CHED 1

Why do we need green chemistry in the classroom?

Edward Brush1, [email protected], Kate Anderson2, [email protected]. (1) Department of Chemistry, Bridgewater State University, Bridgewater, MA, United States (2) Beyond Benign, Wilmington, MA, United States

As the number of chemicals of concern continues to rise the need for solution based green chemistry has never been more necessary than it is today. Green chemistry helps prepare students to engage with their world while connecting chemistry, human health and the environment. Connect core chemistry concepts by using real-world examples of innovation. Learn how green chemistry can be integrated into the high school classroom.

CHED 2

Exploring the 2012 ACS Guidelines and Recommendations for Teaching High School Chemistry

Deborah Cook, [email protected], Carolyn Rulli, [email protected], Brian Kennedy, [email protected] of High School Chemistry, American Chemical Society, Washington, DC, United States

The ACS Guidelines and Recommendations for Teaching High School Chemistry have been significantly revised and are now available for high school chemistry teachers and administrators. Featuring strategies and considerations for teaching high school chemistry in the 21st century to all students, the document is designed to serve as a useful resource for strengthening high school chemistry programs. This symposium has two aims: to communicate the key messages of the document and to explore how high school chemistry teachers and administration can use the guidelines to enhance program activities and leverage for resources. Copies of the ACS Guidelines and Recommendations for Teaching High School Chemistry will be available.

CHED 3

Products of the Target Inquiry project: Quality inquiry materials made for and by high school teachers that stand up to student scrutiny

Ellen J. Yezierski1, [email protected], Deborah G. Herrington2. (1) Department of Chemistry & Biochemistry, Miami University, Oxford, Ohio 45056, United States (2) Department of Chemistry, Grand Valley State University, Allendale, Michigan 49401, United States

The National Science Education Standards, many state science standards, and the newly released Conceptual Framework for New Science Education Standards, call on teachers to develop inquiry-based science programs. Designing such a program can be a daunting task. Three cohorts of high school chemistry teachers have completed a long-term professional development program known as Target Inquiry (TI) at Grand Valley State University. One important product of TI is a peer-reviewed collection of inquiry-based activities for high school chemistry teachers including research-based guides for students and teachers. Not only are these activities teacher-designed and teacher-tested, they have also been edited by chemistry faculty and revised based on feedback from hundreds of teachers who used the activities with more than 30,000 students around the world. An overview of the activities, several specific examples, and instructions to access them will be presented. CHED 4

Health and medicine from a green perspective: Ready-to-use resources from the Journal of Chemical Education

Laura Slocum2, [email protected], Hillary Wilmoth1, [email protected], Deanna Cullen1, Greg Rushton3. (1) Journal of Chemical Education, United States (2) University High School of Indiana, Carmel, IN 46032, United States (3) Department of Chemistry & Biochemistry, Kennesaw State University, Kennesaw, GA 30144, United States

Chemistry is a part of every aspect of health and medicine. However, we do not always think about approaching them in a “green” way. However, the pharmaceutical industry is certainly using greener methods to syntheses many of the medicines they make for use. This presentation will focus on the chemistry of health and medicine – keeping them both “green” – and how it can be integrated into the curriculum using already available teaching materials, including hands-on activities that use low-cost materials from grocery and hardware stores. Presenters will share several ready-to-use resources from the Journal of Chemical Education (JCE) related to the meeting's theme “Chemistry of Health and Medicine” and how we can keep it green. These give educators an opportunity to make stronger connections for their students between the chemical world and the students' "real" world. As time permits, participants will try out a hands-on JCE Classroom Activity related to the theme.

CHED 5

JMU ChemDemo: Lowering the activation energy to do chemistry demonstrations

Casey Rogers, [email protected], Kevin L. Caran, [email protected] of Chemistry and Biochemistry, James Madison University, Harrisonburg, VA 22807, United States

The James Madison University ChemDemo project provides resources for educators interested in using chemistry demonstrations in a variety of venues. Specifically, the program targets college professors, college students and K-12 teachers, largely within the state of Virginia. A website was developed that catalogs over 50 demonstrations, correlated to VA standards of learning (SOLs), including procedures in downloadable and editable formats. In addition the website has lesson plans and problem sets corresponding to selected demos. Annual chemistry demonstration workshops for high school teachers have been held since 2010. The workshops integrate hands- on demonstration instruction, presentations on the value of demonstrations, and opportunities to discuss these activities with other educators. Demonstration videos, including several that require dry ice or liquid nitrogen, were recorded and produced in collaboration with JMU's Center for Instructional Technology. These videos are distributed via YouTube, the ChemDemo website, and DVD. http://sites.jmu.edu/chemdemo/

CHED 6

Fun and chemistry? Yes, they go together!

Todd Smeltz1, [email protected], Karen M. Kaleuati2. (1) ACS ChemClub, Upper Dauphin Area High School, Elizabethville, PA 17023, United States (2) American Chemical Society, Washington, DC 20036, United States

Students can learn about drug testing, urinalysis, and kidney dialysis, while having fun in an after- school chemistry club. The ACS ChemClub provides fun, authentic, and hands-on opportunities to experience chemistry beyond the classroom. ACS provides many valuable resources for this program, but teachers take the resources and transform them into fun and inspiring activities for their students. Participants will hear from a high school teacher and his students on how the ACS ChemClub program has increased students' interests in chemistry and learn about ACS resources available to all teachers willing to start a ChemClub in their schools.

CHED 7

Web-based simulation engine for 2D interactive simulations of molecular systems

Colin A Ashe1, [email protected], David J Yaron1, Michael Karabinos1, Laura Bartolo2, John Portman3, W. Craig Carter4, Donald Sadoway4. (1) Department of Chemistry, Carnegie Mellon University, Pittsburgh, PA 15213, United States (2) Center for Materials Informatics, Kent State University, Kent, OH 44242, United States (3) Department of Physics, Kent State University, Kent, OH 44242, United States (4) Department of Materials Science and Engineering, Massachusetts Institute of Technology, Cambridge, MA 02139, United States

A particularly difficult aspect of chemistry is connecting atomic level interactions to emergent macroscopic properties. To aid students in developing the intuitions needed to make these connections, we have developed a web-based computational engine for simplified two- dimensional simulations of atoms and molecules. The simulation engine is optimized to give results that well represent the nature of motion and interactions at the atomic scale, as opposed to precise integration of the molecular dynamics. This allows students to controlvarious system parameters and observe the effect of their changes on the visualized atoms, as well as attach charts that provide measurements of important system quantities. The software is modular to allow easy construction of simulations. In this talk, we will highlight the capabilities of our system in general and provide specific examples of simulations created to teach a broad range of concepts like osmotic pressure, interatomic potential energy, and heat transfer.

CHED 8

Making their own visualizations: Introducing students to the techniques and applications of biomolecular simulations

Daniel A. Barr, [email protected] of Chemistry and Biochemistry, Utica College, Utica, NY 13502, United States

The pedagogical advantages of visualizations (including animations and simulations) in the chemistry classroom are well-established. Most publishing companies now offer online animations and visualizations to accompany their printed chemistry textbooks and many instructors are becoming familiar with strategies for designing and implementing their own visual aids in their teaching. At Utica College, we are incorporating biomolecular simulation techniques into the biochemistry curriculum that allow students to both visualize and manipulate biomolecules on an atomic scale. By developing their own simulations, students simultaneous learn important principles of physical biochemistry as well as leading-edge research techniques in computational biochemistry. Examples and outcomes of student experiments with biomolecular simulations will be presented.

CHED 9

Visualization and interactivity in the learning of chemistry

Bhawani Venkataraman, [email protected] Sciences and Mathematics, Eugene Lang College The New School for Liberal Arts, New York, NY 10011, United States An essential requirement for learning chemistry is the ability to form mental models of processes at the molecular scale. Yet, students find this to be one of the most challenging aspects of chemistry. An approach that is increasingly being used to help students develop mental models is computer visualizations of molecular systems and processes. This paper presents a set of instructional units that integrate molecular modeling and visualizations to teach fundamental chemical concepts. The units emphasize fundamental chemical concepts and guide students in building, visualizing, interacting, and simulating molecular-level systems and processes. The units help students develop a visual understanding that spans the scale from individual atoms to complex macromolecular systems and highlights the relationship between molecular-scale processes and macro-scale outcomes. Assessment of these units indicates that the students are successfully learning fundamental concepts and value the computer-based instructional units in “visualizing” and developing mental models of the molecular scale.

CHED 10

Boosting laboratory preparedness and experimental comprehension: Integration of online pre-laboratory modules

Danaè R. Quirk Dorr, [email protected], M. Hadley.Department of Chemistry and Geology, Minnesota State University, Mankato, Mankato, MN 56001, United States

All students enrolled in a single semester organic and biochemistry for allied health laboratory received the same written laboratory manual and in-laboratory instruction. However, half of the students were required to complete online pre-laboratory modules prior to participating in the laboratory experiments. The online pre-laboratory modules designed included an audio/visual screen-capture of pre-laboratory instruction that incorporated photographs of the various tools and techniques that would be used in the laboratory. The modules also included interactive problems that provided students with an opportunity to answer questions about the lab based only on the information presented in the laboratory manual and the textbook. Improved student preparedness and experimental comprehension was demonstrated by a comparison of the quantity and type of questions asked during the experiment and the experimental analysis, the time utilized to complete the experiment and analysis, and the laboratory scores.

CHED 11

Visualizing concepts in chemistry: A case study in physical chemistry

Edmund Moses N. Ndip, [email protected] of Chemistry, Hampton University, Hampton, NJ 23668, United States

The development of critical thinking skills as well as the ability to understand abstract concepts in real time is an essential component of the teaching and learning process. Overall, active participation by the learner (the student) and teacher (facilitator) are essential. The underlying principles of this assertion is that people learn best when there is direct personal involvement and by connecting new information to the existing knowledge base. Visualization techniques are essential in helping students discover facts, concepts or principles on their own with guidance from the instructor through hands-on activities. Physical chemistry is a challenging course. A number of practical approaches for visualizing abstract concepts will be presented as part of the computational science pedagogical paradigm.

CHED 12

Single class period activities for the science majors' chemistry course covering an introduction to the gas laws Patricia M Todebush, [email protected] of Natural Sciences, Clayton State University, Morrow, GA 30260, United States

One way for faculty to increase retention, develop classroom enjoyment, and improve student achievement is through the inclusion of active learning activities in their curriculum. I have developed a set of visualization activities to go along with the development of the gas laws in my general chemistry course. The activities are designed to support the theory discussed in a fifty minute class period, including set up and class reflection. These activities demonstrate how active learning can fit nicely into a chemistry curriculum for majors as well as work in a large lecture and convey the fundamental concepts better than the traditional lecture.

CHED 13

Mobile devices and the future of chemical education

Harry E. Pence, [email protected]. of Chemistry & Biochemistry, SUNY Oneonta, Oneonta, NY 13820, United States

More than half of the students in many chemistry classrooms now own smartphones and/or tablet computers and that percentage is growing rapidly. Smartphones are now at the place where electronic calculators were a little more than a decade ago; many instructors are focused more of potential abuse of the device than on the way it will change the learning process. Why are mobile devices so important to the future of chemical education? What are the potential learning capabilities of mobile devices in the classroom, and what are the best learning strategies to take advantage of these new opportunities?

CHED 14

Case study in mobile device usage: Mobile enhanced inquiry-based learning (MEIBL)

Cynthia B Powell1, [email protected], John Hatherill2, Daiyuan Zhang2, Louise Nicholson3. (1) Department of Chemistry and Biochemistry, Abilene Christian University, Abilene, Texas 79699, United States (2) Department of Natural Sciences, Del Mar Community College, Corpus Christi, Texas, United States (3) Department of Biology and Environmental Sciences, California University of Pennsylvania, California, Pennsylvania, United States

Over the past five years, we have used mobile devices (iPods, iPhones, and iPads) to deliver podcasts covering essential laboratory techniques and central conceptual information to students enrolled in General Chemistry laboratories taught with an inquiry-based curriculum. In addition, faculty members have leveraged applications and browser search engines on mobile devices as a support for student activities in both the lecture and laboratory courses. In an effort to scale our approaches to different STEM settings with more diverse populations, we have been working with faculty at two other institutions on the Mobile Enhanced Inquiry-Based Learning (MEIBL) project. This presentation will include data collected on student performance and student approaches to learning at the three institutions, as well as challenges and successes in adapting mobile device use for different curricula.

CHED 15

Blended biochemistry: Using technology outside of class to better reach students in class

Autumn L. Sutherlin, [email protected] of Chemistry and Biochemistry, Abilene Christian University, Abilene, TX 79699, United States Biochemistry is difficult because it requires not only the memorization, but also the interpretation and evaluation of large amounts of material. Technology allowed me to modify a Biochemistry I course to use constructivist techniques. Students did assigned reading followed by Just-in-Time Teaching Warm-up questions which they responded to online before class. The Warm-up questions along with responses to clicker questions followed by Peer Instruction were used to guide class discussion. This allowed me to find the areas of content where the students were struggling and to focus in on areas that require higher order thinking skills. The performance on exams of this year's class was compared to the previous year's class. On two of the four exams the treatment group performed statistically significantly better on exams. Pre- and post-attitudinal studies along with course evaluations showed that the students appreciated the use of the Warm- up and Peer Instruction questions.

CHED 16

Demise of the textbook and rise of ... something else

Doris I. Lewis, [email protected] of Chemistry and Biochemistry, Suffolk University, Boston, MA 02114, United States

Weighty, static, expensive textbooks have become an unsustainable burden on the student and the teacher. What will replace them? Other commercial platforms are being advanced, and some of these will no doubt serve as replacements for the bound sheets of cellulose that have been synonymous with education. It is also possible that the democratization of information we see taking place in society will become the new model in academia, with individualized courses designed by the teacher, even in the highly structured learning environment of science education. This is a report on one teacher's attempts to explore textbook writing in the watershed year of 2012.

CHED 17

Integrating student-created videos into research papers

Lucille A Benedict1, [email protected], Harry E Pence2. (1) Department of Chemistry, University of Southern Maine, Portland, ME 04104, United States (2) Department of Chemistry and Biochemistry, SUNY at Oneonta, Oneonta, NY 13861, United States

Using multimedia (videos and photos) in education has gained popularity. Students increasingly use this content to supplement study materials; students capture videos and photos, disseminate these on social websites, and generate QR codes embedded with a URL linked to the content. For this project, instrumental analysis students created research manuscripts accompanied by short videos focused on research methods developed during independent research performed in the course. Videos were uploaded to YouTube and added to research manuscripts using QR codes. Evaluation of articles and videos was analogous to journal article review; papers that were accepted for publication were incorporated into an online course journal. This project is an extension of published work that had students create videos that were then QR coded and posted to instruments and lab manuals. This project reinforced that having students create a publication increases their engagement and their investment in the finished product.

CHED 18

IM-Chem: The use of instant messaging to improve student performance and personalize large lecture general chemistry courses Derek A Behmke1, [email protected], Charles H Atwood2. (1) Department of Chemistry and Biochemistry, Bradley University, Peoria, IL 61625, United States (2) Department of Chemistry, University of Utah, Salt Lake City, UT, United States

Previous research has linked poor student performance with the depersonalized feeling of large lecture courses. Various forms of enhanced communication have been tried that appear to enhance personalization in large courses. At the University of Georgia we have attempted to enhance communication using 26 instant messaging (IM) devices in large general chemistry courses. A project we called IM-Chem. The general chemistry classes are taught in a 365-seat lecture hall. Implementation of IM-Chem in large lecture general chemistry courses has had a positive impact on student performance. IM-Chem participants had a mean course grade that was 0.14 GPA units higher than non-participants. Gains in student performance are attributed to the active learning environment that IM-Chem participants experienced. Additionally, an overwhelming majority of participants stated that IM-Chem personalized the large lecture setting by providing them with an unintimidating way to ask questions and individualized answers to those questions.

CHED 19

Putting chemistry into the hands of students – chemistry made mobile using resources from the Royal Society of Chemistry

Antony J Williams1, [email protected], Valery Tkachenko1, Will Russell2, Alexey Pshenichnov1. (1) ChemSpider, Royal Society of Chemistry, Wake Forest, NC 27587, United States (2) Royal Society of Chemistry, Cambridge, United Kingdom

The increasing prevalence of mobile devices offers the opportunity to provide chemistry students with easy access to a multitude of resources. As a publisher the RSC provides a myriad of content to chemists including an online database of over 26 million chemical compounds, tools for learning spectroscopy and access to scientific literature and other educational materials. This presentation will provide an overview of our efforts to make RSC content more mobile, and therefore increasingly available to chemists. In particular it will discuss our efforts to provide access to chemistry related data of high value to students in the laboratory. It will include an overview of spectroscopy tools for the review and analysis of various forms of spectroscopy data.

CHED 20

Possibly the nation's (world's?) largest and longest ongoing university chemistry demonstration outreach program

John J. Fortman, [email protected] of Chemistry, Wright State University, Dayton, Ohio 45435, United States

Since the late 70's Wright State University has sponsored chem demo outreach programs done by Rubin Battino and myself. Doing up to 25 shows per year we have reached over a quarter million students. It began with visits to local schools for general assemblies. Currently we do 19 shows each year for over 8,000 students. When we couldn't meet the demand for reservations in 1987 we made a 3 hour video tape set for teachers to use. Additional sets of new demos were recorded in 1991 and 1993 with all being transferred to DVD's in 2004. Presentations have also been done at Science Fairs, Science Museums, Air Shows, and Tech Fests. Video clips from will be shown including some "bloopers". JJF has also given presentations throughout the country.

CHED 21 Students participating in chemical education: Teaching chemistry through interactive demonstration shows

Brendon T Sargent1, [email protected], Andrew Killeen1, [email protected], Holly W Kerby2, Brittland DeKorver1. (1) University of Wisconsin-Madison, Madison, WI 53706, United States (2) Madison Area Technical College, Madison, WI 53704, United States

Students Participating In Chemical Education (SPICE) is a student organization at the University of Wisconsin-Madison. The group's mission is to expose the community to the broad world of chemistry doing activities and performing demo shows that are fun, entertaining, interactive, and educational.

SPICE adopted the Science Concept Investigation (SCI) Demos and Shows developed by Fusion Science Theater (FST) to enhance the learning of their audience members.

In this presentation, members of SPICE will discuss their experiences in adapting, rehearsing, and performing the SCI Demo, “Will it Light?”.

CHED 22

Learning through experiments, awareness, and demonstrations: The chemistry LEAD program at the University of Virginia

Trisha L Vickrey, [email protected], B. Jill Venton, Joseph Houck.Department of Chemistry, The University of Virginia, Charlottesville, VA 22903, United States

In 2009, the graduate students in the Department of Chemistry at the University of Virginia formed a chemistry outreach group called the Chemistry L.E.A.D. (Learning through Experiments, Awareness and Demonstrations) Program. We visit local K-4 elementary schools and facilitate learning through hands-on, inquiry-based activities. The experiments that we engage the students with are aligned with the science standards of learning for the Commonwealth of Virginia, so that it is easy for teachers to fit chemistry experiments into their curriculum. Through our efforts, we have taught over 2,000 students in over 75 classrooms. We have also partnered with two local museums to bring chemistry programming to over 500 visitors, as well as, have hosted a Saturday chemistry camp. This presentation will discuss some of the lessons learned and strategies for managing a successful chemistry outreach organization.

CHED 23

Sustainable-chemistry based outreach to Bay Area schools

Ritankar Das, [email protected] of Chemistry, UC Berkeley, Berkeley, California 94706, United States

Earth's resources are limited, and in order for mankind to survive, future generations must be left with enough resources to sustain basic living necessities. To educate youth about the green chemisty concepts surrounding this issue, and to attract them to STEM fields, student volunteers at See Your Future (SYF) have developed new experiments and demonstrations for K-12 chemistry classes.

SYF is a student-founded and student-run nonprofit organization with approximately 50 volunteers including undergradutes, graduate students, postdocs, lecturers, and faculty in chemisty. SYF works with the Berkeley Center for Green Chemistry and the Department of Energy to develop novel sustainability-based demonstrations and labs. SYF volunteers perform these demonstrations and labs alongside science curriculum in the Bay area schools through in- class and afterschool visits.

Figure 1: SYF Volunteers at Piedmont Middle School

SYF has conducted surveys about techniques of curriculum and demonstrations that connect best to youth from 6th to 9th grade and has discovered two things. First, comparisn of salaries in the chemical sciences versus other professions is an effective attention-grabber. Second, cost is a major barrier for teachers in the Oakland Unified School District to provide demonstrations in chemistry classrooms.

CHED 24

Are you really reaching your public?

Marilynn Sikes, [email protected] of Science, Hawthorne High School, Charlotte, NC 28205, United States

The purpose of most public outreach activities is to promote a positive image of the chemical sciences to those outside of the field of chemistry. But how can you know if your message is coming through to your audience? This session will show how using techniques from the field of informal education can assist you in answering this question. The session will then introduce some evaluation methods implemented by museum professionals to gather data on audience impact.

CHED 25

High School outreach staged demonstrations: Benefits and pitfalls of introducing young students to the process of experimental design

David A Laviska, [email protected], Kathlene D Field, Alan Goodman.Department of Chemistry, Rutgers University, Piscataway, NJ 08854, United States

Now in its sixth year, our outreach program (LEEDAR: Learning Enhanced through Experimental Design and Analysis with Rutgers) exposes high school students to the basic tenets of experimental design – a process through which they can design, conduct, and present the results of their own unique classroom experiments. Funded by the NSF, our central goal has been to forge connections between learning in the sciences at the high school and undergraduate and graduate college levels. While effective experimental design is a critical component of scientific research, there is typically little introduction to the necessary creative and analytical skills prior to the start of graduate-level studies. While many outreach programs rely on experimental demonstrations, we believe that participating in the process of independently forming a hypothesis and testing it will attract more young students to advanced study in the STEM disciplines.

CHED 26 Chemistry for everyone: Teaching, learning, and the power of the human factor

Michelle Shearer, [email protected] National Teacher of the Year, Urbana High School, Ijamsville, MD 21754, United States

“Chemistry is everywhere, and thus chemistry is for everyone.” Michelle Shearer, 2011 National Teacher of the Year, has maintained this philosophy during her fifteen years as a high school chemistry teacher. Her first classroom experience with deaf and hard-of-hearing students galvanized her belief that there is an aspiring scientist in all of us. To fully engage students of all backgrounds and abilities, educators must be conscious of both the chemistry curriculum and the “chemistry” within the classroom, as students need to experience positive rapport, high energy, and high morale to succeed in this traditionally “intimidating” subject area. Mrs. Shearer will discuss strategies for incorporating 21st century skills into chemistry lessons and share insights from her national travels and educational exchanges with chemistry teachers in China, Japan, and Singapore.

CHED 27

Integrating green chemistry into the high school chemistry experience

Teresa Natoli, [email protected] & Technology Magnet High School of SE CT, CT, United States

Learn how to infuse green chemistry into a traditional chemistry course at the high school level. Explore techniques and materials designed specifically to augment the established curriculum and replace laboratory activities that use materials that are not hazardous to human health and the environment. Connecting concepts to real-world examples of innovation and research brings chemistry to life for students.

CHED 28

Teaching equilibrium using safer starting materials

William R Smith, [email protected] High School, Bristol, PA 19007, United States

Many equilibrium labs call for using materials that are unsafe to dump down the drain. Why is that? What if you could teach the same concept while using safer materials? This lesson uses common household products to safely demonstrate and show the properties of equilibrium. This is a great example of how to incorporate the principles of green chemistry into your current curriculum.

CHED 29

Greener approach to endothermic and exothermic reactions for the high school lab

Heather Paul, [email protected] School Chemistry, Friends Select School, Philadelphia, PA, United States

This presentation will include an example of a green chemistry experiment that demonstrates endothermic and exothermic reactions using an enzyme common to many living organisms and popular candy products. In addition to being a greener alternative to some traditional reactions used to illustrate energy transfer, this experiment uses reagents easily identifiable for high school students and commonly found in a supermarket. Participants will gain insight into teaching the experiment through performing portions of the experiment themselves.

CHED 30

Bioplastics in the world today

Sherri Conn Rukes, [email protected], Libertyville High School, Libertyville, IL 60048, United States

As society has evolved, the use of plastics has evolved with it. Plastics have been a fundamental material for many of the devices and day to day items that we use. There are many types of plastics around and those various types are plastics are needed for the many different uses that society depends on. With the push to become greener, bioplastics are emerging more and more. This talk will discuss the various components to what makes a bioplastic, how they are made, the difference between compostable and biodegradable, the various types of bioplastics, properties of these plastics, as well as, learn how to make various types of bioplastics. The idea of making bioplastics as an inquiry lab will be discussed, as well as, how to actually test the material to see the various properties.

CHED 31

Green chemistry in context

Teresa Natoli, [email protected] & Technology Magnet High School of SE CT, New London, CT, United States

This presentation will feature a hands-on activity which pulls from cutting edge research and technology advancements. Explore how this lesson can be streamlined for one class period or expanded to be student-driven project. Challenge your students to connect concepts to recent science headlines such as; advances in medicine, alternative energy and safer cosmetics.

CHED 32

Physical and photophysical properties of [Ru(bpy)3](PF6)2: An advanced inorganic chemistry experiment

D. Paul Rillema, [email protected] of Chemistry, Wichita State University, Wichita, KS 67260, United States

[Ru(bpy)3](PF6)2 , where bpy is 2,2'-bipyridine, can be prepared by reduction of RuCl3xH2O in a reducing solvent such as ethanol or with a reducing agent, isolated as the chloride salt and then - metathesized to yield the PF6 salt. The electronic properties can be examined by visible/UV spectroscopy, emission spectroscopy and electrochemistry. The visible/UV spectrum contains intense metal-to-ligand charge transfer and intraligand transitions and their absorption coefficients can be determined by Beer's law. The emission spectrum contains vibrational structure consistent with an IR ring breathing mode. The molecule undergoes oxidation at the metal center and sequential reduction of the ligands which can be demonstrated by electrochemistry measurements. From the proton NMR spectrum of the complex, one can assign the proton resonances to their locations on the aromatic rings and compare them to those of the uncomplexed bipyridine ligands. This is an upper inorganic chemistry laboratory experiment, but aspects can be adapted for other sub disciplines as well. CHED 33

Coordination chemistry experiments with numerous possibilities, for the undergraduate, inorganic lab course: Including links to the organic lab

Mark A Benvenuto, [email protected], Matthew J Mio.Department of Chemistry & Biochemistry, University of Detroit Mercy, Detroit, MI 48221-3038, United States

Numerous multi-dentate ligands which include at least two primary amines can be combined with multi-functional aldehydes to create highly multi-dentate ligands for use as starting points for coordination chemistry experiments. Their ease of synthesis and rapid visual color changes make them ideal for qualitative or quantitative inorganic chemistry laboratory courses. As well, the organic synthetic step prior to the production of metal-organic complexes makes them very suitable as experiments that can bridge the inorganic and organic chemistry laboratory courses. An examination of the possibilities for such complex formation, and the results, will be discussed.

CHED 34

Solid state experiments for advanced chemistry students

Molly Blanchette, [email protected], Richard Langley.Department of Chemistry, Stephen F. Austin State University, Nacogdoches, Texas 75962, United States

This experiment is a solid-state inorganic experiment designed for fourth-year chemistry majors. Students synthesize a compound and determine its density, measure its magnetic susceptibility, and analyze its powder x-ray diffraction pattern. This experiment differs from other similar experiments in that each student synthesizes a different compound. The examination of different compounds allows students to draw conclusions by using data from other students for comparison. There are three sets of compounds to choose between. One set is primitive cubic (perovskite), one is body-centered cubic (garnet), and the final set is face-centered cubic (spinel). It is also possible to assign syntheses from different sets to illustrate the variations between the different cell types. The syntheses within each group are similar; however, it is possible to include some complications such as distorted structures and ferromagnetic or antiferromagnetic compounds. It is necessary to synthesize less than a gram of material, as all analyses are non- destructive. The small amount of material limits the cost and the amount of waste.

CHED 35

Teaching inorganic concepts through descriptive inorganic chemistry experiments

Richard Langley, Danica Dizon, [email protected], Annalisa Mora, Meagan Cameron, Adrienne Soliz.Department of Chemistry, Stephen F Austin State University, Nacogdoches, Texas 75962, United States

In the early to mid-90's many Chemistry departments added a pre-physical chemistry inorganic chemistry course to their curriculum. In general, this course was a “descriptive” inorganic chemistry course. These courses led to the development of several textbooks. Along with other chemistry courses, it is helpful to have a laboratory component illustrating or emphasizing the lecture material. This paper presents a descriptive inorganic laboratory course that emphasizes student observations and independent work. This course consists of a number of experiments that examine the chemistry of various columns across the periodic table. Some of the experiments, such as “The Amphoteric Properties of Aluminum Hydroxide,” are simple and require only a few minutes to complete. Other experiments, such as “The Oxidation States of Chlorine,” require a full three-hour lab period. One experiment, “Survey of the Transition Elements” requires several consecutive laboratory periods and one major report. There are one or more experiments concerning every column on the periodic table except the noble gases. In lecture students learn the “ideal” reactions, in lab they observe the “real” reactions and must be able to reconcile the possible differences. During the development of this course, it was important to minimize the cost of chemicals required and the cost of disposal. In addition, there will be comments concerning the grading of student results.

CHED 36

Comparision of the transition metals through descriptive inorganic chemistry experiments

Richard Langley, Danica Dizon, [email protected], Annalisa Mora, Meagan Cameron, Adrienne Soliz.Department of Chemistry, Stephen F Austin State University, Nacogdoches, Texas 75962, United States

A series of descriptive inorganic experiments examine the periodic properties of transition metals. This lab differs from “traditional” experiments because it challenges students to make predictions to match their observations. The metal ions surveyed are those of Y, La, Ce, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, and Zn. There are eighteen tests run on each metal ion. This reaction series illustrates how transition metal chemistry changes periodically and varies with oxidation state. Students submit a three-part lab report. The first part is an observation list, followed by the chemical equations for all reactions. Finally and most importantly, each student relates his or her observations/equations to periodicity. In the last section, the students compare how the chemical properties vary across the transition series. Since the students do not know which ions will react, this experiment introduces students to chemical research.

CHED 37

General (microwave) chemistry for first-year undergraduates

Michael J. Karney, [email protected], Grace S. Vanier.Life Sciences Division, CEM Corporation, Matthews, NC 28106, United States

As first year undergraduates, many students have their initial exposure to the field of chemistry in the general chemistry lab. By early introduction of instrumentation such as microwave reactors, students are taught to embrace ideas on the cutting edge of chemistry, and they are better prepared for the technology of the future. Microwave chemistry in the teaching lab offers numerous benefits to conventional methods including safer, faster, and more efficient reactions. Chemistry which was previously not suited for teaching because of dangerous solvents, long reaction times, or low yields can be readily adapted to a microwave format, preparing students for a wide range of chemistry they will encounter an a variety of work environments. This presentation will focus on a sampling of experiments designed for use in the general chemistry lab to supplant and supplement procedures from established curricula.

CHED 38

Engaging students in learning through the use of mobile webapps

Lisa B. Lewis1, [email protected], Ian F. MacInnes2. (1) Department of Chemistry, Albion College, Albion, MI 49224, United States (2) Department of English, Albion College, Albion, MI 49224, United States Our students are addicted to their mobile devices, but so are we. Can we turn this addiction into an opportunity to have students engage longer and more meaningfully with course material? This talk describes our efforts to create mobile web applications for the study of chemistry and English. We will share examples of the webapps that we have developed, our students' experiences using these webapps, and our development process including design and format, pedagogy, and coding challenges.

CHED 39

Development of tablet software for learning Lewis dot structures

Carlo Yuvienco1,2,3, [email protected], Jin Kim Montclare1,2,3. (1) InSchool Apps, LLC, New York, NY 10038, United States (2) Department of Biological and Chemical Sciences, Polytechnic Institute of NYU, Brooklyn, NY 11201, United States (3) Department of Biochemistry, SUNY Downstate, Brooklyn, NY 11203, United States

While electronic devices like cell phones, iPods and touch screen devices are conventionally shunned in the classroom as distractions, we hypothesize that students may be better engaged by developing software that effectively use such devices in the classroom to teach chemistry. We developed an iPad-based App that aims to enhance the learning of Lewis dot structures in secondary and post-secondary classrooms. We posited that the lack of an instructional framework in pencil and paper imposed a learning barrier for students that have not yet fully grasped the concept of Lewis dot diagrams. We present lessons from the design and implementation of the App prototype, which was developed to overcome this lack of guided structure as well as around the basis of creativity in an attempt to migrate students from being information consumers to being producers.

CHED 40

Mobile learning in organic chemistry: Discussion of the student's role in the 21st century classroom

Mai Yin Tsoi, [email protected], Patrick Coppock, Julia Paredes, Sang Park, Richard Pennington, David Pursell, Joseph Sloop, David Gabrell.School of Science & Technology, Georgia Gwinnett College, Lawrenceville, GA 30043, United States

In acknowledging that today's students are very different from those of previous generations, we created a student-centered, mobile learning environment in Organic Chemistry with a suite of electronic course materials which include videos, apps, and a social network. They are formatted for computers and mobile devices and are tuned to the 21st century student's learning needs and lifestyles. Over the last 3 years, we have studied students' interactions with these materials and measured various student attributes; we have found that students bring a distinct set of needs and skills to the learning environment, which impact their use of the mobile learning materials. Some of these qualities, such as self-efficacy, attitude, and technology expertise, were found to significantly affect whether students use mobile devices for learning Organic Chemistry. We will present findings from each year of our study and discuss implications of implementing mobile learning in a student-driven curriculum.

CHED 41

Learning organic chemistry through gaming, Part I: Nomenclature Issam Kobrsi, [email protected] of Arts and Sciences, The Petroleum Institute, Abu Dhabi, United Arab Emirates

A program was designed to train students in organic nomenclature using touch media such as tablets and mobile phones. The concepts required by students to learn nomenclature were identified, and a program was designed to train each concept separately, instead of training all concepts of nomenclature simultaneously. The first concept was identified as the numbering of the longest chain. The program displays one molecule at a time from a customizable database. Students can then tap the carbon atoms in the proper order using their fingers and receive immediate feedback. Preliminary studies showed that, compared to traditional homework, students can go through many more exercises during the same allocated time. In addition, the students were more engaged due to the “video game nature” of the exercise versus the “study nature” of traditional homework.

CHED 42

Chemical structure diagrams, reactions, and data: Anytime, anywhere

Alex M Clark, [email protected] Materials Informatics, Montreal, Quebec H3J2S1, Canada

The creation of chemistry-aware mobile apps presents a significant opportunity to enhance chemical education. Tablets and mobile phones introduce a level of convenience that makes them all but omnipresent. Access to chemistry-oriented learning material is of significant value, and taking it one step further involves providing content-creation capabilities. Being able to create, view, send and receive chemical data, and use it to interact with educational or reference services, can make these devices into powerful interactive learning tools. This presentation will focus on the state of the art for mobile apps for chemistry, and their use in an educational context.

CHED 43

Using HTML5 to build immersive teaching materials

Kevin J Theisen, [email protected], LLC., Somerset, NJ 08873, United States

Students today have access to a wealth of technology for interacting with digital information, made possible through mobile devices. It can be very enticing to take advantage of these platforms in classrooms. However, the ability to distribute information across the wide range of devices students may possess is a significant problem. This barrier restricts most instructors to distributing text and images, since they simply do not have the time to prepare and format coursework for all the existing devices. HTML5 standards present a simpler approach to distributing dynamic graphics and interactive data across all desktop and mobile platforms. We discuss two key HTML5 technologies, and WebGL, and also discuss the open source ChemDoodle Web Components library, which is widely used in education and allows scientists to quickly create rich, interactive scientific media and applications that can be easily deployed to students.

CHED 44

Chemistry magic of toys, polymers, food, and more: 35 years of public outreach

David A Katz, [email protected] of Chemistry, Pima Community College, Tucson, AZ 85709, United States For 35 years, this author has presented chemistry programs, hands-on activities, and workshops in many venues including schools, museums, public libraries, hotels, restaurants, fire houses, parks, and television studios to various audiences from youngsters, to professional scientists, to the general public around the world. Using varied formats, major topics have included “Chemistry in the Toy Store”, “The Science of Soap Bubbles”, “Polymers”, “Magic into Science”, “Cooking With Chemistry”, “Liquid Crystals”, and more. These presentations have resulted in the development of new activities and popularization of others, many of which are utilized in science education throughout the world today.

CHED 45

Week-long interactive science experience for deaf students

Casey Rogers, [email protected], Kevin L. Caran, [email protected], Daniel M. Downey, Gina MacDonald, Daniel K. Havey, Christine A. Hughey, Thomas C. DeVore.Department of Chemistry and Biochemistry, James Madison University, Harrisonburg, VA 22807, United States

In June of 2012 a science camp was held at the Virginia School for the Deaf and the Blind (VSDB) as part of the James Madison University (JMU) Chemistry REU program. Upper elementary and middle school students from Virginia's deaf community participated in this 5 day program. The camp was developed by a JMU alumna along with six JMU Chemistry and Biochemistry faculty members. Additionally, undergraduates from the JMU REU program and teachers from VSBD assisted in the daily activities. Faculty members developed content related to their respective fields of expertise. These topics included water chemistry analysis, colloid chemistry, simulations and polymers. A day trip to JMU's campus highlighted ongoing research activities in the Chemistry and Biochemistry Department, and enabled interaction with college- aged role models from the deaf community.

CHED 46

Validity and application of a pre/post survey assessing children's attitudes and motivation at informal chemistry outreach events

Christopher Bauer1, [email protected], Mary Emenike2,3, Jessica Reed2, Jeffrey Raker2, Thomas Holme2. (1) Department of Chemistry, University of New Hampshire, Durham, NH 03824, United States (2) Department of Chemistry and ACS Examinations Institute, Iowa State University, Ames, IA 05011, United States (3) Catalyst Center, California State University at Fullerton, Fullerton, CA 92831, United States

We have developed a six-item paper-and-pencil survey for chemistry outreach events. Survey items are based on theories of human affective and motivational behavior. The survey is presented on a card with pre items on one side and parallel but not identical post items on the other. Field testing has been done at university “science week” field trips, Festival de Quimica in Puerto Rico, and National Chemistry Week events. Design challenges included what constructs to include (emotional satisfaction, difficulty, interest, self-efficacy, fear, mystery), adjusting language for the grade 3-12 population (and Spanish-speakers), physical form, efficiency and reliability of completion, item performance and symmetry, and construct independence. An additional challenge is providing understandable feedback to event organizers from an instrument that provides rich data. We will present data on the robustness of the constructs in survey items and show a visual color-coded approach for summarizing data.

CHED 47 Chemistry camp: A science outreach project

Joseph D Houck, [email protected], Christopher B Jacobs, Trisha L Vickrey, B Jill Venton.Department of Chemistry, University of Virginia, Charlottesville, VA 22904, United States

The Chemistry L.E.A.D. (Learning through Experimentation, Awareness, and Demonstration) Program at the University of Virginia is designed to promote science education and awareness in the local Charlottesville community. We organized and hosted a Chemistry Camp in cooperation with the Department of Chemistry at the University of Virginia. This five-hour, Saturday camp sought to provide hands-on science to K-4th grade students and excite them with demonstrations. The students completed a rotation of five experiments, were provided lunch, and the afternoon ended with a demonstration show. This camp model could be utilized in a variety of settings to provide enrichment opportunities for young learners.

CHED 48

Redesigning the chemical demonstration show to promote investigation, interaction, and concept learning

Christopher Babiarz1,7, [email protected], Holly Walter Kerby2,7, Joanne Cantor3,7, Brittland DeKorver4,7, Marcia Weiland5,7, Kimberly Megna Yarnall6,7. (1) Environmental Chemistry & Technology Program, University of Wisconsin, Madison, Wisconsin 53706, United States (2) Department of Chemistry, Madison Area Technical College, Madison, Wisconsin 53704, United States (3) Your Mind on Media, Monona, Wiscosnsin 53716, United States (4) Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, United States (5) Attainment Company, Verona, Wisconsin 53593, United States (6) Forward Theater Company, Madison, Wisconsin 53708, United States (7) Fusion Science Theater, Madison, Wisconsin 53704, United States

Can a demo show teach as well as entertain? Can theater be used to communicate accurate, conceptual, and data-driven science? Can a chemical education outreach event provide the audience with an authentic investigative experience? The answer is “yes” on every count, and the proof is the Science Concept Investigation Show (SCI Show), a chemical outreach model developed by Fusion Science Theater. This presentation will explain how and why the elements and structure of theater can be used to redesign traditional demonstration shows, and how SCI Shows promote concept learning by providing the audience with an interactive investigative experience. The presentation will also describe the dissemination of SCI Show scripts to the public, and the Performance Training Program currently being developed to train ACS Undergraduate groups to perform the shows in their own communities. Fusion Science Theater is funded by the National Science Foundation.

CHED 49

Where is Penny the Pony? A forensic investigation for elementary students

Joseph D Houck, [email protected], Trisha L Vickrey, [email protected] of Chemistry, University of Virginia, Charlottesville, VA 22904, United States

The Chemistry L.E.A.D. (Learning through Experimentation, Awareness, and Demonstration) Program at the University of Virginia is designed to promote science education and awareness in the local Charlottesville community. We have developed a unique elementary-level forensic science experiment. Students are presented with two clues: a ransom note and footprint found at the crime scene. Using paper chromatography of pen inks, students are able to determine which pen wrote the ransom note based on their characteristic separation. Additionally, the soil sample is compared to other samples collected from local landmarks. Soil samples have been spiked with metal salts and, when complexed with ammonia, show a characteristic color. Students are able to form conclusions based on evidence to locate Penny the pony and identify a perpetrator.

CHED 50

Murderous molecules: Teaching an introductory toxicology course at an undergraduate institution

Christine H Jaworek-Lopes, [email protected] of Chemistry, Emmanuel College, Boston, MA 02115, United States

An Introduction to Toxicology course, an elective for undergraduate chemistry majors was taught at Emmanuel College, a small liberal arts institution in the spring of 2012. Course design and content will be shared. Particular attention will be paid to two assignments. The first is presentation regarding a primary literature toxicology article. The second is the molecules of murder project in which students present on toxins such as coniine, ricin, snake venom, and thallium. A portion of the molecules of murder presentation focused on what a murder mystery writer needs to know. Finally, lessons learned from teaching such an interdisciplinary course for the first time will be shared.

CHED 51

Evaluating outreach: Results from assessment surveys at National Chemistry Week, Chemists Celebrate Earth Day, and International Year of Chemistry events

George L. Heard1, [email protected], Ressano Machado2, rdesouza- [email protected]. (1) Department of Chemistry, UNC Asheville, Asheville, North Carolina 28804, United States (2) Department of Chemistry, University of Wisconsin La Crosse, La Crosse, Wisconsin 54601, United States

The American Chemical Society's Committee on Community Activities (CCA) have been administering a survey of attendees at public chemistry events for the past four years. We present results of this survey designed to gauge the effectiveness of outreach events, asking questions in age-appropriate language. Initial findings are promising, with attitudes towards chemistry showing a consistent increasing trend comparing pre- and post- event data. The post- event data shows an average 30% increase in the number of attendees who rate chemistry as “awesome” compared to before an event, and a significant decrease in the number of attendees who indicated chemistry was “bad” or “boring”. We will include with this poster details on how you can incorporate evaluation in your outreach events.

CHED 52

Dewey to McKeon to Schwab: Tracing the origins of inquiry science education in the 20th century

Donald J. Wink, [email protected] of Chemistry, University of Illinois at Chicago, Chicago, IL 60607, United States

The concept of inquiry and student-centered instruction is a powerful phenomenon in chemistry education. It seems to have recently come upon the community, emerging most forcefully since the late 1980's. In fact, the philosophical, psychological, and pedagogical roots of inquiry instruction go back to before 1900, in the work of John Dewey. His role in the development of 'meaning-centered' education, its connection to the work of philosopher Richard McKeon and McKeon's subsequent influence on the science educator Joseph Schwab will be discussed. Articulation of these ideas with recent reform efforts, including changes in the AP science exams, and the National Research Council's work on How People Learn and the Framework for the Next Generation Standards in Science will be reviewed also.

CHED 53

Fostering green chemistry through a capstone course

Ingrid Montes, [email protected], Richard Rivera.Department of Chemistry, University of Puerto Rico at Río Piedras, San Juan, Puerto Rico 00931-3346, United States

Green chemistry is designed to reduce or eliminate the use or generation of hazardous materials associated with chemical products. Moreover, it has been around for two decades and numerous breakthroughs in environmental protection and pollution prevention have been realized in recent years. Industry and academia are involving on it and focusing on green chemistry principles, but very few opportunities exist for students and practicing chemists to learn more about green chemistry. To address this, a Capstone Course for graduate and undergraduate students was designed. It includes different activities and foster students to apply the knowledge already acquired during their introductory courses. We aim to assess in the students the development of general intellectual skills (e.g., communication, reasoning/analysis, social and team-work, literacy) as well as discipline-specific essential skills (develop environmentally conscious scientists, experiences in laboratory and research projects). The design, methodology and preliminary findings will be elaborated.

CHED 54

Chemical free chemistry: Can a world without chemicals really exist?

George Ruger1, [email protected], Carmen Drahl2. (1) ACS Mid Hudson, Modena, NY 12548, United States (2) C&EN, Washington DC, United States

In recent years a lot of marketing has focused on products that claim to be chemical free. Not just free of hazardous or toxic chemicals, but free of all chemicals. This is even the case when those items have chemical names listed on the list of ingredients. Of course these items do contain chemicals, as do all products. Examples are shown of some of these items as seen in advertisements for the products. A case is made as to why chemophobia is so prevalent in our society. In the future it is hoped that the scientific community will stand up and point out cases where chemical terms are used improperly. Chemicals are everywhere, and the public needs to understand this.

CHED 55

Renovating general chemistry laboratories: A pain in the...pipes

Elaine K. Haub, [email protected], Jan M. Fleischer, [email protected], Chandashri Bhattacharya, [email protected] of Chemistry, Indiana University Southeast, New Albany, IN 47150, United States

Recent renovations to our 40 year old general chemistry laboratories and preparation room were a learning experience. Layout, cabinetry and flooring design decisions were the easiest part of the renovation process. Additions of backpack cubbies, teacher's desk, cart garage, glass front cabinets and an improved open layout have been of great benefit to the overall appearance and function of the laboratories. Unforeseen consquences of decisions led to delays, complications, flooding and last minute changes. An outline of what has been learned from this experience and suggestions to aid others in future renovations will be provided.

CHED 56

Renovation of laboratories and upgrade of cyber-infrastructure to enhance undergraduate research program

Malcolm J. D'Souza, [email protected], MaryAnn Yaeger.Department of Chemistry, Wesley College, Dover, DE 19901, United States

In 2009 through our portion of an NIH-INBRE grant (2P20 RR016472) to Delaware (DE), we accomplished the gut-renovation of the organic chemistry laboratory. This helped us provide a unique opportunity for undergraduates to begin original research in chemistry within a Directed Research program early on in their careers (some beginning as freshmen). This program was originally designed to deliver a statewide pipeline of capable and competitive medical research personnel and has achieved success because research productivity was enhanced by developing collaborative partnerships with neighboring in-state higher-education institutions and the local biomedical industry.

Success achieved has been outstanding; 38 undergraduates are co-authors on peer-reviewed publications, 42 have earned national recognitions, and several have joined graduate and professional programs on graduation. This undergraduate research program is now expanded to cover environmental topics and is supported through the DE-NSF-EPSCoR grant (EPS-081425), and a NSF ARI R2 grant (0960503).

CHED 57

Formative assessment of student learning in an online community for computational chemistry research

David Yaron1, [email protected], Laura M. Bartolo2, Lovell E. Agwaramgbo5, Gaea Leinhardt4, Lynda R. Louis6, Lynn Y.R. Strong7, Geoffrey J. Gordon3. (1) Department of Chemistry, Carnegie Mellon University, Pittsburgh, Pennsylvania 15213, United States (2) Center for Materials Informatics, Kent State University, Kent, Ohio 44242, United States (3) Department of Machine Learning, Carnegie Mellon University, Pittsburgh, Pennsylvania 15213, United States (4) School of Education, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States (5) Department of Chemistry, Dillard University, New Orleans, Louisiana 70122, United States (6) Department of Computer Science, Dillard University, New Orleans, Louisiana 70122, United States (7) Undergraduate Enrichment Programs, Dillard University, New Orleans, Louisiana 70122, United States

The long-term vision of this project is a community that any novice may join to receive training and participate in computational chemistry research. This broadens participation while providing expert researchers with an expanded workforce. This summer, through a NSF CI-TEAM Demonstration Project, students from Dillard University and other sites will work with researchers at Carnegie Mellon, using a prototype system provided by the Materials Digital Library (MatDL) at Kent State. This prototype cyberinfrastructure supports student learning along with project and data management. Key features needed for success of the long-term vision will be evaluated, including the ability of researchers to work productively with students online, of students to support one another, and of the system to capture work in a manner that can train the next cohort of students. The evaluation effort will use student interviews, existing instruments for evaluating research experiences, and analysis of artifacts from the online environment.

CHED 58

WITHDRAWN

CHED 59

Mentorship program for the freshmen general chemistry course

Juan C Aponte-Santini1, [email protected], Ingrid Montes-González1, Víctor Bonilla- Rodríguez2. (1) Department of Chemistry, University of Puerto Rico-Río Piedras Campus, San Juan, Puerto Rico 00931, Puerto Rico (2) Department of Graduate Studies, University of Puerto Rico-Río Piedras Campus, San Juan, Puerto Rico 00931, Puerto Rico

Students starting their baccalaureate in Natural Sciences are introduced to the Selected Topics in Chemistry course, which is a preparatory program part of the Federal Program Pre-MARC. Graduate students offer mentoring to freshmen students that are enrolled in the General Chemistry course, in a one-hour meeting per week. Different activities are promoted as part of the program, including tutoring in identified topics, as the most difficult ones in the course. This study intends to answer the following research questions: Is there any influence in the students' achievement in the General Chemistry course? Does the course promote, create, and influence the development of fundamental knowledge and general intellectual skills? Does the course environment influence the affective aspects in the students? Do mentors gain general intellectual skills participating in the program? The design, methodology and preliminary findings will be elaborated. The MARC Program, UPR-RP, sponsors this project.

CHED 60

Qualitative to quantitative and from spectrum to report: Developing an instrument-focused research methods course for first-year students

Alyssa Thomas, Michelle Boucher, [email protected], Curtis Pulliam.Department of Chemistry and Biochemistry, Utica College, Utica, NY 13502, United States

Four years ago we designed an Introduction to Research Methods course for our first-year chemistry and biochemistry majors to correlate with our 2nd semester of general chemistry laboratory, which is instrumentation driven and follows an atoms first approach. We take aspirin, a product from their general chemistry lab, and fully characterize it both qualitatively (FeCl3, FT- IR, etc) and quantitatively (1H and 13C NMR, GC-MS, etc). Students prepare a paper detailing their synthesis and analysis of aspirin using their spectra to “defend” their findings. Students also prepare an original proposal detailing the synthesis of another ester. In this proposal presentation students are expected to anticipate the results of qualitative tests and appearance of spectra for their target molecule. This process of hands-on use of instrumentation, report writing, and proposal presentation has resulted in students being more confident in their future classes and research.

CHED 61

Assessment of community college students participation in STEM research projects Candice J. Foley, [email protected], Nina A Leonhardt, [email protected] of Chemistry, Suffolk County Community College, Selden, New York 11784, United States

To address the need for more STEM professionals in the U.S., Suffolk County Community College has obtained grant funding for an inclusive STEM support model. This study focuses on the impact of including social and cultural supports in addition to traditional academic services and internships upon STEM student persistence and success.

Since 2007, Suffolk County Community College has leveraged NSF-S-STEM grants and a Collegiate Science and Technology Entry Program (CSTEP) and a County-funded STEM scholarship program to create a STEM community of scholars.

To date, we have served an average of 128 students each year. For 2010-11, 56% of our students were underrepresented groups and 41% were women. Students have secured research internships in chemistry and related fields at the U.S. Department of Energy's national laboratories and at Stony Brook University. Students are completing their undergraduate/graduate studies and entering STEM careers with a high degree of persistence.

CHED 62

Course-based approach to undergraduate research

Patty Fu-Giles1, Gregory A Moehring2, [email protected]. (1) Division of Science, Governors State University, University Park, Illinois 60484, United States (2) Monmouth University, West Long Branch, NJ 07764, United States

Following many years of low undergraduate student participation in chemistry research at Governors State University, a course-based approach to undergraduate research was implemented to supplement the existing independent study research model. Some reasons for attempting the new approach included the belief that students would be more comfortable working as part of a cohort rather than independently and the belief that students would be more likely to sign up for a course which clearly fulfilled a degree requirement rather than signing up for a free elective. The goals of the course included increasing student participation in undergraduate research, providing students with a preview of what graduate study includes, and improving student abilities in synthesizing information from the primary literature and examining their results critically. The course has now been offered several times and has even migrated from one instructor to a second instructor. The course has resulted in increased undergraduate particdipation in research.

CHED 63

Building bridges: Integrating mathematics, science, and engineering on the South Plains

Erin Oliver, [email protected], Laci Singer, [email protected], Dominick J. Casadonte.Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409, United States

One of the primary themes of Texas Tech University's “Building Bridges: Integrating Mathematics, Engineering, and Science on the South Plains” GK-12 program is the development of deep thinking about the integration of mathematics, science, and engineering in graduate research and in the K-12 environment by STEM GK-12 Graduate Fellows. This is accomplished by the development of “Math/Engineering/Science Bridge Quartets (MESBQ's)”, where a science Graduate Fellow and high school science Teacher Fellow pairs with a math Graduate Fellow and a corresponding math Teacher Fellow at the same school to develop learning/teaching cohorts. The “Building Bridges” program at Texas Tech University is unique within the National Science Foundation's GK-12 program due to its interdisciplinary nature. Besides integrating math and science/engineering, a secondary goal at Texas Tech is to prepare graduate-level STEM researchers and in-service secondary mathematics and science teachers to thrive in an interdisciplinary environment.

CHED 64

Broader impacts of research on student success

David Baker, [email protected] Division, Delta College, University Center, MI 48710, United States

As community college Delta College provides students with opportunities to learn and study core science courses that engage the students in the scientific method and offer students with challenges in problem solving approaches. It equally important that we provide students enrolled with an opportunity to engage in scientific discovery and research that augments these courses. Students should be afforded the opportunity to complete basic research with different perspectives that integrates and reinforces their scientific knowledge and skills. How this scientific research impacts student success at the community college level and beyond will be discussed. The impact of these opportunities on students perspectives on sustainability, general laboratory skills and their understanding of the interdisciplinary nature of science will be presented.

CHED 65

WITHDRAWN

CHED 66

Are we really doing a service to students by teaching dimensional analysis?

Kenneth M Abayan, [email protected], Kevin A. Schug.Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, Texas 76019, United States

In our study, 121 General Chemistry I students completed a series of activities which included three distinct modules, each featuring a different way of teaching stoichiometry. The methodologies were taken from science education literature and included: Dimensional analysis; use of ratios; and an operational method.1-3 The on-line experiment was conducted using a treatment-control model. Pretest results showed that, 73% of the students who participated had pre-existing knowledge on how to solve stoichiometry problems. Constructivism asserts that prior knowledge [of stoichiometry] can lead to better conceptual understanding and learning [of stoichiometry].4 Post examination results revealed that students who used an operational approach to describe how they solved stoichiometry scored statistically significantly higher (avg. 93), on an in-class examination, compared to those who used dimensional analysis (avg. 73). Should we really be teaching our students dimensional analysis? Can we transition our students to become operational thinkers?

CHED 67

Math preparation of undergraduates in general chemistry: A gatekeeper course required for biophysicists Colleen F Craig, [email protected], Cynthia A Stanich, Sarah L Keller.Department of Chemistry, University of Washington, Seattle, WA 98195, United States

Gatekeeper courses for undergraduates wishing to pursue careers in biophysics and other STEM fields include introductory chemistry, physics, and biology. At the University of Washington, as at many other peer institutions, a high level of math is required for enrollment in main sequence General Chemistry. Specifically, students must have fulfilled a calculus requirement or be co- enrolled in calculus. Moreover, the average high school GPA of freshmen entering directly from high school is 3.7. Nevertheless, we find that significant fractions of students enrolled in General Chemistry are unable to complete problems in which they are asked to manipulate exponents (~20%), logarithms (~40-50%), or probabilities (~40%). Researchers at University of Minnesota have documented similar results [Leopold and Edgar, 2008, Chemical Education Research 85:724]. We find that some math deficiencies among undergraduates persist into the senior year, at least for biochemistry majors. Here we track undergraduate math competencies through the first two academic terms of General Chemistry after introducing an intervention of a math quiz and feedback. We separately track competencies after student use of a program called ALEKS, which uses adaptive questioning to determine student competencies and then instruct on deficient topics.

CHED 68

Thermodynamic concentric multipolyhedron diagram and its applications

Zhen-Chuan Li, [email protected] of Physics & Chemistry, Stuyvesant (Math & Science Specialized) HS, New York, NY 10282, United StatesDepartment of Physics & Chemistry, Stuyvesant (Specialized Math & Science) HS, New York, NY 10282, United States

For a one phase single component system, a variety of thermodynamic variables, such as three pairs of natural variables(P~V, T~S, & µ~N), eight thermodynamic potentials (U, H, G, A, Ω, Ψ, Χ, & Φ), their six first order and twenty-four second order partial derivatives (-P, V, T, -S, µ, -N and CPN, CVN, OPN, OVN, JTN, JSN, RTN, RSN, CPµ, CVµ, OPµ, OVµ, JTµ, JSµ, RTµ, RSµ, ΛPT, ΛVT, ΓPT, ΓVT, ΛPS, ΛVS, ΓPS, & ΓVS), were arranged at vertexes of a concentric multi-polyhedron (a cube sandwiches between a pair of octahedrons and it is surrounded by a 26-face polyhedron or rhombicuboctahedron) based on considerations of their physical meanings, such as a neighbor relationship among correlated (corresponding and/or conjugate) variables, the criteria for spontaneous changes & equilibria, the Ehrenfest classification of phase transitions, and symmetry in thermodynamics. It could be found out by this diagram that some quite confused similar derivatives could be easily distinguished by their variable neighbor relationship, that more than ten families of thermodynamic relations (Legendre transforms, Identity equations, Maxwell equations, Maxwell-II & III equations, fundamental equations, important Jacobian equations, Gibbs-Helmholtz equation family. CPN-type variable family, CPN~CVN relation family, two groups of concise relations among 24 CPN-type variables) could be symmetrically expressed by specific movable patterns, that any derivatives, such as Bridgman's equations, Shaw's formulas, Koenig's results etc., could be derived and expressed in terms of T, P, V, S, α, ΚT & CP on the spot by using the fixed diagram as a map and selecting specific movable patterns plus symmetrical operations as different routes to get their destinations, that the symmetry emphasized by Callen in thermodynamics has been visually revealed in development of this foolproof graphic method, and that the thermodynamic symmetry is not as perfect as the geometric symmetry of the polyhedrons is because of Φ(T,P,µ)=0 at a corner of the cube. This generalized elegant diagram might be considered as a model rather than a mnemonic device since it has profoundly distinguished, expressed, derived, and developed a variety of thermodynamic relations, and especially because it has virtually revealed the thermodynamic symmetry being a C3 symmetry about the special conjugate U~Φ pair as a C3 axis, which pivots at Φ=0, and displaying C4 & σ symmetries on three U-containing squares, where the U, H, G, & A square is most important and useful. CHED 69

Teaching of organic chemistry and analogies

Varaprasad R Koganti, [email protected] of Chemistry, New Science College, Ameerpet, Hyderabad, Andhra Pradesh 500073, India

The teaching of organic chemistry, with its ever-changing content, has undergone revolutionary changes over the past few decades. Moreover, the organic chemistry has been systemized to a considerable degree. In this process, analogies with familiar examples help make organic chemistry more interesting. For example, the relative stabilities of various conformations of butane/cyclohexane can be compared with different postures of human body during yoga asanas. Including this, a total of six new examples of analogies will be presented.

CHED 70

Evolution of organic chemistry textbooks: A comparative study of contents and organization over the past 20 years

Phuong-Truc T. Pham1, [email protected], Mamoun M. Bader2. (1) Department of Chemistry, Pennsylvania State University Worthington Scranton, Dunmore, PA 18512, United States (2) Pennsylvania State University Hazleton, Hazleton, PA 18202, United States

In this paper we survey and analyze the evolution of both the content and organization of organic chemistry textbooks over the past 20 years. Special emphasis is placed on the emerging role of using technology, and computational chemistry in teaching organic chemistry. Prices, frequency of releasing new editions and resources available for students and instructors are also compared. The increasingly popular E-books and the extent they have been used by students will also be considered. What prompted us to carry out this study are the many changes organic texts have undergone over the past two decades and how these changes affect the way organic chemistry is taught and learned. The impact of the internet and the vast resources available to both instructors and students present a challenge which we will only briefly consider.

CHED 71

Design of new experiments for the organic chemistry laboratory

Phuong-Truc T. Pham, [email protected] of Chemistry, Pennsylvania State University Worthington Scranton, Dunmore, PA 18512, United States

This work describes a sequence of new experiments developed and used in teaching our undergraduate organic chemistry course. These experiments were selected based on the chemistry commonly used to access various organic functional materials namely: (1) Electrophilic aromatic substitution reactions and (2) Wittig reactions. Both reactions could yield visibly interesting and exciting products when highly conjugated starting materials were employed. By incorporating research with teaching in the organic lab students gained a sense of excitement through preparing and discovering new compounds as well as through collaborative learning. The reaction of activated aromatic compounds with tetracyanoethylene for instance introduced the tricyanovinyl group, a rather strong electron withdrawing group. The resulting products are highly colored, shiny metallic crystalline solids which showed solvatochromism in solution. Wittig reactions using dialdehydes result in highly conjugated fluorescent materials. Examples of simple room temperature experiments, which can be done in less than three hours, will be presented. CHED 72

WITHDRAWN

CHED 73

Modification of the mixed aldol condensation experiment in the introductory organic chemistry laboratory: An inquiry-based approach towards determining unknowns following a systematic thought process

Amy M Balija, [email protected] of Chemistry, Fordham University, Bronx, NY 10458, United States

Introductory organic chemistry students can fail to fully grasp concepts taught in the lecture and their implications in the organic laboratory. This leads to students being frustrated when performing an experiment containing unknowns, especially when they are unable to determine the structure of their product. The mixed aldol condensation experiment described by Hathaway (J. Chem. Educ. 1987 , 64, 367-368) utilizes different unknown aldehydes and ketones to provide highly conjugated products. In an effort to facilitate a more inquiry-based laboratory approach at Fordham University, I have developed a two step learning process for the mixed aldol condensation experiment that encourages students to have a more proactive view of learning. Through the use of chemical drawing programs, melting points, 1H and 13C NMR spectral data, and a post-laboratory worksheet, an increase in students' understanding of the general reaction has been noted. Representative data and student assessment also will be presented.

CHED 74

Chiral analyses of ephedrines, pseudoephedrines, amphetamines and methamphetamines in the teaching lab

Zhaohua Dai, [email protected] of Chemistry and Physical Sciences, Pace University, New York, NY 10038, United States

Ephedrines, pseudoephedrines, amphetamines and methamphetamines are a class of drugs that contain chiral center(s). To help students understand such concepts better and gain hands-on experience in chiral analysis, we have successfully separated and identified these drugs in our Chemical Separations and Analytical Spectroscopy teaching lab exercises. First, our students analyzed these compounds by GCMS using a HP-5 ms column. Then, they derivatized these compounds with L-TPC and analyzed these compounds on the same instrument. They also analyzed these compounds using capillary electrophoresis using b-cyclodetrin as the chiral additive in the running buffer. From these experiments, the students draw their own conclusion to see how enantiomers and diastereomers can be separated. Students analyzed these compound suing NMR and IR as well to see if there is any spectroscopical difference between enantiomers, between diastereomers, and between a pure enantiomer and a racemate. Learning outcomes will be presented.

CHED 75

Analysis of authentic vs. imitation perfumes

Danielle Miceli, [email protected], Bruce Montalbano, Joseph Iorio, Gobind Vaswani, Sasan Karimi.Chemistry, Queensborough Community College of CUNY, Bayside, NY 11364, United States In the years since the Persian chemist Avicenna invented steam distillation in the early 11th century, perfume has become a multibillion dollar industry. Perfume is made of anywhere from 78-95% ethanol, with the rest as essential oils. Compared to toilet water and eau de cologne, perfume is the costliest fragrance, containing as much as 22% essential oils. Our investigation will focus on the number and amounts of essential oils present in the authentic and the imitation and the GC-MS profile of these oils. Our aim is to find out whether imitation perfumes are inexpensive because they contain less essential oil or perhaps different compounds, which may or may not faithfully recreate the fragrance of the original.

CHED 76

Isolation and quantification of FD&C Red Dye #40 from cranberry flavored beverages

Henry F Rossi, Jacqueline Rizzo, Devon C Zimmerman, Karyn M Usher, [email protected] of Chemistry, West Chester University, West Chester, PA 19383, United States

This poster describes an undergraduate analytical chemistry experiment that uses solid phase extraction to isolate FD&C Red Dye #40 (Red 40) from other colorants found in cranberry flavored beverages. Red 40 is commonly added to beverages to enhance their color, making them more attractive to consumers. Although it improves the color of the beverages it does not add flavor. While the natural colorants found in cranberry juice, anthocyanins, have many health benefits, Red 40 has been linked to many negative side effects such as ADHD and hyperactivity. This experiment uses solid phase extraction to extract the Red 40 from the beverages then uses colorimetry to quantify the amount of Red 40 present. It provides students in an introductory analytical laboratory course with experience in solid phase extraction and colorimetry. The solid phase extraction method that is being presented was shown to give recoveries of 99% with a standard deviation of 2%.

CHED 77

Sodium chloride crystallized with sodium ferrocyanide: Powder X-ray diffractometry, scanning electron microscopy, and middle school inquiry

Susan D. Wiediger1, [email protected], Sarah Elkins1, Therese Hembruch2. (1) Department of Chemistry, Southern Illinois University Edwardsville, Edwardsville, IL 62026, United States (2) Triad Middle School, St. Jacob, IL 62281, United States

Crystallization is an engaging topic that does not fit well into the chemistry standards at the middle school level, despite the potential for strong cross-curricular connections. Using low hazard sodium chloride, with a sodium ferrocyanide additive that changes crystal morphology, an inquiry activity has been successfully implemented several times. As an activity early in the year, the nature of the topic engages student interest and the relative safety of the materials permits open-ended experimentation. Scanning electron microscope images and powder X-ray diffraction spectra provide advanced detail about crystal structure as possible extensions.

CHED 78

Development of an aesthetically appealing example of oxymercuration of alkynes

Jonathan C. Quirke, J. Martin E. Quirke, [email protected] of Chemistry and Biochemistry, Florida International University, Miami, Florida 33199, United States The teaching of organic chemistry is hampered by the lack of pictorial evidence of the reactions that form the bulk of the core organic chemistry curriculum. The reason for this is that most reactions involve neither phase change nor color change, making them of no value as a source of pictorial evidence. Furthermore, photographing scientific glassware is very challenging because of glare. In this poster we provide visual evidence for the regiochemistry of the oxymercuration of 1-hexyne. The product of the reaction was distilled onto solutions of bromine in CH2Cl2, which was not decolorized, 2,4-dinitrophenylhydrazone, which formed a precipitate, and chromic acid, which was unchanged. The CH3C=O unit was confirmed by a positive iodoform test. The boiling point coupled with the functional group test confirmed the product was 2-hexanone. The reaction of 1-hexyne with bromine is included for comparison with the product.

CHED 79

Aesthetically appealing benzyne trapping reaction via mixed aldol and Diels-Alder reactions

Jonathan C. Quirke, [email protected], Jaroslava Miksovska, J. Martin E. Quirke.Department of Chemistry and Biochemistry, Florida International University, Miami, Florida 33199, United States

There is a lack of pictorial evidence of the outcome of most reactions in core organic chemistry. This places visual learners at a disadvantage. Photographic evidence is presented for the preparation of 2,3,4,5-tetraphenylcyclopentadienone via the crossed aldol reaction of dibenzyl ketone with benzil. Then the 2,3,4,5-tetraphenylcyclopentadienone was used as a trap for benzyne, which was generated in situ from anthranilic acid and isopentyl nitrite. The effluent carbon dioxide was confirmed by the formation of a milky precipitate with limewater and decolorization of blue basic thymolphthalein. The carbon monoxide byproduct was confirmed by reaction with an iron(II) porphyrin. Finally, the interaction of picric acid with the 1,2,3,4- tetraphenylnaphthalene was compared with the reaction with naphthalene. In addition to supplying students with evidence for the benzyne intermediate, students also learn about the binding of carbon monoxide with porphyrins which is critical to the toxicity of carbon monoxide.

CHED 80

Animations help general chemistry students learn thermodynamics

Xinli Xiao, Deyan Kong, Lijiang Hu, [email protected] of Chemistry, Harbin Institute of Technology, Harbin, Heilongjiang 150001, China

A recent trend at our university has been an increase in the use of animations, particularly for freshmen classes. We have observed that first-year students are interested in studying general chemistry using animations. We've also experienced an increase in the number of students registering for general chemistry, perhaps because of our use of animations. This presentation will provide two examples of animations used for understanding a thermodynamic definition of entropy. The first example is an animation of a building that explodes into a mash of pieces but then becomes a new building. It is easy for students to understand entropy using this analogy. It helps them recognize that the entropy of the universe can be increasing even though there is a probability of local sites of decrease in entropy.

The second example uses an animation of bouncing balls that are initially in disorder but after a certain amount of time become ordered even though the entropy of the system increases during the process.These two animations help students learn general chemistry.

CHED 81 Invitation of professors from the top universities for a short-term visitation

Lijiang Hu1, [email protected], Xiaowei Lv2, Jiang Chang2. (1) Department of Chemistry, Harbin Institute of technology, Harbin, Heilongjiang 150001, China (2) International Office, Harbin Institute of Technology, Harbin, Heilongjiang 150001, China

To construct a science specialty in Department of Chemistry and reach the top specialty level of world-class universities, our university provided a project about invitation of foreign experts for shorter-term visiting. The invited professors can come over HIT anytime as a visiting foreign expert. Our university will pay the international around-trip ticket, free 7-day living expenses and wages for the experts' lectures. There is another invitation project for the longer term (2 months per year), which the payments are much better than the short term. The invited professors will assist our specialty to make a plan about construction of the cultivating and curriculum system and enhancement of the faculty level and so on.

CHED 82

Macromolecule/polymer foundational course content in organic chemistry

Bob A. Howell1, [email protected], Warren T. Ford2, [email protected], John P. Droske3, [email protected], Charles E. Carraher, Jr.4, [email protected]. (1) Department of Chemistry, Central Michigan University, Mt. Pleasant, MI 48859-0001, United States (2) Department of Chemistry, Portland State University, Portland, OR 97207, United States (3) Department of Chemistry, University of Wisconsin-Stevens Point, Stevens Point, WI 54481, United States (4) Department of Chemistry and Biochemistry, Florida Atlantic University, Boca Raton, FL 33431, United States

In the latest CPT guidelines there is a statement that "students should be exposed to the principles of macromolecules across foundational areas". Working to assist CPT, PolyEd (a joint education effort of the ACS divisions of Polymer Chemistry and Polymeric Materials: Science and Engineering) assembled working committees to focus on each of the foundational areas. These working committees are assembling drafts of content materials for each of the foundational areas; putting together material that assists professors to integrate polymer/macromolecule content into foundational course areas; drawing together examples where polymers/macromolecules might assist in conveying the foundational content including laboratory exercises, etc. This content will be available on the PolyEd web site (www.polyed.org) for use by teachers. These efforts are ongoing. One of the efforts is offering free short courses at national ACS meetings to professors that introduce basic/fundamental polymer/macromolecular concepts. Another effort is to offer symposia at national ACS meetings illustrating how polymer/macromolecule topics can be introduced into foundational course content. The initial effort in this venue is organic chemistry.

Much of polymer/macromolecular chemistry builds on a strong foundation in organic chemistry. The chemistry of polymers/macromolecules enhances the study of organic chemistry acting to illustrate and cement fundamentals and real-world applications. Student interest and active participation in the first organic course can be strongly enhanced by inclusion of some discussion of polymeric/macromolecular materials. This should be integrated throughout the course. This presentation focuses on both the dynamics of the foundational course effort and suggestive course content within the organic chemistry framework.

CHED 83

Incorporation of polymeric materials to enhance interest and learning in the foundational organic chemistry course Bob A Howell, [email protected] of Chemistry, Central Michigan University, Mt Pleasant, Michigan 48858-0001, United States

The treatment of alkene chemistry comes early in the first organic chemistry course. The most important societal/commercial reaction of alkenes is polymerization. Discussion of vinyl polymerization provides an opportunity to emphasize the importance of organic chemistry in the daily lives of students. Polymers are important in most of the items that students (and anyone else) encounter daily from food to clothing to home construction to transportation to personal care products- they (and we) simply could not enjoy the standard of living that they are accustomed to were it not for the presence of polymeric materials. Early discussion of the formation and utilization of polymeric materials facilitates student interest and enthusiasm throughout the course.

CHED 84

Extrapolation from small molecules to polymers: A simple and effective way to promote interest in both organic chemistry and polymer chemistry

Eric Bosch, [email protected] of Chemistry, Missouri State University, Springfield, MO 65897, United States

I will describe my approach to the introduction of polymer synthesis throughout both one and two- semester organic chemistry courses over the past 15 years. It is quite apparent as a teacher that students interest level increases each time we I translate simple reactions to polymers – particularly those common yet intriguing polymers. The approach, which will be described in detail, involves the direct extrapolation from the synthesis of discrete small molecules to the synthesis of a variety of polymers. For example we quickly go from amide synthesis to both natural polyamides as well as the early nylons and Kevlar. Other examples include the extrapolation from ethers to polyethers and esters to polyesters. The fact that all students have interest in novel polymers such as the newer non-crease fabrics, flame resistant fabrics, and biodegradable polymers should be used to promote interest in a subject we all know is fascinating.

CHED 85

Using polymer synthesis, reactions and properties as examples of concepts in beginning organic chemistry

David E. Bergbreiter, [email protected], Texas A&M University, College Station, Texas 77843, United States

Polymer chemistry, like environmental chemistry or biological chemistry should be and is easy to integrate into a standard sophomore organic chemistry course. While the details of polymer science may be best left to an advanced course, there are countless ways polymers and their properties can be integrated into a conventional sophomore organic lecture course intended for pre-meds, chemists, chemical engineers or others who are at a stage where they are learning the centrality of chemical principles. Examples where glass transition temperatures are spectacularly related to the conformational energetic of butane can be used very early on in any course. Later in discussing functional group chemistry like the chemistry of alkenes one can relate ring strain and Nobel prize winning work in metathesis polymerization to the synthesis of a 'good' ash baseball bat just as one can relate the properties of rubber balls used in pre-European American cultures to the chemistry of vision. Similar chemistry is equally relevant to the later material with carbonyls where one can relate acetal stability to leaking plastic pipes or amide and ester stability to the properties of tires and molecules which variously serve as materials in construction, materials for transportation or materials relevant to information or energy storage for organisms.

CHED 86

Industrially important polymers offer an excellent didactic tool for learning many of the fundamental principles of organic chemical structure and reactivity

Mark M Green, [email protected] and Biological Sciences, Polytechnic Institute of New York University, Brooklyn, New York, New York State 11201, United States

For several years, at the Polytechnic Institute of New York University, beginning students of organic chemistry have learned many of the fundamental structure and reactivity properties of organic chemistry based on industrially important polymers ranging from polyethylene and polypropylene to polyesters and nylon 6,6. We've discovered that the study of these polymers, and the monomers they are derived from, expand on and introduce new concepts that capture the students' interest, as not encountered before over long years of experience in teaching sophomore organic chemistry. With this approach, students are introduced to, and learn, in rigorous detail, the contextual importance of many of the most important concepts that form the basis of the sophomore organic chemistry course. A text has been created using polymers as part of its approach, “Organic Chemistry Principles in Context” with another existing text “Organic Chemistry Principles and Industrial Practice” of special interest to chemical engineering students.

CHED 87

Polymer chemistry in an undergraduate curriculum

Sarah L. Goh, [email protected] of Chemistry, Williams College, Williamstown, MA 01267, United States

The multi-disciplinary applications that polymers have in biology, chemistry, medicine, and materials science make them ideal vehicles for teaching. They serve as familiar, real-world examples and help to reinforce concepts and reaction mechanisms while introducing developments in current chemical research. Examples of using the topic of polymers in teaching a breadth of classes, including introductory and intermediate organic courses, a non-majors and an upper-level elective course are presented.

CHED 88

Integrating macromolecules into undergraduate organic chemistry courses - it's important and there is room

John P. Droske, [email protected] of Chemistry, University of Wisconsin-Stevens Point, Stevens Point, WI 54481, United States

Much of the matter around us is macromolecular. When we ask students to make a list of things in a room that are made of macromolecules, they often are surprised when the “macromolecules” side of the list ends up longer than the “small molecule” (typical low molecular weight) side. They also are usually surprised to learn that some synthetic polymers were first prepared in an effort to expand on the polymers that already existed in nature, such as wool and silk and other polyamides. While a case can be made for the inclusion of macromolecular topics because they are relevant, including them also helps students appreciate that our modern understanding of chemistry includes both small and large molecules. Importantly, including straightforward macromolecular topics in undergraduate organic chemistry courses helps students prepare for the much more complex macromolecules they will encounter in biochemistry courses, which many of them will take. This presentation will focus on specific examples that take only a few minutes of class time interspersed throughout a semester and help students understand key features of macromolecules such as helices, branching and crosslinking, and glass transition temperatures.

CHED 89

Polymers in organic chemistry – a fine balance

David Baker, [email protected] Division, Delta College, University Center, MI 48710, United States

Delta College is a community college in the heart of the Great Lakes Bay Area. The core organic chemistry courses serve two major student populations. One is for students who need the core chemistry curriculum to transfer to four-year colleges or universities to pursue bachelor's degrees and/or onto professional programs. The second group of students are those who are enrolled in the successful chemical technology program and are completing an associate's degree to gain employment with area chemical companies. How poly-materials both carbon and silicon based are presented to these two different student groups in the same class will be discussed. Why it is important to maintain a balance between chemical reactivity and structure and function relationships will be presented.

CHED 90

Polymer concepts illustrated in the context of biopolymers

Abby L. Parrill, [email protected], Daniel L. Baker.Department of Chemistry, The University of Memphis, Memphis, TN 38152, United States

The foundation course in biochemistry at the University of Memphis includes a strong emphasis on the organic chemistry of biomolecules that serve as the central focus of the course. Among the organic concepts illustrated in the context of biomolecules are polymer concepts in the areas of both synthesis and analysis of biopolymers. Polymer synthesis topics illustrated in the course include condensation polymerization as well as solid-phase polymer synthesis. Polymer purifications and separations discussed include size-exclusion chromatography, ion-exchange chromatography, and electrophoresis. Polymer analysis by mass spectrometry and electrophoresis are also illustrated. The course and preliminary evaluation will be discussed.

CHED 91

Comparison of students' abilities to interpret NMR in discovery-based and traditional organic laboratories

Leah Martin, [email protected], Norma Dunlap.Department of Chemistry, Middle Tennessee State University, Murfreesboro, TN 37132, United States

A number of laboratory experiments have been published that are discovery-oriented and move away from the typical "cookbook" experiments. One multi-week experiment developed at our institution exposes students to distillation, chromatography and spectroscopy. Steam distillation of herbs and spices is done in the first week. In the second week, they analyze and purify the material by chromatography and collect NMR spectra. The third week is devoted to data sharing and analysis of their identification of isolated products.

The analogous traditional labs involve an individual chromatography experiment, and a separate individual spectroscopy lab using NMR and IR to identify unknowns. Students in both the discovery-oriented and traditional labs were given an NMR quiz at the end of the semester, as well as a survey measuring their perceptions of the laboratory experience. Comparison of the two lab procedures and analysis of the students test results will be presented here.

CHED 92

Flash chromatography: A safer method for teaching this important and ubiquitous technique

Brenton DeBoef, [email protected] of Chemistry, University of Rhode Island, Kingston, RI 02881, United States

We have developed a new, low-cost apparatus for performing flash chromatography using pre- packed silica cartridges. The key advantage of this system, when compared to traditional flash chromatography, is its use of commercially available silica cartridges, which obviates the need for students to handle carcinogenic silica gel. The apparatus has been tested for its ability to perform separations that are commonly found in organic chemistry teaching laboratories such as catechol/resorcinol, fluorene/fluorenone and ferrocene/acetylferrocene, as well as difficult separations that are commonly encountered in an organic research laboratory. The performance we observed was comparable, if not superior to, traditional flash column chromatography.

CHED 93

Collaboration and guided inquiry in the organic chemistry laboratory

Susan S Hershberger1, [email protected], Ben W Gung1, Janet Marshall2. (1) Department of Chemistry and Biochemistry, Miami University, Oxford, OH 45056, United States (2) Department of Chemistry and Biochemistry, Miami University, Middletown, OH 45042, United States

Student centered collaboration and guided inquiry pedagogies are being applied to the development of organic laboratory activities. In these activities, students work individually on four complementary laboratory investigations with guided questions and discussion prompts. The similar laboratory experiences build individual student knowledge while the group's collected data allows students to discover patterns and trends. Materials feature tiered tasks with leading discussion questions designed to build and develop student knowledge and laboratory challenges which allow students to apply their knowledge. Several examples of the laboratory activities covering basic organic laboratory and spectroscopy techniques, common reactions, as well as a class research project will be described. These collaboratively designed laboratory activities are being tested against the traditional model of all students in a laboratory doing the same laboratory activities and preliminary results of the benefits of this collaborative guided inquiry model will be presented. CHED 94

Green chemistry metrics for choosing a reaction: Incorporation of independent green chemistry student assessments in organic chemistry lab

James W. Wollack, [email protected] of Chemistry and Biochemistry, St. Catherine University, St. Paul, MN 55105, United States

Since every chemical has some level of toxicity associated with it, no chemical reaction is totally green. Declaring a chemical reaction is green can only be done when comparing one reaction to another reaction. To do this, every aspect of both reactions must be accessed. This includes comparing cost, yield, environmental impacts of the starting materials and products, and energy requirements. Often organic chemistry labs focus solely on techniques which leaves the students lost in regards to what they are actually doing in terms of the impact of their work on scientific advancement and environmental deterioration. The goal of this project was to get students to access the impacts of all components of two chemical reactions that yield the same product. This was done in context of a three-step synthesis of various targets choosen by each student group. Two of the three steps were done twice, once as reported and once with a green modification of a solvent or reagent. Students chose procedures using the journal database SciFinder Scholar and attempted their completion in lab. Before beginning the reactions the students acessed the “greenness” of both reactions using a metrics based point system. Then the students completed both reactions looking at cost, time, and environmental impact in order to determine which reaction is more green. The goal was to get students to think more concretely about what they actually are doing in lab by looking more in depth at each chemical, product, and byproduct. Students became more aware about the environmental and cost impact of scientific research. This helped students undertand that in order for a reaction to be green it also must be cost effective otherwise no one will do it.

CHED 95

Synthesis of organic conjugated polymers in an undergraduate teaching laboratory

Mindy Levine, [email protected], Patrick Marks.Department of Chemistry, University of Rhode Island, Kingston, RI 02881, United States

Reported herein is a procedure to synthesize conjugated polymers in an undergraduate laboratory setting. This robust procedure does not require a strictly inert atmosphere, which eliminates the requirement for a glovebox that is often impractical in teaching laboratories. Once synthesized, the photophysical properties of the resulting conjugated polymers were measured using a portable and inexpensive Microlab spectrometer. Students were also taught how to fabricate thin films of the conjugated polymers and measure the solid-state fluorescence. A variety of potential applications of the polymers were also discussed.

CHED 96

Illustrating the primary kinetic isotope effect in the organic lab: Make your own deuterated cyclohexanone and study its reaction with iodine

Arno Kraft, [email protected], Ai-Lan Lee.Institute of Chemical Sciences, Heriot-Watt University, Edinburgh, Scotland EH14 4AS, United Kingdom

In a reaction where a C–H bond is broken in the rate-determining step, it becomes noticeably slower when a deuterated substrate is used. The kH/kD ratio will be typically 5 to 8, where kD is the rate constant for the reaction of the deuterated compound and kH is the rate constant for the non- deuterated substrate. This is called the primary kinetic isotope effect (PKIE). We have developed a laboratory experiment for advanced students to illustrate the PKIE observed in the halogenation of cyclohexanone in support of a lecture course on Physical Organic Chemistry. Students first make their own deuterated cyclohexanone and determine the degree of deuteration using 1H NMR spectroscopy. In a follow-up experiment, students study the reaction of iodine with cyclohexanone by recording the change of iodine absorbance with time. At identical cyclohexanone concentrations, the reaction takes 4–5 times longer when the deuterated cyclohexanone is used.

CHED 97

Tandem one-pot aldol condensation/Diels-Alder reaction sequence as a green synthesis for the organic chemistry laboratory

Jane E. Wissinger, [email protected], Giang T. Hoang, Tomohiro Kubo, Victor G. Young.Chemistry, University of Minnesota, Minneapolis, MN 55455, United States

The aldol condensation reaction and Diels-Alder reaction have been exploited in the development of green chemical transformations because of their inherent high atom economy and minimal solvent requirements. We have developed a one pot procedure that involves the synthesis of tetraphenylcyclopentadienone (via aldol condensation of benzil and 1,3-diphenylacetone using KOH in triethylene glycol) which is then reacted without isolation with styrene to produce the Diels-Alder adduct. Students use 1H NMR and IR analysis to determine the overall structure and speculate about the endo/exo stereochemistry. The x-ray structure of the pentaphenylbicyclo[2.2.1]hept-2-en-7-one product was solved and provided to the students at the end of the experiment to illustrate the power of x-ray crystallography in unequivocal stereochemical structure elucidation.

CHED 98

Preparation of tetrazines: Undergraduate research for teaching about pericyclic reactions

Melvin Druelinger1, Susan M. Schelble2, [email protected], David Dillon1. (1) Department of Chemistry, Colorado State University-Pueblo, Pueblo, CO 81001, United States (2) Department of Chemistry, Metropolitan State College of Denver, Denver, CO 80217, United States

This laboratory experiment will help the student investigate the synthesis of a novel and useful class of heterocycles (tetrazines) and their application to Diels-Alder chemistry. The student will also learn new aspects of Diels-Alder chemistry, both forward and reverse reactions, and will apply these ideas in a three-step sequence involving heterocyclic chemistry.

CHED 99 One theme, many reactions: An innovative approach to teaching second-semester organic chemistry laboratory

James K. Murray, [email protected] of Chemistry, Immaculata University, Immaculata, Pennsylvania 19345-0660, United States

The second semester organic chemistry laboratory is focused on students conducting reactions to prepare products, using the techniques introduced during the first semester. With the large number of known organic reactions it is very difficult, in a traditional fifteen week semester setting, to do adequate justice to every reaction. We have developed an innovative approach in which laboratory sessions are arranged by reaction type and multiple reactions that fit that theme are conducted during that session. The following laboratory session has an open-forum discussion on how each student/group conducted a “different” reaction, but in reality they all did essentially the “same” reaction. The discussion focuses on the basic commonalities between the reactions in an effort to demonstrate to students that one does not need to physically conduct each reaction in order to understand the workings of reactions that belong to the same theme.

CHED 100

Nano first with atoms-first

David S Heroux, [email protected] of Chemistry, University of Maine at Farmington, Farmington, ME 04938, United States

Many colleges and universities are now implementing an Atoms-First approach to first year chemistry instruction. This change provides the potential to incorporate nanotechnology-based experiments. The use of nanotechnology-based laboratories addresses two issues. First, since Atoms-First teaching necessitates building upwards from electrons, to atoms, to molecules and then to reactions, many traditional, early first-semester labs need to be used only later in the semester. This is not the case with many nanotechnology-based experiments, which can be understood without thorough exposure to general chemistry topics. Secondly, many early semester labs are not engaging or exciting for students. Nano-based experiments introduce students to exciting and modern applications of chemistry in ways typically not illustrated in traditional early semester labs. Therefore, the use of nanotechnology based experiments allow the instructor to lay fundamental principles of chemistry in lecture while students do experiments in lab that builds interest in chemistry.

CHED 101

New advanced nanoscience course at Union College

Michael Hagerman, [email protected], Palmyra Catravas, Rebecca Cortez, Brian Cohen, Samuel Amanuel, Seyfollah Maleki.Union College, Schenectady, NY 12308, United States

We have successfully launched a new advanced nanoscience course funded through the NSF NUE program entitled Advanced Topics in Nanoscience: Microscopy of Self-Assembled Nanostructures. The course features in depth coverage of micro and nanoscale microscopy, including training students to use scanning electron microscopy and atomic force microscopy and their related modes and diagnostic methods to study self-assembled nanostructures for sensors, solar cells and nanoelectronics. Key learning objectives have included: to expand student technical expertise with nanomaterials characterization methods; to enhance student understanding of the synthesis and characterization of self-assembled nanostructures and their materials applications; to encourage student interest in our undergraduate nanoscience research program in engineering and the physical sciences, the nanoscience minor, and career opportunities in nanotechnology and related fields; and to build student technical science writing and communication skills. A key outcome has been building bridges between classroom learning and undergraduate research through peer-mentoring.

CHED 102

Nano science research at Queensborough Community College

Moni Chauhan, [email protected], queensborough community college, Bayside, NY, NY 11364, United States

Nano-science and technology are important concepts that are going to impact our lives in a very big way. It is important to integrate nanoscience research at the community college level and include underrepresented minorities in this initiative. The earlier the students get involved in the research, the better the chances are for them to stay in the STEM fields. We have taken initiatives to educate Queensborough students in this very important endeavor and we provide our students opportunities to study and synthesize metal nanoparticles of silver, platinum and palladium. The students are also trained hands on use of table top scanning electron microscope, energy dispersive unit, UV- vis spectroscopy, 60 MHz NMR and other spectroscopy techniques. This training and education has helped QCC student to very successfully transfer and integrate with the education and research activities of highly rated four year institutions.

CHED 103

Development of a nanoscience research program at a primarily undergraduate institution

Anderson L Marsh, [email protected] of Chemistry, Lebanon Valley College, Annville, PA 17003, United States

Physical chemistry research groups at liberal arts colleges are generally hard to establish not only because of the difficulty of the experiments, but also because of lack of student interest. Nanoscience research topics offer viable projects for faculty at these institutions wishing to establish active physical chemistry research programs. In this talk, I will describe two nanoscience projects in which a number of undergraduate students have participated. In one we are developing platinum and palladium nanocatalysts for performing hydrogenation reactions in water, while in the second we are investigating zinc sulfide nanocrystals in photocatalysis and biological/environmental toxicity. For each project I will provide recommendations on identifying student roles, on designing projects for both summer and academic year research, and on seeking external collaborators to gain access to necessary instrumentation. Finally, I will discuss the success of both projects as measured in student involvement, publications, and placement of students upon graduation.

CHED 104

Nanomaterials for environmental applications: A gateway to chemical education for the non-chemistry undergraduate student

Matthew D. Cathell, [email protected], Melissa Bradley.Department of Technological Studies, The College of New Jersey, Ewing, NJ 08628, United States

Nanoscience, because of its inherently applied nature, puts chemical knowledge into real-world contexts that possess broad appeal. We offer a case study example of how nanoscale investigations can make key principles of chemistry accessible to non-chemistry majors. We describe a research project carried out by an undergraduate student, with no undergraduate chemistry background, who is studying to become a K–12 technology education teacher. The research investigation centers on the production of electrospun biopolymer nanofibers, which are subsequently used to filter and sequester dissolved toxic metals from water.

Through this project, the student is developing meaningful understanding of critical chemistry tenets including laboratory techniques, safety, nomenclature, and foundational reaction mechanisms. The student is gaining proficiency in obtaining and interpreting spectra and has become a skilled electron microscopist. This project, which spans the STEM continuum, could serve as a model for other design+inquiry experiments for non-majors.

CHED 105

WITHDRAWN

CHED 106

Introduction to nanomaterials at primarily undergraduate institutions: Modules for advanced physical chemistry laboratory

Alyssa Thomas, [email protected] of Chemistry & Biochemistry, Utica College, Utica, NY 13502, United States

As nanotechnology becomes part of the everyday vernacular, there is a need for successful introduction of nanomaterials and implementation of laboratory activities that expose undergraduates to this growing field. I have redesigned the advanced physical chemistry laboratory to include three modules on the synthesis and characterization of various nanomaterials using the available instrumentation at Utica College, a primarily undergraduate institution. The students develop a literature-based procedure to synthesize Au and Ag nanoparticles as well as CdSe quantum dots. The resulting nanomaterials are characterized using UV-Visible spectroscopy and the students are guided through a series of qualitative tests, calculations, and inquiries within each module to further explore properties of the nanomaterials. In addition, the students are also assigned a type of nanomaterial (metal nanoparticles, carbon nanotubes, quantum dots) to research and write a review paper of the current literature during the semester to reinforce the concepts.

CHED 107

Enhancing chemical education: Academic-industry collaborations

Richard E Partch, Sr, [email protected], Clarkson University, Center for Advanced Materials Processing, Potsdam, NY, 13699-5814, USA, Potsdam, NY 13699-5814, United States

Favorite quotations of the presenter made by historically famous chemists are “Research is to teaching as sin is to confession. If you don't do one you've nothing to say in the other” and “The only way to get to do real research is to partner with someone”.

Using these words as guides, the only pathway for academic chemists to achieve success in their profession is to partner with persons at government or industrial sources of funding. With such collaborations and financial support the presenter has been privileged to mentor pre-college, undergraduate and graduate students in very diverse areas of chemistry having applications in ceramics, composites, electronics, lighting, medicine, renewable energy and security. This presentation will highlight a few examples of aspects of the presenter's background that led to the collaborations and how the projects enhanced student participant enthusiasm for chemistry as a career.

CHED 108

Benefits of academic-industrial partnership for chemical technonogy programs

Annemarie D Ross, [email protected], Todd Pagano, [email protected] and mathematics, Rochester Institute of Technology/National Technical Institute for the Deaf, Rochester, NY 14623, United States

Partnerships between academia and industry permit a mutually beneficial flow of information to bridge the gap between these two entities. Industry can provide advice related to curriculum modifications, equipment acquisitions, career counseling, and the establishment of cooperative work experiences/internships. They can also participate in student interaction through diverse ways such as field trips to companies, classroom visitations by industrial representatives, and computer mediated communication between students and professionals, in which students are able to interact with discipline-specific professionals and topical experts as they proceed through course material. The ACS's ChemTechStandards Database is a valuable vehicle for the collaboration between the Laboratory Science Technology program at Rochester Institute of Technology's National Technical Institute for the Deaf and industrial partners. Student learning is greatly enhanced by these collaborations, while simultaneously benefitting industry with better prepared graduates entering the workforce.

CHED 109

Talent and technology: Academia as a strategic supplier to industry

John S Manka1, [email protected], David J Moreton2, Roger W Day3. (1) Global Chemical Synthesis, The Lubrizol Corporation, Wickliffe, Ohio 44024, United States (2) Hazelwood Chemical Synthesis, Lubrizol Limited, Hazelwood, Derbyshire DE56 4AN, United Kingdom (3) Corporate R&D, Lubrizol Advanced Materials, Brecksville, Ohio 44141, United States

Since it was founded, The Lubrizol Corporation has closely partnered with universities to develop talent (students) and technology (research and test capability). In the eight decades since then we have continually expanded these partnership programs. We currently partner with over twenty universities across the globe.

The longevity of our academic partnership attests to the programs being fruitful to both Lubrizol and the universities. Our partner universities gain from our financial support and place many of their graduates as permanent employees with The Lubrizol Corporation. Lubrizol profits by obtaining access to state of the art analytical methods, valuable research and top quality graduates.

This presentation describes the programs in which The Lubrizol Corporation participates with universities both locally and abroad. We will share what has been effective and what has been unproductive so that others can learn from our experience.

CHED 110

From academia to industry: Things to know for faculty starting up companies Carl A. Hultman, [email protected] of chemistry, Gannon university, Erie, Pa 16541, United States

Going from being a faculty member who has developed something in a university to being a company owner using the development can seem like a daunting task. The talk will focus on the experiences of the presenter and what's known in the literature about doing technology transfer. Topics covered will include fund raising, who to consult, business plan, legal documentation, negotiating with the university, finding partners, hiring staff, and market analysis. The talk will also emphasize some of the biggest mistakes that can be made in forming a company.

CHED 111

Shimadzu academic partnerships: Translating innovative research projects into powerful new life science platforms and discoveries

Christine Jelinek1, [email protected], Sree Rayavarapu2, [email protected], Faith Hays3, Brian Feild3, Heather Juzwa3. (1) Department of Pharmacology and Molecular Sciences, Johns Hopkins School of Medicine, Baltimore, MD 21287, United States (2) Center for Genetic Medicine Research, Children’s National Medical Center, Washington, DC 20010, United States (3) Shimadzu Scientific Instruments, Inc., Columbia, MD 21046, United States

Shimadzu has partnered with academic researchers to bring together the insight and creativity of academic researchers with the instrument development expertise of Shimadzu to build truly integrated partnerships that translate innovative research into powerful Life Science products and platforms that impact future discovery and increase diagnostic value. This talk will focus on the development of automated protein sample preparation immuno-MS platforms, including a fully- automated workstation. These new research platforms suggest great potential application for development of future cardiac ischemia and Parkinson's Disease diagnostic assays. Academic partnerships aimed at new biomarker candidate discoveries will also be highlighted, including the development of nanoparticle-assisted biomarker discovery platforms. Applications of a new Nanotrap Biomarker Discovery Platform to Duchenne Muscular Dystrophy biomarker candidate discovery will also be discussed. These academic/industrial partnerships result in new products with many applications, and leverage the creativity of academic researchers to expand the frontiers of life science.

CHED 112

Industry-academia partnership in curriculum development for the part-time graduate program on safety engineering in China

Yingnan Sun1, [email protected], Yi Liu2. (1) QHSE Department, Daqing Refining & Petrochemical Company of PetroChina Company Limited, Daqing, Heilongjiang 163411, China (2) College of Chemical Engineering, China University of Petroleum (Huadong), Qingdao, Shandong 266555, China

With the rapid development of petrochemical industry in China, it is urgent for engineers in petrochemical enterprises to master safety knowledge to prevent unexpected accidents. Therefore, many universities in China began to enroll employed engineers with bachelor degree into part-time engineering graduate programs. The presenter will summarize the status of curriculum development for part-time engineering graduate programs, based on the characteristics and development of petrochemical production in China. It is confirmed that strengthening the process safety education in the part-time engineering graduate program is absolutely necessary. Process safety education is emphasized in the curriculum, which features improving safety cognition, optimizing the curriculum, case studies and practical trainings. The deficiency of current curriculum setting for part-time engineering graduates of safety engineering is also addressed.

CHED 113

Partners to products

John C Gebler, [email protected] Corporation, Milford, MA 01757, United States

Waters Corporation has a rich history of partnerships. Most of these have evolved from constructive collaborations where mutual benefits were identified. Analytical capabilities are being driven to the extreme and the requirement for specialized capabilities is increasing. For example, Waters has developed a comprehensive program for the characterization of biopharmaceuticals (proteins, peptides, antibodies, glycans). This application space has benefited from some key partners resulting in new products and capabilities. Examples from these partnerships will be discussed.

CHED 114

Use of historical events and personalities to facilitate the incorporation of polymeric materials into the beginning organic chemistry course

Bob A Howell, [email protected] of Chemistry, Central Michigan University, Mt Pleasant, Michigan 48858, United States

The development and exploitation of polymeric materials since WWII has provided a standard of living for most citizens that is unmatched in history. In countries with advanced economics the lives of all citizens are daily impacted by the presence of polymeric materials – from food packaging to transportation to housing to personal care and far beyond, these materials have a major impact. Incorporation of some of the history, world events, and personalities responsible for the early development of polymeric materials strongly enhances student interest and performance in the beginning organic course. Events that students find fascinating and helpful in identifying with and appreciating the subject matter being addressed abound – the suggestion that polymers are, in fact, macromolecules by Hermann Staudinger, the demonstration that this is indeed correct and the production of “synthetic silk” by Wallace Carothers, the war effort and the development of SBR by the Dow Chemical Company and “synthetic natural rubber” by Firestone, the development of coordination polymerization by Karl Ziegler, the plasticization of PVC by Waldo Semon, and many, many more.

CHED 115

Radical chain reactions in foundational organic chemistry

Warren T Ford, [email protected] of Chemistry, Portland State University, Portland, OR 97207, United States

Radical chain reactions usually are introduced via the chlorination of alkanes. The mechanism of a chain reaction and its selectivity based on thermodynamic stabilities of methyl, primary, secondary, tertiary, allylic, and benzylic alkyl radicals are vital to understanding of much subsequent chemistry. At this time radical chain polymerization is used to introduce polystyrene and poly(vinyl chloride) which, due to their everyday use, are more interesting to students than chloroalkanes. The polymerizations reinforce the importance of radical chain reactions, and the head-to-tail structures of the polymers reinforce the importance of selectivity due to radical stability. Radical chain autoxidation of ethers and lipids and inhibition of both polymerization and food autoxidation by hindered phenols round out the discussion of radical reactions. Time for coverage of polymerization and autoxidation is garnered by omitting radical addition of HBr to alkenes and syntheses based on selectivity of radical halogenation of alkanes and radical addition to alkenes.

CHED 116

Importance of macromolecules in industry: The case for inclusion in the undergraduate chemistry curriculum

Laura L. Kosbar, [email protected] of Physical Sciences, IBM T.J. Watson Research Center, Yorktown Heights, NY 10547, United States

The beginning organic chemistry course and other foundational courses in chemistry often include few aspects of polymer science including many of the features of polymers that make them unique. As a result, most chemistry majors get little exposure to macromolecules as part of their undergraduate education. This despite the fact that most of them will work in industry. The ACS itself estimates "that as many as 50% of all chemists will work in polymer science in some capacity during their careers". Other estimates place this number even higher. While industrial applications of polymers in traditional chemical and materials companies may be expected, there are many less obvious applications in a wide variety of fields - including microelectronics. Some examples of polymer applications in industrial research, including biobased epoxy resins for printed circuit boards and cholesteric liquid crystalline polymers for reflective displays, will be reviewed. The importance of exposing chemistry majors to elements of polymer science as part of their undergraduate training will be emphasized.

CHED 117

Including polymers in organic chemistry

Steven A Fleming, [email protected] of Chemistry, Temple University, Philadelphia, PA 19111, United States

There are several approaches to teaching polymer chemistry in the standard organic chemistry course. One method that ought to be included in every first semester course, is including alkenes as a type of nucleophile that will react with a carbocation. Since all learners retain information in packets, it is useful to show students how carbocations can: 1) add nucleophiles (SN1), 2) eliminate (E1), 3) polymerize, 4) rearrange, and 5) add to aromatic rings. We should all be showing examples of the polymerization of alkenes.

There is a second method of including polymers that is worth considering. It is logical to discuss bio-polymers in a second semester of organic chemistry. Many organic chemistry instructors have a difficult time teaching biomolecules because of the size of the molecules. A teaching tool called Bio-Organic Reaction Animations (BioORA) has been developed to ameliorate the inherent challenges of representing these large molecules. BioORA has several animations that demonstrate the biopolymers. In addition, the DNA polymerase enzyme has been animated.

This presentation will expand on the two methods outlined in this abstract for getting polymers into your organic chemistry course.

CHED 118 Inclusion of polymer concepts in organic and other undergraduate chemistry books

L. H. Sperling, [email protected] of Chemical Engineering and Materials Science and Engineering, Lehigh University, Bethlehem, PA 18015, United States

Somewhere close to a third of all American chemists of all degree ranks are engaged in some kind of polymer activity right now as part of their professional assignment. This may involve some aspects of plastics, fibers, rubber, coatings, or adhesives. Their position may involve research, engineering, sales, etc. Yet only a tiny fraction of these people have had any formal training in polymer science and engineering! Some, amazing enough, seem not to be aware that it is a regular academic topic in a growing number of colleges and universities!

Ideally, all departments should have, and perhaps require, a course in polymer chemistry. An alternate solution would be to have the subject matter introduced gradually, in a natural manner, along with other topic examples. Such examples might include for organic chemistry, when studying synthesizing esters, how about an example for polyesters? (They make great sweaters, for example.) Same for polyamides, which includes Nylon. When showing reactions of double bonds, how about showing polyethylene starting with ethylene and also polystyrene as examples? A brief discussion of molecular weights might follow, which usually run something like 50,000-100,000 g/mol, depending on the polymer and exact concentrations of reactants.

We have noted with significant satisfaction that undergraduate authors have increased their coverage of polymer topics from about 10% to about 70% of such undergraduate organic chemistry textbooks. We laud this progress, and know it will result in better trained professionals in the future. Yet, much more needs to be done. A 5% inclusion of polymer examples in these undergraduate chemistry books would be a goal. Please note that what is not wanted is a token chapter on polymers at the end of the book! Assuming this is done, however, another problem must be solved: Educating professors about polymers so they can teach a bit of the subject, and not skip over the polymer topics!

It should be noted that a fair fraction of universities are now offering something in the way of polymer courses to undergraduates, but liberal arts colleges, with reduced faculty numbers, usually offer nothing.

On a broader subject, it is of interest to observe how U.S. universities and colleges wound up with such a complete separation of polymers from ordinary chemistry, far more than Europe, for example. This results, in significant measure, by industry seeing the utility of research done in Europe, started manufacturing polymeric goods. Now, we must rectify this problem.

CHED 119

Enhancement of the laboratory component of the first course in organic chemistry through the incorporation of polymeric materials

Bob A Howell, [email protected] of Chemistry, Central Michigan University, Mt Pleasant, Michigan 48858-0001, United States

There are a number of readily available polymer experiments which may be utilized to enhance laboratory instruction in the sophomore organic chemistry course. Perhaps the most popular with students (the experiment most remembered by students years later) and faculty is the interfacial polymerization of hexamethylenediamine and sebacoyl chloride to produce nylon 6,10. The polymer which forms at the interface between an aqueous phase containing the diamine and an organic phase containing the acid chloride may be continuously removed as a strand to be rolled onto a cardboard roller (a paper towel roller works well). The ring-opening polymerization of lactide promoted by tin octonoate with benzyl alcohol as initiator is another excellent example that permits a discussion of green chemistry (the polymer is totally derived from a renewable biosource) and molecular weight determination by end-group analysis using proton NMR spectroscopy (may be done with simple instrumentation). Yet another example is the polymerization of L-aspartic acid (a naturally-occurring amino acid) to form poly(succinimide) which may be hydrolyzed to sodium poly(aspartate), a commercial scale inhibitor in water and stream lines. In this case, molecular weight may be determined titrametrically.

CHED 120

Flow chemistry and continuous processing: Teaching the tricky stuff

Robert J. Tinder1,2, [email protected], Charlotte Wiles3,4. (1) Proteaf Technologies, Palos Verdes Estates, CA 90274, United States (2) Bioorganic and Medicinal Chemistry, Northeastern University, Boston, MA, United States (3) Chemtrix BV, Netherlands Antilles (4) The University of Hull, United Kingdom

Flow chemistry techniques have begun to emerge as a synthetic tool for the modern chemist-- challenging the notion that organic synthesis begins in a round bottom flask. With significant advantages demonstrated by industrial researchers, teaching this new technique to future chemists increases awareness and fosters a much deeper understanding of organic chemistry. The presentation will illustrate what flow chemistry can bring to an academic teaching environment both for the student and the instructor. A teaching method that illustrates examples of increased safety, understanding of kinetics, heat, mass transfer and scalability, with the aim of increasing student understanding will be discussed.

CHED 121

Can organic-style arrowpushing be used to teach descriptive inorganic chemistry? Exploring the limits of the approach

Abhik Ghosh, [email protected], Steffen Berg.Department of Chemistry, University of Tromso, Tromso, Norway

In a recent article (J. Chem. Educ. 2011 , 88, 1663–1666), we suggested that arrowpushing, a widely used tool in organic chemistry, could also be profitably employed in undergraduate inorganic chemistry. A number of relatively simple reactions were used to illustrate our thesis, which raised the question whether the same approach could also rationalize a broader range of main-group element reactions that are typically presented in a descriptive inorganic course. In this lecture, we hope to answer this question in the affirmative by way of a number of illustrative examples. The examples chosen will cover hypervalent phosphorus and sulfur chemistry, sulfur nitride rings and cages, and halogen and noble gas chemistry.

CHED 122

Teaching chemistry in the context of a cross-disciplinary research seminar

Rainer E. Glaser1, [email protected], Jennifer Hart2, Jennifer Fellabaum2, Eric Ludwig2. (1) Department of Chemistry, University of Missouri-Columbia, Columbia, MO 65211, United States (2) Department of Educational Leadership and Policy Analysis, University of Missouri- Columbia, Columbia, MO 65211, United States We report on the design, implementation and assessment of the research seminar offered as part of the NSF-PRISM supported “Mathematics and Life Sciences” program at MU. The seminar format aims for 25-minute research talks followed by 25 minutes of defense, discussion and extrapolation. The emphasis on equal time between presentation and scientific discussion is a stratagem of this course to stimulate open and frank discussion and cross- and interdisciplinary brainstorming, exchange and education, and student performance is assessed in this spirit. The seminar grade is affected by the student's attendance, the assessment of the student's research presentation (rubric-based peer review of science content and presentation skills), the assessment of the student's peer reviewer performance (meaningful, balanced, written constructive criticism), and the assessment of the student's discussant performance (attention and comprehension; seeking and providing clarification; content of mini-paper; contribution to discussion). The grading scheme reflects a shift from the traditional assessment of the speaker to an assessment of members of the learning community. The presentation will highlight how such a class is socializing students for research.

CHED 123

Constructing a web of knowledge in organic chemistry through supplemental instruction

Connie Gabel, [email protected], Ryan Fitt, Dustin Politica, Rosemarie Walker.Department of Chemistry, Metropolitan State College of Denver, Denver, Colorado 80217, United States

Supplemental Instruction (SI) through peer-led, group study sessions provides an opportunity for organic chemistry students to work with a peer who has been successful in completing organic chemistry. These sessions are supplemental to the professors' lectures. In SI sessions, the peer leader can work with the students to construct a web of knowledge by developing tables, making diagrams, and creating anticipated spectra for organic molecules. They can analyze organic reactions and problems and list steps and approaches for solving them. The informal setting allows students to ask questions to clarify their understanding of the organic chemistry concepts. A scaffolded approach helps students to create a web of knowledge in organic chemistry, and it reinforces lecture material. Results indicate an improved ABC versus DFWI rate and an increase in ACS scores on the Organic Chemistry I exam for SI attendees.

CHED 124

Peer teaching/lecturing in organic chemistry: Insights gained and lessons learned

Charles M. Bump, [email protected] of Chemistry, Hampton University, Hampton, VA 23668, United States

The idea of “peer teaching” is not new. Most of the recent literature describes small group discussions - Workshop Chemistry, Peer Led Team Learning (PLTL), and Process Oriented Guided Inquiry Learning (POGIL) activities - which reinforce topics introduced in traditional lecture class settings and challenge students to expand their understanding of that material among their classmates. We describe an approach to peer teaching where the students actually teach the lecture class. Two 15-20 minute student presentations are given each class period except for a “review day” before each unit exam which is conducted by the faculty member. Students appear to be more “engaged” as a result of their active participation in the course. We will share our perspective on this type of peer teaching – what went well and what needs to be improved.

CHED 125

Some thoughts on changes in the organic course due to changes in the MCAT Paula Y. Bruice, [email protected] of Chemistry and Biochemistry, University of California-Santa Barbara, Santa Barbara, CA 93106, United States

The revamped MCAT, sheduled for 2015, will be testing on the chemistry of living systems. Since the reactions of living systems are organic reactions, does this material have to be taught in the organic course? Can this be done while preserving that which is central to the discipline known as organic chemistry? Can we increase the content of the one-year course? Do we need to eliminate topics? What topics can go? Or can we just tell students to take biochemistry course?

CHED 126

Organic chemistry principles in context: Backwards learning

Mark M Green, [email protected] and Biological Sciences, Polytechnic Institute of New York University, Brooklyn, New York 11201, New York 11201, United States

A successful, sophomore level, rigorous, organic chemistry course, taken together by both chemical engineering and science students has been developed at the Polytechnic Institute of New York University in which the principles of the science are discovered by the students in the complex phenomena arising from the application of these principles. The two term course is designed so that the fundamental concepts, reactions and mechanisms of organic chemistry are woven into a story telling historical approach with a content ranging from industrially interesting processes, to a disease of infants, to in vivo catabolic and anabolic processes, until finally demonstrating the nature of synthetic work and the discovery of many principles and reactions, in Woodward's and Corey's syntheses of cholesterol and prostaglandin. A text, “Organic Chemistry Principles in Context,” has developed from the experience of taking this approach, which could be altered for AP high school use.

CHED 127

Novice problem-solving of organic chemistry items

Jaclyn M Trate1, [email protected], Jeffrey Raker2, Thomas A Holme2, Kristen L Murphy1. (1) Department of Chemistry and Biochemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53211, United States (2) Department of Chemistry, Iowa State University, Ames, Iowa 50011, United States

Assessment items are ideally designed to test the degree to which a student can successfully demonstrate the knowledge needed to complete a task and these assessment items often will have varying degrees of complexity. Item complexity or the degree of difficulty of an item should translate into student performance on the item. The ability to apply an objective complexity rating can be useful for predicting student performance. A rubric for assigning a complexity rating was utilized to rate multiple choice organic chemistry tasks that were further investigated using novice and experienced students working these items on an eye-tracker. The results of these interviews and student-reported mental effort ratings provide richer information to instructors concerning how students solve organic chemistry multiple choice test questions. This coupled with objective complexity ratings can help instructors gauge the difficulty of possible test questions.

CHED 128

Study of student growth through the use of a practice ACS examination Susan M. Schelble1, [email protected], Kristen Murphy2. (1) Department of Chemistry, Metropolitan State College of Denver, Denver, CO 80217, United States (2) Department of Chemistry and Biochemistry, University of Wisconsin-Milwaukee, Milwaukee, WI 53201, United States

Approximately 300 students have used a non-secure practice organic ACS examination. The examination has student metacognitive ratings. The questions on the practice examination have also been rated for complexity by experts. This talk will look at assets for the students taking this practice examination and at comparisons of question difficulties between examinees and experts.

CHED 129

Lithography of polymer nanostructures on glass for teaching polymer chemistry and physics

Jennifer M Vance, Charles Michael Drain, [email protected], Adi Sahar-Halbany.C, Hunter College of the City University of New York, New York, NY 10065, United States

A variety of inexpensive and creative methods toward communicating the concepts underpinning nanolithography processes in the classroom are necessary, as this technology becomes increasingly important in the devices used in daily life. An experiment that uses simple CD-Rs, C- clamps, an oven, and a freezer is describe to provide concrete examples and insights into the chemistry and principles of nanolithography. The experiment is suitable for a range of classroom levels from high school to more advanced labs in college because there is a range of concepts illustrated and flexibility in terms of assays and methods. Because CD-Rs are composed of grooves of polycarbonate, the experiment provides a basis for discussions and exploration into the chemistry and physics of polymers on the nanoscale.

CHED 130

Research training program for undergraduate students--PbS nanocrystals synthesis and characterization

Yi Pan, [email protected], Henan Zhang, Yueru Li, Daniel L Akins.Department of Chemistry, The City College of New York, New York, New York 10031, United States

A research training program was designed, developed, and implemented for introducing new nanomaterials and technology to senior undergraduate students of chemistry. Monodisperse PbS quantum dots were obtained by a simple, one-step synthetic method. Sulfur dissolved in 1- tetradecene was used as the S precursor and PbCl2 with oleylamine was used as the Pb precursor. The synthetic method was easy to operate and tailored for undergraduate students to learn how to design, synthesize, and characterize semiconductor nanoparticles.

CHED 131

Interfacing nanoresearch to undergraduate physical chemistry laboratory Dong Hee Son, [email protected], Texas A&M University, College Station, TX 77843, United States

This presentation will discuss our recent effort to interface nanoscience in the research laboratory to the undergraduate physical chemistry laboratory. The newly developed laboratory curricula aims to provide the students more research-like experience by focusing on several thematic topics that include nanomaterials and nanocharectization techniques. I will showcase two examples of such laboratory modules currently implemented in the physical chemistry laboratory courses. One is the characterization of photoluminescence, plasmon scattering and surfce- enhanced Rman scattering using semiconductor and metal nanocrystals on user-modifiable optical setup. The other is the scanning tunneling microsopy characterising the morphology of metal surface and I-V characteristics of organic film. I will also present data on the effectiveness of this effort in increasing the students' intellectural engagement in the lab activity.

CHED 132

Single-nanoparticle spectroscopy in the Instrumental Analysis Laboratory: Quantifying oligomers of Alzheimer's amyloid-β peptide

Robin K. Lammi, [email protected] of Chemistry, Physics and Geology, Winthrop University, Rock Hill, SC 29733, United States

As a powerful analytical technique harnessing optical, microscopy, and electronics components, single-molecule fluorescence spectroscopy affords valuable and unique learning opportunities in the undergraduate chemistry curriculum. Following from research in our laboratory, undergraduates in Instrumental Analysis employ single-particle fluorescence to monitor the oligomerization of dye-labeled amyloid-β (Aβ) peptides. Aβ dimers, trimers, and tetramers are linked to synapse loss and memory deficits in Alzheimer's disease. Exploiting quantized photobleaching, students quantify the number of associated peptides (n = 1-5) in individual, surface-tethered oligomers. Student pairs spend one laboratory period acquiring fluorescence intensity trajectories for dozens of Aβ peptide species; the following period is devoted to data- processing and analysis, after which each pair generates an oligomer distribution for the sample environment they investigated. Statistical analyses of distributions from all pairs permit comparison of various physiologically relevant sample environments and assessment of reproducibility across multiple samples.

CHED 133

Engaging undergraduate students with research in nanoscience and its applications to energy and medicine

Mark Ellison, [email protected] of Chemistry, Ursinus College, Collegeville, PA 19426, United States

The discovery of nanomaterials such as nanoparticles, nanowires, and nanotubes has spurred much research into the applications of these materials toward addressing some of the significant challenges facing humankind, such as energy production, pollution abatement, and disease treatment. The intriguing properties of nanoscale objects and their potential to aid in the solutions for these issues make their study particularly attractive to undergraduates. Using examples from over a decade of directing undergraduate research in nanoscience, I will explore the joys and challenges of engaging undergraduates in this field. As expected, research in nanoscience offers students many of the same benefits of chemical research: application of classroom knowledge, development of critical thinking and time-management skills, fostering students' ability to work independently, and the joy of making scientific discoveries. The chief benefit of nanoscience research is its interdisciplinary nature, requiring students to integrate knowledge across multiple fields, such as chemistry, biology, and physics.

CHED 134

Soft nanomaterials as an undergraduate introduction to Poisson distributions

Douglas English, [email protected], Wichita State University, Wichita, KS 67260, United States

This talk will describe undergraduate physical chemistry laboratory experiments and research projects that have been implemented at Wichita State University. These experiments use fluorescence microscopy and spectroscopy to illustrate how nanoparticle distributions can be imaged or measured and thereby provide a unique teaching opportunity to introduce students to the Poisson distribution, nanometer length scales and molecular interactions.

CHED 135

Green chemistry: Theory and practice

John C Warner, [email protected] Babcock Institute for Green Chemistry, Wilmington, MA 01887, United States

Imagine a world where all segments of society demanded environmentally benign products! Imagine if all consumers, all retailers and all manufacturers insisted on buying and selling only non-toxic materials! The unfortunate reality is that, even if this situation were to occur, our knowledge of materials science and chemistry would allow us to provide only a small fraction of the products and materials that our economy is based upon. The way we learn and teach chemistry and materials science is for the most part void of any information regarding mechanisms of toxicity and environmental harm. Green Chemistry is a philosophy that seeks to reduce or eliminate the use of hazardous materials at the design stage of a materials process. It has been demonstrated that materials and products can be designed with negligible impact on human health and the environment while still being economically competitive and successful in the marketplace. This presentation will highlight how Green Chemistry can be integrated in to higher education and provide many opportunities for innovative research, as well as inspiring future scientists.

CHED 136

Green chemistry commitment: Transforming chemistry education

John C Warner1, Amy S Cannon2, [email protected], Kate Anderson2, Edward J. Brush3. (1) Warner Babcock Institute for Green Chemistry, Wilmington, MA 01887, United States (2) Beyond Benign, Wilmington, MA 01887, United States (3) Department of Chemistry, Bridgewater State University, Bridgewater, MA 02325, United States

Green Chemistry represents a significant change in how we design molecules and materials. This moves chemists towards safer, non-toxic, renewable chemistry and materials. In order to advance green chemistry throughout the United States and internationally a significant change must occur in how we are training the current and next generation of scientists.

The Green Chemistry Commitment is an initiative to bring together green chemistry educators around the goal of transforming chemistry education. The commitment aims to bring the field together to agree upon common student learning objectives that departments wishing to incorporate green chemistry will champion. The Commitment is being lead by Beyond Benign, a non-profit dedicated to Green Chemistry education, in partnership with a faculty advisory board representing different colleges and universities from throughout the United States. This presentation will describe the program goals, the work of the commitment's advisory board and resources for interested faculty and institutions.

CHED 137

(gc)2 Green Chemistry @ Gordon College

Irvin J. Levy, [email protected], Dwight J. Tshudy.Department of Chemistry, Gordon College, Wenham, MA 01984, United States

In 2003 a student research paper served as the seed for the development of green chemistry at Gordon College, a small liberal arts college in Massachusetts. Student-motivated enthusiasm has advanced the role of green chemistry at Gordon College to the core of our department and his provided a cohesive theme that is easily shared with our community.

In this presentation we will discuss some of the ways that green chemistry has been incorporated into the fabric of our department in lecture, laboratory, research, outreach, alumni affairs and recruitment.

A robust network of collegial partners has emerged to empower individual faculty and entire departments to embrace green chemistry. Student participation in advancing our mission has grown ever more important in the past decade as undergraduate students recognize that they have the ability to participate in the improvement of chemistry through the transforming power of green principles and practices.

CHED 138

Green chemistry PhD program at the University of Massachusetts Boston

Wei Zhang, [email protected] of Chemistry, University of Massachusetts Boston, Boston, Massachusetts 02125, United States

University of Massachusetts Boston (UMB) has a strong tradition in the development of green chemistry. It launched the first Green Chemistry PhD program in the United States 10 years ago. Over a dozen students have received the PhD degrees and currently working in industry, academic, government and non-profit organizations. UMB also has an established Center for Green Chemistry for promoting education, research, and international collaborations. Recent activities related to ACS Green Chemistry Institute Pharmaceutical Roundtable and Curriculum Committee as well as Green Chemistry Commitment will be presented in this talk.

CHED 139

Committing to green chemistry at Bridgewater State University

Edward J. Brush, [email protected] of Chemistry, Bridgewater State University, Bridgewater, MA 02325, United States

Bridgewater State University (BSU) has made a strategic commitment to integrate sustainability in our curriculum, research opportunities, outreach and campus operations. These initiatives have provided new opportunities to educate the campus and regional community about the impacts of chemicals and chemical products on everyday life. The BSU chemistry department introduced green chemistry labs in organic chemistry several years ago, but progress in other courses has occurred at a much slower pace. This presentation will discuss the challenges many institutions face in teaching green chemistry, and how the Green Chemistry Commitment may help to overcome these challenges and provide the resources educators need to develop a STEM workforce capable of addressing key issues related to the impact of chemicals and chemical products on human and environmental health.

CHED 140

Bringing green chemistry into the curriculum at the University of Minnesota

William B. Tolman, [email protected] of Chemistry, University of Minnesota, Minneaspolis, MN 55455, United States

Integrating green chemistry into the crowded curriculum for chemistry majors and graduate students at a large research university presents special challenges. Recent efforts to address these challenges through the introduction of new courses, new laboratory instruction, and research initiatives at the University of Minnesota will be described.

CHED 141

Using green chemistry principles as the framework to incorporate research into the organic laboratory and the resultant effects on the entire undergraduate chemistry curriculum

Richard Gurney, [email protected], Nancy Lee, Changqing Chen, Cheryl Lavoie.Deparment of Chemistry and Physics, Simmons College, Boston, MA 02115, United States

Simmons College, a strong women's liberal arts college in Boston, was among many institutions teaching organic chemistry the traditional expository way ten years ago. Upon introduction of Green Chemistry Principles in an open-inquiry laboratory experiment in 2003, students and faculty learned the value in open-ended, research-integrated, greening experiences. As a result, both Green Chemistry and Research Integrated curricula grew to be mutually beneficial aspirations in our Department. With these goals in mind and with the help of several grants, we have successfully implemented not only a fully, research-integrated, green organic laboratory, but also re-envisioned the entire undergraduate chemistry curriculum. Students are excited about being a part of the "greening" process and willingly engage in the research as early as their first- semester at Simmons. Herein, we will describe our Undergraduate Laboratory Renaissance Program and our efforts to create an entire undergraduate chemistry curriculum rooted in the 12 Principles of Green Chemistry.

CHED 142

Development of an interdisciplinary green chemistry curriculum at UC Berkeley

John Arnold, [email protected], Martin J. Mulvihill.Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720, United States

To advance green chemistry, new approaches are needed in the design of chemistries, the assessment of health and environmental risks, and the governance of the economy. This requires new forms of cross-disciplinary education and research. We are integrating the chemical sciences, environmental health sciences, and the study of public and private governance into a cohesive educational program in green chemistry starting with introductory chemistry and continuing through graduate curriculum. To-date this approach has been applied to the redesign of introductory chemistry labs and the development of a graduate class. The lab development was catalyzed by the green chemistry education community and the GEMs database. The open- access model for educational resource sharing has been a key factor in our expansion of green chemistry offerings. Educators at BCGC have begun to give back by sharing our interdisciplinary graduate curriculum and partnering to advance social science-natural science partnerships seeking to advance green chemistry.

CHED 143

Investigating the influence of Japanese knotweed diet on the fatty acid content of chicken eggs

Shannon T Krauss, [email protected], James R Kraly, [email protected], Denise M Junge, [email protected] of Chemistry, Keene State College, Keene, New Hampshire 03435, United States

Recently there has been increased interest in the nutritional content of chicken eggs and the influence of chicken's diet on commercially produced eggs. Increased ratios of unsaturated to saturated fatty acids and higher levels of omega-3 unsaturated fatty acids in eggs are known to be beneficial to consumers. This collaborative project between the Chemistry Department and Surry Charter School aims to chemically analyze eggs from chickens with or without a Japanese knotweed diet. Japanese knotweed is an ecologically invasive plant with high levels of the antioxidant trans-resveratrol. The hypothesis that a diet high in trans-resveratrol leads to the production of healthier eggs will be tested. Fatty acid characterization and quantitative chemical analysis were performed using gas chromatography-mass spectrometry. Initial results show a 25% increase in fatty acid ratio for eggs of knotweed fed chickens, and a 260% increase in the relative mass percent of DHA, an important omega-3 fatty acid.

CHED 144

Fate of cooking oil during heating and frying: UV-Vis studies and iodine value determination

Chammi S. Miller, Megan L Murr, [email protected], Beverly Clement.Department of Chemistry, Blinn College, Bryan, Texas 77805, United States

In this study, we have evaluated chemistry of selected cooking oils upon heating and frying. We studied UV-Vis absorptions of these oils after heating at different temperatures. Olive oil, sunflower oil and peanut oil were used to fry onions at 196.56 ºC and UV-Vis absorptions of the frying oils were measured after filtration. Highly unsaturated oils such as sunflower oil showed a drastic bathochromic shift upon temperature changes whereas other oils showed a very slight bathochromic shift. Coconut oil was used as the reference oil. Furthermore, we analyzed the iodine value for olive oil and sunflower oil. Iodine value is drastically changed for fried sunflower oil compare to the olive oil. Further studies, including refractive index of treated oils are being performed for these oils.

CHED 145

5-Hydroxymethylfurfural and 5-sulfoxymethylfurfural: Exploration of metabolic adduct formation with 2'-deoxynucleosides and DNA Cameron Hovey, [email protected], Danaѐ R. Quirk Dorr.Department of Chemistry and Geology, Minnesota State University, Mankato, Mankato, MN 56001, United States

5-Sulfoxymethylfurfural (SMF) is a metabolite of the heat-related food contaminant, 5- hydroxymethylfurfural (HMF). HMF is thought to be converted in vivo by sulfotransferase enzymes into SMF, which is a stronger carcinogen. The conversion of HMF to SMF in mice following administration of HMF has been confirmed. However, no literature yet exists that investigates the structure or prevalence of SMF adducts formed with DNA. In this study, we examined SMF and its potential reactions with 2'-deoxyadenosine, 2'-deoxyguanosine, 2'- deoxycytidine, and thymidine in order to elucidate the structural characteristics of any adducts formed. SMF was synthesized from HMF and combined with the individual nucleosides and with calf thymus DNA. NMR spectroscopy and HPLC utilizing UV detection were used to investigate the results of these reactions.

CHED 146

Open-air mass spectrometry analysis of artesanal hot cocoa aroma by DART-TOFMS

Leonardo Hernandez-Torres1, [email protected], Carlos A. Mejias-Cruz1, [email protected], Michelle Z. Torres-Toledo1, Ruben Cruz-Lucena1, Mayra Ocasio1, John A Dane2, Alvaro Peña1, [email protected]. (1) College of Science-Department of Chemistry, Pontifical Catholic University of Puerto Rico-Arecibo, Arecibo, PR 00614, United States (2) JEOL USA Inc., Peabody, MA 01960, United States

Hot chocolate (hot cocoa) has become one of the most beverages drink in breakfast. Many cultures prepared the cocoa with and without milk. These differences in preparation leave analysis to the aroma of the liquid preparation. Commercial cocoa bars and artisanal cocoa have substantial differences that some persons could identify by their taste or odor. The presence of caffeine could be a useful method of analysis to understand why some commercial cocoa beverages affect people sensitive to coffee and why artisanal hot cocoa does not affect them. During this study, 100 mg of artisanal cocoa were dissolved in hot water and the aroma of the preparation was adsorbed in paper for Direct Analysis in Real Time (DART) TOFMS. Caffeine is typically observed at m/z 195.09 [M+H]+. Also, the removed shells and pure caffeine were treated in a similar in order to see if caffeine can be detected in the aroma of the hot beverages. Comparing organic extractions were taken and analyzed. All products were analyzed by DART- mass spectrometry.

CHED 147

Monitoring denaturation of soluble proteins by near infrared spectroscopy

Erin Morgan, [email protected], Alexander Soderberg, Emil Ciurczak, Cynthia Kradjel, Sunghee Lee.Department of Chemistry, Iona College, New Rochelle, New York 10801, United States

Near-Infrared spectra are strongly affected by hydrogen bonding. That means that a protein in its "natural" state will have a distinctive spectrum in an aqueous solution. The secondary or tertiary structures of proteins, are determined by, in large part, hydrogen bonding. Disruption of this structure can lead to consequences from reduced food value to loss of activity in therapeutic materials such as insulin. As the structures are disrupted by temperature, salt concentration, or pH, the NIR spectra also change. Peaks can increase or decrease in intensity or shift to higher or lower frequencies with structural changes. These spectral changes may be measured and rates of reaction determined. The rates at which this denaturation occurs can allow suppliers and users to understand storage and/or use conditions. CHED 148

Determination of the refractive index of solid compounds by the laser pointer method: Extention method

Jihyun Lee, [email protected], Rebecca Cho, Jun H. Shin.Department of Chemistry, Queensborough Community College, the City University of New York, Bayside, NY 11364, United States

A simple, accurate and inexpensive system using a laser pointer and a chromatography column has been developed to measure the refractive index of solid compounds. In the system, a good linear relationship, which was found between percent mass of solid-solvent mixture and its refractive index, was extended to 100% to determine the refractive index of a solid compound. A graph of refractive index vs percent mass was obtained in low concentration ranges (0 - 15%), The line of the linear plot was then extrapolated to 100% mass (i.e. pure solid) where the refractive index of the solid was calculated. The refractive index of solid compounds such as lauric acid, myristic acid, and p-dichlorobenzene has been investigated in several different solvents using this system.

CHED 149

Ni content of the US nickel coin determined by X-ray fluorescence and visible spectroscopy

Sharda Jagdeo1, [email protected], Esther J. Shin2, [email protected], Jun H. Shin1. (1) Department of Chemistry, Queensborough Community College, the City University of New York, Bayside, NY 11364, United States (2) Roslyn High School, Roslyn Heights, NY 11577, United States

We had successfully measured the copper content of the US penny using X-ray fluorescence, UV-Vis spectrophotometer, and gravimetric method. As a continuous study, nickel content of the US Nickels produced between 1962 and 2011 were determined by two methods: visible spectroscopy and X-ray fluorescence. Originally the five-cent coin was made of silver metal, but the shortage of silver during and after the American Civil War (1857-1864) resulted in the introduction of a new five-cent coin consisted of 12% nickel and 88% copper metals; it is called a 'nickel' because of the nickel metal in the coin. From 1865 the nickel content in the US nickel increased to 25%, and the composition of the US nickel has remained unchanged with the exception during the World War II. The percent nickel in the US Nickels (1962-2011) was found to be 25±1% by visible spectroscopy, and 27±1% according to X-ray fluorescence analysis.

CHED 150

Application of the laser pointer method to determine the refractive index of solid compounds: Out-in method

Suk Ju Ham, [email protected], Rebecca Cho, Jun H. Shin.Department of Chemistry, Queensborough Community College, the City University of New York, Bayside, NY 11364, United States

We have developed a simple, accurate, and inexpensive system for determining the refractive index of various compounds using a laser pointer and a chromatography column. We applied this system to measure the refractive index of a solid compound based on the observation that the refractive index of a liquid remains unchanged on addition of a solid if the refractive index of the solid is the same as the liquid. The refractive index of solid compounds including lauric acid, myristic acid, and p-dichlorobenzene has been determined using an out-in method. The refractive index determined by this new method was found to be close to the literature values for all three solids.

CHED 151

Self-assembly studies of DNA/dendron conjugates for DNA sensor development

Chris N Warner, [email protected], Erik S Vint, Zachary Hunter, Rebekah Jamieson, Brian S Day.Department of Chemistry, Marshall University, Huntington, WV 25755, United States

The surface chemistry involved in immobilizing biological molecules to solid supports is one crucial factor in the success of biochips. Many processes for creating sensing spots on biochips rely on self-assembly of the probe molecules so there is a need to understand the design elements necessary to create reproducible, homogeneous spots on a surface. In this study, we have investigated the basic physical properties of headgroup size and substrate-adsorbate binding strength on the structure and function of DNA monolayers on gold. The self-assembling molecules are prepared by conjugating DNA molecules to dendrimers with their terminal groups functionalized with either thiol groups, acetate groups, or a combination of the two. Dendrimers were chosen to conjugate to the DNA since their generations provide control over the DNA headgroup size and their large number of terminal groups provides control over the number of strong bonds to the gold.

CHED 152

Defensive secretions of the carabid beetle Chlaenius cordicollis: Chemical components and their geographic patterns of variation

Travis M Mattingly1, [email protected], Kathleen M Naccarato1, [email protected], Neil J Holliday2, Alison E Holliday1. (1) Department of Chemistry & Biochemistry, Swarthmore College, Swarthmore, PA 19081, United States (2) Department of Entomology, University of Manitoba, Winnipeg, MB R3T 2N2, Canada

Chlaenius cordicollis are carnivorous ground beetles that live on the shores of large lakes and rivers. When disturbed, they produce a strong-smelling defensive secretion. Adult C. cordicollis were collected in Pennsylvania and Manitoba and induced to discharge defensive secretion in a vial. The headspace was sampled by solid phase microextraction, and samples were analyzed by gas chromatography–mass spectrometry. Five alkylphenolic compounds were detected: all beetles secreted 3-methlyphenol, 2,5-dimethylphenol, and 3-ethylphenol, and most beetles from each locality secreted detectable amounts of 2,3-dimethlyphenol and 3,4-dimethylphenol. In about 80% of beetles, we detected small amounts of the alkoxyphenolic compounds 2-methoxy- 4-methylphenol and 2-methoxy-5-methylphenol. Multivariate compositional analysis of relative peak areas of alkylphenolic compounds revealed geographic variation and sexual dimorphism in defensive secretions.

CHED 153

Imprinted polymers for the detection of metal ions

Brian K. Lindner, [email protected], Shannon M. Fetner, Shannon E. Stitzel.Department of Chemistry, Towson University, Towson, MD 21252, United States The development of chemical sensors for metal ion detection has potential application in environmental monitoring and other areas. The research project described combines photo- switchable spiropyrans with molecularly imprinted polymers to create photo-activated binding pockets for metal ion detection. The selectivity for a metal ion of interest can be achieved by creating a molecular imprinted polymer that contains the spiropyran moieties within the binding pockets, and the photoactive nature of the spiropyran molecule provides an on/off switch that allows the sensor to be reused. Results will be presented for polymers imprinted with cobalt or with zinc as the target analyte. These results indicate that a molecularly imprinted binding pocket can be made within the polymer matrix that has improved selectivity relative to a non-imprinted control polymer.

CHED 154

Impact of polymer cross-linking on spiropyran-based sensors

Shannon M. Fetner, [email protected], Brian K. Lindner, Shannon E. Stitzel.Department of Chemistry, Towson University, Towson, MD 21252, United States

The combination of spiropyrans with polymers has been applied in areas such as photo- controlled surface wettability, memory devices and chemical sensors. Spiropyrans are photochromic compounds which are prone to photo-degradation over time. For the specific application of spiropyrans in chemical sensors, further understanding and control of the photo- degradation process would improve chemical sensor stability, a non-trivial issue when considering environmental monitoring applications where sensors need to be in situ for several weeks or months. The impact of having spiropyran molecules incorporated within highly cross- linked, rigid polymer matrixes used for metal ion detection is the focus of this work. Results will be presented regarding the impact of increased polymer rigidity on the photo-degradation of the spiropyran polymer, as well as the impact on the ability of the spiropyran polymers to detect metal ions.

CHED 155

Determination of the thermodynamics of retention using an octyl HPLC stationary phase under varying mobile phase and temperature conditions

Caitlin Galvin, [email protected], Eric J Williamsen.Department of Chemistry, Ursinus College, Collegeville, PA 19426, United States

The molecular processes underlying HPLC are not completely understood. Using an octyl stationary phase and 10% methanol, 90% water mobile phase, retention of approximately 40 analytes with various functionality was measured at temperatures ranging from 5.0 to 65.0 ˚C. van't Hoff plot were generally linear with a few exceptions. In addition, selectivity plots were made to determine whether the volume phase ratios were constant and multivariate analysis was applied to emphasize retention patterns. Trends in retention, and in the enthalpy and entropy of retention will be presented and compared to results obtained while using other stationary phases (octadecyl and fluorinated octyl), and other mobile phase conditions (varying the organic/water ratio and substituting acetonitrile instead of methanol as the organic component).

CHED 156

Cyclic voltammetric study of an anodically polymerized nickel(II) salen film for catalytic reduction of 1-bromo-5-decyne Kent J. Griffith, [email protected], Dennis G. Peters.Department of Chemistry, Indiana University, Bloomington, IN 47405, United States

Cyclic voltammetry can be used to oxidatively polymerize homogeneous-phase nickel(II) salen onto a carbon electrode in acetonitrile containing 50 mM tetramethylammonium tetrafluoroborate to yield a heterogeneous poly[nickel(II) salen] film. Previously, poly[nickel(II) salen] films were used in our laboratory to catalyze the reduction of simple alkyl halides such as iodoethane. Electrochemical reduction of 1-bromo-5-decyne in the presence of homogeneous electrogenerated nickel(I) salen is reported to yield pentylidenecyclopentane as the major product of reductive intramolecular cyclization. Employing a polymeric film with this alkynyl halide is a novel application, which may lead to a more efficient synthetic route to pentylidenecyclopentane and other reduced species. This study characterizes the behavior of the film in comparison with (i) reduction by homogeneous-phase nickel(I) salen and (ii) direct reduction; in addition, the efficacy of the reduction as a function of catalyst concentration, scan rate, substrate identity and concentration, and addition of a proton donor has been probed.

CHED 157

Constituent analysis of Panadol via paper analytical devices (PADs)

Diana M Vega Pantoja1, [email protected], Toni Barstis1, Marya Lieberman2, Victoria R Darling1. (1) Department of Chemistry and Physics, Saint Mary's College, Notre Dame, Indiana 46556, United States (2) Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, United States

It is projected that in developing countries anywhere from 10% to 50% of the medications sold are counterfeits, which is attributed to a lack of testing equipment and financial resources. This research focused on the detection of counterfeit Panadol (Tylenol®), via Paper Analytical Devices (PADs). A PAD is a device with a modified substrate that uses colorimetric tests to identify constituents in a sample. This analysis is necessary because acetaminophen, the active ingredient of Panadol, may be replaced by cheaper powders (such as chalk) in counterfeit Panadol, and is used itself to replace the active ingredients in counterfeit antimalarial medications. The PAD yields a fast identification of common ingredients found in genuine and counterfeit drugs and also enables a semi-quantification of acetaminophen. The colorimetric tests are analyzed via an imaging tool. This presentation yields the results of series of field tests that examine the reliability of the PAD.

CHED 158

Simple field analysis of antibiotics: The PADs project, antibiotics division

Mary M Bevilacqua1, [email protected], Elizabeth Robbins1, [email protected], James Firth3, Toni L.O. Barstis1, Marya Lieberman2. (1) Department of Chemistry and Physics, Saint Mary’s College, Notre Dame, Indiana 46556, United States (2) Department of Chemistry and Biochemistry, Notre Dame University, Notre Dame, Indiana 46556, United States (3) Marian High School, Mishawaka, Indiana 46544, United States

Antibiotic counterfeiting is a serious problem facing many developing nations. Inadequate dosing may lead to insufficient treatment of infected individuals and an increased rate of antibiotic resistance. The antibiotics division of the project team is developing a series of simple colorimetric tests on PADs (paper analytical devices) to semi-quantitatively and qualitatively analyze antibiotics samples in a non-laboratory environment. The PAD is impregnated with colorimetric indicator reagents, and then exposed to the pharmaceutical analyte to verify active ingredient concentration and check for common counterfeiting agents. This division of the project team has focused its efforts on developing general PADs for types of antibiotics such as macrolides as well as more specific PADs for drugs such as erythromycin-A. These and other PADs may improve health care in multiple settings including developing nations.

CHED 159

Flow behavior in microfluidic devices

Shane M McMahon, [email protected], Ryan M Keltz, [email protected], James M Karlinsey.Department of Chemistry, Penn State Berks, Reading, PA 19610, United States

The past decade has seen a significant increase in the number of reported applications of microfluidic analysis systems, and it is important to recognize the difference in flow behavior on the microscale. This work describes two of the most important considerations in microscale flow, laminar flow and electroosmotic flow (EOF). Laminar flow, which features non-turbulent flow of adjacent fluid streams, is the result of the low Reynolds numbers associated with flow in microchannels having sub-millimeter dimensions. EOF, which enables bulk flow of solution in response to an applied electric field, is dependent upon the interaction of ions in a buffer solution with surface charge on the walls of the microchannel. Both of these phenomena are described in the context of micofluidic systems, with data presented using microchannels fabricated in glass, poly(dimethylsiloxane) (PDMS), and glass-PDMS hybrid devices.

CHED 160

Improved methodology for removing dihalomethane carryover from SPME fibers

Christina M McGuire, [email protected], Edward Harrington, Maria J Krisch.Department of Chemistry, Trinity College, Hartford, Connecticut 06106, United States

Solid phase microextraction (SPME) in conjunction with gas chromatography-mass spectrometry (GC-MS) is a simple and effective way to sample analytes. Typically during desorption in the GC the coated fiber is automatically rid of most compounds, allowing for the analysis of a new sample. This study indicates that simple desorption is not enough to thoroughly clean a Carboxen PDMS 75µm fiber from dihalomethanes, resulting in carryover of the analyte between samples. Our data suggests that heating the fiber in a separate injection port between each run prevents carryover from sample to sample. Calibration curves indicate that heating between samples significantly improves the linearity of the peak area vs. concentration relationship.

CHED 161

Quantitative determination of gallic acid in various tea beverages using HPLC

Mengjia (Michelle) Lin, [email protected], Pedro Irigoyen, Paris Svoronos.Department of Chemistry, Queensborough Community College, Bayside, NY 11364, United States

Gallic acid, C6H2(OH)3COOH, also known as 3,4,5-trihydroxybenzoic acid, is a carboxylic acid, that has been found many applications in the pharmaceutical industry. It is also used as the standard in the spectrophotometric determination of the total phenol content in wines, where results are reported in “gallic acid equivalents”. A procedure has been developed that determines the amount of gallic acid present in beverages, such as tea samples and other fruit and vegetable juices using High Pressure Liquid Chromatography (HPLC). This quantitative measurement uses a calibration curve produced with standard solutions of gallic acid. The preparation of the samples, treatment with sodium dihydrogen phosphate buffers as well as the identification and quantitative determination of the gallic acid content in these beverages will be described and comparisons will be drawn. Preliminary studies on the air oxidation of the same samples indicate a considerable decomposition of gallic acid with time.

CHED 162

Spectrophotometric determination of the total amount of antioxidants in juice beverages

Sandy Enriquez, [email protected], Soraya Svoronos, May Myat Moe, Pedro Irigoyen, Paris Svoronos.Department of Chemistry, Queensborough Community College, Bayside, NY 11364, United States

The Gallic Acid Equivalence method (GAE) measures the total amount of antioxidants in the wine industry (A.L Waterhouse. “Determination of Total Phenolics” in “Current Protocols in Food Analytical Chemistry”, I1.1.1-I1.1.8). The procedure uses the Folin's phenol reagent to oxidize polyphenols into polyquinones, thus allowing the visible spectrophotometric determination of the polyphenols that are present in a beverage. The results are expressed as Gallic acid equivalents and the measurements are made using a Beer-Lambert plot. The procedure has been extended to several commercially available juice and fruit beverages and the semiquantitative measurement of the antiooxidants' decomposition with time was determined.

CHED 163

Use of a microscale freezing point technique to determine the ionization constant of carboxylic acids.

Fathima B. Nazumudeen, [email protected], Pedro Irigoyen, Paris Svoronos.Department of Chemistry, Queensborough Community College, Bayside, NY 11364, United States

The standard freshman General Chemistry laboratory uses freezing-point depression concept to determine the molar mass of a solute using the general equation ΔTF = (KF) x (m) x (i) where ΔTF o o = freezing point depression ( C); KF= the solvent cryoscopic constant ( C/ molal) m = molality of solution (mol solute/kg solvent) andi = van 't Hoff factor, characteristic of the solute degree of ionization We have developed a microscale procedure that uses a LabPro interface and aqueous solutions that are as low as 0.1g of solute in 3 mL water to determine the ionization constant of -1 -2 five carboxylic acids (Ka= 10 -10 ) using the van 't Hoff factor at different concentrations. The data are the first ones reported at the freezing point of water. Moreover our procedure uses much smaller quantities than the standard titration procedures which lead to potentially significant accumulations of waste chemicals.

CHED 164

Use of the Folin-Ciocalteau method to measure the total amount of antioxidants in tea samples

Kaungmyat San, [email protected], Soraya Svoronos, May Myat Moe, Pedro Irigoyen, Paris Svoronos.Department of Chemistry, Queensborough Community College, Bayside, NY 11364, United States

The Folin-Ciocalteu reagent, also known as Folin's phenol reagent or Folin-Denis reagent or Gallic Acid Equivalence method (GAE), is a mixture of phosphomolybdate and phosphotungstate ions. It is used in the colorimetric assay of phenolic and polyphenolic antioxidants in the wine industry. In this project the Beer-Lambert law was applied to measure the intensity of the blue color formed when the reagent is placed in contact with tea sample solutions to measure the total amount of the antioxidants present in the solution using Gallic acid as the standard. The study of tea samples included beverages as well as extracts of tea bags. A comparison of various brands of tea and the effect of air decomposition of the antioxidants with time was measured and compared.

CHED 165

Spectroscopic properties of tetracyclines

Mariya Rozov, [email protected], Elmer-Rico E. Mojica.Dept of Chemistry & Physical Sciences, Pace University, New York,, NY 10038, United States

Tetracyclines (TCs) are an important family of low molecular weight and broad spectrum antibiotics. They have been widely used in the prevention and treatment of infectious diseases and as food additives for growth promotion, as well, in fish farming. Tetracyclines are amphoteric molecules containing several ionizable functional groups that exist predominantly as zwitterions at a given pH value. TCs are reported to undergo a wide variety of reactions at different pH values. As an example, TCs undergo reversible epimerization at position C-4 to form 4-epi-TCs between pH 3 and 6. The formation of anhydrotetracyclines at low pH and isotetracyclines at high pH values are also known. In this presentation, we report on the pH-dependent absorbance and emission properties of several tetracyclines. We also report on the absorbance and emission of some tetracyclines in various alcoholic solvents.

CHED 166

Synthesis and evaluation of non-natural PFTase substrates capable of copper-free bioorthogonal cycloaddition

Kaitlin R. Peterson1, [email protected], Kayla A. Lange1, Kristina R. Poss1, Benjamin Monson2, James W. Wollack1. (1) Department of Chemistry and Biochemistry, St. Catherine University, St. Paul, MN 55105, United States (2) Department of Chemistry, Hamline University, St. Paul, MN 55104, United States

Many non-natural isoprenoid diphosphate analogs have been shown to be substrates for Protein Farnesyltransferase (PFTase). Transferable analogs include azide and alkyne containing isoprenoid derivates which can subsequently be used as handles to perform click chemistry after modification. The limitation for bioconjugations using click chemistry is that these reactions must be completed in the presence of copper which can degrade biological molecules. An alternative method is tetrazine ligation: a bioorthogonal reaction which proceeds through an inverse electron demand Diels-Alder mechanism at a rate comparable to copper-catalyzed click reactions, without cytotoxicity. Here we report the synthesis of cyclooctene and norbornene containing isoprenoids that are substrates for PFTase. Proteins and peptides labeled with these moieties are candidates for tetrazine ligation—a particularly useful bioconjugation method in biological environments.

CHED 167

Ribosomal proteomics in five species: A biochemistry teaching laboratory

Yoshihiro Miura, [email protected], Kestutis Bendinskas.Department of Chemistry, State University of New York at Oswego, Oswego, New York 13126-3599, United States Clean water is essential to human health, yet over a billion people lack sanitary drinking water, resulting in millions of preventable deaths every year. Although there are numerous water-quality issues, nitrates present a significant problem. The widespread use of fertilizers, combined with the high solubility of nitrates, has made nitrates an almost universal contaminant in water sources, especially aquifers. We have been working on the development of an innovative method for the removal of nitrates. This method of purification utilizes microcapsules that hold purified water. The microcapsules are designed to have a polymer-based membrane that is permeable to ions. This process should be relatively inexpensive and work by simple diffusion. We have studied the rate of nitrate removal from water using these microcapsules and have determined the role of chemical structure, concentration gradient and mass of microcapsule to volume of water ratio.

CHED 168

Investigation of the antibiotic mechanisms of bacterial 5'-methylthioadenosine/S- adenosylhomocysteine nucleosidase (MTN) inhibition using enzyme specific inhibitors and targeted gene deletion

Allison Eberly1, [email protected], Reece Knippel2, Seth Eidemiller2, Kenneth A Cornell2, [email protected]. (1) Department of Chemistry, Chestnut Hill College, Philadelphia, PA 19118, United States (2) Chemistry & Biochemistry, Boise State University, Boise, ID 83725, United States

The bacterial specific enzyme 5'methylthioadenosine/S-adenosylhomocysteine nucleosidase (MTN) is essential for production of the universal quorum sensing signal autoinducer 2 (AI-2). AI- 2 is known to influence biofilm formation and virulence in bacteria. This enzyme serves as a target for development of novel antibiotics that would interrupt quorum sensing responsive events that are widespread in bacteria. In E. coli MTN gene knockout (MTN KO) strains, we found alterations to growth, biofilm formation, nutrient utilization patterns, and a loss of AI-2 synthesis. Significant alterations in pyruvate and polyamine metabolism were observed in MTN KO and MTN inhibitor treated cultures that were not reversed by supplementation with exogenous AI-2. The results suggest that loss of MTN activity exerts its principle antibiotic effect through inhibition of radical S-adenosylmethionine dependent vitamin synthesis and product inhibition of polyamine synthase reactions.

CHED 169

Investigating structural changes to green tea extract (EGCG) by monitoring the effect on cells using QCM-D

Danielle E Fagnani, [email protected], Marcela Garcia, Jennifer Chen, Jun Xi.Chemistry, Drexel University, Philadelphia, PA 19104, United States

Epigallocatechin gallate (EGCG) is one of the most abundant and potent antioxidants found in green tea. Research has shown that this compound displays many cancer preventative effects on cells. EGCG contains many hydroxyl functional groups that can be converted to ester groupings by chemical derivatization to make the molecule more hydrophobic. This may increase cell permeability of EGCG and possibly increase its potency. In this study, we compared the biological effects of EGCG and ECGG-peracetate on a cancer cell line A431 by assessing the respective cellular response caused by each of these two compounds with a quartz crystal microbalance with dissipation monitoring.

CHED 170 Inhibition of porcine pancreatic lipase by various tea products

Erin Wolfe, [email protected], Terese Wignot.Department of Chemistry, Wilkes University, Wilkes Barre, PA 18766, United States

Lipase, along with co-lipase, assists the body in the breakdown of lipids. Reducing lipase activity can have a variety of health benefits including reducing cholesterol and weight loss. Consumption of tea has been shown to decrease blood glucose levels and to reduce the risk of cancer. In vitro studies have been performed to test if various types of tea inhibit lipase activity. The addition of black tea (9 mL) to thein vitro lipase assay results in a 62 % decrease in activity. Further studies are being performed to determine if lipase activity is affected by the addiction of white or green tea. The polyphenols in tea will be extracted and separated to determine which, if any, of the individual polyphenols show inhibitory effects.

CHED 171

Bacterial membrane permeability assays for evaluating antimicrobial peptide mechanism of action

Angela L Picciano, [email protected], Sarah M Misenko, [email protected], Zachary M Ridgway, Gregory A Caputo.Department of Chemistry and Biochemistry, Rowan University, Glassboro, NJ 08028, United States

Small molecule permeability assays are an efficient way for detecting membrane disruption by antimicrobial agents. They rely on the hydrolysis of a chromophoric enzyme substrate, which varies depending on the bacteria and membrane. By utilizing a DNA binding fluorophore in these membrane permeability assays, knowing cellular enzyme content is not needed. A broad- spectrum assay that utilizes a fluorescent dye that binds reversibly to DNA was developed to test the ability of the anti-microbial agents in bacteria. We have applied this combination of assays to test the membrane permeabilizing activity of a series of antimicrobial peptides derived from the venom of ponerine ants or from a human platelet factor. In combination with fluorescence spectroscopy and circular dichroism spectroscopy, we have found a correlation between peptide length and structure. We are also able to correlate bactericidal activity with permeabilization of the bacterial membrane implicating it in the peptides' mechanism of action.

CHED 172

Sequence specific DNA binding behavior of GCN4

Danielle M McHarris, [email protected], Daniel A Barr.Department of Chemistry, Utica College, Utica, NY 13502, United States

GCN4 is a basic leucine zipper protein and is the main regulator of the transcriptional response to amino acid starvation in yeast. When bound to DNA, a “chopstick-shape” is formed and an antagonistic folding occurs. By performing computer simulations on the 100ns timescale, we are able to understand how GCN4 recognizes these DNA sequences. To understand the interactions responsible for sequence-specific binding, we are analyzing: hydrogen bonds, electrostatic interactions, RMSF, RMSD, and patterns in atomic fluctuations. Through running these specific analyses, we can conclude why these proteins bind the way they do. In the future, this will lead to continuing investigation in specific mutations and how they affect protein binding.

CHED 173 Mass spectral analysis of glycated cytochrome c

James D Collins, [email protected], Leslie M Frost.Department of Chemistry, Marshall University, Huntington, WV 25755, United States

Spontaneous glycation of protein amines by sugars is a reaction that can lead to protein modification and dysfunction. Carnosine, a dipeptide found exclusively in long-lived animal tissues, has been proposed to act as a naturally occurring anti-glycating agent. Cytochrome c is a protein involved in the electron transport chain and is a key player in the cellular apoptosis process. The glycation of this protein could alter critical functional lysine groups, leading to impaired functions in respiration and apoptosis. We have two main goals for this research project: 1) to determine the effect of carnosine on the glycation of cytochrome c, and 2) to identify the preferential sites of glycation using mass spectrometric techniques when cytochrome c is condensed with D-glucose and D-galactose. We have determined that the addition of carnosine does not disrupt initial glycation reactions and that cytochrome c is glycated at only a few preferential lysine residues.

CHED 174

Understanding the mechanisms of copper induced lipid peroxidation mediated cell death in Saccharomyces cerevisiae

Jasodra Ramlall, [email protected], Nidhi Gadura.Biological Science, Queensborough Community College, Bayside, New York 11364, United States

The long-term goal of this proposal is to understand the mechanisms of copper induced cell death by using Saccharomyces cerevisiae. Our working hypothesis, based on preliminary results is that upon exposure to copper, toxicity is triggered by the increased lipid peroxidation of unsaturated fatty acids in the plasma membrane. In order to determine the relationship between exposure to copper alloy surfaces, lipid peroxidation, and cell death in Saccharomyces cerevisiae quantitative dilutions series were performed to test for cell death levels. Our results indicate a biphasic killing curve when S. cerevisiae is exposed to copper, however this was not seen on steel chips. TBARS assay was used to measure the lipid peroxidation levels. In addition to looking at how copper effects the membrane we characterized the impact of exposure to copper alloy surface by using FM4-64, an amphiphilic styryl dye. Genomic DNA was analyzed to establish how cell death was triggered.

CHED 175

Role of calcium in anionic mixed bilayer

Zuzanna Michalak, [email protected], Nousin Haque, Darius Fartash, Sunghee Lee.Department of Chemistry, Iona College, New Rochelle, NY 10801, United States

In this study, effect of calcium on anionic lipid in bilayers has been investigated by droplet interface bilayer (DIB). DIB is formed when individual pairs of surfactant-monolayer coated aqueous droplets adhere at an interface. The use of varying mole ratios of dioleoylphosphatidylglycerol (DOPG)/1-glyceryl monooleate (GMO) as surfactant dissolved in squalene provides DIB with different anionic charges. The sensitivity to calcium ions was apparent depending on the degree of the negative charge of lipids that constitutes DIB. A possible explanation of the observed phenomena is strong association of calcium ions with the negatively charged DOPG/GMO bilayers leading to reorganization of the two lipids at the molecular level. CHED 176

Staphylococcus aureus cell wall proteins targeted by antibacterial plant extracts

Kathleen A. Leamy1, [email protected], Kaleigh Cote1, Jenna Cunningham1, Shawn Reap1, George Bazinet2, Daniel F. Moriarty1. (1) Department of Chemistry and Biochemistry, Siena College, Loudonville, NY 12211, United States (2) Department of Biology, Siena College, Loudonville, NY 12211, United States

The search for molecules with broad-spectrum antibacterial activity has led to natural sources for new pharmaceutical advances. Plant material has proven to be a reservoir of bacterial inhibition. This research has focused on water-soluble compounds and has found positive bacterial inhibition from multiple sources. This experiment is designed to ascertain a specific mode of action for inhibition. Penicillin inhibits the transpeptidation reaction by binding to the bacterial cell wall proteins. In order to determine plant extract binding to these proteins, isolated cell wall proteins were subjected to SDS-PAGE. Binding of the active extract to a specific protein would alter that protein's electrophoretic mobility, and has identified several possible targets.

CHED 177

Effect of copper surfaces on endospore-forming bacteria Bacillus subtilis

Janet Long, [email protected], Nidhi Gadura.Department of Biology, Queensborough Community College, Bayside, NY 11364, United States

The overall objective of this project is to determine the relationship between exposure to copper surfaces, lipid peroxidation, and cell death in different bacterial strains. In particular, this project explores the impact of copper exposure on the endospore-forming, gram-positive strain, Bacillus subtilis. Different time course trials were preformed to determine the correlation between copper exposure, amount of lipid peroxidation, and rate of cell death. A quantitative dilution series was used to determine bacterial cell death. The TBARS Assay was used to measure the amount of lipid peroxidation that occurs during exposure to copper. Genomic DNA was extracted to study the mode of death. Furthermore, fluorescent microscopy was done using a Live Dead Assay kit. Results indicate that cell death begins within five to ten minutes of copper exposure, except for the endospores. The increase in lipid peroxidation correlates with cell death as well as genomic DNA degradation.

CHED 178

M_ssbauer studies of the dehaloperoxidase enzyme from Amphitrite ornata

Danielle Miller1, [email protected], Codrina V Popescu1, Jonathan Birabaharan1, [email protected], Hongli Chen1, Reza Ghiladi2, Rania Dumarieh2. (1) Chemistry, Ursinus College, Collegeville, PA 19426, United States (2) Chemistry, North Carolina State University, Raleigh, NC 27695, United States

Dehaloperoxidase (DHP) from the marine worm Amphitrite ornata, is a globin exhibiting significant peroxidase acitivity and is of environmental interest as it is involved in the oxidation of dehalogenation of trihalophenols. The active site of this bifunctional enzyme is a heme center, coordinated by a histidine residue in the proximal position. This first Mössbauer study will present the spectroscopic features of DHP in the resting states and the oxyferrous state. His 55 can close the active site in a 5-coordinated form (at low pH) or leave it open to coordinate a water ligand (high-pH). These two ferric forms coexist at all pH values and have different EPR signatures. DHP-A was studied at pH 7 and 5, in variable temperature and variable field conditions. This study will ascertain the spin and oxidation states of the iron in the several catalytic states and will draw comparisons between DHP and other heme proteins.

CHED 179

Purification and characterization of the lectin-like domain of thrombomodulin and complement component C3

Grace R Soloff, [email protected], Amy Schaefer, Kelechi Iro Kalu, Julia R Koeppe.Department of Chemistry, Ursinus College, Collegeville, PA 19426, United States

The goal of this project is to isolate and purify complement factor 3 (C3) and the lectin-like domain of thrombomodulin (TM). This research may help to identify an association between blood clotting and inflammation mechanisms. The TM gene was successfully ligated with a yeast expression vector (pPic9K) and then amplified in E. coli. The resulting plasmid was then successfully transformed into P. pastoris. Small scale growths showed expression of TM. Large scale growths have been performed followed by purification of TM. The TM is purified by a series of chromatographies: hydrophobic interaction, anion exchange, and size exclusion. Purification has been monitored by SDS-PAGE. Multiple attempts to purify C3 from blood serum have been attempted using ion-exchange chromatography. The isolated TM and C3 will be characterized by MALDI-ToF mass spectrometry alone and as an interacting pair.

CHED 180

Characterization and interactions of complement component C3 and the lectin-like domain of thrombomodulin

Kelechi Iro Kalu, [email protected], Amy Schaefer, Grace Soloff, Julia R. Koeppe.Department of Chemistry, Ursinus College, Collegeville, PA 19426, United States

Protein-protein interactions are extremely important interactions in the body responsible for many necessary biological functions. This study aims to specifically look at the interactions between the lectin-like domain of thrombomodulin (TM) and complement components C3 and C3b. Interactions of TM, known to be a regulator of blood clotting, with the complement system, an important part of innate immunity, could play an important role in a link between coagulation and inflammation. To understand the relationship, each protein first needs to be studied individually. The lectin-like domain of TM has been expressed in and purified from yeast. Complement component C3 has been isolated from plasma, purified and activated to C3b. Analysis by SDS- PAGE and mass spectrometry verified that the desired proteins were isolated. Development of a pull-down assay to confirm interaction between the proteins is underway. The proteins will also be studied by hydrogen/deuterium exchange coupled with mass spectrometry.

CHED 181

Impact of plasma membrane unsaturated fatty acid levels on copper surface mediated cell death in E. coli

Robert Hong, [email protected], Tae Y. Kang, Nidhi Gadura.Biology, Queensborough Community College, Bayside, NY 11364, United States

The broad goal of our study is to understand the mechanism(s) by which copper alloy surfaces kill microorganisms. Our results indicate that copper surface mediated cell death of E. coli correlates with increased levels of lipid peroxidation at the plasma membrane. We also determined the relationship between membrane lipid peroxidation levels and cell death in Escherichia coli on both copper and steel surfaces. Quantitative dilutions series were performed to test for bacterial cell death. Our results indicate a biphasic killing curve when E.coli is exposed to copper chips however this was not seen on steel chips. TBARS assay was used to measure the lipid peroxidation levels. Genetically altered bacterial strains show that when exposed to copper surfaces, increased levels of unsaturated fatty acids in the plasma membrane results in faster cell death rates in E.coli. Genomic DNA analysis show a necrotic cell death pattern.

CHED 182

Synthetic and spectroscopic investigations of oligomers of α-aminoisobutyric acid

Timothy Jacisin, [email protected], Matthew A. Kubasik.Department of Chemistry and Biochemistry, Fairfield University, Fairfield, CT 06824, United States

Oligomers of the achiral amino acid α-aminoisobutyric acid are known to form 310 helical secondary structures in solution, even at short (n= 6, 8) oligomer lengths. Additionally, oligomers of this achiral amino acid form racemic mixtures of left- and right-handed helices. Despite the favorable conformational properties of the α-aminoisobutyric acid residue, the geminal methyl groups reduce peptide-coupling efficiency due to steric hindrance. Recent synthetic (e.g., isotopic enrichment) and spectroscopic (e.g., infrared and nmr) results will be presented.

CHED 183

Expression of gamma-synuclein protein in cancer cells

Julia Boroday, [email protected], Urszula Golebiewska.Department of Chemistry, Queensborough Community College, Bayside, NY 11364, United States

Gamma-synucleins (gamma-syn) belong to a small, soluble, highly conserved group of neuronal proteins implicated in both neurodegenerative diseases and cancer. They share sequence homologies and structural properties whose biological functions are still unclear. However their involvement in these diseases may provide insights into the pathological processes resulting from their effect, and present the possibility to serve as potential targets for early diagnosis and treatment. Recently, elevated levels of gamma-syn proteins were detected in advanced stages of cancer. Furthermore, studies to date indicate that overexpression of gamma-syn compromises normal mitotic checkpoint controls, resulting in multinucleation as well as faster cell growth. Gamma-syn has also been shown to promote invasion and metastasis in animal models as well. These observations raise questions about the involvement of gamma-syn in the process of tumorigenesis and metastasis, and current efforts try to use them as markers in assessing breast cancer progression.

CHED 184

Reactivity of tris(trimethylsilyl)phosphite (TMSP): Synthesis of a bisphosphonic derivative of bicine Lena Najjarian, [email protected], Luis Vargas.Department of Chemistry, Queensborough Community College, Bayside, NY 11364, United States

The synthesis of a potential inhibitor of the tyrosine phosphatase is presented.The compound, a bisphosphonic derivative of bicine, uses commercially available bicine as the starting reagent. The O-protected bicine is treated with thionyl chloride to form the corresponding acyl chloride and then reacted with tris(trimethylsilyl)phosphite (TMSP). After hydrolysis to regenerate the hydroxy group and spectroscopic identification, the compound will be tested as a potential inhibitor of the enzyme.

CHED 185

Synthesis and characterization of efficient Nek2 substrates employing solid phase synthesis procedures

Daniel Andre Novoa1, [email protected], Sanjai Kumar2. (1) Department of Chemistry, Queensborough Community College, Bayside, NY 11364, United States (2) Department of Chemistry and Biochemistry, Queens College, Flushing, NY 11367, United States

Nek2, a Serine/Threonine kinase present at the centrosome of the cell, is essential during mitosis and is greatly over-expressed in many forms of cancer. Nevertheless several of its biological functions remain unknown due to the lack of small molecule substrates and biosensors, which can serve in assaying its intracellular activity. C-Nap1, a known in vivo protein substrate of Nek2, has its phosphorylation sites identified by mass spectrometry, an information utilized to synthesize small peptide substrates of Nek2 and assess their catalytic efficiency via Michaelis- Menten kinetic parameters (high kcat and low Km values). In this project, FMOC-based solid phase peptide synthesis procedure is employed for the development of two potential peptide substrates of Nek2 (NAP-3 and NAP-4) which are purified using Reverse Phase-HPLC, and characterized by ESI-MS. The knowledge gained from these studies could be utilized in the development of Nek2 biosensors and small molecule inhibitors.

CHED 186

Enzymatic deglycosylation of bicupin oxalate oxidase

Bridget Immelman, [email protected], Ellen W Moomaw.Department of Chemistry and Biochemistry, Kennesaw State University, Kennesaw, GA 30144, United States

Oxalate oxidase catalyzes the oxygen-dependent oxidation of oxalate to carbon dioxide in a reaction that is coupled with the formation of hydrogen peroxide. Although there is currently no structural information available for oxalate oxidase from Ceriporiopsis subvermispora (CsOxOx), sequence data and homology modeling indicate that it is the first manganese-containing bicupin enzyme identified that catalyzes this reaction. Interestingly, CsOxOx shares greatest sequence homology with bicupin microbial oxalate decarboxylases (OxDC). CsOxOx is expressed recombinantly in Pichia pastoris as a highly glycosylated soluble protein. In this work, we describe experiments to 1) characterize the glycosylation of CsOxOx and 2) prepare a sample appropriate for crystallization trials.

CHED 187

In silico design of sequence-specific DNA-binding peptidomimetic compounds Michael Convertino, [email protected], Suliman Salman, Daniel Barr.Department of Chemistry and Biochemistry, Utica College, Utica, NY 13502, United States

The binding of proteins to DNA often depends very strongly on the interaction of just a few amino acids with specific base pairs in the DNA. Understanding the chemical and physical nature of these interactions will provide important insights for the development of pharmaceuticals that can target specific DNA sequences. Traditional peptides, however, are unlikely to make effective drugs due to the relatively easy hydrolysis of exposed amide bonds in biological systems. In this work we present a series of molecular dynamics simulations of peptides and peptidomimetic compounds that demonstrate clear sequence-specific DNA-binding ability. Our results demonstrate that we can use data on atomic fluctuations, interaction energies, and hydrogen bonding patterns to design novel peptidomimetic compounds that retain sequence-specific DNA- binding ability but take advantage of a backbone that will be more stable in a cellular environment.

CHED 188

Incorporation of green chemistry metrics into independent synthesis projects

Kayla A. Lange, [email protected], Kaitlin R. Peterson, Alexandra E. Jones, James W. Wollack.Department of Chemistry and Biochemistry, St. Catherine University, St. Paul, MN 55105, United States

Green chemistry aims to eliminate hazardous substances with less hazardous substances. With reduction of chemical release by humans, ozone depletion, global warming, smog, and water pollution can be decreased. Also, less hazardous reactions reduce costs. In this curricular study, organic chemistry laboratory students are required to propose their own green alternatives by completing a three-step synthesis in multiple ways and determining the greenest route. To increase the greenness of a reaction, students used alternative solvents and reagents to complete two of the steps of their synthesis. The products were purified, characterized, and compared. A metric system was used to compare the greenness of the reactions. If there were relative decreases in the combination of factors such as cost, environmental factor, yield, and waste produced, the reaction was considered greener. Teaching the importance and relevance of green chemistry is imperative to the future of chemistry and the environment.

CHED 189

Performance differences in life science courses

Leah R Creech, [email protected], Ryan D Sweeder.Lyman Briggs College, Michigan State University, East Lansing, Michigan 48823, United States

This study examined the historical performance of students at Michigan State University in twelve life science courses over 13 years to find variables that impact student success. Hierarchical linear modeling predicted 25.0 to 62.8 percent of the variance in students' grades in the analyses. The primary predictor of a student's course grade was their entering GPA; except for the second course in a series (i.e. Biochemistry II), where the first series grade (i.e. Biochemistry I) was the best predictor, as judged by β values. Student gender was also statistically significant for a majority of the courses studied where female students were found to have GPA's of 0.067 to 0.303 lower than their equivalent male counterparts. Grades earned in prerequisite courses and student major provided minimal additional predictive ability. Ethnicity and involvements in the Honors College or science residential college were generally insignificant.

CHED 190

Green Chemistry: Adaptation of experiments for a laboratory course

Lyanne Valdez, [email protected], Mariya Rozov, Rita K. Upmacis.Chemistry and Physical Sciences, Pace University, New York, NY 10038, United States

Basic research into Green Chemistry is necessary in order to provide alternative ways of generating new and existing products without unnecessary risk to human health and unwanted pollution. A standard of 12 guiding principles by Paul Anastas and John Warner has previously emerged (Green Chemistry: Theory and Practice, 1998) and later increased to 24 (Martyn Poliakoff et al.; Green Chem. 2008). To help improve the innovative thinking behind Green Chemistry, it is important to expose chemistry students to these principles and provide demonstrations in the laboratory. While suitable experiments for a Green Chemistry laboratory course are known (for example, Green Organic Chemistry: Strategies, Tools, and Laboratory Experiments, by Kenneth Doxsee and James Hutchison), the successful implementation requires one to run test trials. Therefore, we have embarked upon the testing and further design of experiments for their implementation into an undergraduate laboratory course and will report our experiences in this endeavor.

CHED 191

Use of coconut water as a better sports drink

Chhandashri Bhattacharya, [email protected], Basudev Swain.Department of Chemistry, Indiana University Southeast, New Albany, IN 47150, United States

Coconut Water (Coconut liquid endosperm) is widely consumed in many countries as a refreshing beverage but its unique chemical composition of electrolytes and nutrients can make it a good natural substitute of sports drink. This study explores the nutrients in Coconut Water (Coconut liquid endosperm) to know how much people were replenishing compared to sports drinks in the market.

CHED 192

Tennessee women in chemistry: The Bio Project

Rachel Davies, [email protected], Marleyna Daughters, Elizabeth Sharp, Angel Talamantes, Judith Iriarte-Gross.Department of Chemistry, Middle Tennessee State Univeristy, Murfreesboro, TN 37132, United States

Tennessee women are currently underrepresented in many STEM fields, including chemistry. Positive role models can likely be an influence on the career choices of women and girls. However, possibly due to a more conservative culture, the history of women in science in Tennessee is especially silent. In an effort to promote women role models in STEM from Tennessee, as well as shine light on the amazing contributions of women to STEM over the years, we have created The Bio Project. For this project, we have researched the lives of Tennessee women in STEM. These women have swum against the stream to create a path for women's participation in the sciences. They have been able to fight discrimination and balance their family and working lives, while helping make great strides in the name of science.

CHED 193

Using a homemade flame photometer to measure sodium in beverages

Ian Pelse1, [email protected], Karina Elvy2, Christopher N. LaFratta1. (1) Department of Chemistry, Bard College, Annandale-on-Hudson, NY 12504, United States (2) Poughkeepsie High School, Poughkeepsie, NY 12603, United States

The purpose of this experiment was to create a simple and inexpensive flame photometer to measure [Na] in beverages, such as Gatorade. We created a nebulizer using small tubing and sprayed the sample into the base of a Bunsen burner. Adjacent to the flame was a photodiode with a filter specific for the emission of sodium. After making a calibration curve, we could detect the amount of sodium in Gatorade to within 10% of the value on the label. The system costs <$500 and can easily be assembled by students for an analytical chemistry laboratory.

CHED 194

Tennessee history and science: An innovative learning community

Ashely M Harvey1, [email protected], Judith Iriarte-Gross1, Mary Hoffschwelle2. (1) Department of Chemistry, Middle Tennessee State University, Murfreesboro, TN 37132, United States (2) Department of History, Middle Tennessee State University, Murfreesboro, Tennessee 37132, United States

We have designed a learning community which incorporates two required general education courses, Tennessee History and Science. Learning occurs "through" a focus on complex problems of civic consequence. This approach is defined by SENCER (Science Education for New Civic Engagement and Responsibilities) as applying the science of learning to learning of science, through civic issues. (www.sencer.net) Students in this class use a variety of pedagogical techniques such as collaborative learning, applied laboratory activities and a case study which involves data collection and analysis as well as writing reports and presentations to the class. In this learning community, we also introduce our students to valuable resources on and off campus. Students learn to work as a team and help each other understand concepts in both subjects. We strongly feel that the SENCER approach to learning of science and history makes both disciplines more real, accessible, and "useful" to our students.

CHED 195

Inquiry based 5E lesson on VSEPR theory, effective modeling in a high-school classroom

Amanda Cook, [email protected], Martha Day.Department of SKyTeach, Western Kentucky University, Bowling Green, Kentucky 42101, United States

This poster presents an inquiry-based 5E Lesson designed to teach VSEPR Theory to general chemistry students at the secondary level. This lesson uses the 5E inquiry model of instruction (Engage, Explore, Explain, Elaborate, and Evaluate) to teach the molecular geometries of molecules and how they are influenced by the VSEPR theory. Students were encouraged to explore and create various shapes associated with molecular geometries of common compounds and will see electron-pair electrostatic repulsion at work in their own balloon models. This activity allows high-school students to understand molecular geometries and VSEPR theory in a meaningful way, which results in deeper conceptual understanding and better retention of this critical, but difficult, general chemistry concept.

CHED 196

Nitration of phenyl benzoate: Development of an undergraduate organic chemistry laboratory

Ethan Sylvain, [email protected], Carolyn Weinreb, Lisa Bonner.Department of Chemistry, Saint Anselm College, Manchester, NH 03102, United States

The nitration of phenyl benzoate is a simple illustration of the effects of activating and deactivating groups on aromatic rings. The laboratory synthesis involves the electrophilic aromatic substitution reaction of phenyl benzoate with nitric acid to make ortho and para- nitrophenyl benzoate. As indicated by GC/MS, the crude isomers exhibit essentially identical fragmentation patterns, so fractional crystallization is necessary to obtain pure samples of the regioisomers. Differentiation between isomers is observable via melting point. The relative simplicity of this synthesis makes it possible for an undergraduate organic student to complete within a three-hour lab session. If done in accordance with lecture, the hands on experience might facilitate an organic student's understanding of the fundamental concepts of electrophilic aromatic substitution in addition to demonstrating the use of fractional crystallization to separate regioisomers.

CHED 197

Limiting reagents: A 5E inquiry lesson

Shelby N. Overstreet, [email protected], Martha M. Day.Department of SKyTeach, Western Kentucky University, Bowling Green, Kentucky 42101, United States

Chemistry addresses many abstract concepts, one of which is limiting reagents. This poster presents an inquiry-based 5E lesson on limiting reagents for general chemistry students. The 5E model of instruction includes Engagement, Exploration, Explanation, Elaboration and Evaluation. This lesson was designed to take the abstract concept of limiting reagents and make it a concrete and hands-on experience for the students. Students are encouraged to explore the idea of limiting reagents using different amounts of baking soda and vinegar, measuring the gaseous product, and comparing results. Students were also asked to create various analogies about limiting reagents with real-life examples. Creating physical and mental models of limiting reagents allows students to develop a deep conceptual understanding of an abstract concept in chemical education.

CHED 198

Development and incorporation of sustainability principles and green chemistry into chemistry curriculum designed to increase undergraduate retention, performance, and interest in chemistry through biodiesel synthesis from the microalgae Botryococcus braunii

Debra Del Castillo, [email protected], Richard W Lee, [email protected], Kalyn Shea Owens.Department of Chemistry, North Seattle Community College, Seattle, WA 98105, United States A multipurpose learning module was created that benefits undergraduate research students and college level chemistry students. The project emphasized and developed rapid, economical methods for quantifying hydrocarbons produced by algae grown by research students at NSCC and laboratory facilities at the University of Washington Seattle. Laboratory exercises introduced first year chemistry students to green chemistry and sustainability while they learned lab techniques within the standard curriculum of undergraduate level chemistry. Student understanding was enhanced by participating in a multidisciplinary research project with a theme based on sustainability and green chemistry. Direct transesterification of lipids to biofuels was conducted using the microalgae Botryococcus braunii. Gas Chromatography and photospectrometry were used to quantify hydrocarbons available for use as fuel sources in the microalgae. The utilization of a theme and analytical techniques can help undergraduates evaluate the success and applicability of chemistry knowledge in a practical matter that enhances student interest and understanding.

CHED 199

Efficacy of teaching alcohol toxicology using the case study approach

Peter Falzarano, [email protected], Kilshore K Bagga.College of Medicine, Drexel University, Philadelphia, PA 19129, United States

As is becoming more evident in the academic community, students learn material in a multitude of ways. Independent learning and case studies have been frequently used in various disciplines as a means of information delivery. In this work, two groups of students were compared in which one was taught alcohol toxicity using the traditional classroom lecture style of teaching; whilst the other used a case study approach. Both groups were assessed using identical evaluations as a means to compare the two groups. The work indicates that those taught using the case study approach had a statistically significant improvement in their scores compared to those taught using the traditional lecture style.

CHED 200

Outliers amongst the minority women scientists: Their challenges and successes, a comparative and investigative case study

Sharay McGann, [email protected], Kilshore Bagga.College of Medicine, Drexel University, Philadelphia, PA 19129, United States

This work explored the historical backgrounds and the contributions to the chemical field made by minority women in science. It discusses the challenges which they each faced, and the attributes which lead them to become successful in their work. An investigative approach was taken to compare these scientists to see if there was any correlation, in terms of factors, which they all shared in common that could have lead to their success. The study indicated that each of the women showed determination and dedication as a means to overcoming their challenges, which ultimately lead to their success.

CHED 201

Contributing factors leading to the success of various women in science through the ages and the struggles they faced and how they overcame them

Lyndsey March, [email protected], Kilshore W Bagga.College of Medicine, Drexel University, Philadelphia, PA 19129, United States Accounts appear to indicate that throughout history women in science have been seen as unusual, atypical and extraordinary. This expression of female success is paradoxical, and leads to a societal perception of a women's general inability to apply themselves and be successful in the sciences. The work here reported examined the lives of a number of renowned female scientists and the various factors such as their upbringing, familial support, encouragement, the impact of the time period in which they lived affected their quest in the chemical field. What is universal despite a variety of differences amongst these women is an underlying desire to learn and work which ultimately lead to them earning the Nobel Prize. However, what is even more compelling is that our research reveals that these women were almost “chaperoned” throughout their evolution into female scientists by their father, husband or colleague(s). Through the discussion in this work, we can potentially understand the challenges women face cross-culturally and identify the characteristics that differentiate them from traditional standards of feminine achievement.

CHED 202

Women do not like competitive environments in the classroom? Group competitive exercises imply not so!

Kevin Cannon1, [email protected], Kathryn Cannon1, [email protected], Maureen Breen2. (1) Department of Chemistry, Penn State Abington College, Abington, PA 19001, United States (2) Department of Finance, Drexel University, Philadelphia, PA 19104, United States

A non-traditional teaching method applied in science courses at Penn State Abington College as a vehicle for engaging students is group-based competitive exercises. These exercises combine cooperative learning in a competitive environment and may be employed to promote subject- and problem-based learning. Concern over potential pitfalls of classroom competitions prompted the development of a survey to evaluate students' attitudes towards the exercises used in organic chemistry and biochemistry courses. The survey primarily consisted of thirty-one statements to which respondents indicated strongly agree, agree, not sure, disagree, or strongly disagree (that is, a five point Likert response scale). The survey also provided students the opportunity to expand upon their answers to the statements. Generally respondents indicated that the group competitive exercises were a positive academic and social experience. However, despite a general positive attitude that continues to be indicated, questions arose concerning the existence of potential gender differences toward the group competitive exercises. An analysis of student survey responses was undertaken to determine if potential gender differences toward group competitive exercises exist. In all of the thirty one questions, there was no instance in which the female response is significantly more negative towards the competitions than the male response. There were actually five questions in which the female response is more positive (significant at the .1 level or less), with one of these questions indicating that competitions made the subject more interesting. This enables an instructor to employ group competitive exercises for student engagement without gender discrimination that was noted in competitive environments by previous studies.

CHED 203

Synthesis of 18-crown-6 and its applications as a phase transfer catalyst for organic chemistry laboratory students

Nicholas R Petre, [email protected], Dell Jensen Jr..Department of Chemistry, Augustana College, Rock Island, Illinois 61201, United States

18-Crown-6 is a useful phase-transfer catalyst (PTC) that can solubilize ionic compounds in non- polar organic solvents for a variety of reactions including oxidation and acid-base reactions. We present a practical synthesis of 18-crown-6 that provides a broad range of topics to teach in the organic laboratory. Topics include bimolecular substitution, leaving group transformation, catalysis and "green chemistry". Additional reactions for the synthesized catalyst such as dichlorocarbene addition and oxidation of alcohols are also explored.

CHED 204

Improvement and expansion of the selective oxidation of alcohols: A greener green chemistry laboratory experiment

Nathaniel G. Chmura2, [email protected], Irvin J. Levy1, Thomas E. P. Safford2, [email protected], Ethan T. Whitman2, [email protected]. (1) Department of Chemistry, Gordon College, Wenham, MA 01984, United States (2) Unaffiliated, United States

The selective oxidation of alcohols to aldehydes traditionally uses toxic reagents and solvents. Previous work from our lab reported a greener synthesis of benzaldehyde from benzyl alcohol using 15% H2O2 in the presence of tetrakis(benzyltriethylammonium) octamolybdate. This preparation was suited for use as a greener organic laboratory experiment.

The current work reports the oxidation of alcohols (benzyl and p-methylbenzyl) using greener conditions (3% H2O2) for the preparation of benzaldehyde and p-tolualdehyde.

Unexpectedly, attempts to oxidize cinnamyl alcohol to cinnamaldehyde resulted in traces of the desired product along with large amounts of unanticipated products: benzaldehyde and 1-phenyl- 1,2-propanedione. Our initial hypothesis for the formation of benzaldehyde from cinnamyl alcohol suggests that cinnamaldehyde may, in fact, form and then undergo a retro-aldol reaction. Results of initial experiments to study that hypothesis will be presented.

CHED 205

Thermodynamics of cellulose solvation in novel solvent mixtures

Ritankar Das1,2,3, [email protected], Adam Gross1, Jhih-Wei Chu1. (1) Department of Chemical and Biomolecular Engineering, UC Berkeley, Berkeley, California 94720, United States (2) Department of Chemistry, UC Berkeley, Berkeley, California 94720, United States (3) Department of Bioengineering, UC Berkeley, Berkeley, California 94720, United States

Biomass contains abundant amounts of cellulose as crystalline microfibrils. A limiting step to using cellulose as an alternative energy source, however, is the hydrolysis of the biomass and subsequent transformation into fuels. Cellulose is insoluble in most solvents including organic solvents and water, but it is soluble in some ionic liquids like BMIM-Cl. This project aims to find alternative solvents that are less expensive and are more environmentally benign than the ionic liquids. All-atom molecular dynamics simulations were performed on dissociated glucan chains separated by multiple (4-5) solvation shells, in the presence of several novel solvents and solvent mixtures, e.g., pyridine-propanol mixture.

The solubility of the chains in each solvent was indicated by contacts calculations after the equilibration of the molecular dynamics. It was discovered that pyridine and imidazole acted as the best solvents because their aromatic electronic structure was able to effectively disrupt the inter-sheet interactions among the glucan chains in the axial direction, and because perturbation of the solvent interactions in the presence of glucan chains was minimal.

CHED 206

Computational chemistry study of the boiling point trend in fluorinated and chlorinated acetic acid dimers

Sydney Herrington, [email protected], Patricia M. Todebush.Department of Natural Sciences, Clayton State University, Morrow, GEORGIA 30260, United States

Hydrogen bonding is a key factor in understanding the boiling points of compounds. When acetic acid is fluorinated, the boiling point increases but unexpectedly decreases when more fluorine is added to the molecule. To explain this observation gas phase molecules of acetic acid, its fluorinated derivatives and their dimers were constructed using the Gaussian 03 Computational Chemistry Program. The ground state molecular geometries, energies and electrostatic potentials were calculated using Density Functional Theory and a B3LYP 6-311G* basis set. In addition a similar study of chlorinated acetic acid compounds was also completed. This work supports the hypothesis that boiling points depend on electrostatic interactions.

CHED 207

Logistics and procedure that ensures New York City's water quality

Feroz Ali1, [email protected], Faye Jacques2, Carol Neptune2, Panayiotis Meleties3, Paris Svoronos1. (1) Chemistry Department, Queensborough Community College, Bayside, NY 11364, United States (2) Microbiology Department, NYC Dept. of Environmental Protection, Newtown Creek Wastewater Treatment Plant, Brooklyn, NY 11222, United States (3) Office of Academic Affairs, York College, Jamiaca, NY 11451, United States

The Department of Environmental Protection (DEP) enforces New York's environmental laws and regulations. Its purpose is to decrease air pollution and protect the river's water quality by assisting in the waste removal, thus ensuring the safety of New York' drinking water. One of the DEP's several divisions is the Monitoring Section that checks out sewer lines for water contamination and possible harmful industrial discharges. As an intern of the Industrial Pollution Prevention (or I.P.P) team, the presenting author was involved with the logistics team evaluating the degree of contaminants' presence. A detailed insight into the I.P.P and the logistics team, the equipment and machines used, the protocol followed and the chemicals used to neutralize the contaminants will be presented.

CHED 208

Iodine doped carbon nitride polymeric photocatalyst with visible light response

Juncheng Yang1,2, [email protected], Sheng Chu1,2, Leilei Luo1,2, Fei Kong1,2, CuiCui Wang1,2, Ying Wang1,2, Zhigang Zou1. (1) Eco-materials and Renewable Energy Research Center (ERERC), Nanjing University, Nanjing, Jiangsu 210008, China (2) Department of Chemistry and Chemical Engineering, Nanjing University, Nanjing, Jiangsu 210008, China

Iodine doped carbon nitride polymer (CNP) is successfully synthesized. FTIR and XRD are used to confirm the crystal structure of polymeric carbon nitride. UV-visible spectra indicate iodine doped CNP have much more visible light absorption than its parent, which accounts for its good photocatalytic ability in degradation of pollutant in water, in this case, methyl orange.

In addition, photoluminescence (PL) spectra of both doped and non-doped CNP are acquired to judge the recombination between photo-generated carriers and holes.

CHED 209

Determination of water quality indicators in the Belmont water supply and Saint Joseph's University campus

Anna Feairheller, Jessica Kesler, [email protected], Luke Serentis, Jean M Smolen.Department of Chemistry, Saint Joseph's University, Philadelphia, Pennsylvania 19131, United States

The Belmont water supply is the water reservoir for West Philadelphia, including parts of the Saint Joseph's University (SJU) Campus. Using Standard Methods, water samples were analyzed for phosphorous, iron, lead, copper, and calcium carbonate. One sample from each site was treated through a water filter system: Brita® or Zerowater®. Water samples were taken from three local creeks which feed the Belmont Water Supply: Indian Creek, Naylor's Run Creek and Cobb's Creek. It was observed that the unfiltered tap water samples had higher concentrations of copper and phosphorous than that of the creek water samples. Lead was not detected in any of the samples. Naylor's Run Creek, Cobb's Creek, and some campus sites fell in the category of hard water. It was also shown that household water filters were effective at removing the ions that may contribute to poor water quality.

CHED 210

Role of cysteine concentration and particle size in the reductive dissolution of goethite and the subsequent transformation of nitrosubstituted compounds

Alex DeBernardo, Andrew Kusterbeck, [email protected], Drew Kaneps, Jean M Smolen.Department of Chemistry, Saint Joseph's University, Philadelphia, Pennsylvania 19131, United States

The reductive transformation of 4-cyanonitrobenzene (4-CNB) was examined in batch suspensions of goethite containing cysteine at pH 6-8. Experimental results demonstrate that cysteine promotes the reductive dissolution of ferric oxides, which in turn, facilitates the reductive transformation of 4-CNB at all pH values examined. Transformation rates are dependent upon cysteine concentrations, surface loading, and pH. In comparing particle size, it was observed that the nano-sized particles facilitated the fastest rates of reduction, followed by the intermediate- sized rods, and the micro-sized rods. The results of this study provide evidence that naturally occurring organic molecules play an indirect role in the transformation of reducible organic compounds. Generally, a neutral pH is less favorable for the reductive dissolution of ferric oxides and more favorable for Fe(II) adsorption, but neutral pH conditions can generate sufficient concentrations of Fe(II). Results of this effort may elucidate the fate of reducible organic compounds in aqueous systems.

CHED 211 WITHDRAWN

CHED 212

Pyrolysis and oxidation kinetics of corn and coal blends for energy generation

Phylicia Cicilio, [email protected], Ana M Celaya, Jillian L Goldfarb.Department of Chemical Engineering, University of New Hampshire, Durham, NH 03824, United States

The incorporation of biomass to coal in coal-fired power plants is an important step to transitioning into a more sustainable energy future. This study looked at the addition of corn stover to Illinois No. 6 coal at different fractions and blend ratios to see how it effects the activation energy and pre-exponential factors for the pyrolysis and oxidation of the solid fuels. The blends studied were 50/50, 80/20, and 90/10 of coal to corn. The samples were oxidized in O2 and pyrolyzed in N2 through thermogravimetric analysis (TGA). Samples were heated at different temperature ramps at 100, 50, and 10K/min. The activation energies approximately ranged from 50-100kJ/mol between hemicellulose, cellulose, and lignin. Increasing the size fraction increased the activation energy.

CHED 213

Fracking fluid in natural gas extraction: What happens to acetaldehyde that is left deep in the earth

Michael D Kilmer, [email protected], Lorena Tribe.Division of Science, The Pennsylvania State University - Berks Campus, Reading, Pennsylvania 19610, United States

Hydraulic fracturing for natural gas in the United States currently requires a special fluid composed of sand, water, and potentially harmful chemicals. Acetaldehyde is a component of the fracking soup, whose fate has not been established. Prolonged ingestion of acetaldehyde can cause cancer and severe organ damage. Upon encountering the Marcellus Shale, the acetaldehyde molecules in the fracking soup may have the ability to be adsorbed to clay minerals. The potential role of montmorillonite, a component of shale, in inhibiting acetaldehyde from entering the watersheds will be researched here using computational methods with density functional theory. Comparisons to experimental data will be made so a realistic surface complex model can be proposed. Models of acetaldehyde, montmorillonite, and both inner and outer sphere surface complexes are energy minimized to propose adsorption energies and for infra red vibrational frequency calculations. The results are analyzed with Molden and correlated with the experimental data.

CHED 214

Cocoa and coal: Pyrolysis kinetics of locally sourced coal-biomass blends in New Hampshire

Lauren E Pappas, [email protected], Ana M Celaya, Jillian L Goldfarb.Department of Chemical Engineering, University of New Hampshire, Durham, New Hampshrie, United States

The Portsmouth, NH power station blends cocoa shells with coal to produce electricity. Pyrolysis kinetics of cocoa shells and coal, the first step in combustion is examined to find optimal blend ratios. Cocoa shells are pyrolyzed in a TGA under nitrogen heating rates of 10 °C/min, 50 °C/min, and 100 °C/min to 750 °C. Mixtures of cocoa shells and coal are pyrolyzed at the same ramp rates with ratios of 50:50, 80:20, and 90:10 to 900 °C. The activation energy is determined for the volitazation of hemicellulose, cellulose, lignin, and the coal. The average activation energy for the pyrolysis of cocoa shells was ~50 kJ/mol for the volitization of hemicellulose and cellulose, and 30-100 kJ/mol for lignin. For the pyrolysis of the cocoa shell and coal blends the activation energy was 20-40 kJ/mol for hemicellulose, 10-70 kJ/mol for cellulose, 30-70 kJ/mol for the lignin, and 13-30 kJ/mol for the coal.

CHED 215

Historical trace metal profile of Lake Michigan sediment

Robert Muterspaugh, [email protected], David Nowicki, Christopher W. Avery, Graham F. Peaslee.Department of Chemistry, Hope College, Holland, Michigan 49423, United States

Trace metals occur naturally in the environment, but elevated levels of trace metals can indicate anthropogenic influence. By analyzing lake sediment cores as a function of depth, historical anthropogenic effects in the surrounding watershed can be determined. Multiple ~50-cm cores were taken from a 65m depth contour in southeastern Lake Michigan and were separated into centimeter segments and dried, then a subset of cores were radiodated using 210Pb and 137Cs. Inductively-Coupled Plasma - Optical Emission Spectroscopy was used to measure metal content of several full cores and a trace metal profile was assembled as a function of depth and date. The resulting metal profiles will be used to identify trace metals in the lake sediment and to indicate their origins.

CHED 216

WITHDRAWN

CHED 217

Analysis of compositing samples of various sewage treatment plants at the Newtown Creek facility of New York's Department of Environmental Protection (DEP) Agency

Nicole Yu1, [email protected], Paris Svoronos1, Faye Jacques2, Abeba Negatu Negatu2, Panayiotis Meleties3. (1) Department of Chemistry, Queensborough Community College, Bayside, NY 11364, United States (2) Department of Microbiology, New York City Department of Environmental Protection, Newtown Creek, Wastewater Treatment Plant, Brooklyn, NY 11222, United States (3) Office of Academic Affairs, York College, Jamaica, NY 11451, United States

The Department of Environmental Protection of New York City, regulates the polluting factors that may affect the water quality. As an intern in the chemistry laboratory at the New Town Creek facility, I was involved with the compositing samples from several different sewage treatment plants, testing for the pH and conductivity of each sample, and measuring the effluent samples for chlorine residual. Part of my duties included helping in the analysis of fecal coliform in citywide samples in order to determine the appropriateness of minimal chlorine use and discharge into the receiving waters. The procedures and the difficulties encountered in every step will be presented.

CHED 218

Analysis of water samples at the marine science department of New York's Division of the Environmental Protection Agency at Ward's Island Mobolaji Giwa1, [email protected], Paris Svoronos1, Naji Yao2, Faye Jacques2, Panayiotis Meleties3. (1) Department of Chemistry, Queensborough Community College, Bayside, NY 11364, United States (2) Department of Microbiology, NYC Department of Environmental Protection, Newtown Creek Wastewater Treatment Plant, Brooklyn, NY 11222, United States (3) Office of Academic Affairs, York College, Jamaica, NY 11451, United States

As an intern at New York City's Division of Environmental Protection (DEP) at Ward's Island I was involved with several processes that dealt with the determination of water quality. Samples that were collected off the boat were analyzed for the amount of dissolved oxygen using the Winkler Method, in addition to determining the pH of different water levels and measuring the light penetration via the Secchi Disk Depth method. Another procedure measured the collected TSS (total suspended solids) from top and bottom levels of water and most importantly used the Membrane Filter Method to collect and analyze bacteria such as fecal coliform and enterococci.

CHED 219

Analysis of the rain water of the Puerto Rico wet season of 2012 using simple electrochemical sensors: Simple on-site methods for fast screening studies

Michelle Z. Torres-Toledo, [email protected], Danny G. Ortiz, [email protected], Mayra Ocasio, Alvaro J. Pena-Quevedo, [email protected] of Science- Department of Chemistry, Pontifical Catholic University of Puerto Rico-Arecibo, Arecibo, PR 00614, United States

Spring of 2012 was a very wet rain season. Several rain episodes were recordedin Puerto Rico. The climate changes suggest that rain water had changed in pH, conductivity and electrolyte components. This study is focus in the analysis of recovered rain water for commercial portable electrodes for analysis. Water samples were analyzed in pH, conductivity, salinity and calcium ions. Most of the water analyzed presented a pH, conductivity and salinity equivalent to pure drinkable water. Most of the rain brought sand particles but these particles does not affect water quality. The rain times does not affect quality.

CHED 220

Infrared spectroscopy of hydrocarbons diluted in nitrogen ice: Implications for planetary and astronomy studies

Sarah E Lee1, [email protected], Rachel Mastrapa3, Monika Kress2, Cynthia Phillips2. (1) Department of Chemistry, San Jose State University, San Jose, CA 95192, United States (2) SETI Institute, Mountain View, CA 94043, United States (3) NASA Ames Research Center, Moffett Field, CA 94035, United States

Geophysical activity taking place on the surfaces of distant objects in our Solar System naturally stirs up curiosity about what might be causing these occurrences. Images from Voyager 2 have provided pictorial evidence of geysers on the southern hemisphere of Triton, Neptune's largest moon. Infrared spectroscopic studies of the chemical composition will assist in interpreting Triton's surface activity. Previous studies of Triton's surface composition have confirmed the presence of nitrogen and methane, and have suggested the presence of ethane. This spectral data has been expanded to a thermal range of 15 to 25 K, which is relevant to the surface temperature of Triton. Binary mixtures of methane and ethane diluted in nitrogen ice will be used for comparison to a ternary sample. A ternary mixture will show how these hydrocarbons interact with one another in a solid nitrogen matrix, and help to identify contributions from ethane.

CHED 221 Synthesis and reactivity of tungsten and molybdenum carbon dioxide complexes

Robert G. Carden1, [email protected], James J. Ohane1, [email protected], Peter M. Graham1, Robert D. Pike2. (1) Department of Chemistry, Saint Joseph's University, Philadelphia, Pennsylvania 19131, United States (2) Department of Chemistry, College of William and Mary, Williamsburg, VA 23187, United States

Tp (Trispyrazolylborate) tungsten nitrosyl complexes that form thermally stable η2-carbon dioxide complexes have been prepared using elevated pressures of carbon dioxide. These complexes have been characterized by X-ray crystallography, cyclic voltammetry, IR, and NMR spectroscopy. The reactivity of these of these and analogous molybdenum complexes have also been investigated.

CHED 222

Using carbon monoxide (CO) as a probe to study the electronic properties of the tris(triazolyl)borate copper(I) complex

Jodi Kraus, [email protected], Natalie A Dixon, Elizabeth T Papish.Department of Chemistry, Drexel University, Philadelphia, Pennsylvania 19104, United StatesDepartment of Chemistry, Youngstown University, Youngstown, Ohio, United States

Recently, tris(triazolyl)borate (Ttz) ligands have emerged as a way to model various enzymes. They offer improved water solubility as well as differing electronic structure from their tris(pyrazolyl)borate (Tp) counterparts. The addition of a Lewis acid to the copper(I) carbonyl species of the ligand alters the electronics at the third nitrogen on the triazole ring, and as such, decreases its ability as an electron donor. Infrared spectroscopy allows for the changing electronic properties to be measured in regards to CO stretch. As the stoichiometric ratio of acid to ligand increases, the CO stretch shifts as well. The reversibility of the reaction can also be demonstrated upon the addition of a base in which the CO stretch shifts to its original position in solution. The ability of the ligand to act as a “switch” at this location on the triazole ring offers practical application in regards to a potential role in catalysis.

CHED 223

Efforts towards the template synthesis of novel hydrogen bonding chelates using tris(3- aminopyrazole)ZnBr2

Lee Serpas1, [email protected], Ismael Nieto1, Matthias Zeller2, Elizabeth T. Papish1. (1) Chemistry, Drexel University, Philadelphia, PA 19104-2424, United States (2) Chemistry, Youngstown University, Youngstown, OH, United States

We are interested on applying template synthesis to the formation of new scorpionates that offer hydrogen bonds near the metal center. The synthesis of tris(3-aminopyrazole)zinc halide salts are known in the literature, but not much is known on whether new reaction pathways can be established with these salts. One such reaction pathway is template synthesis, a reaction involving the activation of the pyrazole ligands by zinc coordination and then linking them to an atom or group. This reaction pathway can lead to the formation of metal complexes coordinated to new pyrazole based chelates. For our study, we used the ditopic salt, tris(3- aminopyrazole)ZnBr2, and performed a series of reactions to determine if template synthesis on this salt is successful. Our future goal is to develop new complexes of zinc and other metals containing hydrogen bonding groups near the metal center in chelates that are linked by B and/or C atoms. CHED 224

Novel synthesis of high-valent and low-coordinate manganese clusters

Sean F. McWilliams, [email protected], Shivaiah Vaddypally, Sandeep Kondaveeti, Michael J. Zdilla.Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, United States

Photosynthetic organisms catalytically oxidize water to dioxygen using an oxo-bridged Mn4-Ca cluster called the Oxygen Evolving Complex (OEC) located within the Photosystem II protein. The manganese metal centers are high valent Mn(IV) and Mn(V) when water oxidation occurs. Our goal is to modify and oxidize manganese clusters previously prepared by the Zdilla group with initial focus on Mn(OPhPh2)2(Et2O)2 and Mn3(µ-OPhPh2)4(NR2)2(THF)2 (R = Me3Si), in which metal atoms are low-valent Mn(II), but biologically active manganese, like those found in the OEC occur in higher oxidation states. Oxidation of these clusters was explored using techniques of ligand exchange and oxygen transfer with focus on labile, non-chelating ligands in order to promote reactivity. Oxidized ligand byproducts were observed from the reaction of the monomer with oxidants. Reactions of the trimer have led to a variety of strongly colored products under various conditions. The products from the trimer oxidations will be characterized and presented.

CHED 225

Formation energetic analysis of gas and solution phase iron(III) aqua hydroxamate complexes

Kayla R Curry, [email protected], Jason L Sonnenberg.Department of Chemistry, Stevenson University, Stevenson, Maryland 21153, United States

Ferrioxamine siderophores are secreted by microbes to gather up essential iron needed within the organism via three hydroxamate binding groups. Unfortunately, the reactive groups can also bind to transuranic metals if present. Understanding the formation energetics within ferrioxamine siderophores could eventually aid in the extraction of nuclear waste from the environment. To understand the plutonium siderophore binding interactions, the iron(III) siderophore binding interactions must first be understood. Therefore, iron(III) hydroxamate complex binding reactions were investigated in both gas and solution phases using scalar-relativistic density functional theory.

CHED 226

Hydroxylated dibenzylideneacetone complexes of palladium as metal sources in the synthesis of organopalladium compounds

Brennen A. Harding, [email protected], William B. Barclay, Patrick R. Melvin, Felix E. Goodson.Department of Chemistry, West Chester University of Pennsylvania, West Chester, PA 19383, United States

Palladium dibenzylidineacetone (dba) complexes, such as tris(dibenzylidineacetone)dipalladium(0) (Pd2dba3), are common sources of palladium in the synthesis of many different organometallic compounds. However, complications can arise when purifying the desired product from the released dba ligands. Past research has shown that when hydroxyl groups are placed in the para position of the benzene rings on the dibenzylideneacetone ligands, the solubilities of both the precursor and the dba ligands are changed, making the purification of the desired products more readily achieved. In this paper, we present the synthesis of a di(3-ethoxy-4-hydroxybenzylidene)acetone palladium(0) complex, as well as the use of this complex as a palladium source in the synthesis of a variety of catalytically useful palladium compounds.

CHED 227

Toward the synthesis of the ansa-metallocenium charge transfer salt [((C5Me4)2(CH2)4)Fe]TCNE

Caleb A. Calvary, [email protected], Michael P. Castellani.Department of Chemistry, Marshall University, Huntington, WV 25755, United States

The ansa-metallocene [(C5Me4)2(CH2)4]Fe may be prepared from commercially available starting materials according to Ogasawara and co-workers (J. Am. Chem. Soc. 2002, 124, 9069) in five steps. Oxidation of this metallocene with tetracyanoethylene (TCNE) should yield the title charge-transfer salt. This material would represent a low-symmetry analog to the known metallocenium charge transfer salt [(C5Me5)2Fe][TCNE]. Progress towards the synthesis of this compound will be presented.

CHED 228

Scalar relativistic density functional theory investigations of M2(COT)2 possible formation reactions

Rebecca Wong, [email protected], Jason L Sonnenberg.Department of Chemistry, Stevenson University, Stevenson, Maryland 21153, United States

Complexes of the form M2(COT)2 (M = Cr, Mo, and W) were investigated computationally using density functional theory with scalar-relativistic effective core potentials. The formation energies were computed and compared for the reactions of M2(COT)2 from M2(COT)3. The bond lengths were tabulated from optimized structures for each reactant and product. The possibility of M2(COT)2 formation reactions may suggest a viable synthetic route for forming double-stuffed actinide sandwich complexes.

CHED 229

Investigation of natural bond orbital partitioning schemes for metallic systems

Kyle R. Diller, [email protected], Jason L. Sonnenberg.Department of Chemistry, Stevenson University, Stevenson, Maryland 21153, United States

Computational chemistry provides a non-toxic surrogate for investigating chemistry of radioactive actinide molecules. One reoccurring question in actinide chemistry is the location of valance electrons. The Natural Bond Orbital method employs a partitioning scheme to assign atomic orbitals into one of three categories: core, valence or Rydberg. A partitioning scheme designed for the actinides was investigated to determine a scheme to accurately represent chemistry for transition and actinide metals. The metallic systems were in the form ML where M is a first-row transition metal, scandium through zinc, and L is a ligand. The ligands employed to form five - - - complexes for each metal were CO, CN , NH3, F and OH . These small-molecule ligands range from π-bond acceptors to π-bond donors respectively. By analyzing atomic charge trends across the first-row transition metals and across the π-donor ligands, the most chemically relevant partitioning scheme was elucidated. CHED 230

Metal-organic frameworks with triangular Cu3-pyrazolato building units

Raquel Cruz, [email protected], Logesh Mathivathanan, Raphael Raptis.Department of Chemistry, University of Puerto Rico - Rio Piedras, San Juan, Puerto Rico 00936-8377, Puerto Rico

Energy and environmental needs for cost-efficient and effective sorbent materials have led to the discovery of a new class of porous materials now widely known as metal-organic frameworks (MOFs). MOFs are prepared by connecting clusters or metal ions (secondary building units, SBUs) by polytopic ligands (linkers). We synthesized and characterized a cationic MOF (1 ) based on triangular trinuclear Cu3-pyrazolate with 4,4'-bipy as the linker. 1 is an 8-fold interpenetrated MOF, and has been shown to preferentially sorb CO2. With improved functionality and porosity in mind, we have used 4,4'-azobispyridine and 4,4'-bispyridylethylene as linkers to obtain two iso-structural 3-fold interpenetrated MOFs (2 and 3 ) that are of mog topology. 2 and 3 have an interesting [Cu3(µ3-O)]-core and photoactive linkers. We describe the design, syntheses and structures of the two new MOFs, 2 and 3 .

CHED 231

Syntheses, characterization, DFT calculations and activity of tridentate SNS or NNN zinc pincer complexes based on bis-imidazole or bis-triazole precursors

John R Miecznikowski1, [email protected], Wayne Lo2, Jerry P. Jasinski3, Matthew A. Lynn4, Elizabeth E Butrick1, [email protected], Anne Elise R Drozdoski1, Kerry A Archer1, [email protected], Brianne E O'Loughlin1, Amanda P DiMarzio1, Lauren C Keilich1, Erin A Powers1, Jason T Panarra4. (1) Department of Chemistry and Biochemistry, Fairfield University, Fairfield, CT 06824, United States (2) Department of Chemistry, Boston College, Chestnut Hill, MA 02467, United States (3) Department of Chemistry, Keene State College, Keene, NH 03435, United States (4) Department of Science and Mathematics, Rochester Institute of Technology, National Technical Institute for the Deaf, Rochester, NY 14623, United States

Liver alcohol dehydrogenase (LADH) is a zinc metalloenzyme that catalyzes the oxidation of alcohols to aldehydes and ketones, and the reduction of a ketone or an aldehyde to an alcohol. The resting enzyme has a zinc(II) metal center which is pseudo-tetrahedrally ligated with one N- histidine side chain, two S-cysteine side chains, and one water molecule. Our work involves the syntheses, spectroscopic and electrochemical characterizations, quantum chemical calculations, and activity screening of potential functional models of the zinc active site in LADH. We model the zinc active site using a family of tridentate pincer ligands coordinating S,N,S or N,N,N donor atoms. DFT calculations are performed to better understand the geometries about the zinc center. A detailed description of the syntheses and characterization of the ligand precursors and model complexes will be presented along with reactivity findings and DFT calculations.

CHED 232

Alkylated 1,10-phenanthrolines and the photochemistry of their copper(I) complexes

Kurstan L.H. Cunningham, [email protected], Jacob Schneider, Louis Ayensu- Mensah, Steven Kraft.Department of Natural Science, St. Norbert College, De Pere, WI 54115, United States From analytical protocols to luminescent metal complexes, 1,10-phenanthroline and its derivatives can be found throughout the literature. The reason for this interest has been the wide variety of possible substitutions along the backbone. Our current work has found that a direct relationship exists between the electronic properties of the phenanthroline ring and the ratio of mono-substituted to di-substituted products when using alkyl lithium reagents as nucleophiles. The resulting ligands allow for direct comparison of effect that a simple methyl group can exert on the photochemistry of these 1,10-phenanthroline complexes of copper(I). We find that methyl groups in the 3,8-positions on the phenanthroline ring have a steric effect that enhances luminescent intensity while the 4,7-positions have no electronic effect on the luminescent copper(I) complexes.

CHED 233

Synthesis of bis-tropolonate tungsten complexes and their reactivity towards 4-electron donor ligands

Andrew B. Jackson1, Joseph Becica1, [email protected], William Dougherty2, W. Scott Kassel2, Nathan M. West1. (1) Department of Chemistry and Biochemistry, University of the Sciences, Philadelphia, PA 19104, United States (2) Department of Chemistry, Villanova University, Villanova, PA 19085, United States

The addition of two equivalents of tropolone to tetracarbonyltriiodotungsten(II) results in the formation of W(CO)3(trop)2. This 7-coordinate 18 electron species will react with alkynes, nitriles, and ketones to lose two equivalents of CO and form 4-electron donor complexes with the ligands bound in an η2-fashion. Single crystal x-ray diffraction studies have confirmed the seven- coordinate geometry for both the parent tricarbonyl compound and the bound 1-phenyl-1- propyne. The parent tricarbonyl compound forms complexes with (CH3)2CO, PhCCMe, and PhCH2CN. These tropolonate complexes react readily with oxygen at room temperature to form tungsten(IV) and tungsten(VI) oxo compounds.

CHED 234

Solid state synthesis and crystallization kinetics of mixed metal oxide surfaces

Tyler Potter, [email protected], Virginia Martelli, Karen Downey, [email protected] of Chemistry, SUNY Cortland, Cortland, NY 13045, United States

Current erbium-doped optical amplifiers require working lengths of 10-50 meters. A more efficient erbium ion hosting material could be integrated into optical circuitry and replace some existing electronic circuitry. A successful erbium host material must have a low rate of crystallization and prevent agglomeration of the erbium ions. Two promising candidates for planar optical amplification are Zn0.91Si0.07Ge0.01Er0.01O1.1 (ZSG-low) and Zn0.45Si0.16Ge0.16Er0.23O1.7 (ZSG-high). Powdered reagents were sintered into circular discs at temperatures up to 1040°C for up to 50 hours. Sputtering targets were fashioned by shaping these discs to fit a conductive backing; thin films were created by sputter deposition of the mixed metal oxide targets. Annealing studies were done on the thin films and the percent crystallinity as a function of annealing time was measured using x-ray diffraction. Upon measuring kinetics of annealing at multiple temperatures, the Arrhenius equation enables calculation of the activation energy of crystallization.

CHED 235

Reductive elimination from aminotropiminate dimethyl platinum(IV) complexes promoted by sterically hindered Lewis bases Elise Traversa2, Joseph L Templeton2, Hiu Yan Cheng1, Megan M Mohadjer Beromi1, [email protected], Peter S White2, Nathan M West1. (1) Department of Chemistry and Biochemistry, University of the Sciences, Philadelphia, PA 19104, United States (2) Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599, United States

II IV II Various Pt and Pt complexes have been synthesized from (N-tolyl-ATI)Pt(CH3)(SMe2), a Pt species. This starting compound itself was obtained from the reaction of +[N-tolyl-ATI]- with IV (Me)(Cl)Pt(SMe2)2. Reaction with methyl triflate results in the cationic Pt species (N-tolyl- ATI)Pt(CH3)2(O3SCF3)(SMe2). The triflate ligand, can be replaced by isocyanides, cyanide, and azide. Phosphine ligands with small cone angles can displace the triflate anion and yield the substitution product [(N-tolyl-ATI)Pt(CH3)2(PR3)(SMe2)][OTf]. On the other hand, reactions with larger cone angle phosphorus ligands result in reduction to form PtII(ATI), like (N-tolyl- IV ATI)Pt(CH3)(L). Intermediate sized phosphines initially result in a stable Pt adduct followed by reduction to PtII. The mechanism of this reductive elimination has been studied by NMR.

CHED 236

Spectral studies of the solvation equilibria of proximally-substituted copper(II) bis- phenanthroline derivatives

Adam T. Krakowiak, [email protected], John E. Lusignan, Stephen P. Watton.Department of Chemistry and Biochemistry, Central Connecticut State University, New Britain, CT 06050, United States

Copper phenanthroline complexes have been extensively studied for their uses as nucleases in molecular biology and their interesting photophysical and photochemical properties. Due to significant variations in geometric arrangements and coordination numbers in the complexes, along with the characteristic d-orbital transitions due to the phenanthroline and solvent ligands, solvation equilibria between these complexes of different coordination numbers becomes of significant interest. Past studies have demonstrated that cupric complexes bearing substituents at the 2- and 9-positions of the ligands impose steric congestion close to the copper centers. These substituents directly affect the favorability of the complex to form either the five-coordinate (green) or four-coordinate (purple) complexes. We will report on the influence of various proximal substituents in determining the extent of formation of the four and five-coordinate cupric complexes both in solution and in the solid state through various electronic spectra of these complexes.

CHED 237

De novo protein models of binuclear non-heme iron enzymes

Connor L Kanya, [email protected], Susan E Butch, Sabrina N Cimerol, Amanda J Reig.Department of Chemistry, Ursinus College, Collegeville, PA 19426, United States

De novo four-helix bundle proteins are uniquely suited for studying the structure-function relationships in binuclear non-heme iron enzymes due to their simplicity, stability, and ease of mutation. Correlations between catalytic function and the number and orientation of active site His residues suggest that they play an important role in tuning the reactivity of the enzymes. To demonstrate the potential for using de novo proteins as scaffolds for investigations into the geometric and electronic factors that influence catalytic tuning of di-iron active sites, a de novo di- iron carboxylate protein from the due ferri family (containing two active site His residues) has been rationally redesigned to contain one, three, and four active site His residues. As the active sites of the models differ by only a single His residue, observed changes in the spectroscopic and functional properties can be linked to the charge and/or coordination number at the iron site. Comparisons of the spectroscopic and functional properties of these proteins provide insight into the roles of individual amino acids in tuning catalytic activity.

CHED 238

Oxidation of phenols by (µ-oxo)diiron(III) complexes of 1,10-phenanthroline and tris(2- pyridylmethyl)amine

Christine A Bange, [email protected], Kaitlyn A Perez, [email protected], William D Kerber.Department of Chemistry, Bucknell University, Lewisburg, PA 17837, United States

The two related oxo-bridged diiron(III) complexes [(phen)2(H2O)Fe-O-Fe(H2O)(phen)2](NO3)4 (1 , phen = 1,10-phenanthroline) and [TPA(H2O)Fe-O-Fe(H2O)TPA](NO3)4 (2 , TPA = tris(2- pyridylmethyl)amine) are shown to abstract hydrogen atoms from 4-hydroxyphenol (hydroquinone) and 4-methylphenol (p-cresol). Quantification of the organic products shows that hydroquinone is oxidized to benzoquinone, while oxidation of p-cresol yields the o,p'-dimer of 4- methylphenoxyl known as Pummerer's ketone. Pummerer's ketone is usually accompanied by an o,o'-biphenyl dimer, which is not observed in this case. Hydrogen atom transfer from phenols is generally faster with 1 than with 2 , and kinetic data on both complexes will be presented. In particular, the clean conversion of p-cresol into Pummerer's ketone allows kinetic analysis of a reaction that is still not well understood nearly 100 years after it's initial discovery.

CHED 239

Rhenium(I) pentylcarbonato complexes as anticancer agents

Brent V Powell, [email protected], Santosh K Mandal.Chemistry, Morgan State University, Baltimore, Maryland 21251, United States

Many research groups are actively engaged in synthesizing rhenium(I) tricartbonyl (α-diimine) complexes because such complexes exhibit fluorescence in solutions and solid-states. Recently we have synthesized a series of rhenium(I) tricartbonyl (α-diimine) pentylcarbonato complexes from one-pot reactions of Re2(CO)10 with the corresponding α-diimines in 1-pentanol. As expected, the pentylcarbonato complexes exhibit fluorescence in various solvents. Interestingly, each of these pentylcarbonato complexes are cytotoxic against lymphosarcoma, myeloid leukemia, breast (both estrogen-receptor positive and negative), colon, and prostate cancer cell lines.

CHED 240

Kinetics of the reaction between cycochrome C and copper(II) dioxime complexes

John T Schmidt, [email protected], Michael J Prushan.Department of Chemistry and Biochemistry, La Salle University, Philadelphia, PA 19141, United States

The reaction between bovine heart ferrocyctochrome C and a series of copper(II) dioxime complexes was studied. The kinetics of the reactions were measured spectrophotometrically under anerobic conditions. The data was fit using a biphasic model and the values of the two rate constants were found to vary widely from complex to complex. Possible mechanisms consistent with this data will be explored.

CHED 241 Intramolecular ligand exchange at chiral eight coordinate rhenium polyhydride complexes

Stephanie Dos Santos1, [email protected], Geetha Birudala2, Adit Patel1, Gary Mejia1, Gregory A Moehring1. (1) Department of Chemistry, Medical Technology, and Physics, Monmouth University, West Long Branch, New Jersey 07764, United States (2) Department of Chemistry, Texas A&M University - Kingsville, Kingsville, Texas 78363, United States

Previous work with eight coordinate rhenium polyhydride complexes has suggested that hydride ligand exchange occurs either through a pairwise exchange of hydride ligands or through a pseudorotational ligand rearrangement involving the entire coordination sphere. Some recent work in our group involving rotational isomers which arose due to unsymmetrical aromatic amine ligands in the rhenium coordination sphere led to the suggestion that pseudorotational rearrangement was unlikely. Further study of a neutral rhenium(V) pentahydride compound which included a chiral aromatic amine ligand demonstrates that pseudorotation is indeed the primary mechanism for hydride ligand exchange. Our examination of ligand exchange at eight coordinate rhenium polyhydride complexes has expanded to include ligand exchange at tetrahydride rhenium(V) centers, including rhenium tetrahydride centers which are stabilized by a chiral ligand.

CHED 242

Carbonic anhydrase as a model for matrix metalloproteinase inhibition

Tessa M Woodruff, [email protected], David L Tierney.Department of Chemistry and Biochemistry, Miami University, Oxford, OH 45056, United States

Carbonic anhydrase (CA) is being used to model matrix metallproteinases (MMPs), as both are zinc-dependent enzymes that bind to zinc in a His3(OH) environment. CA is being used to screen potential zinc chelators, such as maltol, thiomaltol, acetohydroxamate and benzylacetohydroxamate, via spectroscopic examination of their binding to Zn-CA and cobalt substituted CA, using UV-visible. Detailed comparisons between carbonic anhydrase and small molecule analogs will be presented.

CHED 243

Use of molecular micelles modified kaolin for lead and cadmium remediation

Shantel D Cosby, [email protected], Ashley M. Taylor, Sayo O. Fakayode.Chemistry, Winston-Salem State University, Winston-Salem State, NC 27110, United States

Elevated concentrations of heavy metals in humans has been implicated in various health issues including, low child intelligent quotient, cardiovascular disease, cancer, and death. The toxic consequences of high heavy metal concentration in humans necessitate the urgent need for the development of a more effective remediation strategy, capable of heavy metal remediation of contaminated sites. This study investigated the potential utility of molecular micelles modified kaolin for remediation of lead (Pb) and cadmium (Cd). The effects of time, pH, and two molecular micelles: poly (sodium N-undecanoyl-glycinate) and poly (sodium N-undecanoyl-alanate) modified kaolin on Pb and Cd remediation were also investigated. In general, the observed remediation capability of molecular micelle modified kaolin is metal and molecular micelles dependent. Besides, the pH of solution and time of remediation were found to have influenced on heavy metal remediation efficiency. The none toxicity, large surface area, and high solubility of molecular micelles in diverse matrixes make molecular micelles promising and practical heavy metal remediation agent in environmental study CHED 244

Remediation of chromium, copper, and nickel using SDS and Poly SUS-modified kaolin

Yasmeen Pauldin, [email protected], Sri Lanka S. Owen, Casey Myers, Austria Taylor, Sayo O. Fakayode.Chemistry, Winston-Salem State University, Winston-Salem, NC 27110, United States

Heavy metals including chromium (Cr), copper (Cu) and nickel (Ni) are emerging environmental contaminants with considerable health hazards in humans. Several chelators have been well developed for heavy metal remediation. However, most of these chalators suffer from low remediation efficiency, low selectivity, and/or poor solubility in aqueous and organic solvents, limiting their practical application. This study investigated a comparative analysis of the use of unmodified kaolin, sodium dodecyl sulfate (SDS) modified kaolin, and poly (sodium N- undecanoyl-sulfate) poly-SUS-modified kaolin for Cr, Cu, and Ni remediation. In addition, the influence of experimental factors on remediation abilities of SDS-modified kaolin or poly-SUS modified kaolin to achieve optimum Cr, Cu and Ni remediation was investigated. The results of the remediation efficiency obtained in this study are not only metal specific, but it also depends on the type of chelator employed for kaolin modification for remediation. In general, poly-SUS modified kaolin was observed to have a comparable or better remediation capability for the investigated heavy metals than the corresponding SDS-modified-kaolin. Overall, the result of Cr, Cu, and Ni remediation using poly-SUS modified kaolin obtained in this study is promising with practical field and environmental remediation of contaminated sites.

CHED 245

Spectroscopic investigation of the binding mechanism of arsenic on human serum albumin

Austria Taylor, [email protected], Ashley M. Taylor, Casey Myers, Sayo O. Fakayode.Chemistry, Winston-Salem State University, Winston-Salem, NC 27110, United States

Arsenic (As) is an emerging toxic heavy metal contaminant, causing severe health problems including, diabetes, skin, lung, and urinary bladder cancer, kidney and renal failure, oxidative DNA damage, hypertension, stroke, and neurological disorder at chronic and/or acute concentration. Humans can be exposed to arsenic through various routes including, occupational, environmental (air, water, and soil), foods, or industrial activity. The harmful health consequences of elevated arsenic concentration in humans necessitate the need for the investigation of the interaction and binding mechanism of arsenic with biological specimen such as human serum albumin (HSA). The high volatility of arsenic at room temperature precludes the use of conventional flame atomic absorption spectroscopy for arsenic analysis. Analysis of arsenic is often achieved using a more specialized and relatively expensive hydride generation-AAS technique. However, the high cost of hydride generation-AAS instrument hinder routine arsenic analysis in most research and medical laboratories. In this study explore the use of Fourier transformed infrared (FTIR) to investigate the binding site of arsenic with human serum albumin. In addition, the study investigated the UV-visible absorption and fluorescence property of arsenic and human serum albumin complexes. The result of FTIR analysis indicated the binding of arsenic at HSA amide I and amide II sites. In general, the binding of arsenic with HSA resulted in a decrease of HSA absorbance and dramatic quenching of HSA fluorescence emissions.

CHED 246

Synthesis of large lanthanide-manganese complexes Michael R. Azar, [email protected], Curtis M. Zaleski.Department of Chemistry, Shippensburg University, Shippensburg, PA 17257, United States

The field of single-molecule magnetism is dominated by transition metal complexes, in particular manganese-based molecules. However, single-molecule magnets (SMMs) that contain lanthanide ions have become an interesting target for chemists. Lanthanide ions possess a large number of unpaired f electrons and are magnetoanisotropic due to relativistic spin-orbit coupling. SMMs have been made containing only lanthanide ions, while other complexes are hybrids of transition metal and lanthanide ions. One of these hybrid SMMs is a Dy6Mn6 complex first reported by Pecoraro and coworkers.1 While the dysprosium-manganese complex is a SMM, the gadolinium and terbium analogues are not SMMs. In an attempt to understand the magneto- structural properties of this family of complexes, a series of Ln6Mn6 complexes has been synthesized and characterized with single-crystal X-ray diffraction. 1. Zaleski, C. M.; Depperman, E. C.; Kampf, J. W.; Kirk, M. L.; Pecoraro, V. L. Angew. Chem. Int. Ed. 2004 , 43, 3912

CHED 247

Inhibition of quinone reductase 2 by novel resveratrol analogs

Jillian M Jespersen, [email protected], Joseph G Hood, Craig N Streu.Department of Chemistry and Biochemistry, St. Mary's College of Maryland, St. Mary's City, Maryland 20686, United States

Quinone reductase 2 (QR2) has been identified as an enzyme that plays a role in the reduction of reactive quinone molecules. Unlike QR1, which contributes toward the detoxification of quinones and protection of cells, QR2 activity has been linked to increased cellular damage due to the production of more reactive compounds. This suggests that the inhibition of QR2 may be beneficial for cell protection. Resveratrol, a polyphenol found in certain kinds of grapes, has been shown to be a potent competitive inhibitor of QR2, potentially explaining its observed antioxidant effects. We have therefore synthesized novel reseveratrol analogs and examined their potency for QR2. Enzyme inhibitory constants (Ki) were measured via an absorbance assay using N- methyldihydronicotinamide as an electron-donor to prime QR2 and menadione as a substrate.

CHED 248

Progress towards synthesis of a transition metal coordination complex analog of the neocarzinostatin metabolite core

Paul R Di Iorio1, [email protected], Nicholas Anzideo2, Craig Streu1. (1) Chemistry/Biochemistry, St. Mary's College of Maryland, St. Mary's City, Maryland 20686, United States (2) Department of Chemistry, Pennsylvania State University, United States

RNA has gained tremendous attention recently due to its recently discovered functions. The functions of RNA depend on its conformation and overall structure. RNA binders have also been validated as therapeutics, most notably as binders to the Rev response element (RRE) and trans- activating response region (TAR) in HIV. These conformations can be altered by RNA binders used to better stabilize one conformation. Neocarzinostatin is an antibiotic with a metabolite of well characterized RNA binding. Modifications of neocarzinostatin using traditional medicinal chemistry approaches are very cumbersome. We herein disclose progress towards the synthesis of a transition metal analog of the neocarzinostatin metabolite core and discuss its potential applications.

CHED 249 Synthetic ligands that modulate the quorum sensing receptor BmaR1 in Burkholderia mallei

Jacob W Brummond1, [email protected], Danielle M Stacy1, Charlotte D Majerczyk2, E. P. Greenberg2, Helen E Blackwell1. (1) Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, United States (2) Department of Microbiology, University of Washington, Seattle, Washington 98195, United States

This poster describes our discovery of the first synthetic N-acyl-L-homoserine lactones (AHLs) capable of modulating quorum sensing (QS) in the pathogen Burkholderia mallei. Many bacteria regulate transcription of target genes through a process known as QS. Gram-negative bacteria naturally produce AHL signals at basal levels. As the bacterial population grows, the concentration of native ligand increases and receptor-AHL dimers promote the transcription of genes to induce phenotypic changes. B. mallei, a soliped and human pathogen, displays QS- regulated virulence. We sought to identify ligands capable of blocking or promoting B. mallei QS for use as chemical tools to study virulence in this organism. Here, we report modulators of the B. mallei QS receptor, BmaR1. Among these are potent agonists that promote QS with low nanomolar EC50 values and antagonists that inhibit QS with low micromolar IC50 values. These ligands could provide a route toward new anti-virulence therapeutics for B. mallei infections.

CHED 250

Synthesis of hydroxylamines as indoleamine-2, 3-dioxygenase inhibitors

Maisha M Rahman, [email protected], William P Malachowski.Department of Chemistry, Bryn Mawr College, Bryn Mawr, PA 19010, United States

Indoleamine-2, 3-dioxygenase (IDO) is an enzyme that catalyzes the addition of oxygen to the essential amino acid tryptophan to form N-formylkynurenine. It has been found in high levels among cancer patients and linked to a decline in T cells. Inhibiting the function of this enzyme with small molecule inhibitors could improve the effectiveness of chemotherapy by promoting a more robust immune response to developing tumors. Hydroxylamines have been found to be successful inhibitors of IDO. Based on the results of tested compounds and computer modeling, compounds with diphenyl rings and electron withdrawing groups have been found to be particularly effective. A variety of these hydroxylamine compounds were synthesized using several different methods, including the Mitsunobu reaction and transition metal catalyzed hydroalkoxylation.

CHED 251

General diastereoselective preparation of N-tert-butanesulfinylaziridines via organocatalysis

Gavanne J Davis2, [email protected], Michael Schulte1, Craig Lindsley1. (1) Department of Pharmacology, Vanderbilt University, Nashville, Tennessee 37240, United States (2) Department of Chemistry, Southern Methodist University, Dallas, Texas 75275, United States

Organocatalysis offers many advantages over their metal-based counterparts, including their lack of sensitivity to moisture and oxygen and low toxicity. Previously, we have developed a general route to chiral N-alkyl terminal aziridines via organocatalysis. Our current efforts are focused on preparing activated aziridines bearing two stereogenic centers. We envisioned a synthesis through a-chlorination of an aldehyde followed by condensation with an enantiopure N-tert- butylsulfinamie to form an a-chlorinated N-tert-butanesulfinyl-imine. Addition of excess Grignard reagent results in a directed addition to the imine, followed by intramolecular SN2cyclization, providing the chiral aziridines. Previously, to optimize conditions for the enantioselective a- chlorination of an aldehyde, our lab surveyed a set of fifteen organocatalysts, using NCS for the chlorine source and DCM as the solvent. While the JØrgensen catalyst was the most favorable, with >97% conversion and 95%ee, it is commercially scarce. We decided to synthesize and screen additional catalysts for the enantioselective chlorination of aldehydes.

CHED 252

Synthesis of modafinil analog 2-(benzylsulfinyl)acetamide and its derivatives: A series of potential dopamine transporter inhibitors

Jennifer R. Pace, [email protected], Lisa A. Bonner.Department of Chemistry, Saint Anselm College, Manchester, NH 03102, United States

The neurotransmitter dopamine regulates cognition and promotes reinforcing behaviors. The dopamine transporter (DAT) protein moves dopamine back into neurons and is responsible for regulating synaptic dopamine levels. Dysfunctions in dopamine levels are associated with conditions such as Parkinson's disease, schizophrenia, and addiction. DAT inhibitors prevent DATs from regulating dopamine levels and prevent termination of neurotransmission. DAT inhibitors are interesting pharmaceutical targets to treat psychiatric and neurodegenerative diseases and addiction. Modafinil, a known DAT inhibitor, is a cognitive enhancer and wake- promoting agent approved by the U.S. Food and Drug Administration. We have synthesized a modafinil analogue, 2-(benzylsulfinyl)acetamide, as a novel potential DAT inhibitor. Additionally, six derivatives of this parent compound have been synthesized: 3-chloro-, 3-bromo-, 3-methoxy-, 3-nitro-, 4-bromo, and 4-chloro-2-(benzylsulfinyl)acetamide. Two more derivatives, 4-methoxy and 4-nitro-2-(benzylsulfinyl)acetamide are underway. These DAT inhibitors can be used to further understand the dopamine-signaling pathway, and hopefully provide pharmaceutical treatments for Parkinson's disease, schizophrenia, and addiction.

CHED 253

Synthesis of the quaternary form of mecamylamine

Julie V Cristello, [email protected], Joseph Troisi, Lisa Bonner.Department of Chemistry, Saint Anselm College, Manchester, New Hampshire 03102, United States

Nicotine increases dopamine levels in the brain, enhancing levels of satisfaction and pleasure. To keep levels elevated, nicotine is consumed in unregulated dosages and activates cholinergic neurons in the central and peripheral nervous system, communicating with neurons through acetylcholine. This communication occurs through the release of glutamate, a neurotransmitter associated with learning. This procedure strengthens the connection between various neurons, a process called memory. Mecamylamine, a nicotine antagonist, prevents the drug from binding to acetylcholine receptors, and as a result may inhibit drug addiction. This research was a study designed to synthesize the quaternary form of mecamylamine, a potential nicotine antagonist that cannot cross the blood-brain barrier and promotes its effects only in the peripheral nervous system. A Ritter Reaction was performed as well as reduction of an amide to an amine. Various spectroscopy tests confirmed the structure of the compound, such as infrared spectroscopy and nuclear magnetic resonance spectroscopy.

CHED 254

Towards the synthesis of novel boronates as potential HIV-1 protease inhibitors Michael D. Frank, [email protected], Andrea L. Faulkner, Julia J. Jennings, Kristin Sigurjonsson, John D. Schreiber, Levente Fabry-Asztalos.Chemistry, Central Washington University, Ellensburg, Washington 98926-7539, United States

Drug discovery for HIV/AIDS has resulted in many life-saving therapies, making a profound impact on modern medicine. Current drug therapies exist, but are susceptible to resistance development, have poor bioavailability, and cause several side effects. For this reason, there is an urgent need to develop new types of inhibitors that address those problems. We are synthesizing novel boronates as potential dual-mode, competitive and associative, inhibitors of HIV-1 protease. Recent studies showed that boron-modified inhibitors have a higher affinity for the protease than their corresponding non-boronated analogs. Furthermore, the boron-modified structures were inhibitory to an HIV-1 protease variant that is resistant to several HIV-1 protease inhibitors. A library of both straight chain and cyclic boronates are being synthesized.

CHED 255

Toward the synthesis of a novel dopamine transport inhibitor

Daniel Martin, [email protected], Lisa Bonner.Department of Chemistry, Saint Anselm College, Manchester, NH 03102, United States

Dopamine (DA) is a very important chemical in the brain when it comes to the functionality of cognition. A low concentration of dopamine in the synapses can lead to slow, weakened signals sent from the brain to the rest of the body. The levels of DA in the brain are regulated by dopamine transporters (DATs), which remove dopamine from the synapse. Dopamine transport inhibitors can be used to block the reuptake of dopamine into the neurons, causing an increased concentration of dopamine in the synapse. This increased concentration can lead to stronger, faster brain messages sent throughout the rest of the body. Based on the structure-activity relationships of two known DAT inhibitors, bupropion and methylphenidate, a novel DAT inhibitor structure was designed and a short synthesis from known intermediate species was attempted.

CHED 256

Antimicrobial activity of plants traditionally used in Puerto Rican folkloric medicine

Rafael Maldonado2, [email protected], Ileana I Rodriguez1. (1) Department of Chemistry, University of Puerto Rico at Humacao, Humacao, Puerto Rico 00792, United States (2) Department of Biology, University of Puerto Rico at Humacao, Humacao, Puerto Rico 00792, United States

Medicinal plants are commonly used worldwide for the treatment of many health conditions. However, in many cases folkloric knowledge do not necessarily matches with scientific proof. In this study, we selected 30 plant species traditionally used in Puerto Rico for the treatment of cold symptoms, skin infections, and digestive problems. In order to study the antibacterial potential of these plants, their polar crude extracts (methanol, H2O, H2O + heat) were screened using in vitro microbial inoculation techniques against five bacterial strains: Serratia marcescens, Escherichia coli, Staphylococcus aureus, Salmonella sp., and Bacillus subtilis. Several extracts with specific antimicrobial activities showing 8 mm or larger areas of inhibition were detected. The results obtained in this ongoing project will be presented in detail.

CHED 257

Chemical profiling of fungal endophytes of the genus Xylaria isolated from Coffea arabica Angel L. Placeres, [email protected], Samuel O. Figueroa, [email protected], Ileana I. Rodriguez.Department of Chemistry, University of Puerto Rico at Humacao, Humacao, Puerto Rico 00792, United States

Endophyte fungi species live symbiotically in plants and provide them with protection against herbivorism and pathogens. Recent studies comparing the endophytic fungal communities associated with leaves of coffee (Coffea arabica) in Puerto Rico have led to the isolation of different strains of the genus Xylaria. Secondary metabolites isolated from Xylaria sp. exhibit a wide variety of biological activities. TLC, 1H-NMR and 13C-NMR were used to perform the initial chemical profiles of two strains of Xylaria (M12 and M34) cultivated in different growth conditions. Results suggest that varying the growth media causes a difference in the chemical contents of these strains. The extracts were screened using antibiotic susceptibility assays against Serratia marcescens, Bacillus subtilis, Staphylococcus aureus, and Escherichia coli. Although no activity was detected in these assays, further analysis for the detection of activity is in progress.

CHED 258

Synthesis and evaluation of potential amyloid-β aggregation inhibitors

Craig B. Stevens, [email protected], James M. Hanna, Jr., Robin K. Lammi.Department of Chemistry, Physics and Geology, Winthrop University, Rock Hill, SC 29733, United States

Amyloid-β peptide (Aβ) is known to aggregate into insoluble fibrils, the primary component of extracellular senile plaques characteristic of Alzheimer's disease. As such, it may be therapeutic to inhibit Aβ aggregation. We have synthesized four potential inhibitors – the para-, meta- and ortho- isomers of terphenyl-3,3˝,4,4˝-tetrol (PTT, MTT and OTT, respectively), as well as biphenyl-3,3',4,4'-tetrol (BPT). Inhibition was evaluated using the Congo Red spectral shift assay. Congo red (CR) binds selectively to Aβ containing beta-sheet structure, resulting in a red-shift in the visible spectrum for the bound CR-Aβ complex; quantifying this spectral shift permits tracking of Aβ aggregation. Measurement of CR-Aβ levels in the absence and presence of varying inhibitor concentrations permits determination of inhibitor efficacies. All four compounds synthesized inhibit Aβ aggregation when present in excess. BPT is most successful, providing complete inhibition of aggregation at one molar equivalent and dose-dependent inhibition at sub- stoichiometric concentrations.

CHED 259

Design and synthesis of inhibitors of ornithine decarboxylase using hydroxamate functionality in the polyamine biosynthetic pathway

Amanda L Genzling, [email protected], Hyunshun Shin.Department of Chemistry and Biochemistry, McMurry University, Abilene, TX 79697, United States

Ornithine decarboxylase (ODC) is the first and rate limiting step of the polyamine biosynthetic pathway. ODC catalyzes ornithine to produce putrescine, which is the precursor of polyamines such as spermidine, and spermine . These polyamines are necessary for cell growth and proliferation. Studies have shown that tumor cells have higher concentrations of these polyamines than other cells. ODC has become an ideal target for tumor treatment due to regulationg polyamine concentrations in abnormal cells. Here we present the microwave-assisted synthesis of (S)-2-amino-5-(hydroxyamino)-5-oxopentanoic acid (AHOPA) as a potential inhibitor of ODC. Biological activity will be under investigate in the future work in collaborative works with other institutes.

CHED 260 Design, synthesis, and biological evaluation of novel small molecules as antifungal agents

Michael J Williams2, Michael A Corsello1, M. A. Alam2, Christopher E Sleet1, [email protected], Grady L Nelson2, Bella P Wight1, [email protected], Bryan J Penczuk1, [email protected], Kathleen M Twomey1, [email protected], Subash C Jonnalagadda1, Venkatram R Mereddy2. (1) Department of Chemistry and Biochemistry, Rowan University, Glassboro, NJ 08028, United States (2) Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812, United States

Systemic fungal infections may be life threatening for people with impaired immune systems. Although there are several antifungal agents currently in clinical use, the efficacy of many of them is low (30 to 80%) and drug resistance is a common problem. Hence, there is a critical need to develop novel drugs that can overcome the resistance and are more efficacious. Baylis-Hillman reaction is an important C-C bond forming reaction and it offers densely functionalized alcohols and amines in one step. The reaction is highly atom efficient, compatible with wide variety of functional groups and it does not require any organic solvents, thus making it environmentally benign. Baylis-Hillman reaction offers a unique template with high tunability at three different places to afford valuable synthetic intermediates. Recently, we synthesized several Baylis- Hillman based amine, which have been tested for their efficacy as anti-fungal agents. Our synthetic and biological studies will be presented.

CHED 261

Design, synthesis, and evaluation of novel small molecules as mono carboxylate transporter 1 inhibitors

M. A Alam1, [email protected], Shirisha Gurrapu1, [email protected], J. Sravan Kumar1, [email protected], Grady L Nelson1, [email protected], Matthew J Just1, Christopher E Sleet2, [email protected], Lester R Drewes1, Subash C Jonnalagadda2, Venkatram R Mereddy1. (1) Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812, United States (2) Department of Chemistry and Biochemistry, Rowan University, Glassboro, NJ 08028, United States

Advanced stage tumors were once thought to contain uniform cell types throughout. This theory was recently discovered to be a myth and in fact these advanced tumors contain oxygen rich (aerobic) and oxygen deficient (hypoxic) regions. Once this advanced stage tumor develops the hypoxic region it is generally resistant to standard chemotherapy and radiation protocols, resulting in treatment failure, relapse and patient mortality. Hypoxic and aerobic regions of the tumor each have unique metabolic processes that are essential to their survival. Under hypoxic conditions, cancer cells metabolize glucose into lactate, whereas nearby aerobic cells take up this lactate for oxidative phosphorylation for ATP production. The transport of these metabolites occurs through a membrane transporter called the mono-carboxylate transporter 1 (MCT1). Inhibition of this MCT1 transporter has remarkable clinical potential. Recently, we have designed, synthesized and evaluated several small molecules as MCT1 inhibitors. Our synthetic and biological studies will be presented.

CHED 262

Chemokine production in inflammatory bowel diseases

Ricky Loh1, [email protected], Yuanyuan WU2, Elaine Lin2, Andrew Nguyen1. (1) Department of Biological Sciences and Geology, Queensborough Community College, Bayside, NY 11364, United States (2) Department of Medicine Montefiore Hospital, Albert Einstein College of Medicine, Montefiore Hospital, Albert Einstein College of Medicine, Bron, NY 10467, United States

Inflammatory bowel diseases (IBD) are a series of circumstance which lead to the inflammation of the colon and small intestine. IBD begin when the body initiates an abnormal immune response to normal bacteria flora. In many cases of IBD, a link has established that chemokines as one of the key factors regulating IBD pathogenesis. Chemokines are a family of small cytokines that facilitate the migration of circulating leukocytes to the inflamed site. Chemokines such as, monocyte chemotactic protein 1, macrophage protein 1-a, MIP-1b, RANTES, and interferon inducible protein 9 and 10 are reported to express in larger quantities during the active phase of the disease. Many of these chemokines are produced by immune cells. However, little is known about the role of colonic epithelial cells in immune cell recruitment. We evaluated these chemokine productions from isolated colonic epithelial cells using real time PCR in mouse model of inflammatory bowel diseases.

CHED 263

Effect of various compounds on the prevention and degradation of staphylococcus aureus biofilms

May Myat Moe1, [email protected], Mengjia Lin1, Engred Vanegas1, Nidhi Gadura1, Kristen LaMagna2, David Maloney2. (1) Department of Biological Sciences and Geology, Queensborough Collunity College, Bayside, NY 11364, United States (2) Department of Biochemistry and Cell Biology, Stony Brook University, Stony Brook, NY 11794, United States

Methicillin-Resistant Staphylococcus aureus (MRSA) is responsible for up to 19,000 annual US deaths via this skin infection. MRSA is a strain of Staphylococcus aureus, a bacterium which produces a biofilm necessary for its survival and proliferation. Studies have shown that the serine protease ESP from S. epidermidis can destroy the formation of this biofilm. We examined the effectiveness of various compounds on both the prevention and destruction of the such as the supernatant from S. epidermidis and Biotene mouth wash. S. aureus was cultured and treated with Biotene PBF, Biokleen, Propolis and serine protease from S. epidermidis compounds. Our results indicate that Propolis did not show any impact on the biofilms. Results from S. epidermis serine protease treatment were not conclusive. However, the Biotene PBF mouthwash treatment was the most effective in the destruction of biofilm whereas Biokleen treatment had the most impact against preventing the formation of biofilm.

CHED 264

Effect of O-acetyl L-carnitine hydrochloride on MDA-MB 231 cells

Deandra Dacosta, [email protected], Michael Regan, Regina Sullivan.Department of Biological Sciences and Geology, Queensborough Community College, Bayside, NY 11364, United States

Many cancer cells rely on glycolysis for ATP production even in the presence of oxygen, a phenomenon known as the “Warburg Effect”. A number of studies have suggested that ATP production via aerobic glycolysis may alter the production of reactive oxygen species leading to evasion of apoptotic pathways. In our studies we investigated the ability of O-acetyl L- Carnitine Hydrochloride (a derivative of L-Carnitine) to induce cell death in MDA-MB 231 cells, a metastatic human cell line. L-Carnitine is a quaternary amine with important mitochondrial functions including the transport of lipids into mitochondria for oxidation and the export of toxic compounds from the mitochondria. Preliminary results show MDA-MB 231 cell death is increased at L- Carnitine concentration of 100µM The effect of O-acetyl L-Carnitine Hydrochloride on cell death was investigated. Further studies will determine if this metabolic pathway could be a target for cancer drug development.

CHED 265

Effects of resveratrol analogs on cell proliferation and migration of mouse melanoma cells

Fathima B. Nazumudeen1, [email protected], May Myat Moe1, Valery Morris1, Carmela Spatafora Spatafora2, Corrado Tringali2, Susan A. Rotenberg3. (1) Department of Chemistry, Queensborough Community College, Bayside, NY 11364, United States (2) Dipartimento di Scienze Chimiche, Universita di Catania, Catania, Italy (3) Department of Chemistry and Biochemistry, Queens College, Flushing, NY 11367, United States

Resveratrol (3, 5, 4'-trihydroxy-trans-stilbene), found in red wine and other foods, occurs naturally as both the trans and cis isomers and has both anti-oxidant and anti-cancer properties. This project examines the inhibitory effect of 50 µM resveratrol and analogues on proliferation and motility of metastatic mouse melanoma B16 cells using a fluorescence assay. Proliferation was inhibited substantially by of the trans isomer (A), while the cis-trimethoxy (B-OMe) analogue was similar to the parent compound (B) and more potent than (A). Motility was also substantially decreased by the (B-OMe), while (A) had no effect. While none of the analogues are more potent than the parent compound as inhibitors of proliferation, (B-OMe) shows novel and potent activity and therefore potential as an anti-metastatic agent. The phosphorylation of the PKC substrates, alpha-tubulin and MARCKS is associated with motility in these cells and is being analyzed by Western blots of lysates of resveratrol-treated cells.

CHED 266

Reactivity of tris(trimethylsilyl)phosphite (TMSP): Synthesis of a bisphosphonic derivative of β-alanine

Tai Lildar, [email protected], Luis Vargas.Department of Chemistry, Queensborough Community College, Bayside, NY 11364, United States

The synthesis of a potential inbitor of the tyrosine phosphatase is presented.

The compound, a bisphophonic derivative of β-alanine is synthesized using commercially available alanine. The protected β-alanine is reacted with thionyl chloride followed by reaction with tris(trimethylsilyl)phosphite (TMSP). After hydrolysis and spectroscopic identification the product will be tested as a potential inhibitor of the enzyme.

CHED 267

Identification of mycotoxin and chemotherapeutics by FDA Northeast Region Laboratory

Fathima Nazumudeen1, [email protected], Shelema Cox2, Hendri Chauca2, Jose Obando2, Paris Svoronos1. (1) Department of Chemistry, Queensborough Community College, Bayside, NY 11364, United States (2) Food and Drug Administration Northeast Region, Jamaica, NY 11433, United States

One of the goals of The Food & Drug Administration is to test for drug residues, contamination of food and animal feed items and prevent the consumer and public from adverse effects. In Chemotherapeutic and mycotoxin lab, as a first step the collected samples as listed on current Fiscal Year ORA Field Work Plan by CFSAN (Center for Food Safety and Applied Nutrition) is composited. Then the composited sample is extracted for further analysis of drug residues. Chemotherapeutic is an antibiotics used in aquaculture and the analysis for chemotherapeutics include Fluoroquinolones, Quinolones, Ivermectin and Malachite Green. Mycotoxin is a fungal toxin and its analysis includes Alfatoxin, Patulin, Deoxynivalenol, Fumonisins and Ochratoxin.

CHED 268

PCR and statistical analyses of the observed variations in the CCR5 gene

Fidel E Raposo1, [email protected], Jennifer B Palenchar1, Barry S Selinsky1, Joseph Rucker2. (1) Department of Chemistry, Villanova University, Villanova, PA 19085, United States (2) Department of Research and Development, Integral Molecular, Philadelphia, PA 19104, United States

CCR5 is a G protein-coupled receptor that, along with CD4, is involved in HIV entry into cells. A deletion mutation, CCR5Δ32 results in a receptor protein that is no longer on the cell surface. Those individuals heterozygous for CCR5Δ32 have a low level of resistance to HIV; homozygous carriers are highly resistant. We have designed an undergraduate laboratory experiment in which students isolate their cheek cell DNA using Gatorade and InstaGene matrix (BioRad). DNA samples were randomized and the CCR5 gene analyzed by PCR, using primers flanking the deletion region, and agarose gel electrophoresis. Our initial results indicate 1 homozygous (3%) and 5 heterozygous (14%) samples out of 35 total samples, consistent with the expected population frequency. Students will carry out statistical analyses based on their class results, as well as data from previous laboratory sections that we will make available online

CHED 269

Photonic crystal fiber bending loss sensitivity for design of fiber sensors

Andrew Lee, [email protected], Gilberto Constantinez, [email protected], Leonardo Mora, [email protected], Dimitrios Kokkinos.Department of Physics, Queensborough Community College, Bayside, NY 11364, United States

Fiber macro-bending loss is very important in telecommunications and the design of optical fiber sensors. Determining the bend loss sensitivity, would enable the design of optical fiber sensors with optimum bend conditions, including bend radii range and patterns, depending on the application. Reported results show that the bend loss sensitivity for standard Single Mode Fiber (SMF) is not uniform and increases as the bend radius decreases. SMF bend loss sensitivities reported are in the range of 0 to 15 dB/turn-mm bend radius, corresponding to a bend radius range of 3 to 15 mm. This study investigates the effects of optical fiber bend radius on bend loss sensitivity in Photonic Crystal Fibers (250mm coated) operating at 1550 nm, compared to SMF. The results show that the bend loss sensitivity is in the range of 0 to 3 dB/turn-mm bend radius, corresponding to a bend radius range of 3 to 7 mm.

CHED 270

Relationship of hydrogen bond interactions of inhibitors in the active site of HIV-1 integrase and Lipinski's rule of five for drug-like properties

Julie B. Ealy, Sarah Israel, [email protected], Robert Huff, [email protected], Talia Katz, [email protected] State Lehigh Valley, Center Valley, PA 18034, United States The computational software ICM Pro (Molsoft, La Jolla, CA) was used to assess the hydrogen bond interactions of inhibitors of human immunodeficiency virus type 1 (HIV-1) integrase with the active site of the enzyme (Protein Data Bank entry 1BIS). Many of these inhibitors have drug-like properties that follow Lipinski's rule of five that was introduced for predicting oral bioavailability. These rules include the following: 1) Molecular mass less than 500 g/mole, 2) Log P (the partition coefficient, defined as the ratio of the concentration of a drug inoctanol to its concentration in water) less than 5, 3) No more than 5 hydrogen bond donors, and 4) No more than 10 hydrogen bond acceptors. Some integrase inhibitors, however, do not follow these rules. Thus three questions are being addressed: Is there a difference in the number of hydrogen bond interactions of drugs that follow Lipinski's rule of five and those that do not? Is there a difference in the amino acid contacts for the two groups of inhibitors? Is there a difference in the average number of amino acid contacts for the two groups of inhibitors?

CHED 271

Synthesis, characterization, and applications of ferrocene-functionalized multiwalled carbon nanotubes

Steven W Caudle, [email protected], Ryan Spidle, Ken Ofosu, Adam Wanekaya.Department of Chemistry, Missouri State University, Springfield, Missouri 65807, United States

This presentation describes the covalent binding of ferrocene (a compound with unique electrochemical properties that acts as an excellent electron mediator) to multi-walled carbon nanotubes (MWNTs). MWNTs are nanomaterials with large apparent surface area and versatile electrical and catalytic and extraordinary mechanical strength). The resulting ferrocene-modified multi-walled carbon nanotubes (ferrocene-MWNTs) were subsequently investigated and characterized via various spectroscopic, microscopic and electrical techniques such as Fourier Transform Infrared Spectroscopy, Energy-dispersive X-ray spectroscopy, Solid-state Nuclear Magnetic Resonance Spectroscopy, Scanning Electron Microscopy and Cyclic Voltammetry. Preliminary results suggest that the ferrocene-MWNTs possess properties of the individual components with a synergistic effect. Potential analytical applications of the ferrocene-MWNTs nanomaterials in clinical, biomedical, environmental and other sectors will be discussed.

CHED 272

Surface engineering and roughness study of SAM surfaces of 1-mercaptoundecanoic acid and 1-undecanethiol towards biosensing

Rose L. Pasquale2,4, [email protected], Lauren N. Swiger2,4, Reshani N. Senevirathne3, Indrajith C. Senevirathne1, [email protected]. (1) Department of Geology and Physics, Lock Haven University, Lock Haven, PA 17745, United States (2) Department of Chemistry, Lock Haven University, Lock Haven, PA 17745, United States (3) Department of Research and Development, Dons Food Products, Schwenksville, PA 19473, United States (4) Department of Biology, Lock Haven University, Lock Haven, PA 17745, United States

Thiolated surfaces have a high capacity to engineer surface chemistry by changing terminus of the chain and by utilizing thiol mixtures. Clean, flat Au(111) on mica surfaces were used for self assembly to obtain Self Assembled Monolayers (SAM). A simple system of 1- mercaptoundecanoic acid and 1-undecanethiol were used at total 5 mM solutions in varying concentration ratios, in 200 proof ethanol solution. Thiol SAM layers were investigated for surface corrugation, morphology, roughness and structure variation at different thiol ratios. Observations will be discussed, quantitatively and qualitatively. Eventual mixture ratios were so selected towards optimum conditions for confining Bacillus subtilis as a model system. SAM surfaces were investigated using intermittent contact, noncontact, lateral force and contact modes of Atomic Force Microscopy (AFM).

CHED 273

Investigation of tetracycline-functionalized single-walled carbon nanotubes as a drug delivery agent

Kara DiJoseph, [email protected], Matthew Chorney, [email protected], Mark Ellison.Department of Chemistry, Ursinus College, Collegeville, PA 19426, United States

Single-walled carbon nanotubes (SWNTs) have shown promise for applications in biosensing and drug delivery. We have researched the possibility of using SWNTs to deliver antibiotics to bacteria. Specifically, oxidized SWNTs were covalently functionalized with the antibiotic tetracycline, as verified with FTIR and UV/vis spectroscopies. Then, Escherichia coli cells were incubated in a growth medium that contained tetracycline-SWNTs, and the viability of the cell cultures were assessed using absorbance measurements. The results showed that a concentration of 50 µg/mL of tetracycline-nanotubes was as effective as plain tetracycline at killing E. coli. Current experiments use fluorescein isothiocyanate, FITC, as a fluorescent tag to track the movement of the oxidized carbon nanotubes to investigate the method by which the SWNTs deliver tetracycline to E. coli. If the nanotubes carry the antibiotic through the membrane, it opens up new opportunities to study the effectiveness of tetracycline-SWNTs against tetracycline-resistant E. coli.

CHED 274

Functionalization of single-walled carbon nanotubes with the antiviral drug acyclovir

Chris Goodwin, [email protected], Greg Lewis, Mark Ellison.Department of Chemistry, Ursinus College, Collegeville, PA 19425, United States

In this study, we produced and purified quantities of acyclovir-functionalized single-walled carbon nanotubes (SWNTs) for use as a novel antiviral medication delivery system. Preliminary trials have shown that acyclovir-functionalized nanotubes exhibit significant antiviral activity in vitro, so our next step was to purify and conclusively determine the identity of the product and generate enough products for future analysis. To synthesize acyclovir-functionalized SWNTs, both oxidized nanotubes and acyclovir were attached to boc-L-cysteine, which then formed disulfide bonds to create acyclovir-functionalized nanotubes. FTIR spectra provided evidence of successful attachment, which was further verified using beta mercaptoethanol as a reducing agent followed by FTIR analysis. Purification of the product was achieved through repeated sonication, centrifugation, and filtering to remove excess reactants from solution. Our results indicate that acyclovir-nanotubes were the primary product of our synthesis, containing an easily-reduced sulfide bond to cleave the medication from the nanotubes and provide effective delivery.

CHED 275

Surfactant assisted high energy ball milling of γ-Fe2O3 nanoparticles for bionanotechnology Philip S. Burnham1, [email protected], Calvin H. Li2, Arthur J. Viescas1, Norman Dollahon3, Georgia C. Papaefthymiou1. (1) Department of Physics, Villanova University, Villanova, Pennsylvania 19085, United States (2) Department of Mechanical Engineering, Villanova University, Villanova, Pennsylvania 19085, United States (3) Department of Biology, Villanova University, Villanova, Pennsylvania 19085, United States

Sub-single-magnetic-domain γ-Fe2O3 nanoparticles (8 to 16 nm diameter) were prepared via high energy ball-milling of commercial powders. Hexane was used as carrier liquid and oleic acid as surfactant. TEM micrographs revealed spherical particle morphology and the effect of the oleic acid shell formed around the particles. Milling times of 3, 6, 9, and 12 hours with mass ratios (oleic acid):(γ-Fe2O3) of 0:1, 1:5, 1:10 and 1:20 were used. Optimal particle size distributions were obtained for 6 to 9 milling hours for 1:10 oleic acid to γ-Fe2O3 mass ratio. At room temperature, a reduced internal magnetic field (~480 kOe) was recorded via Mössbauer Spectroscopy compared to bulk γ-Fe2O3 (~500 kOe), due to magnetic relaxation effects. Ferrofluid stability was examined via particle hydrodynamic radius measurements and thermal transport characteristics, of relevance to hyperthermia cancer therapy research applications, were determined via Specific Absorption Rate (SAR) measurements upon nanoparticle exposure to alternating magnetic fields.

CHED 276

Development of a method to manipulate movement of actin bundles within a hybrid microfluidic device

Catherine B Higgins1, [email protected], Rebecca Ragland1, Michael Tanner1, Eric Blough2, Brian S Day1. (1) Department of Chemistry, Marshall University, Huntington, WV 25755, United States (2) Department of Biology, Marshall University, Huntington, WV 25755, United States

A current goal for researchers in the field of bionanotechnology is the development of a nanotransport system that uses biomolecular motors for controlled cargo manipulation and could be used for the sorting, purification, and assembly of materials on a molecular scale. Our group has developed an actin bundle-myosin motor system for use within a hybrid PDMS/glass microfluidic device. In this system, ATP fuels the movement of the actin bundles along the myosin-coated device floor within the channel to ensure the directional movement of the bundles. To further enhance the development of a nanotransport system, we use the microfluidic device to start and stop the filaments, which will be needed for cargo manipulation. Along the channel we have implemented orthogonal intersections designed to start and stop the bundles by using laminar flow of ATP and ATP-free solutions.

CHED 277

Computational study of the adsorption of glycine to the surface of single-walled carbon nanotubes

Erin McCarthy, [email protected], Ronald C Brown.Department of Chemistry & Biochemistry, Mercyhurst University, Erie, PA 16546, United States

The adsorption energy of glycine to single-walled carbon nanotubes was investigated computationally. Calculations were performed with Gaussian09 using density functional theory at the B3LYP//6-31G(d,p) level. Models of length 3.7 Å- 18.5 Å were designed for (3,3), (4,4), and (5,5) armchair nanotubes. The adsorption of both N-centered and C-centered glycine radicals to the models was studied. Full optimizations were performed on the clean and glycine adsorbed models and adsorption energies were calculated. Calculated adsorption energies ranged from - 46.0 kcal/mol to -2.7 kcal/mol. Trends in adsorption energy with regards to the size and geometry of the tube models were observed. As expected, the adsorption was more favorable on smaller radii tube models. Comparisons between the N-centered and C-centered adsorptions and armchair versus zigzag tubes were also made. Finally, partial optimizations were performed to elucidate the contributions of the bonding energy and tube relaxation energy to the overall adsorption process.

CHED 278

Self-assembling hydrogen bonded aromatic diimides for optoelectronic devices

Dayne F. Swearer, [email protected], Noah M. Johnson, Haifeng Ji.Department of Chemistry, Drexel University, Philadelphia, Pennsylvania 19104, United States

Using solvent evaporation techniques a wide variety of large self-assembling hydrogen bonded nanostructures made of a variety of aromatic diimides can be attained. Our studies have shown that nanostructures including wires, blocks, and pillars are possible from aromatic diimide crystallization. These nanostructures are characterized with scanning electron microscopy, infrared, thermal analysis, and fluorescence. Nanowires of 1,4,5,8- naphthalenetetracarboxydiimide (Fig. 1) exhibits electrical conductivity along the length of the wires; optical and electrical properties of these self-assembled nanostructures may hold promise of organic light-emitting diodes and other optoelectronic devices.

CHED 279

Generation and analyis of glycine polymorphs: Micro and macro approaches

Allyson Moffat, [email protected], Jaclyn Robustelli, [email protected], Courtney Veilleux, [email protected], Peter Vitale, [email protected], Sunghee Lee.Department of Chemistry, Iona College, New Rochelle, NY 10801, United States

The understanding and control of polymorphic form and crystal size is important in materials science. In this study, we outline various micro- and macro-scale approaches to control of crystallization of the model compound, glycine. We have applied the following three methods to generate various glycine polymorphs: an isothermal microdroplet crystallization method; a hanging drop method; and an emulsion crystallization method. Crystal form was characterized by microscopic image analysis and by ATR-IR spectroscopic technique. It was found that for these methods, rate of evaporation, surfactant type, and additive type appears to contribute to the observed polymorphic form.

CHED 280

Preparation of silver nanoparticles conjugated to siloxane gels

Moni Chauhan, [email protected], Sebastien Delva.chemistry, Queensborough Community College, Bayside Ny, NY 11364, United States Metal nanoparticles are unique because of their physical and chemical properties. They represent great potential for application as catalyst, biosensor and nonlinear optical devices. Novel nanoporous architecture with conjugated metal nanoparticles are usually synthesized via bottom up approach and have been in great demand due to emerging applications in green catalysis, drug delivery, light harvesting material, gas storage and sensors. In our approach, the condensation of silanes and in situ reduction of metal salts was the methodology of choice to synthesize the polysiloxane with homogenous distribution of nanoparticle within the glass or polymer frame work. Tris [3-trimethoxysilylpropyl] isocyanurate was the reducing and stabilizing agent for the nanoparticles and it was further cross linked with alkoxysilanes to generate a solid or gel like matrix. The details of the procedure and analysis of the material will be discussed.

CHED 281

Preparation and study of molecular single source precursor containing cavitnads

Kourtney D Wright, [email protected], Niranjan Adhikari, Joshua J Pak.Chemistry, Idaho State University, Pocatello, ID 83209, United States

Our research has been centered on the synthesis of I-III-VI (e.g. CuInS2 and CuInXGa1-XS2) nanoparticles made from various bimetallic molecular single source precursors. Our current efforts involve size-selective preparation of I-III-VI nanoparticles by employing functionalized cavitands thereby engineering bandgaps of resulting nanoparticles. With judicious placement of functional groups on the upper rim of cavitands, we can prepare molecular single source precursors containing cavitands. Due to its size and rigidity, these functionalized cavitands allow size selective formation of desired nanoparticles by changing reaction parameters such as concentrations and reaction temperatures.

CHED 282

Partial sulfonation of polyaniline nanofibers by co-polymerization: Effects of monomer ratio and polymerization initiator

Jaspreet Kaur, [email protected], David M. Sarno.Department of Chemistry, Queensborough Community College of CUNY, Bayside, New York 11364, United States

Nanocomposites of polyaniline nanofibers and metal nanoparticles (NPs) are of interest for catalysis, sensors, organic electronics, etc. We have observed increased deposition of NPs onto polymer nanofibers via electrostatic interaction between negatively charged sulfonated polyaniline and positively charged Au-NPs. However, since sulfonation increases water solubility, the nanofibers are degraded. To limit solubility, yet provide sufficient charge to attract Au-NPs, we have partially sulfonated polyaniline by co-polymerizing aniline and sulfonated aniline. SEM reveals similar morphology for nanofibers synthesized using 10% and 20% sulfonated monomer. However, as the quantity of the polymerization initiator is increased, fibers become increasingly fused and FTIR peaks related to the sulfonic acid group grow slightly in intensity. This suggests greater solubility via increased sulfonation. The synthesis of pure polyaniline does not require an initiator, but in its presence, fused nanofibers are obtained. This is also consistent with increased solubility and may represent a simpler route towards sulfonation.

CHED 283

From nano to macro: Constructing free-standing papers from inorganic nanosheets Richard D Weimar, [email protected], Matthew Davidson, Tina Salguero.Department of Chemistry, University of Georgia, Athens, Georgia 30602, United States

Because of their anisotropic dimensions, nanosheets have great potential in the modern-day search for nanostructured yet scalable materials. The two-dimensional morphology of nanosheets allows us to handle them as colloidal dispersions, which can be processed into large thin films or free-standing, multilayered papers. An example of a titanium dioxide nanosheet-based paper is shown in Figure 1. We describe the preparation of various additional inorganic nanosheet papers, including those based on metal oxide, boride, and chalcogenide materials, as well as their characterization by microscopy and spectroscopy techniques. The results indicate that these papers have many interesting electronic, optical and physical properties with promising applications in the fields of electronics, sensors, and display devices.

CHED 284

Synthesis and property investigation of single-walled carbon nanotube-magnesium nanoparticle composites (SWNT-Mg)

Loren Condon, [email protected], Tirandai Hemraj-Benny.Department of Chemistry, Queensborough Community College, Bayside, New York 11364, United States

Single-walled carbon nanotubes (SWNTs) are graphene sheets consisting of single-layered hexagonally packed carbon atoms which are rolled into tubes. Due to its strength, it is ideal for use in composites and other protective materials. Herein we prepared single-walled carbon nanotubes magnesium nanocomposites (SWNT-Mg) wherein the SWNTs were coated with magnesium metal at the nanoscale. The structural properties of the composites were investigated using Scanning electron microscopy (SEM), transmission electron microscopy (TEM), Fourier transform infrared (FT-IR) and energy-dispersive X-ray spectroscopy (EDS). Mechanical strength of the SWNT-Mg composites was also investigated for application in strong and lightweight material.

CHED 285

Screening of various nanomaterials for the removal of lead ions in aqueous samples

Arianna J Porrata-Doria, [email protected], Amanda A Falade, Elmer-Rico E Mojica.Department of Chemistry and Physical Sciences, Pace University, New York, New York 10038, United States

Nanomaterials are materials possessing grain sizes on the order of a billionth of a meter (nanometer). Nanomaterials possess unique, beneficial chemical, physical, and mechanical properties and they have been used for a wide variety of applications. They have been used as a remediation material in removing pollutants, such as chlorinated solvents (polychlorinated biphenyls) and heavy metals (chromium). In this study, nine commercially available nanomaterials have been screened for removal od lead ions (Pb2+) in aqueous solutions. Fixed amount of the nanomaterials were added to Pb2+ solution of known concentration. The amount of the Pb2+ that bound to the nanomaterials was determined using atomic absorption spectroscopy (AAS). The effect of pH and the presence of humic acid on the aqueous solution containing the metal ions was also performed to determine the optimal conditions in the removal of lead out of the aqueous solutions.

CHED 286

Characterization of noble metal nanoparticles: Study of pH effects

Sai Han Myo Tun, [email protected], Alyssa Thomas.Chemistry & Biochemistry, Utica College, Utica, New York 13502, United States

A nanometer is one billionth of a meter (10-9 m) and represents the collection of few molecules or atoms. At this scale (1-100 nm), the properties of materials become dependent on their size and shape compared to the bulk state. The physical and optical properties have very unique features due to electron confinement and high surface to volume ratios. Among these are noble metal (copper - Cu, gold - Au and silver - Ag) nanoparticles (NPs) that to the naked eye will appear colored in solution from pale red to black, depending on the NPs size and distribution. These colors are due to surface plasmon resonances which are sensitive to small changes in the particle size. This work will analyze the relationship between size and size distribution of synthesized Au NPs and initial concentration of reagents as well as the stability of the synthesized Au NPs in various pH environments.

CHED 287

Investigation of the use of double-walled carbon nanotubes in organic solar cells

Emma Cave, [email protected], Paige Fronheiser, [email protected], Mark Ellison.Department of Chemistry, Ursinus College, Collegeville, PA 19426, United States

The work to be presented focuses on the use of double-walled carbon nanotubes as electron acceptors in the production of organic photovoltaic solar cell devices. Double-walled carbon nanotubes (DWNT) are of interest because of the possibility of selectively functionalizing the outer wall to increase solubility while leaving the inner wall remains intact and maintaining its electrical properties, therefore increasing the efficiency of the solar cells. The electrical conductivities of DWNT and DWNT/poly(3-hexylthiophene) (P3HT) blends were measured at 2% and 5% doping levels. The DWNT and DWNT/P3HT blends were tested in solar cells as well. The conductivity and solar cell measurements suggest that the use of DWNT in organic solar cells could improve the efficiency of the devices.

CHED 288

What is the best bimetallic nanoparticle catalyst for alcohol oxidations

Adam Earle, [email protected], Troy Mahon, Rebeka Mitchell, Janet Petroski.Division of Natural Science, Mount Saint Mary College, Newburgh, NY 12550, United States

Alcohol oxidations under mild conditions using polyvinylpyrrolidone (PVP)-stabilized bimetallic AuPd, PtPd, and AuPt nanoparticles catalysts in aqueous solutions have been previously shown to be effective catalysts. Bimetallic nanoparticles can be synthesized in a heterogeneous or core- shell configuration of varying ratios of the two metals. A heterogeneous arrangement is a random distribution throughout while a core-shell configuration pertains to one of the metals concentrated in the inner core of the structure and a coating shell of the other metal. The oxidation of 2-butanol to 2-butanone under mild conditions was investigated using these catalysts. The reaction was followed using Gas Chromatography. The time of the reaction for maximum product formation was determined for each bimetallic nanoparticle synthesized. The results for optimum arrangement of the nanoparticle including the most efficient catalytic ratio, the most effective bimetallic nanoparticle, and the optimum configuration type will be presented.

CHED 289

Investigation of the use of single-walled carbon nanotubes to deliver an antifungal drug to common yeast

Katherine Greco, [email protected], Mark Ellison.Department of Chemistry, Ursinus College, Collegeville, PA 19426, United States

Recent advances in drug development have revolutionized the biomedical field. However, the delivery of drugs to their target cells remains a formidable challenge. Our goal for this project was two-fold: discover whether (i) single-walled carbon nanotubes (SWCNTs) are able to enter yeast cells, and (ii) if novel antifungal compounds could become more effective in the presence of SWCNTs. SWCNTs were functionalized with fluorescein isothiocyanate to provide visual evidence of cellular uptake using confocal microscopy. To examine the effect of SWCNT on antifungal compounds, growth rates of S. cerevisiae were measured in the presence of antifungal compounds, with and without oxidized SWCNT. Our results suggest that functionalized nanotubes are promising potential transporters for other molecules into S. cerevisiae and other fungal species.

CHED 290

Binding of proteins with different nanomaterials

David B Collins, [email protected], Elmer-Rico E Mojica.Department of Chemistry, Pace University, New York, New York 10038, United States

Nanomaterials are of great interest lately due to their wide variety of applications.The extremely fascinating and useful properties of nanomaterials, which can be exploited for a variety of structural and non-structural applications, made them versatile materials in various fields of science ranging from material science, energy and medicine. Because of this, knowledge on the interactions of nanomaterials with different biomolecules must be known. Phaseolus vulgaris lectin or phytohemagglutinin, a glycoprotein commonly found in legumes, was used as the binding biomolecule. The binding interactions were monitored using various spectroscopic techniques such as UV-Vis, fluorescence and infra-red (IR). Results showed the preferential binding of some nanomaterials with the phytohemagglutinin. This study will report on the binding of the nanomaterials with the lectin and the effect of different parameters (pH, ionic strength and presence of denaturants) on the binding interactions.

CHED 291

Binding of different proteins with different nanoparticles monitored by spectroscopy

Claudia Sobolewski, [email protected], Elmer-Rico E Mojica.Department of Chemistry and Physical Sciences, Pace University, New York City, New York 10038, United States

The interactions of several proteins such as bovine serum albumin (BSA), human serum albumin (HSA) and hemoglobin with nanoparticles (metal oxides) was monitored by various spectroscopic techniques (i.e., absorbance, fluorescence, infra-red). Serum albumins were selected and used because both served as a model protein in many and diverse biophysical, biochemical and physicochemical studies due to its role in the transport and deposition of a variety substance in blood. Results showed the preferential binding of some nanomaterials with the proteins. This study will report on the binding of the nanomaterials with the three proteins and the effect of different parameters (pH and ionic strength) on the binding interactions.

CHED 292

WITHDRAWN

CHED 293

Reactivity of tris(trimethylsilyl)phosphite (TMSP): Synthesis of the bisphosphonic acid of 3-(Trifluoromethyl) phenyl chloroformate

Marjorie Morales, [email protected], Luis Vargas.Chemistry Department, Queensborough Community College, Bayside, NY 11364, United States

A novel bisphosphonic derivative is proposed using an alternative reagent which increased the yield of our desired product – the bisphosphonic derivative of 3-(Trifluoromethyl) phenyl chloroformate. The degenerative disease osteoporosis is caused by a combination of both decreased hormone levels and steady osteoclast activity. Using 3-(Trifluoromethyl) phenyl chloroformate allows us to monitor and study the chloroformate group in the reactivity of Tris(trimethylsilyl) Phosphite. With this reaction, the corresponding bisphosphonate derivative of 3-(Trifluoromethyl) phenyl chloroformate is followed by spectroscopical analysis in hopes that this nucleophilic reagent will create the P-C-P bond that is characteristic in inhibiting the natural metabolic process of biological phosphates. Fosamax, a bisphosphonate drug that inhibits osteoclast-mediated bone resorption, has an amino group in which osteonecrosis of the jaw was strongly correlated with the use of aminophosphates. Thus we will test the reactivity of TMSP to synthesize new bisphosphonates that do not contain amino groups.

CHED 294

Reactivity of tris(trimethylsilyl)phosphite with chloroformates containing electron withdrawing groups

Kevin Chavez, [email protected], Luis Vargas.Chemistry Department, Queensborough Community College, Bayside, NY 11364, United States

Bisphosphonates are a class of drugs used, not only in the treatment of osteoporosis but also, to inhibit both in vivo and in vitro experimental angiogenesis. Studies have shown that nitrogen- containing bisphosphonates (N-BP) can focus on bone density and strength thanks to their antiresorptive properties and affinity to inhibit osteoclasts. Osteoclasts are tissue cells that control bone formation by breaking up mineralized matrix from the organic bone. The degenerative disease osteoporosis is caused by a combination of both decreased hormone levels and steady osteoclast activity. A novel approach in the synthesis of N-BP from 2-Nitrophenyl chloroformate using Tris(trimethylsilyl)Phosphite (TMSP) is discussed. TMSP is an alternative, highly nucleophilic reagent in place of the conventional trialkyl phosphites used in synthesizing bisphosphonic acids.

CHED 295

Synthesis and evaluation of a non-natural PFTase substrate capable of photoreaction with diaryl tetrazole Jennifer L Rowe, [email protected], Klara Zelikman, James W Wollack.Department of Chemistry and Biochemistry, St. Catherine University, St. Paul, MN 55105, United States

Protein Farnesyltransferase (PFTase) has the ability to site-specifically transfer a variety of non- natural isoprenoid groups to proteins ending in the amino acid sequence CVIA. Here a non- natural isoprenoid was synthesized containing a vinyloxybenzene moiety in six steps. This vinyloxybenzene tag allows for the creation of a fluorescent probe after photoreaction with a diaryl tetrazole. The fluorescent tag can be seen within a cell, thus a protein movement and interactions can be assessed. In the past, protein tags have often been large. The inclusion of a large tag may obscure a protein from it's normal functions, and its ability to interact with other proteins. The vinyloxybenzene modification after reaction with diaryl tetrazole allows for a fluorescent tag that should have less of an impact on protein interactions and functions.

CHED 296

Synthesis of oxyallyl silanes and their application as homoenolate equivalents

Donald E Mitchell, [email protected], Fatima Y Moslimani, Julie A Pigza.Department of Chemistry, Queensborough Community College, Bayside, NY - New York 11364, United States

New methodology is proposed in which the alkene will act as a homoenolate equivalent in the addition to electrophiles. Unlike the standard method using allyl silane, oxyallyl silane addition furnishes the vinyl group at an increased oxidation state. This circumvents the need for an additional alkene oxidation step and will allow for quick conversions to complex substrates. The synthesis of ester derivatives of oxyallyl silanes is described as well as initial work to convert the products to alkyl-protected oxyallyl silanes.

CHED 297

Total synthesis of (-)-tatarinoid A

Olga Inozemtseva, [email protected], Claudia G. Lucero.Chemistry, CSU Sacramento, Sacramento, California 95831, United States

(-)-Tatarinoid A (1 ) is one of nineteen compounds that has been isolated from the rhizome (stem) of the plant Acorus tatarinowii. Used in Chinese medicine Acorus tatarinowii possesses pharmacological effects on the central nervous system. Currently there is no reported synthesis of (-)-Tatarinoid A and we have developed the first expeditious and efficient route towards this natural product (in 3 steps). (-)-Tatarinoid A was accessed from the nucleophilic addition of an aryl lithium, resulting from the treatment of 1-bromo-2,4,5-trimethoxybenzene (2 ) with n- butyllithium, to Weinreb amide (3 ) to yield ketone 4 in 32% yield. Treatment of the ketone (4 ) with tetrabutylammonium fluoride (TBAF) at 50 °C for 4 hours removed the tert-butyldimethylsilyl (TBS) protecting group and afforded (-)-Tatarinoid A in 37% yield. The total synthesis was accomplished in 3 steps in a 12% overall yield.

CHED 298

Total synthesis of (+)-tatarinoid B

Yuriy Slutskyy, [email protected], Claudia G. Lucero.Chemistry, CSU Sacramento, Sacramento, California 95819-6057, United States

(-)-Tatarinoid B (1a ) is one of nineteen compounds that has been isolated from the rhizome (stem) of the plant Acorus tatarinowii. Used in Chinese medicine Acorus tatarinowii possesses pharmacological effects on the central nervous system. Currently there is no reported synthesis of (-)-Tatarinoid B and we have developed the first expeditious and efficient route towards the construction of the racemic mixture of this natural product (in 1 step). (+)-Tatarinoid B (1b ) was accessed, in 56% yield, from the crossed acyloin condensation between 2,4,5- trimethoxybenzaldehyde (2 ) and acetaldehyde (3 ) using an achiral triazolium salt (4 ). In an effort to afford (-)-Tatarinoid B, in high yield and enantioselectivity, chiral triazolium salts 5a-e are also being investigated.

CHED 299

Total synthesis of (-)-tatarinoid C

Tyler Johnson, [email protected], Claudia G. Lucero.Chemistry, CSU Sacramento, Sacramento, California 95819-6057, United States

(-)-Tatarinoid C (1 ) is one of nineteen compounds that has been isolated from the rhizome (stem) of the plant Acorus tatarinowii. Used in Chinese medicine Acorus tatarinowii possesses pharmacological effects on the central nervous system. Currently there is no reported synthesis of (-)-Tatarinoid C and we have developed the first expeditious and efficient route towards this natural product (in 4 steps). (-)-Tatarinoid C was accessed from the nucleophilic addition of an aryl lithium, resulting from the treatment of 1-bromo-2,4,5-trimethoxybenzene (2 ) with n- butyllithium, to TBS protected methyl ester (3 ) to yield tertiary alcohol (4 ) in 67% yield. Deoxygenation of the tertiary alcohol with NaBH3CN and BF3·OEt2 at -78 °C for 10 minutes afforded precursor (5 ) to (-)-Tatarinoid C in 51% yield. Treatment of the silyl ether (5 ) with tetrabutylammonium fluoride (TBAF) at 50 °C for 3 hours removed the tert-butyldimethylsilyl (TBS) protecting group and afforded the natural product in 38% yield. The total synthesis was accomplished in 4 steps in a 13% overall yield.

CHED 300

Synthesis and photochemical studies of substituted diarylnorbornadiene derivatives Kyle J. Spivack, [email protected], Jesse V. Walker, Benjamin R. Rupert, Karyn M. Usher, Felix E. Goodson.Department of Chemistry, West Chester University of Pennsylvania, West Chester, PA 19383, United States

Substituted diarylnorbornadiene compounds can be synthesized in two steps from simple aryl iodide, aryl boronic acid, and norbornadiene precursors. Several examples have been synthesized with different electron donating and electron withdrawing groups in the 3 and 4 positions of one of the aromatic rings. In this paper, we discuss their synthesis, purification, and photochemical properties. We also note how the stability (as determined by kinetics experiments) of the corresponding quadricyclanes (which result from the 2+2 photochemical cycloaddition) varies with the identity and position of the substituent.

CHED 301

Synthesis of substituted diarylnorbornadiene derivatives: Variation of the groups on the norbornadiene skeleton

Maria J. Sanford, [email protected], Jesse V. Walker, [email protected], Karyn M. Usher, Felix E. Goodson.Department of Chemistry, West Chester University of Pennsylvania, West Chester, PA 19383, United States

While our other research focuses on the synthesis of norbornadiene diesters, here we investigate whether the synthetic strategies utilized previously can be applied towards the formation of derivatives without the ester groups. This would then allow us to determine how the presence and absence of the ester groups affect the photochemical properties of these compounds. In particular, we discuss the synthesis of derivatives where the ester groups are replaced by simple hydrogen atoms as well as hydroxymethyl groups.

CHED 302

Solid state synthesis of a series of tetra-substituted porphyrins

Paula Mackin, [email protected], Tamara D. Hamilton.Department of Physical Sciences, Barry University, Miami Shores, FL 33161, United States

Solvent-free chemistry is becoming more important due to the industrial demand for waste reduction and cost efficiency. Traditionally porphyrins are synthesized using large amounts of solvent by way of an acid-catalyzed condensation between pyrrole and an aldehyde. The reaction mixture is then oxidized to produce the porphyrin. We are investigating a solvent-free approach involving grinding of reactants with an acid catalyst in a Retsch MM300 ball-mill grinder to produce significant amounts of porphyrin after oxidization. The method has proven effective using benzaldehyde as a reactant to produce tetraphenylporphyrin in significant yields. To investigate the general applicability of the approach, a series of substituted benzaldehydes were ground in the presence of pyrrole and toluenesulfonic acid as a catalyst. Each reaction is carried out 3 times to determine the yield and the product is characterized using UV-Vis Spectroscopy and 1H Nuclear Magnetic Resonance to confirm the presence of the porphyrin.

CHED 303

Diastereoselective synthesis of tetrahydropyridines via rhodium-catalyzed C-H bond activation Colin Lu, [email protected], Simon Duttwyler, Jonathan Ellman.Chemistry, Yale University, New Haven, CT 06520, United States

The ability to synthesize substituted nitrogen heterocycles is essential because of their prevalence in pharmaceutical products. Previously, efficient rhodium-catalyzed C-H bond activation methods were developed in the Ellman lab to selectively synthesize highly substituted dihydropyridines through alkenylation/cyclization reactions between alkynes and α,β -unsaturated aldimines or ketimines. The current project expands the substrate scope of the C-H activation reaction and focuses on the subsequent borohydride reduction of the dihydropyridine under acidic conditions to afford the tetrahydropyridine. Several reducing agents and Lewis acids were tested for efficiency and diastereoselectivity. After optimizing conditions, a variety of tetrahydropyridines were successfully isolated in high yield and purity, and their configurations were determined through X-ray crystallography.

CHED 304

Studies toward the total synthesis of quinazoline alkaloids: Vasicinone, luotonin, and nigellastrine

Jeffrey A Boerth1, [email protected], Sivappa Rasapalli2. (1) Department of Chemistry, University of Massachusetts Amherst, Amherst, MA 01003, United States (2) Department of Chemistry and Biochemistry, University of Massachusetts Dartmouth, Dartmouth, MA 02747, United States

Among a variety of natural compounds produced by the plant Peganum Nigellastrum, three closely related families of quinazolinone alkaloids have been discovered: vasicinone, luotonins, and nigellastrines.

The quinazolinone core is common to each and has been known to have medicinal properties in treating diseases such as cancer. Most importantly, the compounds nigellastrine A and B have been shown to inhibit the enzyme acetylcholinesterase, reducing the effects of Alzheimer's disease. Intrigued by the interesting biological activities, we set out to develop a synthetic route that would provide access to these natural products and their analogs. We proposed that bicyclic quinazolinone ketone could serve as a linchpin to access a library of tricyclic ketones via a key aldol reaction with various aldehydes. Our efforts towards the synthesis of the precursors and efforts to develop a common synthetic route to the natural product type library will be presented.

CHED 305

Synthesis and characterization of naphthalene based fluorescent conjugated polymer chemosensors

Manar Alherech1, [email protected], Davis U. Anugo1, [email protected], Abigail M. Oakes1, [email protected], Megan E. A. Fegley1, Sherryllene S. Pinnock1, Anne Pfeifle2, Jetty Duffy-Matzner2, Wayne E. Jones Jr.1. (1) Department of Chemistry, Binghamton University, Binghamton, New York 13902, United States (2) Department of Chemistry, Augustana College, Sioux Falls, South Dakota 57197, United States Fluorescent conjugated polymers have been of interest for use as chemosensors to detect harmful contaminants in environmental systems. Previously, our group has worked with two classes of fluorescent conjugated polymers, “turn-off” sensors containing a tolyl-terpyridine (ttp) receptor ligand and “turn-on” sensors containing a trimethylethyldiamino (tmeda) receptor ligand. In an attempt to expand the variety of detectable metals, we have synthesized 2,6-diethnyl 1,5- didodecyloxy naphthalene, which is used to alter the original conjugation of the polymer backbone. The monomer was incorporated into the backbone containing the “turn-on” receptor ligand as well as the “turn-off” receptor ligand. Photophysical tests were completed for each polymer and the peak absorbance and emission frequencies were blue shifted for the polymers containing the naphthalene monomer. The resulting change in the donor energy gap caused shifts in analyte selectivity.

CHED 306

Asymmetric synthesis of primary amine and its conversion to new calcimimetic analogs

Ileanne Martinez, [email protected], Sandraliz Espinosa-Diaz, [email protected], Jaime L Alvarez, Margarita Ortiz-Marciales.Department of Chemistry, University of Puerto Rico at Humacao, Humacao, Puerto Rico 00792, United States

Primary amines are used as intermediates for the synthesis of a variety of pharmaceutical products. The enantioselective synthesis of nonracemic amines is the most important method for the production of enantiopure drugs. Previously, we developed a higly enantioselective method for the synthesis of enantiopure amines by the reduction of O-benzyl oxime ethers with a spiroborate ester/borane system. Using 10% of the catalyst derived from diphenyl valinol and ethylene glycol, (R) and (S) naphtyl-1-ethylamines were obtained in good yield and excellent enantiopurity (>99% ee). Secondary hyperparathyroidism is a dangerous disease characterized by an excessive secretion of the parathyroid hormone due to low calcium levels in the body. Calcimimetic agents are new drugs, whose name reflects their major action: to mimic the effect of calcium on calcium receptors, and have the potential to control hyperparathyroidism. A new approach for the synthesis of novel class calcimimetic analogs from enantiopure amines will be presented.

CHED 307

Investigation of various synthetic pathways using methyl salicylate and menthol isolated from over-the-counter topical pain creams

Joseph M Henain, [email protected], Jodie T Wasacz.Division of Natural Science, Mount Saint Mary College, Newburgh, New York 12533, United States

Many athletes suffer from joint and muscle pain, and may use over-the-counter (OTC) topical salicylates to alleviate symptoms. The major brands researched were IcyHot®, Bengay®, and a generic brand all containing methyl salicylate and menthol as the active ingredients. This research focuses on the extraction, purification, and quantification of methyl salicylate and menthol from the OTC creams. The methyl salicylate will be hydrolyzed to aspirin while the menthol will be used in additional synthetic pathways. Upon successful completion of this research a multi-week laboratory experiment for undergraduate organic chemistry experiments will be written and implemented. Results will be presented in this poster. CHED 308

Synthesis of precursor dipeptides for the coordination of Pt(tpy) in the formation of mono- and di-metallic peptides

Aaron K Le, [email protected], Lindsey Ray, Lauren A Levine.Department of Physical Sciences, Kutztown University of Pennsylvania, Kutztown, Pennsylvania 19530, United States

Peptide nucleic acids (PNA), which contain an aminoethylgylcine (aeg) backbone functionalized with nucleobases, have been used as antisense drugs for their ability to bind to DNA through base pair formation. The aeg backbone provides a stable skeleton due to the increased stability of peptide bonds that spatially mimic the negatively charged sugar-phosphate backbone of DNA without the electrostatic repulsion between phosphate groups. Alternatively, metal coordinating ligands have been used in place of nucleobases, dubbed iDNA (inorganic DNA) replacing hydrogen bonding with metal ligand coordination. Our research aims to synthesize dipeptides utilizing an aeg backbone functionalized with metal ligands. FMOC/t-butyl ester protected acetyl and pyridyl monomers have been selected for the synthesis of two dipeptides, pyridine-pyridine and acetyl-pyridine combinations. The dipeptides are purified by column chromatography and characterized with mass spectrometry and NMR spectroscopy. The pyridyl subunits will subsequently be functionalized with platinum terpyridine ligands.

CHED 309

Green oxidation methods for porphyrin synthesis

Hannah Shy, [email protected], Tamara D. Hamilton.Department of Physical Sciences, Barry University, Miami Shores, FL 33161, United States

Solvent-free chemistry is becoming more widespread because of increased emphasis on waste reduction and lessening cost. Porphyrins are cyclic, organic compounds that have become important in the construction of larger, self-assembled systems. The traditional synthesis of porphyrins consists of an acid-catalyzed condensation of pyrrole and aldehyde to produce a precursor: porphyrinogen, which is then oxidized to become porphyrin. The traditional process produces yields lower than 30% and requires high-dilution solvent conditions to ensure the proper reaction takes place. We have been successful in developing a solvent-free approach using either a mortar and pestle or a ball mill to produce the cyclized product, porphyrinogen, which needs to be oxidized in a second step to produce a porphyrin. Here we present the results of our studies to develop a green oxidation method for pophyrinogen oxidation, leading to an entirely green methodology for synthesis of these important organic molecules.

CHED 310

Greener synthesis of subphthalocyanines using microwave heating

David Nissenbaum, [email protected], Chris McConnell, [email protected], Matthew Jurow, Charles Drain.Department of Chemistry and Biochemistry, CUNY Hunter College, New York, New York 10065, United States

Sub-phthalocyanines (SubPc) are moderately stable macrocyclic systems consisting of three isoindole rings. SubPc are used in diverse technologies ranging from displays to solar cells to phototherapeutic agents because of their photonic properties. The goal of this work is to develop a greener synthesis of subPc by using the microwave heating, using less solvent, and reduced reaction time. We report an efficient procedure using a microwave heating to produce a range of SubPc with different substituents with yields similar to or greater than conventional heating. The method involves microwave heating three equivalents of the phthalonitrile with one equivalent of BCl3 in a minimum amount of toluene. The optimization of the reaction parameters and a diversity of phthalonitriles, such as the tetrafluorophthalonitrile, will be presented. The results of using phthalic acids and urea to form the subPc using the above methods will also be presented.

CHED 311

Dual Br_nsted acid/nucleophilic activation of carbonylimidazole derivatives

Tingting Fu, [email protected], Stephen T Heller, Richmond Sarpong.Department of Chemistry, University of California, Berkeley, Berkeley, California 94720, United States

Carbonylimidazole derivatives have been established as an important and versatile class of acylation reagents. In the presence of pyridinium salts, carbonylimidazole derivatives have been found to be highly reactive under mild conditions. These reactions are thought to involve both Brønsted acid and nucleophilic catalysis. This mode of activation has been applied to the synthesis of oxazolidinones, as well as esters and amides.

CHED 312

Applying solvent-free conditions to the synthesis of ferrocenyl chalcones derivatives

Fernando J. Correa Delgado, [email protected], Juan C. Aponte-Santini, Ingrid Montes-González.Department of Chemistry, University of Puerto Rico, Rio Piedras Campus, Rio Piedras, Puerto Rico 00931-3346, Puerto Rico

Because of its intriguing structure and numerous uses, ferrocenyl derivatives had captivated and attracted the scientific community since its discovery in 1951. Our interest is mainly focused in ferrocenyl chalcones that also exhibit remarkable stability in their structure and magnificent properties. Based on their attributes, ferrocenyl chalcones core can be considered as potent inhibitory agents, which promise treatments to human diseases and as synthetic precursors for other biological active compounds. Numerous syntheses for chalcone core have been explored, but some of these organic reactions generate a significant amount of waste. This research studies solvent-free conditions and how they compare to the traditional Claisen-Schmidt condensation reactions. So far, our research is showing positive results where reaction times have been reduced from hours to minutes, obtaining good to moderate percent yields. The synthetic methodology, characterization and potential applications of these compounds will be elaborated. Work supported by UPR-RP RISE Program.

CHED 313

Spectroscopic studies of a new ion-pair receptor

Alisha Contractor, [email protected], Kristin N. Skala-Jordan, Farooq A. Khan, Megumi Fujita.Department of Chemistry, University of West Georgia, Carrollton, GA 30118, United States Ion-pair receptors bear recognition sites for both an anion and a cation. Such receptors may bind a cation and an anion either as an intact ion pair or as separate ions. We have synthesized bis(3- bromoindol-2-ylmethyl)(2-pyridylmethyl)amine (1), in which two indolyl NH groups bind an anion and two amine/pyridine N atoms bind a cation. The cation and anion binding behavior in solution, as separate ions or an ion-pair, was demonstrated using ESI-MS, 1H NMR and UV-Vis spectroscopy. Titrations, by 1H NMR, were performed to determine the association constants of the various ions binding to the synthesized receptor 1. A cooperative binding of an ion pair was demonstrated. DFT (density functional theory) calculations support the ability of receptor 1 to bind an intact ion pair. Colorimetric studies were performed to ascertain the possibility of using the synthesized receptor 1 as an ion-specific sensor.

CHED 314

Structural studies of oxazinoquinolinespirohexadienone “photochromes” and related molecules

Benjamin J Pollock, [email protected], Jason G Gillmore.Department of Chemistry, Hope College, Holland, MI 49423, United States

Creating electron deficient perimidinespirohexadienone (PSHD) photochromes to “gate” sensitivity toward photoinduced charge transfer (PICT) reactions has been performed, including replacement of the of the naphthalene moiety in the PSHDs with a quinoline, resulting in quinazolinespirohexadienones (QSHDs). In the present work, oxazinoquinolinespirohexadienones (OSHDs), QSHD analogs in which a bridging nitrogen atom is replaced with an oxygen, have been prepared and studied. Calculations predict these to be more potent photochromic photooxidants. Unfortunately NMR, UV-vis, and X-ray analyses indicate these analogs are not photochromes but rather exist exclusively in their ring-opened, long wavelength (LW) form. Two tautomeric structures of this LW isomer are possible. Contradictory NMR and cyclic voltammetry evidence for the structure in solution will be presented and compared with X-ray diffraction data on the crystalline solid state structure. Our current understanding of these molecules, as well as future directions envisioned for the QSHD and PSHD families of photochromes will be presented.

CHED 315

Synthesis of aspernigrin A and analogs

Kirsten Eldredge, [email protected], William Tidwell, Zachary Cureton, Anne Reeve.Department of Chemistry and Biochemistry, Messiah College, Grantham, PA 17027, United States

Aspernigrin A (1 ) is a cytotoxic pyridone natural product isolated from various strains of fungi, including Aspergillus niger. In order to study the structure-activity relationship for cytotoxicity, a flexible synthetic scheme was developed. We obtain the pyridone from reaction of a pyrone precursor (such as 2 ) with DMF dimethyl acetal followed by an amino donor. To date, we have synthesized several anlogs of the natural product in good overall yield employing only simple reagents and mild reaction conditions. Furthermore, our process requires no or minimal protecting groups, depending on the desired R groups, and operates with very good atom efficiency.

CHED 316

Organocatalyzed reactions for the asymmetric synthesis of Fmoc-protected β2-amino acids

Justin M. Kontra, [email protected], Nicholas C. Boaz, Samantha J. Bowen, Timothy J. Peelen.Department of Chemistry, Lebanon Valley College, Annville, PA 17003, United States

We have investigated organocatalytic strategies for the synthesis of Fmoc-protected β2- amino acids, which are useful building blocks of peptidomimetics. Our goal is to develop asymmetric methods that are compatible with the base-labile Fmoc-protecting group and result in the construction unnatural β-amino acids. Using enamine and SOMO catalysis, we have explored additions to Fmoc-protected 3-aminoproionaldehyde. The resulting enantioenriched products can be directly oxidized to the corresponding β2-amino acids.

CHED 317

Synthesis of chiral amines via reduction of oxime ethers with spiroborate ester

Kiara M Santiago Fidalgo, [email protected], Valerie E Torres Claudio, [email protected], Margarita Ortiz-Marciales.Department of Chemistry, University of Puerto Rico at Humacao, Humacao, Puerto Rico 00792, Puerto Rico

Enantiomeric pure amines are specially valuable organic compounds that have been used as amphetamines, antihistamines and antibiotics. The enantioselective borane reduction of oxime ethers to primary amines has been studied under catalytic conditions using the spiroborate esters derived from diphenylvalinol and ethylene glycol. Effective conditions were achieved by using only 10% of catalyst resulting in complete convertion to the corresponding primary amine in up to 99%ee. Recently our group is studying the reduction of several O-benzyl oximes and their conversion to primary chiral amines.

CHED 318

Development of a novel asymmetric alkylation of superquat-derived glycolyloxazolidinones and its application toward the synthesis of majorenolide and majorynolide

Jade Bing, [email protected], Danielle L. Jacobs.Department of Chemistry, Biochemistry & Physics, Rider University, Lawrenceville, NJ 08648, United States

Asymmetric glycolate alkylations have been traditionally limited to primary, sterically- unencumbered electrophiles; our laboratory accordingly seeks to increase the scope of compatible electrophilic partners, potentially reinvigorating the utility of this valuable alkylation in organic synthesis. Primary investigations into the asymmetric alkylation of (S)-p- methoxybenzylglycolyl-i-propyl-2-oxazolidinone, with both t-butyl and i-butyl-2- (methyliodo)acrylates, provided products in good yields yet poor diastereoselective ratios. Ethyl acrylates provided multiple products, likely a result of competitive alkylation at the alkene terminus and ester carbonyl. These initial results prompted us to employ less common Superquat chiral auxiliaries to induce higher diastereo- and regioselectivity via enhanced rigidity of the enolate transition state. Our current progress and results are reported toward this end. Upon optimization, this methodology should enable the synthetic preparation of unique γ-lactone natural products bearing exo-methylene functionality at the γ position, as showcased in our laboratory's progress toward the first total synthesis of the cytotoxic natural products majorynolide and majorenolide.

CHED 319

Thiomorpholin-3-ones via a solvent-free tandem amidation/cyclization

Carl-Johan Wallentin, James E. Park, [email protected], Corey R. J. Stephenson.Department of Chemistry, Boston University, Boston, MA 02215, United States

Evident by the ubiquitous nature of heterocycles in biological systems, these building blocks, through their rigidity and either hydrophobic or hydrophilic interactions, play key roles in drug development. As a consequence, new synthetic sequences for their construction are essential. This study highlights the facile, solvent-free coupling of various diallylamines with methyl thioglycolate to generate an assortment of thiomorpholin-3-ones.

CHED 320

Synthesis of 3, 4, 9, 10-tetracarbooxylic acid derivatives as a chelating agent

Katterin G. Colon, [email protected], Kenneth Yamaguchi.Department of Chemistry, New Jersey City University, Jersey City, NJ 07305, United States

Perelyene-3, 4, 9, 10-tetracarboxylic acid bisimide is an organic compound that is useful due to its variety of scientific and industrial applications, such as: polymers, n-type semiconducting materials, photovoltaics, OLEDS, fluorescent tags, and dyes. The goal is to find an easy and successful route for the reaction of Perelyene-3, 4, 9, 10-tetracarboxylic acid bisimide and 4- Iodoaniline, which in turn will be coupled to a chelating ligand via Suzuki coupling reactions which can ultimately generate a variety of new and useful compounds.

CHED 321

Rapid synthesis of N-(4-isopropylbenzyl)formamide

Joel A. Collins, [email protected], Halee Namanny, Lioudmila I. Bobyleva, Mikhail M. Bobylev.Division of Science, Minot State University, Minot, ND 58707, United States

Substituted benzylformamides are important intermediates in the synthesis of numerous biologically active compounds, including agrochemicals and pharmaceuticals. Recently, we developed an accelerated procedure for the synthesis of formamides. It was important to investigate if the procedure can be successfully applied for the synthesis of benzylformamides with electron-donating substituents, for example N-(4-isopropylbenzyl)formamide. Column chromatography was used for the isolation of the products of the reaction. NMR, MS, and elemental analysis were used to determine the structure of the products. The reaction was completed in 1 minute and produced N-(4-isopropylbenzyl)formamide in good yield. Three byproducts were isolated and their structures were determined. The new reaction opens the way for the fast synthesis of N-(4-isopropylbenzyl)formamide and its derivatives. The project is supported by NIH grant P20 RR016741 from the NCRR and by the Great Plains Center for Community Research and Service as funded by the US Department of Education Grant Award P1 16Z100151

CHED 322

Byproducts in the rapid synthesis of N-(4-chlorobenzyl)formamide

Kowan O’Keefe, [email protected], Misty Huesers, Lioudmila I. Bobyleva, Mikhail M. Bobylev.Division of Science, Minot State University, Minot, ND 58707, United States

N-(4-chlorobenzyl)formamide is an important intermediate in the synthesis of medicinally active compounds. Recently, we developed an accelerated procedure for the synthesis of formamides and successfully used it for the synthesis N-(4-chlorobenzyl)-formamide. In this work, the newly developed reaction was investigated for the purpose of isolation and investigation of the reaction by-products. Column chromatography was used for the isolation of the products of the reaction. NMR and MS spectra and elemental analysis were used to determine the structure of the products. The reaction was completed in 1 minute and produced N-(4-chlorobenzyl)-formamide in good yield. Three byproducts were isolated and their structures were determined. The results will help to better understand the mechanism of the Leuckart reaction. The project is supported by NIH grant P20 RR016741 from the NCRR and by the Great Plains Center for Community Research and Service as funded by the US Department of Education Grant Award P1 16Z100151

CHED 323

Rapid synthesis of N-(2,4-dichlorobenzyl)formamide

Mitchell A. Falkenberg, [email protected], Arie W. Bauer, Lioudmila I. Bobyleva, Mikhail M. Bobylev.Division of Science, Minot State University, Minot, ND 58707, United States

Substituted benzylformamides are important intermediates in the synthesis of numerous biologically active compounds, including agrochemicals and pharmaceuticals. Recently, we developed an accelerated procedure for the synthesis of formamides. It was important to investigate if the procedure can be successfully applied for the synthesis of benzylformamides with electron-withdrawing substituents, for example N-(2,4-dichlorobenzyl)formamide. Column chromatography was used for the isolation of the products of the reaction. NMR, MS and elemental analysis were used to determine the structure of the products. The reaction was completed in 1 minute and produced N-(2,4-dichlorobenzyl)-formamide in good yield. Three byproducts were isolated and their structures were determined. The new reaction opens the way for the fast synthesis of N-(2,4-dichlorobenzyl)amine and its derivatives. The project is supported by NIH grant P20 RR016741 from the NCRR and by the Great Plains Center for Community Research and Service as funded by the US Department of Education Grant Award P1 16Z100151

CHED 324

Rapid synthesis of N-[1-(1-naphthyl)ethyl] formamide Luke W Uran, [email protected], Mikhail M Bobylev.Department of Science, Minot State University, United States

N-[1-(1-naphthyl)ethyl]-formamide is an important intermediate in the synthesis of biologically active compounds, including calcimimetics (allosteric enhancers of calcium-sensing receptors). Recently, we developed an accelerated procedure for the synthesis of formamides. In this work, the accelerated procedure was applied for the synthesis of N-[1-(1-naphthyl)ethyl]-formamide. The reaction was conducted on 10 mmol scale at 190-192ºC. Column chromatography was used for the isolation of the reaction products. NMR-spectroscopy and elemental analysis were used to determine the structure of the products. The reaction was fully completed in 5 minutes and produced N-[1-(1-naphthyl)ethyl]-formamide in good yield. One by-product was isolated and its structure was determined. The new reaction opens the way for the fast synthesis of N-[1-(1- naphthyl)ethyl]-formamide and its derivatives. The project is supported by NIH grant P20 RR016741 from the NCRR and by the Great Plains Center for Community Research and Service as funded by the US Department of Education Grant Award P1 16Z100151

CHED 325

Unprecedented azine formation via proton tautomerismof isoquinolyl-1-hydrazones

Kevin Cannon, [email protected], Samantha Lauro, [email protected], Ann Schmiedekamp, Clayton Wang.Department of Chemistry, Penn State Abington College, Abington, PA 19001, United States

Previously reported structures of isoquinolyl-1-hydrazones were subjected to electronic structure calculations using density functional theory (DFT). For six targeted compounds, calculations were applied to multiple conformations for both azine and hydrazone tautomers in order to determine the relative energies of the possible conformations. Then calculations were performed using the hybrid functional B3LYP and a 6-31G**++ basis set using the program Jaguar. The lowest gas phase Gibbs free energy conformation was a function of substitution. In some instances, an azine tautomer was the lowest energy conformation,and in others it was a hydrazone. Compounds which showed a significant calculated preference for either the azine or hydrazone tautomer was synthesized and characterized by x-ray crystallography. Compounds characterized thus far possess solid state structures which agree with those based on the lowest energy conformations.

CHED 326

WITHDRAWN

CHED 327

Stereoselectivity of Diels-Alder reactions in protic ionic liquids

Suzanne Szewczyk, [email protected], Donald E. Mencer.Department of Chemistry, Wilkes University, Wilkes-Barre, PA 18766, United States

Alkylammonium ionic liquids as solvents for Diels-Alder reactions have shown higher endo to exo stereoisomer ratios of the products compared to common organic solvents. GC-MS and 1H NMR analysis were used to determine the isomer ratios of the products in ethylammonium nitrate, propylammonium nitrate, and tributylammonium nitrate as well as de-ionized water as a reference. Cyclopentadiene was used as the diene for all the Diels-Alder reactions with various dienophiles including acrylic acid, methyl acrylate, methyl vinyl ketone, 1-hexene, and styrene to examine the effects of steric hindrance and electronics on the reactions and to compare to literature results. The polarity of the solvents was determined using solvatochromatic dyes to define a relationship between the endo to exo ratio and the polarity of the solvent. It was found that there is a direct correlation with solvent polarity and the endo to exo ratio of the corresponding Diels-Alder products.

CHED 328

Wet-lab approach to stereochemistry using 31P and 1H NMR spectroscopy

Bianca R. Sculimbrene, [email protected], Owen S. Fenton.Department of Chemistry, College of the Holy Cross, Worcester, MA 01610, United States

Understanding stereochemistry is an important and difficult task for students to master in organic chemistry. In both introductory and advanced courses, students are encouraged to explore the spatial relationships between molecules, but this exploration is often limited either to the lecture hall or the confines of the library. As such, we sought to develop an experiment-based approach that would facilitate investigation of stereochemical principles in an organic chemistry laboratory. Herein is reported a 31P NMR and 1H NMR-based experiment that allows students to explore the different stereochemical outcomes when enantiopure or racemic alcohols are coupled to an achiral phosphorous center.

CHED 329

Modeling muscle contraction as a stochastic ratchet

Steven G. Desjardins, Alex Finnegan, [email protected], Frederick LaRiviere.Department of Chemistry, Washington and Lee University, Lexington, Virginia 24450, United States

Contraction of skeletal muscle arises from interaction of the proteins actin and myosin. The myosin filaments contain tiny “head” pieces that crawl along depressions in the actin filaments. This study models the actin/myosin interaction as a stochastic ratchet similar to a plastic cable tie. The “one-way” nature of the head groups acting as a ratchet causes motion in only one direction to be captured, resulting in the steady contraction of the muscle. The contraction is powered by random thermal energy and the energy released by ATP hydrolysis at the head groups. Simulation results track energy used as a function of time as the fiber contracts. Modulation of the specific directional forces also allows us to determine the effectiveness of a purely random motion as opposed to a model with largely directional forces. These simulations were performed in the graphical modeling software MapleSim.

CHED 330

Chain length dependence tribological properties of self-assembled monolayers of alkyl carboxylic acids

Jacob M Walbridge1, [email protected], Tiffany A Mcclain1, Min S Lim1, Ellen S Gawalt2. (1) Department of Chemistry, Slippery Rock University, Slippery Rock, PA 16057, United States (2) Department of Chemistry and Biochemistry, Duquesne University, Pittsburgh, PA 15282, United States

The interfacial properties of SAMs are decisive criteria for good lubricants which are significantly dependent upon their molecular structure, chain length, packing order, packing density, chemical composition, and molecular termination. The influence of the systematic variation of chain length of SAMs on the interfacial properties has been investigated in the present study. Self-assembled monolayers (SAMs) of n-alkylcarboxylic acids have been grown on single crystalline surfaces of sapphire because the surfaces provide both physically and energetically homogeneous conditions for the formation of SAMs. An atomic force microscope (AFM) has been used for the measurements of interfacial friction and adhesion in the force range of 0 – 30 nN from monolayers. Bonding nature of a SAM monomer to a substrate surface and backbone chain ordering of SAM has been also explored with Diffuse Reflectance Infrared Fourier Transform Spectroscopy (DRIFT).

CHED 331

Measurement of heterogeneous rate constants during the reaction of allyl chlorides at indium surfaces

Katherine M. Delaney, [email protected], Gabriella Mylod, Tessa Sullivan, Alexa N. Hill, Walter Bowyer.Department of Chemistry, Hobart and William Smith Colleges, Geneva, NY 14456, United States

Indium mediated allylation has proven to be an extremely versatile reaction that offers regio- and stereoselectivity; furthermore, it proceeds in aqueous solutions, which are much safer than the solvents used in alternative reactions. Recently, we developed a novel strategy using photomicroscopy to measure the kinetics of the heterogeneous reaction at the indium surface. We now show that the reaction of indium with various allyl chlorides is first order in allyl chloride, and the absolute heterogeneous rate constants range from 3×10-5 to 3×10-4 cm/s, depending on the substituents on allyl chloride. Also, we report preliminary measurements over a range of temperatures to estimate the energy of activation. The potential for broader application of our technique to determining rate constants of other heterogeneous reactions is discussed, and we describe preliminary results on the dissolution of gold metal.

CHED 332

Pyrolysis products from the thermal decomposition of butyraldehyde

Courtney D. Hatten, [email protected], Allison B. Combs, Kristen M. Keown, Laura R. McCunn.Department of Chemistry, Marshall University, Huntington, WV 25755, United States

A hyperthermal nozzle was used to induce thermal decomposition of butyraldehyde and matrix- isolation Fourier transform infrared spectroscopy (MI-FTIR) was used to analyze the products. The thermal decomposition of gas-phase butyraldehyde occurred in an oxygen-free environment and the immediate products were trapped and isolated in a cold argon matrix. This technique allows the capture of radical intermediates formed in pyrolysis. The MI-FTIR spectrum of the products from pyrolysis of butyraldehyde was compared to the MI-FTIR spectrum of butyraldehyde in the absence of pyrolysis in order to identify the various reactions of thermal decomposition. The products of butyraldehyde pyrolysis were also compared to the products of acetaldehyde pyrolysis, which was studied in an experiment conducted by another laboratory. The results will aid in the prediction of products formed in thermal decomposition reactions of aldehydes that may occur in the course of biofuel production.

CHED 333

Can current forcefield models accurately simulate peptoids Christopher R Michel, [email protected], Vincent A Voelz.Department of Chemistry, Temple University, Philadelphia, PA 19122, United States

Peptoids (N-substituted glycine oligomers) are synthetic foldamers. Peptoids are similar to peptides, except the side chain normally found on the alpha carbon is bonded to the nitrogen. Because they are easily synthesized, peptoids have been used in a variety of biomimetic applications, including antimicrobials and surrogate antibodies. Can current forcefield models be used to predict peptoid solution structure? To answer this, we used UCSF Chimera to build a model of a small peptoid pentamer shown to have a stable folded conformation in solution (Armand et al. PNAS 1998). We then applied the GAFF forcefield with partial charges computed by the AM1-BCC method, along with a Generalized Born implicit solvent model (GBSA). Using this model, we simulated replica-exchange molecular dynamics (REMD) using the OpenMM package. In this investigation, we assess the accuracy of the model by comparing the simulation results to experimental distance restraints obtained by NMR.

CHED 334

Interactions of osmolytes with neutral lipid membrane

Nousin Haque, [email protected], Zuzanna Michalak, Darius Fartash, [email protected], Sunghee Lee.Department of Chemistry, Iona College, New Rochelle, NY 10801, United States

We have studied individual pairs of surfactant-monolayer coated aqueous droplets which adhere at an interface to form a droplet interface bilayer (DIB). Droplets are generated and manipulated by micropipet. The use of 1-glyceryl monooleate (GMO) as surfactant dissolved in squalene medium provides droplet pairs which have a large contact zone, the size and area of which is amenable to an optical microscopy study. We report investigations of the variability of the contact angle of the DIB as a function of the nature and concentration of ions present in the aqueous microdroplet. Specific anion effect has been observed. Possible explanations for the observed effects will be explored.

CHED 335

Reaction kinetics of Colorado, Chinese, and Estonia oil shale semi-cokes in air

Anthony A D'Amico1, [email protected], Jillian L Goldfarb1, Indrek Külaots2. (1) Department of Chemical Engineering, University of New Hampshire, Durham, New Hampshire 03824, United States (2) Department of Chemical Engineering, Brown University, Providence, Rhode Island, United States

As concern about reducing the impact of energy productions increases, it is important not only to study alternative energy sources, but also to examine methods of reducing the environmental impact of more traditional energy sources on the environment. To this end the reaction kinetics of semi-coke, the primary by-product of oil-shale processing, were studied. The samples were pyrolized at 500 °C and 1000 °C and then heated in air. The activation energies for the samples pyrolized at 500 °C ranged from 81 to 157 kJ/mol and 147 to 187 kJ/mol for the samples pyrolized at 1000 °C. These results indicate that semi-coke could be used as fuel source, thus reducing the overall waste output of oil-shale processing.

CHED 336

Single-pair FRET analysis of structures and dynamics in amyloid-β dimers Emily Amenson, [email protected], Abigail Bradner, Robin K. Lammi.Department of Chemistry, Physics and Geology, Winthrop University, Rock Hill, SC 29733, United States

Amyloid-β (Aβ) is a self-associating protein of 39-43 amino acids that is linked to Alzheimer's disease (AD). Recently, it has been discovered that Aβ oligomers as small as dimers are closely correlated to the symptoms and progression of AD; however, little is known about their structures. We have used single-pair Förster Resonance Energy Transfer (spFRET) to investigate structures and dynamics in surface-tethered dimers, determining FRET efficiencies (EFRET) between associated donor- and acceptor-labeled peptides. A histogram of characteristic dimer EFRET values reveals two peaks near 0.38 and 0.58, perhaps representing two preferred dimer structures. Single-dimer histograms reveal that approximately 70% of dimers exhibit one characteristic EFRET value; the other 30% show two or three characteristic EFRET values, likely indicative of structural dynamics. Collectively, these investigations provide some of the first experimental insights into structures of neurodegenerative Aβ dimers, and may lead to improved understanding and treatment of Alzheimer's disease.

CHED 337

Computational study of the adsorption of cationic and zwitterionic lysine to a mineral clay surface: Adsorption energy and vibrational frequencies

Meserret Zekarias, [email protected], Lorena Tribe.Division of Science, The Pennsylvania State University - Berks Campus, Reading, Pennsylvania 19610, United States

The interactions of amino acids with mineral clays are fundamental in fields as diverse as soil remediation, bone bio-materials, and Origins of Life theories. Theoretical atomistic models of cationic and zwitterionic lysine, of montmorillonite clay, and of surface complexes of both forms of lysine with the clay were developed and energy minimized. Adsorption energies are proposed for inner and outer sphere complexes in both cases. The IR adsorption frequencies for the free species and the surface complexes are determined with Density Functional Theory calculations using the Gaussian 09 software package. The values are compared to experimental determinations from the literature to provide an independent assignment of the vibrational modes, and therefore, of the structure of the potential surface complexes.

CHED 338

WITHDRAWN

CHED 339

Effect of capping agent molecular weight on catalytic activity and selectivity of nanoscale palladium catalysts for aqueous phase hydrogenations

Kyle M Gross, [email protected], Anderson L Marsh.Department of Chemistry, Lebanon Valley College, Annville, PA 17003, United States

A key concern that arises with using colloidal nanoparticles as catalytic materials is the effect of the stabilizing polymer on the kinetics of the reaction. We are currently studying the effect of the capping agent poly(vinylpyrrolidone), or PVP, on the activity and selectivity for the hydrogenation of phenol. As model catalysts we are using Pd nanoparticles in the 1-10 nm size range capped with PVP in the 10,000 to 55,000 g/mol molecular weight range. We are measuring particle sizes by transmission electron microscopy (TEM) and determining the amount of capping agent through matrix assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS). We are performing catalytic reactions at moderate temperatures and hydrogen pressures, with the kinetic data being used to calculate turnover frequencies, reaction orders, and apparent activation energies. Taken together, this information will allow us to elucidate the role of the capping agent during catalytic reactions in aqueous solution.

CHED 340

Theoretical study of the adsorption of L-cystine and L-cysteine on layered double hydoxide surfaces

Trung Huynh, [email protected], Lorena Tribe.Division of Science, The Pennsylvania State University - Berks Campus, Reading, Pennsylvania 19610, United States

Layered double hydroxides (LDHs) are host-guest materials with special intercalation properties with a wide variety of anions. Biomolecules or pharmaceutical agents such as amino acids, DNA and vitamins (A,C,E) are some interesting molecules intercalated into LDHs. L-Cystine and L- Cysteine are amino acids that are widely used in the industrial world, for example in the food industry and pharmaceutical industry. From a theoretical point of view, LDHs provide an interesting counterpoint to smectite clays, having similarly layered structures but with positively charged internal surfaces. In this work we calculate the binding energy of the amino acids to the LDH surface, and we determine the best surface complex models for L-Cystine and L-Cysteine by calculating the vibrational frequencies and comparing them to experimental data. All models are developed with GausView, using density functional theory with Gaussian 09 to energy minimize and to calculate the IR vibrational frequencies.

CHED 341

Electron transfer kinetics in ionic liquids using DMPD-coumarin and a series of coumarin derivatives as controls

Megan Harries1, [email protected], Raluca Musat2, James Wishart2, Rouba Abdel Malak Rached1. (1) Department of Natural Science, Fordham University, NY, New York 10023, United States (2) Department of Chemistry, Brookhaven National Laboratory, Upton, NY 11973, United States

Model Donor-Bridge-Acceptor molecules have been used to investigate intramolecular electron transfer reactions. Our work describes kinetic experiments performed to study photoinduced electron transfer in DMPD-Coumarin where the DMPD-donor and the Coumarin-acceptor are separated by a single amide bond. This compound and two controls were characterized by MS and steady-state spectroscopic techniques. Preliminary results for the photoinduced electron transfer reaction were obtained by excitation of the Coumarin at 380 nm and its reductive quenching was monitored by transient absorption spectroscopy as well as time-resolved fluorescence techniques. Electron transfer kinetics were studied in such common solvents as acetonitrile and methanol and compared to those in ionic liquids, which are essentially non- volatile and recyclable solvents and therefore potential candidates to be used in energy related applications such as solar cells and batteries... Multiexponential kinetics were observed using ionic liquids which could be attributed to slower solvation dynamics in these media compared to conventional solvents.

CHED 342

Photolysis at the liquid-vapor interface of dihalogenated methane solutions Andres E Delgadillo, [email protected], Christina M McGuire, Baltazar Ramos, Edward Harrington, William T Nebel, Maria J Krisch.Department of Chemistry, Trinity College, Hartford, CT 06106, United States

Chemistry at the liquid-vapor interface of solutions can differ from that of bulk solutions. These differences were studied with droplets of chloroiodomethane and diiodomethane solutions in water and salt water. Streams of droplets were formed with a vibrating-orifice aerosol generator. The diameter was controlled from 50-140 µm to change the droplets' surface area to volume ratio, thereby increasing any interfacial effects. Droplets were exposed to ultraviolet light using a Pen-ray lamp (254 nm) or lasers (224 nm, 266 nm). Analysis was conducted using gas chromatography-mass spectrometry; the amount of dihalogenated methane in UV exposed samples was compared to unexposed samples. Although smaller droplets showed greater ranges of reaction than larger ones, variability in the results has rendered them inconclusive. One potential reason is that the droplets were not sufficiently small to demonstrate interfacial effects. Experiments on smaller droplets made with another technique are underway and will be discussed.

CHED 343

Accelerated curing method for the synthesis of nanoparticle embedded organic monoliths

Britney Bell1, [email protected], Robert Hougas1, Shannon Lum1, Stephen Gross1, Erika Pfaunmiller2, David S Hage2. (1) Chemistry, Creighton University, Omaha, NE 68178, United States (2) Chemistry, University of Nebraska at Lincoln, Lincoln, NE 68588, United States

Organic monoliths provide an opportunity for efficient separations or as a support for solid phase chemistry. Novel nanoparticles offer the possibility of significant improvement in separations. A method that rapidly incorporates nanoparticles functionalized with bioactive molecules at room temperature can avoid complications from the prolonged heat exposure in classic thermally polymerized systems. We have developed an accelerated radical curing method for the generation of an organic monolith system that can be done at room temperature on the timescale of 30 seconds to 30 minutes depending on the ratio of initiator and accelerator chemistry. The conversion of the vinyl groups in the organic monoliths by this approach in both “microcolumns” and microfluidic devices has been monitored by IR spectroscopy and confocal laser Raman microscopy, respectively. Current efforts focus on the comparison of separations by this new method relative to classic thermal systems and the effect of embedded nanoparticles on targeted separations.

CHED 344

Visible light curing method for the synthesis of nanoparticle embedded organic monoliths

Shannon Lum1, [email protected], Robert Hougas1, Theresa Greving1, Stephen M. Gross1, Erika Pfaunmiller2, David S. Hage2. (1) Chemistry, Creighton University, Omaha, NE 68178, United States (2) Chemistry, University of Nebraska at Lincoln, Lincoln, NE 68588, United States

Novel nanoparticles offer the possibility of significant improvement in separations. Organic monoliths provide an opportunity for efficient separations or as a support for solid phase chemistry. A method for the rapid, direct incorporation of nanoparticles functionalized with bioactive molecules can be complicated by the high temperatures associated with the classic thermal polymerization of organic monoliths. Additionally, classic thermal polymerization of organic monoliths requires a significant amount of time. We have developed a visible light cured organic monolith system that can be formed at room temperature on the timescale of minutes. The conversion of the vinyl groups in the organic monoliths by visible light curing in “microcolumns” and microfluidic devices has been monitored by IR spectroscopy and confocal laser Raman microscopy, respectively. Current efforts focus on the comparison of separations by this new method relative to classic thermal systems and the effect of embedded nanoparticles on targeted separations.

CHED 345

Ion permeable microcapsules for water purification

Grayson L Jackson, [email protected], Stephen Gross.Chemistry, Creighton University, Omaha, NE 68178, United States

Clean water is essential to human health, yet over a billion people lack sanitary drinking water, resulting in millions of preventable deaths every year. Although there are numerous water-quality issues, nitrates present a significant problem. The widespread use of fertilizers, combined with the high solubility of nitrates, has made nitrates an almost universal contaminant in water sources, especially aquifers. We have been working on the development of an innovative method for the removal of nitrates. This method of purification utilizes microcapsules that hold purified water. The microcapsules are designed to have a polymer-based membrane that is permeable to ions. This process should be relatively inexpensive and work by simple diffusion. We have studied the rate of nitrate removal from water using these microcapsules and have determined the role of chemical structure, concentration gradient and mass of microcapsule to volume of water ratio.

CHED 346

Diazaborole-linked 3D covalent organic frameworks

Spencer D. Brucks, [email protected], David N. Bunck, William R. Dichtel.Chemistry and Chemical Biology, Cornell University, Ithaca, NY 14853, United States

Covalent organic frameworks are an emergent class of crystalline materials entirely composed of light elements linked by covalent bonds which form two-dimensional stacked structures or three- dimensional networks. We developed 3D covalent organic frameworks, linked by diazaboroles, an aromatic linker with pH sensitive hydrolysis rates. Herein we report the first characterization of these materials with an eye towards payload release and network hydrolysis rates.

CHED 347

Investigating the photophysics of fluorescent conjugated metallopolymer chemosensors in the solid state

Sarah Dill, [email protected], Davis Anugo, Megan Fegley, Sherryllene Pinnock, Wayne Jones.Department of Chemistry, State University of New York at Binghamton, Binghamton, New York 13902, United States Fluorescent conjugated polymers (FCP's) have received attention for their potential to detect metal cations with selectivity and sensitivity, allowing identification of toxicants in environmental and biological systems. Transitioning these chemosensors from solution to solid state allows for increased portability and usability. Two polymers previously synthesized and characterized in solution, poly[2,5-(3-[N-methyl-N-(N',N'-dimethyl-2-ethanamino)methylamino]thiophenediyl)-1,2- ethynediyl-1,4-(2,5-didodecoxyphenylenediyl)-,2-ethynediyl] (tmeda-PPETE) and poly[2,5-(3-[N- methyl-N-(N',N'-dimethyl-2-ethanamino)methylamino]thiophenediyl)-1,2-ethynediyl-1,4-(2,5- didodecoxynaphthylenediyl)-,2-ethynediyl] (tmeda-PNETE), have been explored in the solid state. These thin films were made by dispersing each FCP in PMMA and PVA from room temperature solutions of THF. For tmeda-PPETE thin films, absorbance and emission spectra showed red shifts and peak broadening consistent with aggregation of the polymer chains. In solution, polymer fluorescence was completely quenched after addition of Cu2+, creating a polymer/Cu2+ hybrid sensor which showed particular sensitivity and selectivity towards iron cations. Preliminary testing has shown the polymer in PVA also quenches in response to Cu2+, with intensity dependent on exposure time.

CHED 348

Crystallization of poly(ethylene oxide)-b-poly(caprolactone) diblock copolymer films at varying temperatures

Elliott C. Hasenkopf, [email protected], Ryan M. Van Horn.Department of Chemistry, Allegheny College, Meadville, PA 16335, United States

The crystallization of diblock copolymers is greatly influenced by the melting temperature of each block. When melting temperatures are very similar, as in PEO-b-PCL, the length of each block has been shown to dictate which block crystallizes more readily. Samples of PEO-b-PCL copolymer films were cast from THF and allowed to crystallize at temperatures ranging from 20- 45°C (below Tm of both blocks). The crystalline state was observed by FTIR and DSC. The relative crystallization between PEO and PCL was analyzed. Results provide insight into the kinetics and solvent quality for each block as a function of temperature.

CHED 349

Preparation of poly(o-toluidine) as highly porous micron-scale spheres

Daniel LaFaurie, [email protected], David M. Sarno.Department of Chemistry, Queensborough Community College of CUNY, Bayside, New York 11364, United States

Substituted polyanilines can improve upon certain properties of the parent polymer. Though nanofibers of these materials are now widely reported, our own investigations of poly(o-toluidine), the methyl-substituted analog, have revealed additional and unexpected morphologies. The crude product, a thick precipitate produced in 1M HCl, rapidly agglomerates when exposed to ammonium hydroxide (1M and greater). By varying the concentrations of the monomer, oxidant, and base, we can obtain discrete, porous micron-scale spheres; clusters of highly fused, porous spheres; or low porosity slabs and “wrinkled” spheres. Notably, if the crude product is purified prior to adding the base, only a granular material is obtained. This indicates that the unusual structures are formed after the polymerization is complete and specifically under the conditions of the acid-base neutralization. In general, more concentrated base favors the formation of discrete spheres. Their porosity may make them useful in composite materials as encapsulants for other smaller particles.

CHED 350 Vapor phase polymerization of poly(3,4-ethylenedioxythiophene) using copper(II) catalysts

Nicholas A Ravvin, [email protected], Kenneth H Skorenko, Kyle LaFever, Peter N Kariuki, Joe Weiss, Lucas Sabalka, Peter Borgesen, Wayne E Jones.Department of Chemistry, Binghamton University, Binghamton, New York 13902, United States

Recently, the conducting polymer poly(3,4-ethylenedioxythiophene) (PEDOT) has been investigated as a transparent electrode and hole conducting material for photovoltaic devices due to its high conductivity and transmittance in the visible region. Vapor phase polymerization (VPP) of PEDOT has shown greater conductivity over solution based applications of PEDOT or copolymerization of PEDOT with poly styrenesulfonate. We have previously shown that the use of iron(III) tosylate as an oxidant produces VPP PEDOT films with conductivities as high as ~600 S/cm. While highly conductive, the iron oxidant causes degradation of titanium dioxide nanoparticles in the adjacent electron conducting layer of the solar cell. By utilizing copper(II) oxidant we have obtained films of VPP PEDOT with conductivities of ~30 S/cm without TiO2 degradation. We present results on VPP PEDOT growth control and effects on conductivity.

CHED 351

Synthesis and characterization of 1,3-bis(4-vinylbenzyl)thymine and its polymerization with vinylbenzyl triethyl ammonium chloride

Ngoc Chau H Vy, [email protected], Nancy E Lee, Richard W Gurney.Department of Chemistry and Physics, Simmons College, Boston, MA 02115, United States

1-(4-Vinylbenzyl)thymine (VBT) is a monomer that has attracted much attention in polymer research due to the versatile characteristics of its structure such as aromatic stacking, derivative site for functional group, photosensitive cross-linking site, and two or three parallel hydrogen bonding sites. During the synthesis of the monomer, we have isolated and characterized a byproduct, 1,3-bis(4-vinylbenzyl)thymine (bisVBT), a di-substituted VBT. This novel compound exhibits similar characteristics to VBT but unique properties upon polymerization due to the two vinyl groups in its structure compared to the single vinyl group on VBT. The synthesis and properties of the copolymer of bisVBT with vinylbenzyl triethyl ammonium chloride (TEQ) of different ratios will be described and compared to the known copolymer 1:8 VBT-TEQ.

CHED 352

Isocyanate functional benzoxazine cross-linking agent with model reactions to glycerin and poly(vinyl alcohol)

Kevin Chiou, [email protected], Erin Hollinger, Tarek Agag, Hatsuo Ishida.Department of Macromolecular Science and Engineering, Case Western Reserve University, CLEVELAND, Ohio 44106, United States

Benzoxazine thermoset is a material that exhibits unusual and advantageous properties, such as near zero volume change upon curing. A by-product of bio-fuel production from waste oil, glycerin, is used to model the reaction of cross-linking agent based on the benzoxazine chemistry. 4-hydroxybenzyl alcohol and aniline benzoxazine was reacted to 2,4 toluene diisocyanate followed by reaction to alcohols. FT-IR demonstrated formation of urethane bond by reaction between isocyanate functional benzoxazine and glycerin by disappearance of the isocyanate peak (2297cm-1) and doubling of urethane signal strength in comparison to known benzoxazine peak (937 cm-1). Nuclear magnetic resonance showed methyl group adjacent to isocyanate group at 2.20ppm shifting upfield to 2.10ppm, while benzoxazine signals remain unchanged (4.65ppm and 5.44ppm). This reaction was then used to characterize side-chain type polymer made of isocyanate functional benzoxazine and poly(vinyl alcohol). The resulting poly(vinyl alcohol) compound showed improved char yield as determined by thermogravimetric analysis.

CHED 353

Photosensitization of water-soluble polystyrene copolymers of vinylbenzylthymine and vinylphenylsulfonate

Veronica Nowakowski1, [email protected], Rich Gurney1, Debora M. Martino2. (1) Department of Chemistry and Physics, Simmons College, Boston, MA 02115, United States (2) Departamento de Física, Facultad de Bioquímica y Ciencias Biológicas, Instituto de Desarrollo Tecnológico para la Industria Química, Santa Fe, Argentina

Thymine-based polymers are especially interesting due to the photoinitiated cross-linking functionality of thymine that increases the polymers' strength and adhesion to surfaces. It is of great importance to determine whether sensitizer molecules promote photocrosslinking/immobilization of the thymine-based, water-soluble, polystyrene copolymers using low-energy irradiation (500 nm) as compared to the UV irradiation (280 nm) necessary for the standard photoinduced process to take place. Using a sensitizer, vinylbenzylthymine−vinylphenylsulfonate (VBT-VPS) copolymers were immobilized on polyethylterephthalate (PET) after exposure to visible irradiation. By exciting the sensitizer molecules in the presence of VBT copolymers at a wavelength where absorption by the latter does not occur, the triplet state of the sensitizer will be generated in high yields, and consequently, polymer photocross-linking takes place. UV−vis spectroscopy will be used to study the effect of irradiation dose, copolymer composition, and sensitizer concentration on the photoreactivity of VBT polymers.

CHED 354

Terminal functionalization of atactic-polypropylene oligomers: Toward the development of polymer-bound ligands and catalysts

Ben Lin, [email protected], Devin Lawler, [email protected], Christopher E Hobbs.Department of Chemistry and Biochemistry, Angelo State University, San Angelo, Texas 76904, United States

The development of terminally-functionalized atactic-polypropylene (ATPP) oligomers is described. Commercially available, olefin terminated, oligomers of ATPP can be converted into various functional groups utilizing straightforward organic transformations. Various methods (such as Friedel-Crafts alkylation) turned out to be a general route for the preparation of many of these derivatives. Acid-catalyzed electrophilic aromatic substitution reactions of ATPP with both activated and unactivated arenes was possible. Other chemistries associated with olefins can also be performed. A hydroboration/oxidation reaction of ATPP generates the primary alcohol in good yield. This species can be further transformed into other functional groups as well. Such species can serve as “Greener” ligand precursors for the development of polymer-supported catalysts that can be used as recoverable catalysts/reagents in thermomorphic/latent biphasic reaction conditions as they are shown to possess high phase selective solubility for nonpolar solvents.

CHED 355

Examination of functional group placement in dendritic structures: Preparation of "mixed" dendrimers for the encapsulation of pyrene from an aqueous environment Olivia N Monaco, [email protected], Amy M Balija.Department of Chemistry, Fordham University, Bronx, NY 10458, United States

Dendrimers provide a unique scaffold to examine how composition impacts macromolecular properties because functional groups can be strategically positioned within the dendrimer's highly branched architecture. Recently, we have discovered that combining 'Fréchet-type' benzyl ether groups with novel benzyl amine monomers result in stable dendrons containing both functionalities in a fixed arrangement. A series of 'mixed' second generation dendrimers from these dendrons have been developed. The synthesis and characterization of these dendrimers will be discussed. The ability of the 'mixed' dendrimers to entrap pyrene from aqueous environments will be disclosed, and the results will be compared with the properties of previously known 'Fréchet-type' benzyl ether dendrimers.

CHED 356

Allegheny College ACS student members encourage students to follow their dreams through “Women in Science” program

Brittany M Rauzan, [email protected] of Chemistry, Allegheny College, Meadville, PA 16335, United States

Women represent approximately 50% percent of the world population, but only 25% of the STEM (Science, Technology, Engineering, and Math) workforce. At the BA/BS degree level about 40- 50% of all STEM degrees are awarded to women. However, only one third of these women obtain a STEM PhD. In addition, there is a decrease in the number of women in STEM positions. Therefore, Allegheny College ACS student members sponsor a collaborative interdisciplinary support group with the chemistry, physics, biology, and neuroscience departments entitled “Women in Science” (WiS). WiS is designed to support students interested in pursuing a variety of careers related to the natural sciences and health professions. As an independent affiliate of the chapter, the WiS group puts on unique events tailored to needs expressed by the students. These types of events include discussion of recent articles in the media, guest speakers, and networking opportunities with faculty members.

CHED 357

University of Maryland, Baltimore County student chapter

Joyce Yoon, [email protected], Tara Carpenter, Scott Johnson.Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, MD 21250, United States

The Student Chapter at UMBC is a very active chapter with over 100 members. Our chapter spends time bringing chemistry awareness to campus, doing K-12 outreach and contributing to the community through events coordinated by our chapter as well as with the local Maryland section and national ACS. In the fall semester, all of our fundraising efforts went towards raising money for Pennies for PUR. We raised over $800 through beaker mug sales, a bake sale, pie-a- professor and more to donate to the cause. K-12 and community outreach included events at local elementary schools and the Maryland Science Center. The chapter also enjoys a pizza party at the end of every semester to celebrate accomplishments and get ready for finals week.

CHED 358

Chemistry outreach at Iota Sigma Pi: Hydrogen Chapter at the University of California at Berkeley Rebecca A. Murphy, [email protected], Jessica K. Kisunzu, [email protected], Piper J. Klemm, Jessica D. Douglas, Olivia P. Lee, Hoang Doan, Kaitlyn M. Weeber, Leah Rubin.Department of Chemistry, University of California at Berkeley, Berkeley, CA 94720, United States

Founded in 1902 at the University of California at Berkeley, Iota Sigma Pi is a national honor society for women in chemistry. We promote the professional development and personal growth of women in chemistry and related fields through recognition, community outreach, and the formation of supportive networks. In 2011, we supported the scientific community through outreach projects with the Girl Scouts of America, the Bay Area Science Festival, and local elementary and middle schools. In an effort to promote women chemists in the community, we also participate in joint events with the Women's Chemist Committee. Within the UC Berkeley College of Chemistry, we work to support undergraduate and graduate students through our Choosing a Research Group Panel and First Year Graduate Student Mixer. We also participate in joint events with the Women Chemists Committee. We also atrive to promote unity in our own department through brown bag lunches with faculty members.

CHED 359

Benzene and Benedictines: Saint Anselm College's chemistry club

Kathryn Demirdjian, [email protected], Jennifer Pace, [email protected], Julie Cristello, [email protected], Timothy Cooke, [email protected], Katharine Lunny, Ryan King, Nicole Eyet, Lisa Bonner.Department of Chemistry, Saint Anselm College, Manchester, NH 03102, United States

The Saint Anselm College Chapter of the American Chemical Society affords an opportunity for our chemistry students to become better aquatinted with their central science. The professional association provides intellectual stimulation and allows us to obtain experience in preparing and presenting technical material before chemical audiences. The chapter serves the community in a number of ways including performing demonstrations at local high schools and holding review sessions for the General Chemistry courses offered at Saint Anselm. Club members work towards the common goal of bringing “positive chemistry” to our campus through Periodic Table Cupcake bake sales and an annual Halloween demonstration. The Saint Anselm Chemistry Club also offers a means of networking throughout the members and faculty, as well as throughout the American Chemical Society. This chapter hopes to continue to foster a professional spirit among its members and to cultivate pride in the chemical sciences.

CHED 360

ACS Student Affiliate Chapter the Molloy Chemical Society from Saint Joseph's University

Brady O Werkheiser, [email protected], Eutchen Ang, [email protected] of Chemistry, Saint Joseph's University, Philadelphia, Pa 19131, United States

The Saint Joseph's University Molloy Chemical Society has recently reestablished itself as an active student body club. The Molloy Chemical Society consists of student associates of the American Chemical Society and is involved in organizing guest lectures, fundraising, campus and community awareness, and holding regular club meetings. This year we have organized two guest lectures; one on the topic of Protein Crystallography and one on Computational Chemistry in a Pharmaceutical Setting. Molloy Chemical Society fundraises through the sale of t-shirts and our Valentine's Day Test Tube sale. The money from these fundraisers go toward future Molloy events; such as attending the 2nd Annual Science Carnival in Philadelphia and attending the Regional ACS event in Philadelphia. The ultimate goals of the Molloy Chemical Society are to encourage scientific curiosity, establish a university and community presence, and provide students with opportunities to learn and experience all that is chemistry.

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UC Berkeley ACS chapter this year: Research, tutoring, outreach, and student-led class

Ritankar Das, [email protected] of Chemistry, UC Berkeley, Berkeley, California 94720, United States

The UC Berkeley ACS Chapter has started four major initiatives this year: Berkeley Chemical Review (BCR) undergraduate research journal, Undergradute Chemical Tutoring Program (UCTP), outreach in collaboration with student-run non-profit See Your Future (SYF), and student-taught course (CUIR) in the opportunities in industry and academia for the chemical sciences.

The BCR journal accepted over 40 submissions from undergradutes for its first issue, and was edited by a panel of 18 gradaute students and 12 faculty at UC Berkeley. It featured the breadth of chemical research from nanocrsytals to battery chemistry to polymers science. Also the BCR crew hosted a research journal symposium with the College of Chemistry and handed out cash prizes to the best submissions.

The UCTP program provided chemistry tutoring by upper-classmen in lower-division chemistry classes to over 600 students in 2012. Tutors were assigned to labs, held drop-in sessions, and/or hosted midterm and final exam reviews.

Outreach to various Bay area schools were done in collaboration with the SYF nonprofit. ACS student members worked with SYF volunteers to develop new demonstration and lab curriculum for K-12 in areas of green chemistry and sustainability, and perfomed those demos and labs at schools. Also, the chapter partnered with BESSA (Black Engineering and Science Student Association) for on campus high-school science recrutiment events.

The CUIR course was student led by four ACS officers and included guest speakers and field trips. Field trips were taken to UC San Francisco and Lawrence Berkeley National Labs. Guest speakers from local industry incldued Dow Chemical, Amyris, Peppertree Engineering, San Francisco Surgery, Kilpatrick Law and others. Speakers from academia included Prof. Jeffrey Reimer (Dept. of Chemical Engineering), Prof. Terry Johnson (Dept. of Bioengineering), Dr. Ron Zuckerman (LBNL), among others.

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Loyola University Maryland Chemistry Club

Emily Schehlein, [email protected], James Hoos.Department of Chemistry, Loyola University Maryland, Baltimore, MD 21210, United States

The intent of this poster is to outline the Loyola University Maryland Chapter's activity both on campus and as a part of the surrounding Baltimore community. This poster will provide details regarding how Chapter meetings are conducted, the ways in which the Chapter fosters intellectual curiosity in the chemical sciences, how the Chapter helps prepare members for careers in chemistry and for pursuing higher education in the chemical sciences, and finally the roles of service and social justice in the Chapter's community involvement. In addition to providing a summary of the Chapter's goals, the poster will also describe in full detail the activities in which the Chapter engages as an organization. These activities include peer tutoring, Chemistry Week demonstrations, and Project Clean Stream. Furthermore, the poster will address how the Chapter incorporates both the goals of the ACS and the Jesuit core values of Loyola University Maryland in devising and implementing its mission statement.

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Bridging the gap: Getting local 8th graders interested in science

Madison Fletcher1, [email protected], Yi Liu1, Amanda Stoddard2, Larra Agate2, Erin Cannan1, Christopher N. LaFratta1. (1) Department of Chemistry, Bard College, Annandale-on-Hudson, NY 12504, United States (2) Department of Science, Lincoln Avenue Middle School, Red Hook, NY 12504, United States

The Bard student chapter of the ACS worked with the Red Hook 8th grade class to strengthen their interest in science. The project took place in three phases: i) a field trip for the 8th graders to visit the science facilities at Bard in September, ii) guest lectures by Bard students in the 8th grade classroom throughout the year, and iii) an 8th grade science fair in April of 2012. In this poster, we will describe the outcome of each of these phases and share our thoughts on how similar community outreach projects may be structured. This project was sponsored by the ACS- Innovative Activities Grant.

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Urban student affiliate group integrates activities with public schools and technical colleges

Nicholas Nelson1, [email protected], Angelique DeCatur2, Jennifer Lathan2, Susan M. Schelble1. (1) Department of Chemistry, Metropolitan State College of Denver, Denver, CO 80217, United States (2) Department of Pharmacy, Heritage College, Denver, CO 80212, United States

The ACS Student Affiliate Chapter of Metro State College of Denver continues to be active on the campus and in the urban community. They have spearheaded the Earth Day celebration for the largest school distric in Colorado. This includes a contest that will collect food for local agencies that help the homeless. Former members of the Chapter who are now on the faculty at technical colleges in Denver have worked with new ACS students to bring science enhancement to institutions in the community.

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Student Affiliate Chapter of the American Chemical Society: Minot State University

Luke W Uran, [email protected], Joel Collins, Kowan O'Keefe, Mitchell Falkenberg, Mikhail Bobylev.Department of Science, Minot State University, Minot, ND 58707, United States

The Student Affiliate Chapter of the ACS at Minot State University is a fairly new organization that received its Charter in 2008. Working closely with the campuses Science Club, the students interact with the community through events such as the MSU at the Mall event, demonstrations to local schools and the annual Science Open House. All members of the Chapter have been very active in conducting research in chemistry and in presenting the research results at various science meetings including the National Meetings of the American Chemical Society. For the past four years the students made over eighty original research presentations at the national, regional, and local level. For two years in a row, in 2009 and 2010, MSU chemistry students were selected by the national Council for Undergraduate Research to present their research results to the members of the United States Congress at the Posters on the Hill session.

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Science Society honored by the American Chemical Society's ChemLuminary Award for the outstanding student event in the nation

Jacqueline Araujo, [email protected], Janet Osorio, Vanessa Arredondo, Sofia Pappatheodorou.Chemistry and Biochemistry, California State University- Dominguez Hills, Carson, CA 90747, United States

At the fall 2009 ACS National Meeting, the Southern California Section of the American Chemical Society (SCALACS) received the ChemLuminary Award for the best student program in the nation: CSUDH Science Society's National Chemistry Week (NCW) event ―Having a Ball with the Chemistry of Sports. This program, commemorating the preceding Summer Olympics, was a team effort among the Science Society, Athletics Department, and Student Health Center. A courtyard buffet was served, while cheerleaders furnished the spirit, and SCALACS officers described the purpose of NCW and the importance of volunteerism. The athletics department followed, linking chemistry to effective athletic training; our student health educator explained the importance and composition of diet; a Science Society Officer (chemistry student) explained the importance of chemistry throughout the history of the Olympics; and a CSUDH alumnus, former athlete, now dentist, demonstrated the materials and process for making custom mouth guards for athletes. The festive program ended with several games relating chemistry and sports.

CHED 367

Strategies for the discovery of innovative therapeutics

Magid Abou-Gharbia, [email protected] Center for Drug Discovery Research, Temple University, Philadelphia, PA 19140, United States

Drug Discovery and Development is a challenging and complex process that involves the dedicated multidisciplinary efforts of many discovery and development functions. Despite of the breakthroughs in innovations and process refinements that have dominated drug discovery during the last two decade, the number and diversity of new chemical entities (NCE's) approved for human use has not kept pace from the 1980's to now. Pharmaceutical industry is currently facing enormous challenges, such as reduced efficiencies, declining innovation and the industry's perceived tarnished image. There is a clear need for change in the paradigms designed to address these challenges. While Pharma have embarked on a range of initiatives, other sectors have also responded. Several academic drug discovery centers have also recently been established to facilitate the transition of innovative academic ideas and breakthroughs into attractive drug discovery opportunities. The presentation will highlight challenges facing the pharmaceutical industry with emphasis on the impact of chemical sciences and academic Drug Discovery Centers in addressing the innovation gap.

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Evolving role of chemistry in small molecule drug discovery Peter R. Bernstein, [email protected] LLC, Rose Valley, PA 19086, United States

Over the last several decades the role of chemistry in small molecule drug discovery has changed dramatically. The function that chemists fill in R&D efforts have become more diverse, complex and specialized, all at the same time. However, at the end of the day an effective small molecule drug is a chemical with a very specialized set of properties that allow it to be safely administered to people. Using examples from 30+ years of Drug Discovery this talk will illustrate how from a starting point at which synthetic organic chemistry was the “core” chemical science it is now but one part of a complex amalgam. Now the medicinal chemist is more of a conductor/composer who designs and develops a drug via the integration of input from synthetic, analytical, computational, structural biological, physical, and informatics chemists.

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Structure-based discovery of a novel Factor Xa inhibitor, Eliquis_/Apixaban, as a new anticoagulant and the discovery of Chan-Lam coupling reaction

Patrick Y. Lam, [email protected] Drug Discovery Consulting, LLC; formerly at BMS, Chadds Ford, PA 19317, United States

Thrombosis is the leading cause of death in developed countries and there is significant need for novel antithrombotics with an improved safety profile. Factor Xa is at the junction of the intrinsic and extrinsic pathways of the coagulation cascade. Preclinical data has demonstrated that blocking FXa is an effective approach for anticoagulation with improved safety profile. Utilizing structure-based drug design tools, we at Bristol-Myers Squibb have discovered a novel class of potent, selective and orally bioavailable Factor Xa inhibitors culminating in Eliquis®/Apixaban. Eliquis® is being evaluated in a series of ongoing or completed Phase III clinical trials.

During the optimization process, we have also discovered the powerful Chan-Lam Coupling reaction of copper promoted C-X bond cross-coupling via boronic acids, a complementary reaction to Suzuki-Miyaura Coupling.

CHED 370

Chemistry of inflammation and cancer: Lessons from inflammatory bowel disease

Steven R. Tannenbaum, [email protected] of Biological Engineering, Chemistry, and Toxicology, Massachusetts Institute of Technology, Cambridge, MA 02139, United States

When tissues are exposed to Inflammatory stimuli such as bacterial infections, inflammatory cells, including macrophages and neutrophils migrate to and invade the infected or damaged tissue. In a mouse model of inflammatory bowel disease (IBD) and colon cancer, bacterial infection leads sequentially to chronic inflammation, dysplasia and cancer, by a process that is promoted by pro- inflammatory cytokines/chemokines, oxidative and nitrosative stress and DNA/protein damage. The invading inflammatory cells produce a complex mixture of chemicals, including NO, H2O2 , HO•, CO3−•, HOCl, and NO2•, which damage and lead to degradation of proteins, lipids and nucleic acids, ultimately inducing mutation and/or cell death. Mass spectrometric analysis of protein and nucleic acid damage in the mouse and human validates the model. Application of the results to the discovery of serum biomarkers of the disease can monitor disease severity and activity in IBD patients.

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Chemistry and regulatory in drug development

Bonnie A. Charpentier, [email protected] of Directors, American Chemical Society, United StatesMetabolex Inc., Hayward, CA 94545, United States

The process of turning a molecule into a medicine involves not only good science, but the ability to meet regulatory requirements for development and approval. Regulations and guidances have grown and changed over time, often as a result of public safety disasters.

Chemistry is important at every step of the discovery and development of new medicines. Chemistry is directly involved in drug design, synthesis, isolation, formulation, manufacturing of drug products (e.g., tablets, capsules, injectables), quality testing, and measurement of drugs and drug metabolites in animal testing and in human clinical trials. Training in chemistry, in particular analytical thinking skills, can be very helpful in guiding drug development, not only in the laboratory but in such careers as regulatory affairs.

This presentation will describe some of the history of drug regulations and the current role of chemistry in the development and approval of new drugs.

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Susan Hixon and her support of NSF projects for community college students and faculty

Thomas B. Higgins, [email protected] of Physical Sciences, Harold Washington College, Chicago, IL 60601, United States

The role of two-year colleges in higher education is important and growing, and Susan Hixon played a key role in expanding NSF support for these institutions. This presentation will describe two community college based projects that have had positive impacts on both students and faculty: The STEM-ENGINES Undergraduate Research Collaborative (URC) and the ChemEd Bridges (CEB) project. The URC supported authentic undergraduate research opportunities for almost 300 community college undergraduates. The observed impacts of this early research experience were increased skill development, enhanced transfer rates, and students' greater realization of their potential to earn STEM degrees. Students from underrepresented groups and first-generation college students were strongly impacted. CEB targeted community college faculty and scaffolded their development as teacher-scholars through travel support, symposium organization, network building, and mentoring. Almost 60 faculty were impacted, and many were empowered to become leaders at their colleges and within their professional societies.

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PLTL implementations: Different environments, different issues, similar outcomes

Pratibha Varma-Nelson, [email protected] for Teaching and Learning, IUPUI, Indianapolis, IN 46202, United States Using PLTL as an example, a discussion of what it takes to implement the same pedagogy at three different institutions (a liberal arts college, a comprehensive public urban university and a urban research university) will be included. While critical components for successful implementation of PLTL were articulated early on what was not clear was how they need to be interpreted and modified in the context of the culture of the institution, institutional type, and the demographics of the students. The result, not surprisingly was that implementation of PLTL at different institutions ended up being quite unique. Adapting PLTL to the cyber environment presented yet another set of unique and interesting challenges, which promise to shed light on what it takes to transform an established face-to-face pedagogy for successful online learning.

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Still becoming: A career born in systemic reform

Jennifer E Lewis, [email protected] of Chemistry, University of South Floride, Tampa, FL 33620, United States

The systemic initiatives changed my life. The opportunity to serve as a post-doctoral associate for ChemConnections introduced me to the challenging task of curriculum reform, and the need to support reform efforts has influenced my career ever since. Spending two formative years in the reform community, listening to faculty share their successes as well as their failures, helped me to understand why the NSF has continued to find ways to support college chemistry faculty in their desire to improve college teaching. From my own small NSF-supported reform efforts as a faculty member to the broader stage of coordinated national projects, developing new skills to address the complex problem of curricular change has driven my career forward. Now, with formal evaluation and measurement training to support my practice, I hope that I am continuing to further the prospects for successful curricular reform in my ongoing work as a project evaluator.

CHED 375

Trajectories of reform: The role of chemistry content

Angelica M Stacy, [email protected] of Chemistry, University of California,Berkeley, Berkeley, CA 94720, United States

More than 15 years ago, the National Science Foundation launched a major initiative to reform the undergraduate chemistry curriculum. A key goal has been a paradigm shift away from memorization of a laundry list of facts to deeper understanding of key ideas in chemistry. This has required an examination of course content from a viewpoint of building knowledge and promoting understanding. In this regard, starting with meaningful contexts, data, and observations is important both to situate the learning, and to allow students an opportunity to derive patterns and develop explanations. Studies of student learning in classes that promote such understanding will be presented.

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At least they don't throw things anymore: One chemist's views on curricular reform in undergraduate chemistry over the past twenty years

Rick Moog, [email protected] of Chemistry, Franklin & Marshall College, Lancaster, PA 17604, United States Over the last two decades, a culture change has been occurring with respect to the acceptance and use of alternative teaching methods in the undergraduate chemistry curriculum. Much of this progress has been due to the generous support of the National Science Foundation. In this presentation, I look back on what has transpired over the past twenty years in terms of both new instructional methods that have been introduced and the extent to which they have been accepted.

CHED 377

Cooperative chemistry laboratories: A 20-year study

Melanie M Cooper, [email protected], Santiago Sandi Urena.Department of Chemistry, Clemson University, Clemson, South Carolina 29634, United States

Over the past 20 years the NSF Division of Undergraduate Education has funded a wide range of curriculum reform projects in chemistry. During that time, the body of knowledge and research upon which we can call has grown considerably, allowing us to make more informed decisions about how curricula should be designed and assessed. In this presentation I will discuss how a project that was funded by NSF-DUE 20 years ago (NSF 9155954) has been institutionalized and disseminated, and how, during the course of the next 20 years, we developed assessment methods that allowed us to investigate and assess a range of outcomes for both participating students and graduate teaching assistants.

CHED 378

Effect of the SFFP report on the MCAT exam and medical school admissions

Karen Mitchelll, [email protected] Office, Association of American Medical Colleges, Washington, DC 20037, United States

The 2009 AAMC/HHMI report on the Scientific Foundation for Future Physicians (SFFP) has been foundational both for the work of the MR5 (fifth comprehensive review of the MCAT) committee and in medical school admissions generally. The SFFP committee advocated for the preparation of entering medical students to be based on the attainment of science competencies rather than the completion of a set of pre-requisite courses. The SFFP committee described and recommended a set of scientific competencies for entering medical students. The MR5 committee used these competencies as an organizing framework for testing the natural sciences on the next version of the MCAT exam (scheduled for release in 2015). Within medical school admissions, there is now a move to consider dropping historic pre-requisites and going to a competency basis for evaluating entering medical students.

CHED 379

NEXUS: Developing competency-based undergraduate science curricula

Cynthia M Bauerle, [email protected] Education, Howard Hughes Medical Institute, Chevy Chase, MD 20815, United States

The 2009 Scientific Foundations for Future Physicians (SFFP) report, sponsored by HHMI and the AAMC, recommends competency-based approaches for the preparation of undergraduates who will become medical students, and medical students who will become physicians. At the undergraduate level, the challenge is to develop strategies to implement the recommendations. The National Experiment in Undergraduate Science Education (NEXUS) is a multi-year institutional collaboration to develop shared strategies toward implementation and assessment of competency-based science curricula. Objectives are to consider and enact the recommendations for undergraduate premedical education set forth in the SFFP report; to develop tools to evaluate competencies across undergraduate science curriculum; and to contribute information to broader conversation about impact of the SFFP recommendations. Project teams are developing competency-based curricular modules and working together to coordinate pilot experiments.

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New model for physician education: Opportunities for curricular change in premedical education

Bradford D Pendley, [email protected] of Biomedical Engineering, University of Memphis, Memphis, TN 38152, United States

The education of contemporary physicians requires a paradigm shift in premedical and medical education. To skillfully practice medicine in the 21st century, physicians must develop competency in several domains: basic scientific principles and their application to medicine; clinical observational skills grounded in the scientific method; the ability to extract and integrate pertinent information from an array of data; and the emotional intelligence and communication skills to understand a patient's needs and articulate the physician's thoughts regarding a diagnostic or therapeutic plan to address these needs. The current curricular focus on content should evolve into a competency based curricula with particular emphasis on the extraction and integration of pertinent data in the problem solving process, as this skill distinguishes physicians from other health care professionals. In this talk, I will present specific ideas related to curricular reform that can facilitate these changes.

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Chemistry for pre-professional and biological science students: A 1-2-1 approach

Marc Loudon, [email protected] Chemistry and Molecular Pharmacology, Purdue University, West Lafayette, IN 47907, United States

We will discuss the Purdue approach for revising the general chemistry and organic chemistry offerings for pre-professional students. The Purdue model is a 1–2–1 semester model for general chemistry, organic chemistry, and biochemistry. This plan has been actively implemented for pre- pharmacy students, with the expectation that it will be also implemented for qualified pre-medical and biological science students in the near future. Although the component courses have retained their traditional names for administrative convenience, there is considerable integration across this curriculum. We will discuss the general chemistry/organic chemistry sequence, in which we have taken the approach of developing specific modules for areas that have not necessarily been available in traditional courses and textbooks. The challenges for implementation and assessment are important, and these will be discussed.

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Developing a one semester course: Organic biological chemistry

Karin S Åkerfeldt, [email protected] of Chemistry, Haverford College, Haverford, PA 19041, United States The first two years of introductory chemistry at Haverford College are undergoing major changes, in part in response to the new guidelines put forth by AAMC-HHMI. I will describe our restructuring efforts, emphasizing the second year organic chemistry curriculum. Some introductory organic chemistry is now included in the first year of our curriculum. Spectroscopy is also emphasized, particularly in lab, where all students get hands-on experience with a variety of techniques, including IR and NMR. This setup allows an intermediate treatment of organic chemistry at the sophomore level. The first semester, which is the only semester required for our pre-health students, predominantly emphasizes the properties, reactivity and biochemical transformations of biomolecules in an aqueous environment. Additionally, with the goal of getting the students into the current scientific literature, they read articles and write short essay/commentaries on "Key Concepts," such as "Why phosphorus and not arsenic?" The second semester of organic chemistry is then focused on organic synthesis, including stereoselective aldol condensations and some metalorganic chemistry.

CHED 383

Response to MCAT2015: New chemistry and biochemistry major course sequences at Washington and Lee University

Lisa T Alty, [email protected] of Chemistry, Washington and Lee University, Lexington, VA 24450, United States

Washington and Lee University is a small liberal arts college that has more bioscience and chemistry majors pursue careers in health professions than Ph.D. studies in the disciplines. As a result, the announcement of the new biochemistry requirement for MCAT2015 inspired us to redraw our chemistry and biochemistry major course sequences, producing a path that allows all pre-health students to enter biochemistry in the fall of the junior year. This new path begins with a one-semester general chemistry course covering the majority of the general chemistry competencies on MCAT2015. Adjustments were made to the analytical and physical chemistry courses to regain topics “lost” from the current year-long general chemistry course. I will present the syllabus for the new one-semester general chemistry course, the course sequence for the major, and the evolution of the discussions that led to this outcome.

CHED 384

Changes in science faculty demographics FY2002 - FY2012, as quantified by the Nelson surveys

Donna J Nelson, [email protected] of Chemistry and Biochemistry, University of Oklahoma, Norman, OK 73019, United States

The Nelson Surveys determine national faculty demographics in the "top 100" departments in each of 15 science and engineering disciplines. These surveys have been carried out four times over the last 10 years -- FY2002, FT2005, FY2007, FY2012. Each was conducted by using the same methodology, which enables a valid comparison of demographics over this 10-year time period. This comparison will be presented, and results for disciplines will be compared and contrasted.

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Supporting women scientists via the NSF ADVANCE program Georgia A. Arbuckle-Keil, [email protected], Pamela Gleason.Department of Chemistry, Rutgers, The State University of New Jersey, Camden, NJ 08102, United States

Rutgers, The State University of New Jersey, received a five year award from the National Science Foundation (NSF) ADVANCE program in Fall 2008. This program seeks to increase the participation and advancement of tenure-track women in academic science via institutional transformation. The goals of the RU FAIR (Rutgers University Faculty Advancement & Institutional Re-imagination) project are to improve recruitment & retention; enhance communication between schools & campuses; encourage interdisciplinary research; improve visibility of women faculty; and enhance resources for dual career families as well as families with children. On the Camden campus, Arbuckle-Keil is one of only three tenured female faculty in the physical sciences (including math & computer science). RU FAIR professors were selected (competitive application) to implement grassroots solutions for women in SEM fields on each of the geographically diverse campuses of the university. Both accomplishments and challenges will be discussed.

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Studying the climate for female faculty at a teaching focused school with increasing research expectation

P. Denise Cobb, Susan D. Wiediger, [email protected], Lynn M. Maurer, Leah C. O'Brien, Danice L. Brown, Christa C. Johnson.Southern Illinois University Edwardsville, Edwardsville, IL 62026, United States

A team at Southern Illinois University Edwardsville has been gathering data about the climate and environment for tenured and tenure-track faculty, particularly women and underrepresented minority women in social, behavioral, and natural sciences as well as engineering and mathematics. Results from surveys, interviews, and institutional data sources suggest that, while there are similarities, there may be significant differences between this regional comprehensive public master's institution and other types of institutions that have done similar studies. Funded by a National Science Foundation grant through the ADVANCE IT-Catalyst program, the findings raise interesting questions about ways to support female faculty.

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Solutions to problems women in chemistry face in their career advancement

Elizabeth Ann Nalley, [email protected] of Physical Sciences, Cameron University, Lawton, OK 73505, United States

This presentation will review the progress women chemists have made in attaining leadership position in both academics and industry during the past seventy years. It will also discuss problems women in academic positions have faced during this period. There are many problems which are common to women around the world. Factors which affected their progress and problems that women had to deal with in overcoming obstacles in their path will be discussed. Although the proportion of women in the chemical community has increased significantly during this period, women still have not achieved parity with men. Strategies for developing a network and for solving these problems will be discussed.

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Careers in college teaching in non tenure track positions Laura S Sremaniak1, [email protected], Amy L. Nicely2, [email protected]. (1) Department of Chemistry, North Carolina State University, Raleigh, NC 27695, United States (2) Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, United States

Careers in college and community college teaching off the tenure track will be discussed from multiple viewpoints and dimensions, including appointment types and lengths, availability of benefits, the ability to participate in governance, academic freedom, and work-life balance. Women are disproportionately represented in lecturer positions nationwide, and nearly 1/3 of all chemistry faculty are non-tenure track. Survey results from the ACS, AAUP, and COACHE will also be reviewed and put in the context of the authors' experiences on this career track.

CHED 389

What I wish someone had told me: Managing your own professional life

Lisa M Balbes, [email protected] Consultants LLC, Kirkwood, Missouri 63122, United States

From organic chemistry graduate student to computational chemistry researcher to freelance technical communication consultant, Lisa has had a very nontraditional career. Along the way, she has learned a lot of lessons, and her side job now is helping younger scientists learn how to manage their own professional lives. This presentation will detail those lessons, and what current scientific professionals can learn from them. Chief among the skills described will be flexibility, perspective, and the importance of networking, communication and other soft skills. Specific examples of the importance of each, along with tips for improving your own professional destiny and resources for more further study will be provided.

CHED 390

WITHDRAWN

CHED 391

From career inception to career progression: Turning obstacles into opportunities

Angela K. Wilson, [email protected] of Chemistry, University of North Texas, Denton, Texas 76203, United States

The numbers of chemists encountering career challenges, from career location decisions due to personal situations to extended time periods in postdoctoral positions is on the rise. Unfortunately, many chemists must make these decisions very early in their careers, preventing traditional pathways to their desired career opportunities from being pursued, and, many of these chemists believe their situations are futile. This presentation provides an account of how a number of career obstacles (i.e. challenges of a two-body problem in a non-ideal location) resulting in a perceived lack of career options can be turned around into desired career opportunities, albeit a somewhat tortuous pathway.

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Science teaching for the new economy Miyong Hughes, [email protected], Suzanne Lunsford, [email protected], Wright State University, Dayton, Ohio 45435, United States

Wright State University offers summer and academic year science professional development workshops for teachers of grades 4-12 to experience the integration of geology, chemistry and biology in an inquiry-based field, lab and distance learning setting. The goal of the two week summer field experiences and a four-week internet course is to allow science and math educators the opportunity to build their knowledge on important environmental issues that impact their world. These field experiences allow teachers to collect samples for their own classrooms and make connections with industry to utilize needed instrumentation skills (XRF, SEM, IR). The need for learning the new technology and instrumentation is vital part to succeed in the STEM fields of study and teach their students the new techniques to develop their own inquiry-based classrooms.

The challenges of working to build a strong science education program with little to no funding will be discussed in relation to departmental issues and conflicts with being a female in science.

CHED 393

Health by design: Dow Wolff cellulosics excipient innovations for the pharmaceutical industry

Bob Maughon, [email protected] Materials Business Group, Dow Wolff Cellulosics, United States

Dow Wolff Cellulosics delivers high-performance cellulose derivatives and companion chemistries used for formulations across a broad variety of applications in the Food & Nutrition and Pharmaceutical markets. Our goal is to tailor polymer chemistry, morphology, and blending into solutions that enable our customers to provide consumers healthier outcomes. In Modified Release, our research is targeted towards enabling formulators and manufacturing teams to address the regulatory and sustainability initiatives from dosage form development through commercialization. Focus areas include modeling the performance design space to better predict structure-property relationships enabling enhanced Quality-by-Design, the development of materials that can deliver direct compression which can reduce processing and energy consumption costs by as much as 30%, and improved technologies for Osmotic Delivery Systems. In Immediate Release, recent developments in low viscosity HPMC polymers and their applications to improve product performance and sustainability vs. conventional methods in coatings, capsules, and granulation will be discussed.

CHED 394

Development of blockbuster drugs in the 21st century: A personal journey

Mick Hurrey, [email protected] Physics & Analytics, Materials Discovery and Characterization, Pharmaceutical Development, Vertex Pharmaceuticals, Cambridge, MA 02139, United States

Turning a drug candidate into a world-class medicine takes a number of years and a number of smart people. Some pharmaceutical scientists, hampered by factors beyond their control, spend their entire careers without launching a successful drug. During my eight years at a medium-sized biotech company, I've had the privilege of helping launch two, both of them successful. In this talk, I'll take you through my perspective on the key factors needed to develop a drug through clinical trials and eventually to launch it. I'll also give you examples of the inevitable blood, sweat, tears, and luck it takes to succeed.

CHED 395

Forensics in the pharmaceutical industry

Nancy Lewen, [email protected] & Bioanalytical Development, Bristol-Myers Squibb, New Brunswick, NJ 08903, United States

Pending

CHED 396

Chemists, chemistry, and the FDA: Building quality into drug manufacturing

Elizabeth Pollina Cormier, [email protected] Standish Place, US Food and Drug Administration, Rockville, MD 20855, United States

It is fair to say that most scientists entered their fields of study with the idea that they would improve the life of those around them. Throughout the last century, FDA staff, many of them chemists, have been striving to both protect and promote public health. A fundamental component of any drug application is the Chemistry, Manufacturing, and Controls (CMC) technical section. The ultimate goal of the CMC section is to ensure that drug manufacturers have built quality into their products so that the drugs our children take tomorrow are as safe and effective as the ones we approve today. This talk will explore the importance of quality controls and the role FDA plays in the drug development process.

CHED 397

Interdisciplinary projects in DUE

Herbert H Richtol, [email protected] Undergraduate Education, National Science Foundation, Arlington, VA 22230, United States

This presentation will cover a number of NSF supported interdisciplinary projects that are chemistry related. Many recent DUE proposals now are partnerships between chemists and other discipline people. Some personal remembrances of Susan Hixson's contributions to chemistry education will also be discussed.

CHED 398

Improving STEM student success and beyond: One STEP at a time

Maureen Scharberg, [email protected] Academic Success Services, San Jose State University, San Jose, CA 95192-0018, United States

Five years ago, San José State University (SJSU) received a NSF STEM Talent Expansion Program (STEP) grant (Type 1A, Grant #0653260). With Susan Hixson's support, we embarked on a journey to transform our STEM student culture by implementing a comprehensive support program. Our College of Science STEP program has the following elements: mandatory academic advising, progress to degree program, College of Science Advising Center (COSAC), supplemental instruction, a probation course, and peer advising and tutoring. In the final year of our project, we have had a measurable increase in the retention of STEM majors. It is important to note that many of these key elements have been institutionalized. Four other SJSU colleges have started their own student success centers, following the COSAC model, with support from the Provost's Office. The overall effect of our STEP grant along with Susan's support has definitely transformed the student success culture at SJSU.

CHED 399

Preparing the next generation of STEM faculty: Integrating research, teaching, and learning (CIRTL)

Robert D Mathieu, [email protected] of Astronomy, University of Wisconsin - Madison, Madison, WI 53726, United StatesCenter for the Integration of Research, Teaching and Learning, University of Wisconsin - Madison, Madison, WI 53726, United States

Graduate students and post-doctoral scholars will shape future undergraduate STEM education in the United States. The Center for the Integration of Research, Teaching and Learning (CIRTL), comprising 25 major research universities, seeks to enhance excellence in undergraduate education through the development of future and current faculty in STEM who have the skills to implement and advance effective teaching practices for diverse learners. CIRTL is founded on three core ideas: teaching-as-research; learning community; and learning-through- diversity. This talk will provide an overview of effective models and resources for programs to prepare future faculty for careers as both excellent researchers and excellent teachers; and will present research findings on the outcomes of such professional development.

CIRTL has benefited immeasurably from the guidance and wisdom of our NSF Program Officer, Dr. Susan Hixson. It is our great pleasure to honor her contributions to the future STEM faculty of the United States.

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Emerging best practices in assessment: What constitutes a good measure of a good measure?

Stacey Lowery Bretz, [email protected] of Chemistry and Biochemistry, Miami University, Oxford, OH 45056, United States

Several chemistry education research (CER) groups have emerged with expertise in assessment over the last 20 years, due in no small part to support from the NSF Division of Undergraduate Education. This presentation will describe the trajectory of one of those groups, namely the author's, across several NSF-funded projects. The creation of tools to advance our understanding of how students learn to think like chemists, as well as their understanding of this thinking, will be discussed. Emerging insights regarding the underlying assumptions and appropriateness of psychometrics are gradually replacing routine statistics to establish reliability and validity. Ultimately, CER must not only answer the question of what do students know, but also the question of how do we measure the quality of our measures?

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Leadership of Dr. Susan Hixson in DUE at NSF Bert E. Holmes, [email protected], University of North Carolina-Asheville, One University Heights, CPO # 2010, Asheville, NC 28804, United States

During 19 years of leadership in the Division of Undergraduate Education at NSF Susan Hixson has had an inordinate impact on chemistry education. A summarily account of Susan Hixson's contributions will be presented and an “insiders look” at her leadership style will be chronicled.

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Trends in NSF-supported undergraduate chemistry education, 1992-2012

Susan H. Hixson, [email protected], United States

When support for undergraduate STEM education was reestablished at the National Science Foundation in the 1980's, the initial focus was on providing instrumentation for the improvement of undergraduate laboratory courses. Over time, support through the Division of Undergraduate Education broadened to encourage the development of materials, pedagogies, and strategies for faculty development that would improve courses in the STEM curriculum; emphases on systemic approaches to curricular changes; focused efforts in assessment, evaluation, and educational research; and institutional efforts in technician education, teacher preparation, and increasing the number of STEM graduates. Trends that occurred during the period 1992-2012, and their impact on undergraduate chemistry education, will be highlighted and discussed.

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Second semester organic chemistry options: "Bioorganic Chemistry" or "Organic Mechanisms and Synthesis"

Albert Matlin, [email protected], Jason Belitsky.Department of Chemistry and Biochemistry, Oberlin College, Oberlin, Ohio 44074, United States

In 1994 the Oberlin Chemistry and Biochemistry Department completely redesigned its curriculum. As part of this change the traditional 2-semester course in organic chemistry (where half of the text is covered in the first semester and the second half of the text is covered in the second semester) was dropped. We replaced these two courses (Chem 205/206) with three courses: Chem 205, Principles of Organic Chemistry; Chem 254, Bioorganic Chemistry; Chem 325 Organic Mechanism and Synthesis. Chem 205 is a rigorous overview of the traditional 2- semester course and is the prerequisite for Chem 254 and Chem 325. Chem 254 is a cross between organic chemistry and introductory biochemistry. Chem 325 is a second pass at the more traditional organic topics skipped in Chem 205. The details of these courses will be presented.

CHED 404

Building a stronger foundation: Redefining the chemistry core curriculum at the University of Memphis

Abby L. Parrill, [email protected] of Chemistry, The University of Memphis, Memphis, TN 38152, United States

Chemists today often work at the interfaces of the traditional chemical subdisciplines. The Department of Chemistry at the University of Memphis recently restructured its curriculum to provide all majors with a common foundation in the five traditional subdisciplines of chemistry with advanced electives at the interfaces of several traditional chemical subdisciplines in order to better reflect how modern chemistry is practiced. In addition to providing students with strong foundations and a realistic picture of modern chemistry, the curriculum was designed to better prepare students for health professional programs and reduce the longest sequence of courses to aid students who select the chemistry major later in their academic career to complete their degree in a timely fashion. The curriculum revisions and our preliminary assessments will be described.

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Development of a foundation course that integrates organic, inorganic, and biochemistry

Chris P Schaller, [email protected], Kate J. Graham, Brian J Johnson, Edward J McIntee, Alicia A Peterson.Department of Chemistry, College of Saint Benedict/Saint John's University, Saint Joseph, MN 56374, United States

The Chemistry Department at the College of St. Benedict/St. John's University has developed a new course focused on the reactivity of organic, inorganic and biomolecules (Chem 250, Reactivity I). This course is the first of a sequence of foundation courses in a curriculum revised to fit the new ACS CPT guidelines. In addition, we specifically designed the course to help students achieve competencies in concepts needed for subsequent professional programs such as graduate programs in chemistry and health sciences. In order to build on common themes in chemistry and reduce artificial boundaries between subdisciplines, the course is built on themes of Lewis acid-base concepts, thermodynamics and carbonyl reactivity. Topics include metal- ligand complex formation, nucleophilic addition to organic carbonyls, and biochemical pathways such as glycolysis and the TCA cycle. We will provide an overview of the content of this course sequence within the context of the entire curriculum. Preliminary assessment data will be provided.

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Evaluation of W&J's realigned “organic first” chemistry curriculum and the potential benefits for MCAT2015 preparation

Mark F Harris, [email protected], Steven M Malinak, [email protected] of Chemistry, Washington & Jefferson College, Washington, PA 15301, United States

In 2005 the chemistry department at Washington & Jefferson College instituted a new curriculum which involved a realignment of topics traditionally taught in a four-course general/organic chemistry sequence, resulting in organic being taught in the first year followed by courses in inorganic and analytical in the second year. Assessment data will be presented that suggest the net impact of this change has been positive. For example, the department has attracted more majors and the biology program reports greater student success in introductory biology in part because of the organic background students now acquire earlier. The new curriculum allows for expanded coverage of analytical topics, facilitates conceptual learning by addressing disjointed “general chemistry” concepts within the context of major chemistry subdisciplines, and fosters interdisciplinary connections between biology and chemistry by introducing organic molecules in the first semester. All of these may assist students in their preparation for MCAT2015.

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Organic chemistry teaching at the University of Oklahoma Donna J Nelson, [email protected] of Chemistry and Biochemistry, University of Oklahoma, Norman, OK 73019, United States

Research in Organic Chemistry teaching and recent changes in the Organic Chemistry curriculum at the University of Oklahoma will be discussed.

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Juniata College “Organic First" chemistry curriculum: Addressing the needs of the premedical student

Richard R. Hark, [email protected] of Chemistry, Juniata College, Huntingdon, PA 16652, United States

For nearly 20 years freshmen at Juniata College have taken a two-semester organic chemistry sequence that emphasizes material particularly relevant to the needs of students in the life sciences and pre-professional areas. The “Organic Chemical Concepts” courses and the associated textbook, which are specifically designed for first-year students, eliminate the vast majority of topics that are less important for life scientists while integrating as many biology- related topics as possible. Such an approach has several advantages over the more traditional sequence beginning with “general chemistry” and aligns well with recent recommendations for changes in the premedical chemistry curriculum. In particular, biochemistry can be introduced earlier and biology courses can begin building on organic chemical concepts in the sophomore year. Anecdotal and quantitative evidence of the advantages and effectiveness of this curriculum will be shared.

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You do not look like a chemist – periodically speaking

Ruth A Woodall, [email protected] Scholars, Tennessee Chamber of Commerce & Industry, Nashville, TN 37203, United States

Have you ever been told that you do not look like a chemist? What does a chemist look like? There is a simple way to tell what a chemist should look and act like by using the characteristics of the elements on periodic table. The physical and chemical characteristics of the elements can help you in recruiting more women in the chemistry field.

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Don't let the men have all the fun, being a female prof rocks! Advice (for men and women) on how to reach your full potential

Elizabeth T Papish, [email protected] of Chemistry, Drexel University, United States

Despite the increase in chemistry degrees being awarded to women, the percentage of female faculty at research schools is still low, ~17%. This scarcity of women is baffling to me, since I have greatly enjoyed being on the faculty at both a PUI and a research school. At both schools, women are supported and the jobs are highly rewarding, though quite different. I will give advice on succeeding as a faculty member, while having a family or other activities. I have followed Sheryl Sandberg's guidelines in that I have 1) sat at the table, 2) made my partner a real partner, and 3) did not leave until I had to leave (due to the birth of my daughter). These methods worked for me because I love chemistry as much as I love my family, and I believe these methods can work for other young women who are passionate about chemistry.

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Collaboration is critical for the success of women in STEM

Judith M. Iriarte-Gross, [email protected] of Chemistry, Middle Tennessee State University, Murfreesboro, TN 37132, United States

The continuing success of the American workforce requires the full participation of women in STEM. It is apparent that our economic future is linked to STEM education. Yet only 21.8% of women in Tennessee hold a four year degree or better. After examining the data concerning the status of women in STEM education and careers, the Women in STEM (WISTEM) Center at Middle Tennessee State University (MTSU) was established. MTSU already plays a strategic role in encouraging young women in STEM through several successful K-16 programs such as the MTSU Expanding Your Horizons Conference, GRITS (Girls Raised In Tennessee Science) Collaborative Project, and WISE. The WISTEM Center provides a “home” for these signature programs, resources and STEM mentors. WISTEM plays a critical role in the STEM education for girls and women in Tennessee today and in the future.

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Ethical issues facing women in academia

Susan M. Schelble, [email protected], Kelly M..Department of Chemistry, Metropolitan State College of Denver, Denver, CO 80217, United States

This talk will illustrate actual conflicts that women in academia currently face. The issues will include, but are not limited to managing pregnancies, double standards for career advancements and student expectations of women versus men.

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An industrial chemist's perspective

Diane Grob Schmidt, [email protected] & Gamble Company, Cininnati, OH 45241, United States

The perspective and experience of a chemist in inductry will be described.

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Malta Conferences: Helping to improve the professional status of women scientists in the middle east

Zafra Lerman1, [email protected], Elizabeth Ann Nalley2. (1) 1911 Grant Street, MIMSAD, Evanston, IL 60201, United States (2) Department of Physical Sciences, Cameron University, Lawton, OK 73505, United States

Over the past ten years we have organized a series of conferences in the Middle East entitled “ Frontiers of Chemical Sciences: Research and Education in the Middle East-A Bridge to Peace and International Development.” The purpose of these conferences is to create a forum where scientists from Middle East countries can come together to discuss common problems in education, energy, environment and water resources, and to develop research collaborations to solve these problems. These conferences bring scientists together who would not ordinarily have the opportunity to meet with one another under normal circumstances because of political strife. Many of these scientists are in positions to influence policy in their home countries. Because of the location of the first two conferences, these conferences have become known as the “Malta Conferences. The first conference had only four female scientists from the Middle East but over the ten years the involvement and leadership roles of women in these conferences has greatly increased. This presentation will discuss the participation of Middle Eastern Women Scientists in the Malta Conferences and the impact their participation has had on their careers.

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Saudi women in science: Challenges and opportunities

Samira Ibrahim Islam, [email protected] Monitoring Unit, King Fahd Medical Research Centre, Jeddah, Jeddah 21411, Saudi Arabia

Due to Saudi conservative society, official primary schools for girls were established in 1960 while Saudi universities allowed women to be officially enrolled in 1970.

Despite of the various restrictions on Saudi women, currently the Kingdom has seen an influx of female students taking interest in Science nationally & internationally The World Bank & Saudi government's figures show that 58 % of the total students at universities are women. In term of gender gap in university registration, Saudi Arabia ranks the 25th among countries.

Saudi Arabia produces higher percentage of women graduates in science than U.S.A. Fifty-six percent of the Saudi working women have earned a degree in higher education, and 26 % are working in the medical field.

With the approval of the 25-year plan for development of university education, Saudi women's higher educational & scientific research opportunities are expected to increase

CHED 416

Support for women scientists in Japan

Yoshie Souma, [email protected] of Science, Kobe University, Kobe, Hyogo 657-8501, Japan

The status of Japanese women scientists is significantly behind when compared to that of the USA, Europe or Asian countries. In order to improve this condition, the Japan Inter-society Liaison Association Committee for Promoting Equal Participation of Men and Women in Science and Engineering (EPMEWSE) was established in 2002 among the academic societies of natural science. Seventy societies have now joined EPMEWSE. EPMEWSE sent a recommendation to the government for the 3rd Science and Technology Policy in Japan (2005-2010) to realize gender equality. Most of the EPMEWSE recommendations were accepted in the 3rd Science and Technology Policy in 2006, and the target number of hiring women scientists was proposed to be 25% (20% in Science, 15% in Technology, and 30% in Agriculture). Based on these basic plan, a new budget for the promotion of women in science was funded by the Government. Now 65 Universities have been carrying out model programs to support women faculties balancing research and family. Recently 12 Universities have been carrying out new program to accelerate an appointment of women faculties.

CHED 417

POGIL and The POGIL Project: An introduction

Rick Moog, [email protected] of Chemistry, Franklin & Marshall College, Lancaster, PA 17604, United States

POGIL (Process Oriented Guided Inquiry Learning) is a student-centered, group learning approach to instruction based on research on how students learn best. The POGIL Project is an organization that promotes the use of POGIL and other student-centered pedagogies, and the dissemination of POGIL materials for use at the college and high school levels. This presentation will provide a brief introduction to the key principles of POGIL pedagogy and its effectivenss, and will also describe the activities of The POGIL Project across the country to support student- centered instruction at all levels. More information is available at www.pogil.org.

CHED 418

Incorporating POGIL in the chemistry of food and cooking

Gail H. Webster, [email protected], Anne G. Glenn.Department of Chemistry, Guilford College, Greensboro, NC 27410, United States

Since 2002, The Chemistry of Food and Cooking has been offered as a lab science course in the general education curriculum at Guilford College. The course gives “science phobic” students an opportunity to learn chemical concepts through the study of different food types and cooking processes. It allows them to see chemistry as an integral part of their everyday experience. In the spring of 2012, the course was modified to incorporate Process Oriented Guided Inquiry Learning (POGIL) pedagogy. Approximately ten learning cycle activities addressing course-specific chemical concepts, such as the structure and properties of fats, carbohydrates, and proteins were developed and used throughout the semester. The design and objectives of the POGIL activities will be discussed as well as student response to the format of the class. Initial assessment of student learning with the POGIL format of the course will also be presented.

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Revolution in university science education: Integrated Concentration in Science (iCons) at UMass Amherst for today's students and tomorrow's leaders

Scott M Auerbach, [email protected] of Chemistry, University of Massachusetts Amherst, Amherst, MA 01003-9336, United States

Our society faces daunting challenges in areas such as renewable energy and biomedicine, requiring collaboration among leaders in science, engineering, and social science. Despite this need for multidisciplinary integration, university science education remains rooted in separate silos. We are tackling this issue through the Integrated Concentration in Science (iCons) program, a new model of integrative education that sets multidisciplinary student teams to work on significant societal problems. iCons aims to produce the next generation of leaders in science with the attitudes, knowledge, and skills needed to solve the multidisciplinary problems facing our world. iCons does not replace science or engineering majors, which remain important for imparting disciplinary expertise. Instead, iCons enhances disciplinary knowledge by training students to excel in diverse teams, cross disciplinary boundaries, and exert leadership in their search for technical solutions to societal problems. iCons achieves these objectives through a four-year program of case studies, student-driven lab work, and research, as will be described in this talk.

CHED 420

Global climate change: POGIL activities for the general chemistry curriculum

Daniel King1, [email protected], Jennifer E Lewis2, Karen Anderson3, Douglas Latch4, Susan Sutheimer5, Gail Webster6, Cathy Middlecamp7, Richard Moog8. (1) Drexel University, United States (2) University of South Florida, United States (3) Madison College, United States (4) Seattle University, United States (5) Green Mountain College, United States (6) Guilford College, United States (7) University of Wisconsin, Madison, United States (8) Franklin and Marshall College, United States

Climate change interests many students and will affect their lives for the foreseeable future. It is also a topic that has strong connections to a large number of general chemistry topics. Through an NSF-funded project, we are developing a series of in-class activities that use climate change topics to teach general chemistry concepts using the POGIL (Process Oriented Guided Inquiry Learning) methodology. It is expected that these new activities will help engage students in learning fundamental general chemistry concepts. We will also be investigating student discourse during the activities and using that information to inform revisions of the activities so they better promote both the development of scientific concepts and discussion of related socio-economic and environmental issues. Thus far, first drafts of a set of activities have been written. Classroom testing will begin this coming Fall term. The key features of the activities will be described in this presentation.

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Development and implementation of guided inquiry experiments for physical chemistry

Sally S Hunnicutt1, [email protected], Alex Grushow2, Robert Whitnell3. (1) Department of Chemistry, Virginia Commonwealth University, Richmond, VA 23284-2006, United States (2) Department of Chemistry, Rider University, Lawrenceville, NJ 08648, United States (3) Department of Chemistry, Guilford College, Greensboro, NC 27410, United States

The NSF-funded POGIL-PCL project implements the principles of Process Oriented Guided Inquiry Learning (POGIL) in order to improve student learning in the physical chemistry laboratory (PCL) course. POGIL principles are being used to develop inquiry-based physical chemistry experiments emphasizing macroscopic and molecular models of chemical phenomena. We describe our initial work with physical chemistry experiments in areas such as chemical kinetics, computational chemistry, and phase transition behavior. We also discuss how we are building a community of instructors who will collaborate on generating and using POGIL-PCL experiments. This presentation will discuss the general structure of a POGIL physical chemistry experiment with specific examples, review the results of three workshops in 2012, give an overview of future workshops, and discuss ways in which interested physical chemistry laboratory instructors can become involved in POGIL-PCL.

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Assessing the impact of roles as they relate to student learning styles in the POGIL laboratory Danaè R. Quirk Dorr, [email protected], M. Hadley.Department of Chemistry and Geology, Minnesota State University, Mankato, Mankato, MN 56001, United States

Student learning styles were gauged at the beginning of the semester and used to create teams. After each experiment, students independently completed online surveys in which they reported their roles as well as their teammates' roles in completing the experiment and experimental analysis. At the end of the semester, students identified the role that they would choose if they were asked to work in a team and commented about possible effects of roles assigned by the instructor. In addition, end-of-the-semester survey responses also included student reflections about the challenges and benefits of working in teams and the perceived impact that the team had on their laboratory scores. Correlations were made between survey responses and the individuals' learning styles.

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Student evaluation of POGIL in large chemistry courses

Suzanne M Ruder, [email protected], Sally S Hunnicutt, Susan Polich.Department of Chemistry, Virginia Commonwealth University, Richmond, VA 23284-2006, United States

Course evaluations were collected and focus group interviews were conducted with students from two large chemistry classes. In both general and organic chemistry classes, students were taught using POGIL in combination with interactive lecturing and online homework. We expected that students' responses would show that there is a distribution of novice to expert learners in each class, but that the distribution is skewed toward more expert learners in the organic class. In depth follow up focus group interviews with students and written comments on the evaluations revealed students with varying degrees of metacognitive abilities in both classes. Students from both courses thoughtfully discussed how they learned, but general chemistry students were more likely to be less logical and coherent in their learning strategies.

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Evaluation of the chemical origin of life as a context for teaching undergraduate chemistry

Bhawani Venkataraman, [email protected] Sciences and Mathematics, Eugene Lang College The New School for Liberal Arts, New York, NY 10011, United States

This paper describes a chemistry course that uses the 'origin of life' as a context and examines how this context supports students' interest in learning chemistry. The selection of this context and the course design are consistent with research on context-based approaches in chemistry. A study was conducted to evaluate the effectiveness of this context in supporting students' (i) interest in chemistry, (ii) learning and application of fundamental chemical concepts (iii) understanding the relevance of molecular processes and interactions. Data were collected through pre- and post course surveys, conceptual questions on tests and assignments, student reflections and research papers. Qualitative analysis of student reflections, surveys, and research papers reveal that the context motivates students to learn chemistry. Quantitative analysis of pre and post course questions, tests, and assignments demonstrate students are learning concepts and apply their understanding to connect molecular-level processes to macro-scale outcomes.

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Comparison of two online learning systems in general chemistry at the University of Washington Colleen Craig, [email protected], Andrea Carroll, Phil Reid.Chemistry, University of Washington, Seatle, WA 98195, United States

This study compares exam scores for students in general chemistry versus performance in two online learning systems: WebAssign, which presents problems in a traditional manner, and ALEKS (Assessment and LEarning in Knowledge Spaces), which is an adaptive, tutorial-based system. Comparisons are made for students taking the same general chemistry course, taught by the same instructor, in the same quarter in subsequent years, where WebAssign was used one year, and ALEKS the next. Preliminary results for first-quarter general chemistry show a strong correlation between ALEKS performance and exam performance (Pearson coefficient = 0.79, N = 508), and weak correlation between WebAssign performance and exam performance (Pearson coefficient = 0.40, N = 496). In addition, correlations between exam and ALEKS performance are observed early on such that ALEKS performance can be used by students and instructors as an early-time, low-risk metric of student learning.

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The question, understand, do you? Divergent interpretations of exam items by faculty and students in general chemistry

Eliscia L. Fought, [email protected], Nathan J Barrows.Department of Chemistry, Grand Valley State University, Allendale, MI 49401, United States

When instructors dedicate time and energy into creating focused, carefully-worded questions only to have a significant fraction of students misinterpret them, all parties to the assessment can become frustrated. This case study investigated the nature of misinterpretations through a series of semi-structured interviews with faculty and students. Participants were asked to comment on a set of problematic questions identified by instructors in the second-semester, general chemistry course. The interviews were transcribed and inductively coded using ATLAS.ti. The results indicate that although clarity and difficulty are related constructs, faculty and students view them differently; for example, to students a question's clarity was unrelated to the underlying chemical knowledge required to answer it. This study reinforces the need for faculty to consider “accessibility” when designing assessment items, so that students' scores accurately represent their content knowledge and are not conflated with their ability to interpret the language used in the questions.

CHED 427

Student outcomes from undergraduate chemistry laboratory innovations: A review of projects funded by the NSF between 2000-11

Hannah Sevian1, [email protected], Gavin W Fulmer2,3. (1) Department of Chemistry, University of Massachusetts Boston, Boston, MA 02125, United States (2) Curriculum, Teaching and Learning Group, National Institute of Education, Singapore (3) Division of Research on Learning, National Science Foundation, Arlington, VA 22230, United States

Many efforts in implementation of novel curriculum, instruction, and assessment in undergraduate science laboratory courses in the U.S. have been funded by the National Science Foundation. A mixed-method review and analysis was conducted of all awards in the CCLI/TUES programs funded and completed between 2000 and 2011 that focused on undergraduate chemistry laboratory learning. The study was concerned with characterizing the types of interventions that occurred, and what was studied related to student learning and associated outcomes. The results offer an overview of the current 'state of the art' of chemistry education; this permits suggesting gaps and opportunities for further efforts. The findings are also contrasted with a recent summary of the state of chemical education research, largely focused at undergraduate level teaching and learning, that was presented in a review paper commissioned by the National Academies of Science as part of the consensus study on discipline-based education research.

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Quantitative analysis of the ANAPOGIL project

Renee Cole1, [email protected], Wendy Schatzberg1, Juliette Lantz2. (1) Department of Chemistry, University of Iowa, Iowa City, IA 52242, United States (2) Department of Chemistry, Drew University, Madison, NJ 07940, United States

In this study, process oriented guided inquiry learning (POGIL) activities are being developed and implemented in the analytical chemistry classroom (the ANAPOGIL project). The objective of this broad mixed methods study is to analyze the impact of ANAPOGIL activities on student learning and attitudes at different universities and over several semesters. The focus is on understanding student learning related to targeted course content and process skills, determining students' learning expectations, and their learning gains perceptions. Qualitative and quantitative data were gathered using interviews, open-ended exam responses, student reviews of activities, as well as American Chemical Society (ACS) Exam, CHEMX, and SALG (Student Assessment of Learning Gains) scores. Statistical analysis of the quantitative results will be presented. Of particular interest is the impact of the lecture materials on students' perception of learning gains in laboratory skills.

CHED 429

Luminescence spectroscopy in molecular assemblies and new energy conversion materials: Integration across the undergraduate curriculum

Jeanne E Pemberton1, [email protected], John Pollard1, Dee Belle-Oudry1, Oliver Monti1, Scott Saavedra1, Judy Jenkins1, Emily Grumbling1, Elliott Smith1, Ingrid Novodvorsky2. (1) Chemistry and Biochemistry, University of Arizona, Tucson, AZ 85721-0041, United States (2) College of Science Teacher Preparation Program, University of Arizona, Tucson, AZ 85721, United States

We have developed and implemented a vertically integrated, cross-disciplinary modification of our undergraduate chemistry and biochemistry laboratory curriculum that focuses on light absorption, luminescence decay, energy transfer, and charge transfer in macromolecular and supramolecular assemblies. The target audience is undergraduate students at the sophomore through senior levels in analytical, physical, inorganic synthesis, and biochemistry lab courses. Using steady- state luminescence and time-correlated single photon counting instruments purchased with DUE funding, newly developed experiments in five undergraduate courses introduce students to luminescence for quantitation of analytes and measurements of binding affinity, resonance energy transfer and emission anisotropy in biochemical and supramolecular assemblies, kinetics of photoinduced reactions obtained from fluorescence lifetime studies, and synthesis and spectral characterization of semiconductor nanocrystals. The latter topic has been designed and implemented as a cross-course, two-semester activity that introduces the students to emerging concepts in solar energy capture and conversion. The authors gratefully acknowledge the financial support of the NSF (DUE 0837398) for this project.

CHED 430

Professional readers for STEM student writers: How university alumni and professional staff can help STEM students develop communication and reasoning skills Cary Moskovitz1, [email protected], Chris Roy2, Todd Woerner2. (1) University Writing Program, Duke University, Durham, NC 27708, United States (2) Chemistry, Duke University, Durham, NC 27708, United States

A new approach to providing students with quality feedback on STEM writing projects, capitalizing on an untapped educational resource: university alumni and employees with scientific or technical backgrounds who normally play no direct role in the institution's educational mission. Students get feedback on drafts from volunteers whose backgrounds fit their writing assignments. Volunteers are instructed in giving “reader-based” feedback--describing their reactions to drafts as users of the texts, rather than editing or evaluating. Instructors consult with project personnel to develop assignments and work out timing for student-reader interactions for their course. Results include survey data from students, volunteer readers, and instructors, along with examples of feedback from volunteer readers. Preliminary analysis suggests that this approach can indeed improve STEM students' engagement with STEM writing tasks, the development of their writing skills, and foster a more mature writing process. The authors gratefully acknowledge the financial support of the NSF (DUE 1043674) for this project.

CHED 431

Integrating science for preservice elementary teachers through foundational big ideas

Jane Rice1, [email protected], Laura Markham2, Susan Jackson2, Diane Wilson2, Patricia Maldonado2, Jennifer Doherty3, Charles W. Anderson3. (1) Department of Geological Sciences, Michigan State University, East Lansing, MI 48824, United States (2) Center for Integrative Studies in General Science, Michigan State University, East Lansing, MI 48824, United States (3) Department of Teacher Education, Michigan State University, East Lansing, MI 48824, United States

The foundation of science literacy, in terms of content and practice, is laid during the elementary school years. This foundation, which underlies life, Earth, and physical science, is often taught by K-8 teachers' whose preparation and training does not match the responsibility they face. We designed a course for elementary and middle school preservice teachers (non-science majors) based on three foundational big ideas (matter conservation, energy conservation, and the interaction between matter and energy). These ideas are then used to build a coherent framework for learning and teaching any topic in the K-8 science curriculum. We supported students' learning with consistent teaching strategies and instructional activities, including physical models for matter and energy. Students' ability to apply these foundational big ideas to new contexts and to integrate them across disciplines will be discussed. The authors gratefully acknowledge the financial support of the NSF (DUE 0941820) for this project.

CHED 432

ChemPRIME/ChemPaths: Using an online resource for chemistry teaching

John W. Moore1, [email protected], Justin M. Shorb2, Donald Storer3, David Carter4, Lisa Smith5, Jeffrey Schwehm6. (1) Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States (2) Department of Chemistry, University of the Virgin Islands, St. Thomas, U.S. Virgin Islands, United States (3) Department of Chemistry, Southern State Community College, Hillsboro, Ohio, United States (4) Department of Chemistry, Angelo State University, San Angelo, Texas, United States (5) Department of Chemistry, North Hennepin Community College, Minneapolis, Minnesota, United States (6) Department of Chemistry, Lakeland College, Sheyboygan, Wisconsin, United States In the Chemical Education Digital Library (ChemEd DL), we have created ChemPRIME, an online wiki text that develops the concepts of a general chemistry course in logical progression, and ChemPaths, an online resource that allows an instructor to select content from ChemPRIME and present it to students in whatever order the instructor wants. We have used ChemPRIME/ChemPaths to supplement in-class POGIL activities, to provide exemplars for a non-science-majors, pre-nursing course, to aid the teaching of dimensional analysis, and to develop a lesson on intermolecular forces and properties of liquids. These applications and evaluation studies of them will be reported. The authors gratefully acknowledge the financial support of the NSF (DUE 1156433 and 1044239) for this project.

CHED 433

Promoting learning through authentic and relevant research experiences in environmental monitoring and remediation across ten chemistry and biology laboratory courses

Stephen G Cessna1, [email protected], Lori H Leaman2, Tara S Kishbaugh1. (1) Department of Chemistry, Eastern Mennonite University, Harrisonburg, VA 22802, United States (2) Education Department, Eastern Mennonite University, Harrisonburg, VA 22802, United States

We have introduced several multi-week mini-research projects to several chemistry and biology courses. Each project engages students in authentic research in environmental analysis and remediation, from copper remediation in General Chemistry to agricultural soils analysis in Sustainable Agriculture. Our hope is that participation in these projects will promote student learning beyond content knowledge, including gaining a better understanding of the nature of science, and enhancing critical thinking and scientific communication skills. For each project, students produce an authentic research product: a research paper, oral report, or poster. We have developed a rubric bank to enhance learning and assess the development of non-content skills and knowledge. We have found significant improvement in nature of science understanding. Students and participating teachers also report improved scientific communication skills and enhanced quality of student research products. The authors gratefully acknowledge the financial support of the NSF (DUE 0837578) for this project.

CHED 434

Coupled science core courses: Designing, delivering, and evaluating interdisciplinary courses for non-majors

Lawrence K Steffen1, [email protected], Kathy A Nantz2. (1) Department of Chemistry and Biochemistry, Fairfield University, Fairfield, Connecticut 06824, United States (2) Department of Economics, Fairfield University, Fairfield, Connecticut 06824, United States

We developed and delivered multiple coupled science core courses. By coupling thematically related science courses or science and closely related fields, students were participated in a dense, interdisciplinary learning experience that helped make explicit the nature of science. Students learned material across disciplinary lines in ways that illustrated the power of scientific thought to address important societal concerns and how science works. We also developed one course couple, between a physics course on the nature of light and color and photography course, that immersed students in a creative exploration from both the scientific and artistic perspectives. We provided workshops on statistical thinking, development of laboratory activities, and on assessment in the sciences. Our workshop series culminated in a regional SENCER workshop on Science Education held at Fairfield University in May, 2011. The authors gratefully acknowledge the financial support of the NSF (DUE 0736985) for this project.

CHED 435 Analysis of halomethane water disinfection by-products by GC/MS and negative chemical ionization (NCI)

Paul Chiarelli1, [email protected], Thomas Higgins2, Charles Abrams3. (1) Department of Chemistry, Loyola University, Chicago, Illinois 60660, United States (2) Department of Physical Science, Harold Washington College, Chicago, Illinois 60601, United States (3) Department of Physical Science and Engineering, Truman College, Chicago, Illinois 60640, United States

As part of the NSF project “Introducing Mass Spectrometry to the Chicago City Colleges”, we have been introducing faculty and students to GC/MS and LC/MS/MS experiments via web access in the belief that exposing chemistry students in two-year colleges to advanced instrumentation will encourage more of them to pursue a BS degree in chemistry. We have designed several experiments that familiarize students with chromatography coupled with mass spectrometry detection. We will describe a new undergraduate experiment based on the analysis of halomethanes and other water disinfection by-products using GC/MS coupled with negative chemical ionization (NCI) that has been developed for the undergraduate laboratory. Students from Harold Washington and Truman Colleges, and Loyola University in Chicago, were asked to analyze different water samples of their own choosing for four halomethanes using GC/MS and NCI. The authors gratefully acknowledge the financial support of the NSF (DUE 0837344) for this project.

CHED 436

Integration of NMR into chemistry curriculum at WKU and ECTC and assessment of factors leading to a successful collaboration between 2- and 4-year colleges

Rui Zhang1, [email protected], Darwin Dahl1, Lester Pesterfield1, Cathleen Webb1, Shawn Kellie2, Sue Ballard2. (1) Department of Chemistry, Western Kentucky University, Bowling Green, Kentucky 42101, United States (2) Elizabethtown Community and Technical College, Elizabethtown, Kentucky 42701, United States

In this NSF-supported project, two Anasazi FT-NMRs are being integrated simultaneously across the chemistry curriculum at Western Kentucky University (WKU) and Elizabethtown Community and Technical College (ECTC). The collaborative project adds to a new curriculum initiative by integrating NMR throughout the undergraduate chemistry curriculum with the ultimate aim of enhancing both programs. For the first time, students at ECTC now are able to gain on-site access to an NMR that has dramatically enhanced the community college student's educational experience. The project has been found to stimulate WKU and ECTC' efforts to establish an equal and sustainable partnership in a broad range. The outcome and viability of the partnership between ECTC and WKU has been critically assessed. As a result, new insights for the future of the WKU/ECTC chemistry partnership have been generated. The success of the partnership between WKU and ECTC can serve as a model for other institutions. The authors gratefully acknowledge the financial support of the NSF (DUE 0942088) for this project.

CHED 437

Improving the biochemistry curriculum through innovative and collaborative hands-on and virtual laboratory experiences

Frank H Bellevue III1, [email protected], Taina Chao1, Joanne Kivela Tillotson2, Joseph Skrivanek1, Mark Condon3. (1) Chemistry Board of Study, Purchase College, State University of New York, Purchase, NY 10577, United States (2) Biology Board of Study, Purchase College, State University of New York, Purchase, NY 10577, United States (3) Department of Allied Health and Biological Sciences, Dutchess Community College, Poughkeepsie, NY 12601, United States

To improve the success of students in the Biochemistry major, we are increasing instrumentation experience, hands-on and virtual, in the lower level courses in our program. Since many of the students in this major transfer from community colleges, we also provided six community colleges with UV-Vis and fluorescence instruments. Workshops on the theory and operation of these instruments as well as hands on experience were provided to the community college faculty. An online clearinghouse was implemented for sharing information among the faculty at the various schools. An online training module that allows students to become familiar with the use and theory of the instruments has been developed to supplement course content and further increase student success. Students that progress to become chemistry and biology majors are also expected to benefit. The authors gratefully acknowledge the financial support of the NSF (DUE 0941855) for this project.

CHED 438

Relationship between the history of synthetic chemistry and artists' materials

Eric Bosch, [email protected] of Chemistry, Missouri State University, Springfield, Missouri 65897, United States

The links between the development of pigments and dyes through the ages will be presented. This will start with an overview of the extraction of organic colorants from natural sources and the use of inorganic minerals. This will be followed by the early, serendipitous, discovery of the syntheses of inorganic and organic colorants in particular zinc oxide, Prussian blue and mauveine. The close relationship between the isolation and subsequent availability of transition elements like chrome and cadmium and the synthesis of brightly colored inorganic pigments will be presented. Similarly, the development of synthetic organic chemistry and new organic colorants will be explored. Particularly interesting decomposition processes of both organic and inorganic colored compounds will be highlighted. The role of polymers as pigment medium will also addressed. The paper will close with brief a look at the role of the chemistry of colorants in evaluating the provenance of artwork.

CHED 439

Chemical matter and the vision of artists: Three exhibits at the Chemical Heritage Foundation

Christy J Schneider, [email protected], Roy Eddelman Institute, Chemical Heritage Foundation, Philadelphia, PA 19106, United States

The shape-shifting nature of matter is hard to represent. Chemists have created tools such as diagrams and tables; some artists have also developed a passion and skill for visualizing chemistry. “I grew up seeing beauty in Science -- fractals, genomes, quarks -- as well as the chemistry of artistic media—drying times, glazes, pigments,” said artist Jennifer Schmitt, whose Periodic Table Printmaking Project was included in a recent exhibit, Elemental Matters: Artists Imagine Chemistry, at the Chemical Heritage Foundation in Philadelphia (CHF). This talk focuses on how and why artists represent chemical themes of past and present science, as evidenced in three CHF exhibits, Elemental Matters, Sensing Change (art about climate), and Alchemical Quest. Also discussed are the goals of a history of science institution that seeks to engage a broad audience through these exhibits, programs, and community partnerships.

CHED 440 Chemistry and contemporary visual art

Tami I Spector, [email protected] of Chemistry, University of San Francisco, San Francisco, CA 94131, United States

Relative to physics, mathematics and biology the intersections of chemistry and contemporary visual art have been relatively neglected. I will begin this presentation with a brief historical perspective on chemistry and art and the possible reasons for chemistry's relative neglect by artists. I will subsequently explore how modern and contemporary artists reveal the art-chemistry connection, focusing on the unique material and conceptual aspects that chemistry and the visual arts share. I will discuss specific works by artists who self-define their art in relation to chemistry, and others whose art can be recontextualized through the lens of chemistry, including those who work with issues related to chemical properties, transformation and chemistry's cultural impact.

CHED 441

Chemical worlds, chemical senses: Building a sniffing booth

Siddharth Ramakrishnan1, [email protected], Victoria Vesna2. (1) Department of Electrical Engineering, Columbia University, New York, New York 10027, United States (2) Department of Design Media Arts, University of California, Los Angeles, Los Angeles, CA 90095, United States

As humans we interact with the world around us relying primarily on visual information. This gives us a very anthropocentric perspective of our environment. Many of us are unaware of the different sensory potentials that other animals possess, which paint a very different picture of the world around us. We wish to raise awareness of this aspect of sensory perception by using the dog, an animal ubiquitous to the human home environment for centuries, as a model. In this work, we contrast the perception of objects by us with the perception of a dog. As an interface, we use cards/ invisible-imprints that have olfactory representations of objects that people encounter in everyday life. By making it an interactive game, we engage the audience and evoke curiosity, and begin a dialog about the human umwelt in comparison to that of the dog.

CHED 442

Art as a catalyst for connections in chemistry

Rebecca Kamen, [email protected] of Liberal Arts, Northern Virginia Commuity College, Alexandria, VA 22311, United States

Art and chemistry share much in common. Both use visualization models as a means for making the invisible visible, both strive for representation and expression to capture some essential truth, and central to both fields is the transformation of materials. This presentation will examine a unique sculpture installation inspired by the periodic table. The project has been informed by wide ranging research into chemistry, cosmology, spirituality and philosophy and serves as a catalyst for connections between art and science, and a resource for pedagogical and outreach purposes.

CHED 443

Teaching chemistry to community college non-science majors by active learning methods utilizing art related topics Tirandai Hemraj-Benny, [email protected], Queensborough Community College, Bayside, New York 11364-1497, United States

It has been an established fact that in the U.S. there is a great need to improve the scientific literacy of undergraduate students, especially those who are non-science majors. Amongst the several pedagogical techniques developed to solve this problem, active learning and relating to real-world examples have shown to significantly improve students' interest and knowledge in science. Moreover, it has been recently argued that an effective way to “hook” non-science students into science is by using interdisciplinary themes. Herein, we investigated the outcomes of active learning utilizing art related topics such as light, color mixing, paints, dyes, photography and art conservation on students' learning and understanding of scientific theories and concepts. Students worked in groups to complete worksheets, mini experiments and created art work. It was concluded that active learning with visual artistic exercises aided students in better grasping important scientific relationships.

CHED 444

Using theater-based learning to engage children in chemistry

Christopher Babiarz1,7, [email protected], Holly Walter Kerby2,7, Joanne Cantor3,7, Marcia Weiland4,7, Kimberly Megna Yarnall5,7, Brittland DeKorver6,7. (1) Environmental Chemistry & Technology Program, University of Wisconsin, Madison, Wisconsin 53706, United States (2) Department of Chemistry, Madison Area Technical College, Madison, Wisconsin 53704, United States (3) Your Mind on Media, Monona, Wisconsin 53716, United States (4) Attainment Company, Verona, Wisconsin 53593, United States (5) Forward Theater Company, Madison, Wisconsin 53708, United States (6) Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, United States (7) Fusion Science Theater, Madison, Wisconsin 53704, United States

Funded by the National Science Foundation, Fusion Science Theater (FST) is a cross-disciplinary project that creates new forms of presentation and performance that engage young audiences in chemistry. Dramatic elements like spectacle, character, theme, and dramatization of metaphor are adapted and integrated into FST shows to give a playful, aesthetic, and visceral experience of science. These methods also leverage the parallels between the dramatic structure of plays and the inherent structure of the scientific method. For example, the dramatic question of a play is replaced with an investigation question to create the desire to know the concept behind an intriguing chemical phenomenon. As the “plot” unfolds, the question is answered by children's observations of demonstrations, their participation in kinesthetic models of underlying concepts, and group problem solving. Data generated by embedded assessment shows this arts-based method yields significant learning gains in children.

CHED 445

Drawing the similarities between scientific and dramatic prose to improve students' technical writing skills

Reuben Hudson, [email protected] of Chemistry, McGill Univserity, Montreal, QC H3A 0B8, Canada

As scientists, we intimately understand that a machine should have no extra parts, a procedure no extra steps, and a comparison no extra variables. We do, however, often forget that a word should contain no extra letters, a sentence no extra words, a paragraph no extra sentences, and a manuscript no extra paragraphs. This is not to say that a scientist must write in short, generalized sentences, but that every word should carry meaning—if not for the stringent page limits for lab reports or manuscripts, then at least to provide clarity for the reader. By drawing on the similarities between scientific and dramatic prose, we can foster a generation of students who cherish concise chemistry writing as an art form.

CHED 446

Finding NEMA's vinyl protons: Unusual chemical shift variability in 1H NMR spectra at low concentrations

William A. Price1, [email protected], Alexander M. Abud1, Robert F. Dyer1, Matthias Zeller2, Allen D. Hunter2. (1) Department of Chemistry and Biochemistry, La Salle University, Philadelphia, PA 19141, United States (2) Department of Chemistry, Youngstown State University, Youngstown, OH 44555, United States

Our research on the preparation and characterization of compounds that are specific Michael acceptors for thiol and thiolate portions of cysteine residues in proteins has unveiled some remarkable NMR data in one particular synthetic precursor. N-ethylmaleamic acid (NEMA) gives rise to a rather ordinary 1H NMR spectrum. Upon close examination, the vinyl protons give rise to a pair of well-resolved doublets that have tremendous chemical shift variability at low concentrations in CDCl3. The chemical shifts of these two protons at a variety of decreasing concentrations eventually give rise to a coalescence of chemical shift(s) (Δν=0) followed by a “cross-over” of the doublet signals. The high degree of inter- and intramolecular hydrogen bonding found in a single crystal X-ray structure of NEMA will be used as a structural reference point. Additionally, observations of the 1H NMR spectra of NEMA in more polar solvents as well as 13C NMR data will be discussed.

CHED 447

Strategies for incorporating multinuclear NMR in coursework and undergraduate research

Robert Stockland, [email protected] of Chemistry, Bucknell University, Lewisburg, PA 17837, United States

This presentation will describe strategies we have used to incorporate multinuclear NMR spectroscopy into coursework and undergraduate research. For entry level courses, the course material remains focused on the fundamentals of NMR spectroscopy and spectral interpretation. As students progress to upper level courses, they are introduced to advanced topics such as spectrometer design, multinuclear NMR, and pulse programs. Students who enroll in undergraduate research often use NMR spectroscopy to monitor the progress of reactions, establish the connectivity of organic and organometallic products, facilitate the collection data for kinetic studies, and probe reaction mechanism through the observation of reaction intermediates. Several examples of these techniques will be highlighted.

CHED 448

Understanding the liquid structure of ionic liquids: Some examples of NMR-based undergraduate-powered research

Guillermo Moyna, [email protected] & Biochemistry, University of the Sciences in Philadelphia, Philadelphia, PA, United StatesDepartamento de Química del Litoral, UdelaR, Paysandú, Paysandú 60000, Uruguay The liquid structure of ionic liquids (ILs) has been the subject of numerous experimental and theoretical investigations. Understanding it is not only critical in the study of these materials, but also for the rational design of new ILs with specific solvent properties. In this presentation we will describe NMR-based studies aimed at deciphering interionic interactions in neat ILs as well as the interactions of ILs with certain solutes. The work ranges from the use of 13C and 35/37Cl relaxation measurements in the study of IL/solute systems to deuterium isotope effects in the determination of intraionic hydrogen bonds. The common denominator to all the work presented in this talk is that it was carried out, and in many cases thought out, almost entirely by undergraduate researchers.

CHED 449

Solution structure and function of the Ig1 domain of the giant muscle protein Obscurin

Nathan T Wright, [email protected] of Chemistry and Biochemistry, James Madison University, Harrisonburg, Virginia 22807, United States

Striated muscle architecture is complex by necessity; the myocyte must balance contrasting needs of structural integrity and motion. The giant muscle protein obscurin assists myofibrils in this task through sarcomere organization, stretch signaling, and linking of the muscle contractile apparatus with the sarcoplasmic reticulum (SR). Here, we present the preliminary structure of the extreme N-terminus of this molecule. NMR data indicate this region folds as an Ig-like motif, with one face showing a large number of solvent-exposed hydrophobic residues. Chemical shift analysis to a known binding partner, the M10 domain of titin, suggests a protein-protein binding event primarily at this hydrophobic face of the obscurin domain. Binding specificity is likely achieved through several charged residues near the hydrophobic patch. Mutations of the M10 domain are associated with limb-girdle muscular dystrophy, and thus fully understanding this obscurin-titin interaction may help elucidate the biochemical mechanism behind this disease.

CHED 450

Use of NMR in determining the absolute configuration of glycerol menthonide isomers

Anthony Kiessling, [email protected] of Chemistry, Mansfield University, Mansfield, PA 16933, United States

Glycerol menthonide has been prepared by reaction of glycerol and menthone in acidic medium and exists in up to 6 isomers. The mixture of isomers was difficult to separate until converted into the 4-bromobenzoate derivatives which were then separated by chromatography. Once purified, two of the isomers were further derivatized and studied by various NMR techniques to understand the absolute configuration of the two menthonides. The final proof of the absolute configuration came through a combination of NMR and x-ray diffraction studies. The synthesis, NMR spectra, x-ray diffraction and structures of the glycerol menthonides will be discussed.

CHED 451

Understanding high school chemistry teachers' reflection during planning

Michael Dianovsky1,3, [email protected], Donald Wink1,2. (1) Learning Sciences Research Institute, University of Illinois at Chicago, Chicago, IL 60607, United States (2) Department of Chemistry, University of Illinois at Chicago, Chicago, IL 60607, United States (3) Department of Educational Psychology, Rutgers University, New Brunswick, NJ 08901, United States This paper describes urban high school chemistry teachers' reflective planning. This study was comparative cases study of the methods teachers use during planning, associated with detailing their reflective practice. The theoretical framework for this study consisted of work on reflection done by Dewey and Schön. Data sources included think-alouds, interviews, artifact collection, and classroom observations. The findings from the description and analysis of the two cases produced two different, complex, structured models of reflective planning. Both teachers had a unique way of planning for a lesson. Although there were differences between the two planning models, both models had structure. It was this structure that allowed for reflective planning to occur. There was not one essential model of teacher reflective planning. A teacher's use of resources was associated with indications of reflection. Three different types of reflections occurred by both teachers. These types included reflection-for-action, reflection-on-action, and reflection-for-action.

CHED 452

Students' views of chemistry as a science and of chemistry studies in their classes

Frackson Mumba1, [email protected], Asiana Banda2, Vivien M Chabalengula2. (1) Chemistry and Biochemistry, Southern Illinois University Carbondale, Carbondale, IL 62901, United States (2) Department of Curriculum and Instruction, Southern Illinois University Carbondale, Carbondale, IL 62901, United States

This study assessed 250 high school students' views of chemistry. Chemistry was further defined into two constructs: Chemistry as a science, and Chemistry Studies in my Class. The term view was defined in terms of three aspects: Image, Cognitive, and Affective. Data was collected through a modified 44 item questionnaire developed by Shwartz, et al. (2006) that has semantic differential statements on Image, Cognitive, and Affect. Each statement was valued in a range from 1 to 5, where 1 indicates “Strongly Disagree” and 5 indicates “Strongly Agree”. Data was analyzed using descriptive statistics, correlations and t-tests. Results show significant correlations between image, cognitive, and affect and ranged from moderate (0.51) to strong (0.79). Students recognized the value and importance of chemistry as a science and chemistry studies despite their perceived low cognitive ability to learn it, and moderately indifferent interest in chemistry. Results have implications for chemistry teaching and learning.

CHED 453

Implementation of a research-based lab module in a high school chemistry class: Examining student-student and student-teacher interactions

Matthew Pilarz, [email protected], Rebecca L Pritchard, Gabriela C Weaver.Department of Chemistry, Purdue University, West Lafayette, IN 47907, United States

The Center for Authentic Science Practice in Education (CASPiE) was developed to provide research experience for undergraduates as part of their general chemistry laboratory. Over the past few years, CASPiE has expanded to include module implementation in high school chemistry classes. This study examines how the high school chemistry classroom environment is affected by the incorporation of a research-based lab module. More specifically, this project focuses on student-student and student-teacher discourse in the various phases of the module and how this impacts the classroom environment. Data were collected via semi-structured interviews with students and teachers at the completion of each of the four phases of the module. Results of this study show how lab group and classroom dynamics change throughout the use of the research-based module.

CHED 454 Zambian pre-service science teachers' interest in and conceptual understanding of electrochemistry concepts

Asiana Banda1, [email protected], Frackson Mumba2. (1) Department of Curriculum and Instruction, Southern Illinois University Carbondale, Carbondale, Illionis 62901, United States (2) Department of Curriculum and Instruction, Southern Illinois University Carbondale, Carbondale, Illionis 62901, United States

Studies show that teachers have misconceptions on electrochemistry and negative attitude towards chemistry. However, studies have not compared pre-service science teachers' interest in and conceptual understanding of electrochemistry. Yet, research shows both interest and conceptual knowledge have influence on teachers' instructional practices, and student achievement. Therefore, this study examined 66 Zambian junior high school pre-service science teachers' (a) conceptual understanding of twenty six electrochemistry concepts prescribed in Zambian school curriculum, and (b) levels of interest in learning more about these electrochemistry concepts. Chemistry is a mandatory subject in Zambian high schools. Quantitative and qualitative data collection and analysis procedures were used. Teachers scored higher on basic than advanced electrochemistry concepts. Furthermore, most teachers expressed high levels of interested in learning more about electrochemistry concepts. In particular, teachers were more interested in learning more about the advanced than basic electrochemistry concepts. Results have implications for chemistry teacher education.

CHED 455

Teachers' abilities to identify misconceptions on electrolysis

Asiana Banda1, [email protected], Frackson Mumba2. (1) Department of Curriculum and Instruction, Southern Illinois University Carbondale, Carbondale, Illionis 62901, United States (2) Department of Curriculum and Instruction, Southern Illinois University Carbondale, Carbondale, Illionis 62901, United States

Several chemical education studies have reported misconceptions on electrochemistry among students and teachers. However, there is a dearth of research on teachers' abilities to identify students' misconceptions on basic electrochemistry concepts. Therefore, this study explored 66 Zambian pre-service science teachers on their abilities to identify junior high school students' misconceptions on electrolysis. Qualitative data collection and analysis procedures were used. Teachers were given a survey that had four scenarios on electrolysis which contained students' misconceptions. Teachers were asked to identify students'misconceptions in each scenario, provide correct explanations of the concepts, and suggest the best instructional practices for addressing such misconceptions in middle school science classrooms. Most teachers acknowledged students' misconceptions in the four scenarios. However, teachers provided incorrect, partially correct or correct explanations of the concepts. Teachers suggested both access and knowledge delivery modes as the best instructional practices for addressing students' misconceptions on electrolysis identified in each scenario.

CHED 456

Chemistry within the NSF's Division of Undergraduate Education

Pamela Brown, [email protected], Joseph Grabowski.Division of Undergraduate Education, National Science Foundation, Arlington, Virginia 22230, United States

The National Science Foundation Division of Undergraduate Education (NSF DUE) has the broad mission of promoting excellence in undergraduate science, technology, engineering and mathematics (STEM) education for all students. DUE's targeted programs provide significant national funding, across the range of institutions of higher education, to support activities which forward these goals, including curricular and pedagogical development and adoption, educational research, teacher preparation, scholarships, workforce development and fostering collaborations. In addition to a summary of programs that support undergraduate education, perspectives beyond those found in the solicitations, and new directions within DUE, will be highlighted. Opportunities for chemists to contribute to the mission of NSF DUE will be presented.

CHED 457

University of Wisconsin-River Falls organic first curriculum

David B. Rusterholz, [email protected], Ross Jilk, Michael Kahlow, Daniel Marchand, Barbara Nielsen, Magdalena Pala, Karl Peterson, Jeff Rosenthal, Jamie Schneider, Stacey Stoffregen.Department of Chemistry, The University of Wisconsin-River Falls, River Falls, WI 54022, United States

In 2008 UWRF implemented an alternative “organic first” curriculum. This curriculum was designed for students who need at least four semesters of chemistry (typically chemistry, biology, and preprofessional majors). Our program goals were to increase student progression, retention, learning, and interest.

The first course introduces the general principles of chemistry through the lens of organic chemistry; the second is similar to a standard second semester organic course with special emphasis on biologically relevant compounds. The third course covers principles of chemistry (mostly general chemistry II topics) and the fourth is a standard analytical chemistry course. We are assessing this program alongside our traditional curriculum through measures of student learning (ACS standardized exams), student grades, retention, and progression. Descriptions of the courses and curriculum along with results of student assessment will be presented. The authors gratefully acknowledge the financial support of the NSF (DUE-0736504) for this project.

CHED 458

Creating a student-centered sophomore organic lab curriculum using microwave-assisted organic synthesis (MAOS)

S. Shaun Murphree, [email protected], Jeremy D. Mason, Theodore G. Bean.Department of Chemistry, Allegheny College, Meadville, PA 16335, United States

A sophomore-level organic laboratory curriculum has been developed using microwave-assisted organic synthesis (MAOS). Fifteen potential chemistries were developed, representing many of the major canonical reaction types in the sophomore organic sequence, some of which are of interest in their own right as workhorse synthetic protocols. A few of these reactions, selected for their tie-in to the classroom material, were crafted into student-driven group-based activities incorporating experimental design and reaction optimization. Thanks to the rapid microwave protocols, these activities could be completed in the regularly scheduled lab period.

The revised curriculum is supported by a variety of new materials, including: a) pre-lab activities; b) “technique primers”, one-page resources for specific lab techniques; c) case studies which frame the particular laboratory activity; and d) instructor materials. To assess the new lab curriculum, a survey instrument was constructed using items from the Attitudes Toward Science Inventory, the Views on Science and Education (VOSE) Questionnaire, the Views of Nature of Science Questionnaire, and the Science Laboratory Environment Inventory. The presentation will address: 1) the development of new synthetic methods adapted to microwave reactors; 2) the construction of new laboratory materials to support the modified curriculum; 3) issues regarding implementation; and 3) assessment results. The authors gratefully acknowledge the financial support of the NSF (DUE 0837640) for this project.

CHED 459

Integrated, instrument intensive project-based biochemistry laboratory for enhanced student learning and research

Todd P. Silverstein, [email protected] of Chemistry, Willamette University, Salem, OR 97301, United States

Our two-semester laboratory course is integrated with an upper-level Instrumental Analysis lecture course, and represents an ambitious extension of our project-based laboratory centered on tRNAPhe structure and dynamics (J. Chem. Educ. (2008) 85 , 666-679). This course is distinctive in that: students work extensively with three of the four major biomolecules; experiments involve the use of nine important methods of instrumental analysis; laboratory skills are developed, then reinforced over two semesters; and we begin with skill-based labs, progressing to guided-inquiry and problem-based labs. Biochemistry experiments draw on the expertise of organic, inorganic, analytical, and physical chemists. We aim to improve learning outcomes, and to replicate the scientific research workplace; this in turn prepares students for independent senior research in biochemistry. We will describe the structure of the course, how learning outcomes are addressed, including critical thinking and scientific communication, and report on initial student responses to the course. The authors gratefully acknowledge the financial support of the NSF (DUE 1044737) for this project.

CHED 460

Applied energy curriculum at the University of Southern Maine

Daniel M Martinez, [email protected], Travis Wagner, [email protected] of Environmental Science, University of Southern Maine, Gorham, Maine 04038, United States

This project focuses on the development of an applied energy curriculum including field and laboratory training. The curriculum is comprised of traditional coursework, laboratory work, field study, internships, and analysis in energy efficiency, production, and life cycle assessment. Undergraduates use various instruments in the energy courses and in conducting research projects under the umbrella of existing faculty research programs. A number of simply designed experiments ranging from determining the heating load of a model domestic hot water heater, to using Infrared thermography to explore how different objects absorb and emit radiation with applications in residential energy auditing. Through the integration into course curricula and use in undergraduate research, purchased energy equipment offers powerful pedagogical tools for helping students learn and perform investigations in energy and sustainability. The authors gratefully acknowledge the financial support of the NSF (DUE 0941778 ) for this project.

CHED 461

Experimental structure determination in the undergraduate curriculum

Dean H. Johnston, [email protected] of Chemistry, Otterbein University, Westerville, OHIO 43081, United States Advances in computing power and detector technology have made single-crystal X-ray structure determination a routine technique in the research laboratory. But relatively few opportunities exist for undergraduate students to analyze data obtained using crystallography. Laboratory exercises in experimental structural chemistry have been introduced into the first and second-year chemistry curriculum at Otterbein University. In the first-year laboratory, students grow crystals of amino acids and selected samples are analyzed using the Bruker SMART X2S diffractometer. Students then use the 3D structural data to analyze molecular geometry, hydrogen bonding, unit cells, density and crystal packing using the Mercury software package. This activity serves as an integrated exercise to reinforce concepts of chemical bonding, molecular structure, intermolecular forces and the nature of crystalline materials. In the second-year chemistry laboratories, students use X-ray diffraction as a tool for structural characterization of products from an independent synthesis project (inorganic) and a qualitative organic exercise (organic). The authors gratefully acknowledge the financial support of the NSF (DUE 0942850) for this project.

CHED 462

Breadth and depth in elemental analysis: A tale of transformation

Michelle M Bushey1, [email protected], Benjamin E Surpless2. (1) Department of Chemistry, Trinity University, San Antonio, TX 78212, United States (2) Department of Geosciences, Trinity University, San Antonio, TX 78212, United States

This project requested funds for a handheld X-ray fluorescence spectrometer and an inductively coupled plasma – optical emission spectrometer. Funds for laboratory development and assessment activities were included. These instruments are used in Chemistry and Geosciences courses that serve lower and upper division science majors, premedical profession, science education, and non-science major students. Both instruments have been used for undergraduate research projects. The use of these instruments builds expertise in faculty and students that has laid the foundation for new collaborations spanning the science departments, extending to non- science departments, and linking with off-campus collaborators. Assessment results for the first two years show that project goals addressing student learning, appreciation, and engagement are being achieved. In addition, this project has spurred additional faculty collaborative activities that includes new curricular activities, undergraduate research, and grant writing. The authors gratefully acknowledge the financial support of the NSF (DUE 0942940) for this project.

CHED 463

Raman spectroscopy implemented into undergraduate science education

Maria Hepel, [email protected] of Chemistry, State University of New York at Potsdam, Potsdam, NY 13676, United States

The innovative coursework based on the Raman scattering spectroscopy involving hands-on experiences with Raman instrumentation has been developed for students of two science departments, chemistry and biology. In series of new experiments incorporating advanced technologies for use in lower division undergraduate courses, the new instrumental capabilities have been utilized to engage students in nanoscience exploration. Also, the demonstrations have been carried out to attract students to undergraduate research and to disseminate information about the unique features and outstanding possibilities of compound identification and microscale analysis. The new hands-on experiences for students create the opportunity to enhance student's comprehension of chemistry at the nanoscale and enables them to gain new laboratory skills in high resolution Raman imaging techniques and chemical identification of species down to single molecule level. These experiences integrated across the curriculum are advancing the learning process to the challenges of the nanoscience and emerging nanotechnology. The authors gratefully acknowledge the financial support of the NSF (DUE 0941364) for this project.

CHED 464

Collaborative teaching innovation in freshman chemistry laboratory

Li-Qiong Wang, [email protected], Kristina Klara, Ning Hou, Allison Lawman.Chemistry, Brown University, Providence, RI 02912, United States

Collaborative efforts between the faculty and the undergraduate students play an important role in developing or improving the freshman chemistry laboratory course at Brown University. Brown University offers Undergraduate Teaching and Research Awards (UTRAs) for students interested in researching with faculty or improving the curriculum for an existing course. Many universities offer undergraduates the opportunity to work in faculty's research groups, but few offer a program that allows undergraduates directly work with professors to improve teaching. The UTRA award allows us to involve outstanding freshmen who just took the lab course to help the faculty in developing and improving the freshman chemistry labs that are aligned with the student's learning level and interests. For example, with the UTRA awards, we have developed a new fuel cell car lab module to illuminate connections between chemical energy, thermodynamics, electrolysis, and a hydrogen based transportation economy. A new and inexpensive circuit board was designed to attach to the fuel cell car kit enabling students to make electrical measurements during the fuel cell operation under different loads. This innovative design allows students to make a series of electric measurements while watching a car and mini cell phone vibrator running. The fuel cell car lab was successfully implemented into the curriculum with a class of 450 students and generated very positive responses from the students. This is an example of the new labs that we are developing for stimulating students' interest in learning as a result of collaborative teaching innovation.

CHED 465

Purification techniques as the theme for two foundation laboratories

Kate J Graham, [email protected], Edward J McIntee, Alicia A Peterson.Department of Chemistry, College of Saint Benedict/Saint John's University, Saint Joseph, MN 56374, United States

The Chemistry Department at the College of Saint Benedict/St. John's University has received NSF funding to fully revise our first year laboratory sequence. These foundation labs introduce students to the laboratory through the practice of purification techniques. The first semester course (Purification 1) focuses on methods such as distillation, filtration and extraction, whereas the second semester laboratory (Purification 2) introduces a wide variety of chromatographic techniques. In both laboratories, students purify a set of unknowns via prescribed methods and then analyze them through NMR, IR and UV spectroscopy, mass spectrometry, and gel electrophoresis. This presentation will focus on the implementation and assessment of these two laboratories.

CHED 466

X-ray powder diffraction for the quantitative analysis of a solid-state mixture: An undergraduate laboratory module Kimberly A. Rosmus, [email protected], Carl D. Brunetta, Jennifer A. Aitken.Department of Chemistry and Biochemistry, Duquesne University, Pittsburgh, PA 15282, United States

While there are many chemical and physical methods that can be used for analyzing materials and mixtures, most of these methods are limited in phase identification and/or providing spatial information with regards to chemical composition. With this in mind, an undergraduate laboratory module was developed to demonstrate the capacity of X-ray powder diffraction (XRPD) as an analytical tool for phase fraction determination of a solid-state mixture. The students performed traditional analytical methods, such as the method of standard addition and the internal standard reference method using a solid-state mixture. Additionally, the whole pattern fitting method of Rietveld analysis was conducted. Scanning electron microscopy was utilized to observe the differences in morphology and particle size between NaCl and KCl. Energy dispersive X-ray spectroscopy was employed for estimating the elemental composition of the NaCl/KCl mixture and providing elemental maps of the samples. Specific learning objectives will also be discussed.

CHED 467

Setting the stage for the development of critical thinking skills and green chemistry metrics using catalytic hydrogenation in the organic chemistry lab

Kenneth J O'Connor, [email protected], Derek Fry.Chemistry, Marshall University, Huntington, West Virginia 25755, United States

Catalytic hydrogenation is often employed for the conversion of alkenes to alkanes. Undergraduates typically conduct these reactions using either a homogeneous or heterogeneous transition metal catalyst. A green hydrogenation experiment of methyl trans-cinnamate and dimethyl fumarate performed in our organic chemistry laboratory classes will be presented; this experiment uses 2% Pd nanoparticles entrapped in an aluminum oxy-hydroxide matrix (Pd/Al(O)OH) as the transition metal catalyst. To address the development of critical thinking skills, the same chemical transformation using 5% Pd/C as the transition metal catalyst is used; however, students are responsible for the experimental design as well as determining how to monitor the reaction by TLC. A hydrogen balloon is used as the hydrogen source.

CHED 468

University/community college collaboration in professional development experiences and sequential research-based laboratories to engage community college organic chemistry students

Stephen D. Starnes1, [email protected], Bukuo Ni1, Ben Jang1, William Whaley2, Larry Brough3, Fred Jury4. (1) Chemistry, Texas A&M University-Commerce, Commerce, Texas 75429, United States (2) Chemistry, Tarleton State University, Stephenville, TX 76402, United States (3) Chemistry, Northeast Texas Community College, Mt. Pleasant, TX 75455, United States (4) Chemistry, Collin College, TX, Plano 75074, United States

This talk will detail the efforts of the NSF TUES (CCLI) project at Texas A&M-Commerce to engage students in chemistry at the University and Community College level. Our approach is multi-pronged, with 3 main components: 1. Professional development workshops between community college students in organic chemistry and a diversity of professionals in the chemistry field. 2. Joint laboratory exercises between community college students and university student mentors which are research based projects; community college students work with their university student mentors on an experiment using a combinatorial approach to the synthesis of nitroalkenes and another experiment in asymmetric organocatalysis. 3. Community college students receive hands-on training on a multitude of scientific instrumentation not readily available to community colleges including a 400 MHz NMR, polarimeter, IR, UV/vis, and chiral HPLC. Training in computational molecular modeling is also utilized. Our approach and successes will be presented.

CHED 469

Checklists as a means to decrease error in the organic chemistry laboratory course

Kishore K Bagga, [email protected], Peter Falzarano.Health Sciences, Drexel University, Philadelphia, PA 19102, United States

Checklists have been used increasingly in a number of fields especially by the aviation industry in order to increase communication between the pilot and co-pilot, and thereby decrease errors which in the past if over looked could potentially lead to a disaster. This approach was employed in the organic chemistry laboratory course to evaluate the frequency of errors made by those students without a checklist, and compared to those who were provided with one. The data in this work indicates that those without a checklist were prone to make more errors during various steps in the synthesis, and as a result have reduced yields of the desired material along with greater amount(s) of unreacted starting material compared to those with checklists. Additionally, those without checklists asked more questions about the procedure during their laboratory sessions. These factors may have contributed to the larger number of errors observed in those without checklists.

CHED 470

Use of virtual labs for electrochemistry

Ian C Hawkins, [email protected], Amy J Phelps.Chemistry, Middle Tennessee State University, Murfreesboro, Tennessee 37132, United States

The use of virtual labs in the teaching of chemistry has received renewed focus due to the increasing cost of hands-on labs, and the increased incidence of distance education. Recent studies have looked at the use of virtual tools for lab to supplement the hands-on laboratory environment but few have been used as replacements for the laboratory portion of the course. Many questions about virtual labs can not be addressed unless we set up a virtual versus hands- on scenario and collect data on the relative effect of each method. We separated our General Chemistry II students into two groups randomly assigning them to either a virtual or hands-on group for their electrochemical lab experiment. Pre- and post- test data were collected for both groups. The post test included a practical task of constructing a galvanic cell given certain solutions and metals. Preliminary results suggest that each group of students significantly improved from the pre-test to the post-test but there were no significant differences between the virtual lab and hands-on lab experiences based on the paper and pencil portion of the post test.

CHED 471

Microwave induced demulsification of cooking oil as potential source of biofuels

Anjali Mitra1, [email protected], Smruti Ragunath2, Somenath Mitra2. (1) Department of Biology, New Jersey Institute of Technology, Newark, New Jersey 07102, United States (2) Department of Chemistry & Environmental Science, New Jersey Institute of Technology, Newark, New Jersey 07102, United States The conventional approaches for the de-emulsification of biological colloids include chemical and physical methods. The former requires the addition of a demulsifier in order to achieve separation, while the latter involves heating or electrical techniques. De-emulsification using these methods tends to be expensive in terms of the cost of chemicals and energy requirements. Microwave induced demulsification of cooking oil water mixtures is presented for suspensions stabilized by surfactants. Microwave induced de-emulsification was completed in a matter of minutes and at very low temperatures. The particles size of the colloids thus formed varied from 400 nm to 6.5 microns. The separation efficiency increased with decrease in the percentage of oil content. The 90 % and 75 % oil-water emulsions, which represented reverse micelle structures reached separation efficiency of 50% using microwave heating but could not be separated by conventional heating. On the other hand, the 50 % and 25% oil-water mixtures were relatively easy to demulsify, where separation efficiency was as high as 100%. We postulate that the microwave couples differently with the polar molecules in the biocollids, leading to breakdown of its stability. The effectiveness of the microwave demulsification is quite evident from this data.

CHED 472

Creating the first forensic science course and the first forensic chemistry course for Walsh University

Amy J. Heston, [email protected] of Math and Sciences, Walsh University, North Canton, OH 44720, United States

Modern technology and group activities were essential in the creation of Introduction to Forensic Science (NS 114) and Forensic Chemistry (NS 215) at Walsh University. These courses offer a unique opportunity for non-majors to meet the general education science requirement. By implementing classroom activities that incorporate the scientific method, both courses meet the requirements in the Walsh University General Education Curriculum. The introductory course now serves as a foundation course for the forensic studies minor. Due to increasing popularity, Forensic Chemistry was created and currently serves as an elective for the minor. Both courses give students a greater appreciation for scientific detail in real life situations. Learning outcomes, including critical thinking and data analysis, were assessed and the data showed that the use of technology as well as group activities enhanced learning and were critical in the success of this course. These actions also increased student self-efficacy and aided in academic success.

CHED 473

Energy! A general education science course

Sally Hunnicutt1, [email protected], Alison Baski2. (1) Department of Chemistry, Virginia Commonwealth University, Richmond, VA 23284-2006, United States (2) Department of Physics, Virginia Commonwealth University, Richmond, VA 23284, United States

Energy!, developed by a chemist and physicist as a study of global energy demands, how these are being met, and environmental consequences is designed to meet the university's science and technology breadth requirement. Topics include energy, work, heat, and power; fossil fuels; combustion; global climate change; renewable energy sources; and nuclear energy. Themes of numeracy, physics, and chemistry are woven throughout the content, and new topics are added each semester based on current events. The course enrolls about 900 students each semester with faculty from both departments co-teaching multiple sections. The students represent a range of majors and comprise freshmen to seniors. In-class “clickers" questions are used and reinforced with online homework. Analysis of student scores will be presented showing that student GPA is the best predictor of success but that classroom participation and completion of homework assignments are also effective means of learning for this group of students. CHED 474

Getting more biochemistry into organic chemistry

Steven A Fleming, [email protected] of Chemistry, Temple University, Philadelphia, PA 19122, United States

There is a push for more biochemistry to be included in organic chemistry courses. This pressure is partially a result of the ACS recommendation to include topics on biochemistry in the undergraduate curriculum. In addition, we have been informed that the organic chemistry questions on the MCAT will be more bio-oriented in the soon to be released version of the exam. Many of the topics of biochemistry can be handled in an organic chemistry course. Dealing with enzymes, lipids, carbohydrates, and nucleic acids is possible after a student has a solid background in the chemistry of alkenes, alcohols, amines, aromatic rings, ketones, aldehydes, and carboxylic acids. We have developed a teaching tool that can assist students as they make the step from the small molecules in organic chemistry to the biomolecules that are involved in life. The tool is called BioORA. It is a software program that is accessible online at no cost. BioORA is divided into 4 chapters: enzymes, lipids, carbohydrates, and nucleic acids. We will present the software and discuss its assessment. We will address whether this tool will meet the need of including more biochemistry in organic chemistry courses.

CHED 475

Teaching an organic/biochemistry semester course to non-majors in the health science fields: Putting the biochemistry first!

Deanna L Warner, [email protected] of Chemistry and Physics, Salem State University, Salem, MA 01970, United States

In the traditional two semester chemistry course sequence for non-majors in the health science fields, the first semester is devoted to general chemistry and the second semester is devoted to a mixture of organic and biochemistry. In that second semester course, the organic chemistry portion is traditionally presented first to the student, followed by the biochemistry portion. Unfortunately this approach sometimes results in the loss of interest by the student, as no immediate, clear connection is established between chemistry and the health science fields. The focus of this presentation is to lay out a pathway to presenting the biochemistry portion of the course throughout the entire semester, with organic chemistry given a supporting role.

CHED 476

Organic chemistry and the "structure-mechanism-reaction" paradigm: Structure knowledge is a powerful predictor of student performance

Steven M Graham, [email protected] of Chemistry, St. John's University, Queens, NY 11439, United States

Much of organic chemistry presupposes knowledge of chemical structure; indeed structure is the foundation upon which mechanistic theory and chemical synthesis rest. For a number of years we have been assessing which types of exam questions – those dealing with chemical structure, reaction mechanisms, and synthetic outcomes – students find most difficult, with the goal of designing an intervention that would address this difficulty. One such intervention was the use of personal response systems ('clickers') to create a numeric representation of organic chemistry mechanism arrows (Ruder and Straumanis, J. Chem. Educ., 2009 , 86, 1392-1396). Post-clicker introduction, we observed a significant improvement on mechanism-based exam questions. More dramatic, however, was the observation that a student's score on structure-based questions is tightly correlated to their overall exam score. This finding suggests that an increased emphasis in the classroom on the structure of organic molecules may be beneficial.

CHED 477

Natural bond orbital model for teaching chemical bonding: Bonding teaching with research

Mohamed Ayoub, [email protected] of Chemistry, University of Wisconsin-Washington County, West Bend, Wisconsin 53095, United States

We report a comprehensive, step-by-step approach for teaching the chemical bond throughout the chemistry curriculum. This approach is guided by modern electronic structure theories available to generate wavefunction (Ψ), the ultimate knowledge for any chemical system of interest. We apply natural bond orbital (NBO) methods to analyze Ψ in Lewis-type (bonding, lone- pair) and non-Lewis-type (anti-bonding, rydberg) language very familiar to students and professionals interested in investigating molecular structures for environmental, biological and material science applications. In addition, we illustrate how to implement NBO graphical capabilities to produce contour and surface plots (2d, 3d) for all NBOs, which can guide students and professionals alike to follow the structure-reactivity relationship for the chemistry at hand.

CHED 478

Electronegativity and the chemical bond

Peter Wepplo, [email protected], United States

Linus Pauling introduced the term electronegativity in 1932 to explain the difference in bond energy from that predicted. It may be the most cited topic in chemistry. However, its predictions of ionic character do not match the the ionization and acidity of the haloacids. The bond energies of metal hydrides refute the principle that ionic character can only increase bond strength.

I will offer a theory to explain why bonds have greater than expected bond strengths and why the metal hydrides should be weaker than predicted.

CHED 479

Drug discovery, human rights, and protecting the intellectual property of indigenous groups

Alexander Greer, [email protected], Brooklyn College of CUNY, Brooklyn, New York 11210, United States

In this talk, I present a description of indigenous groups' right to the benefits of their knowledge and protection against biopiracy and patents that take it. I will describe the situation where drug discovery researchers often do not consider traditional knowledge as intellectual property (IP) that should be protected and benefits shared. Pharma can come into indigenous communities to gain empirical knowledge of decades-old, traditional remedies and leave to do further research and patent it. Aspirin provides one example, where traditional knowledge was the starting point in its discovery. The UN General Assembly has adopted the Declaration on the Rights of Indigenous Peoples in 2007 for greater self-determination. The declaration may lead to more equitable outcomes of IPs, but improvements can be very slow and injustices can remain institutionalized and invisible. I present possible solutions seeking an “enlightened” view against biopiracy, where protecting the IP rights of indigenous medicines is a difficult task and chemists would have a role in such a movement.

CHED 480

Enhancing STEM education via the creation of student-constructed STEMWikis

Delmar Larsen, [email protected], University of California, Davis, Davis, CA 95616, United States

Student authorship of Wiki-based textbooks addresses many needs in contemporary education, including collaboration, critical thinking, and writing and publishing. Rapidly rising undergraduate fees and textbook costs are factors impeding access to higher education for many students, and have a defeating effect on many under-served, at-risk students. Although an problem of great concern, the growing expenses of post-secondary education provide an opportune incentive for greater engagement of students in their education. STEMWiki participation provides students with an attainable (yet loftily) goal of an empowering mechanism to reduce out of pocket expenses. As students create functionally instructional STEMWiki materials, they acquire 21st-century skills including critical thinking, communication, collaboration, and creativity and they organize knowledge with other students and for other students. The ChemWiki (http://ChemWiki.ucdavis.edu) is the pilot STEMWiki developed to demonstrate efficacy of the DTP, and currently has a visitor traffic of 7.5 M visits and 11.25 M pageviews per year with an estimated 512 hours of reading/writing occurring daily.

CHED 481

Practical perspectives: Learning chemistry in a chemical technology program

David Baker, [email protected], Michael Faleski.Science Division, Delta College, University Center, MI 48710, United States

As part of the Chemical Technology program, students are expected to learn and to demonstrate competencies in a broad spectrum of laboratory techniques. In order to evaluate student abilities in these competencies, a number of assessment experiments and tools have been developed. All of the program's core assessment outcomes eventually will be evaluated, but the initial focus is on student ability to apply chemical principles for solving scientific questions. A discussion of the methods employed to evaluate our students' learning, the data collected, and possible future teaching approaches will be presented.

CHED 482

Learning outcomes-based assessment of individual performance gains in general chemistry courses as part of the Emerging Scholars Program at the University of Texas at Arlington

Kevin A Schug, [email protected], Sarah E Hardee, Priscila M Martinez, Emmanuel Varona, Kenneth M. Abayan, Doug D. Carlton, Abegayl L Thomas.Department of Chemistry & Biochemistry, The University of Texas at Arlington, Arlington, TX 76019, United States

As part of a NSF-funded STEM Talent Expansion Program (STEP) at U.T. Arlington, an Emerging Scholars Program (ESP) was instituted to improve retention of STEM majors in high loss courses. For General Chemistry 1 and Chemistry for Engineers, a learning-outcomes based assessment has also been devised to track individual mastery of course content. From the beginning, students in ESP have passed (grade of “C” or better) these courses at a significantly higher rate than non-ESP students. In fall 2011, a learning outcomes-guided approach was adopted. This has included tracking the progression of each student's knowledge through regular quizzes, which are not part of the course grade, and formal lecture exams, which are. Each question was coded to a particular outcome, and the results show a progression toward topic mastery. This is likely due to the ability to identify and address weaknesses in specific material early in the assessment process.

CHED 483

Application of clickers in a small inorganic chemistry lecture class

James F. Kirby1, [email protected], Jeremy J. Anderson2. (1) Department of Chemistry and Physical Sciences, Quinnipiac University, Hamden, CT 06518, United States (2) Department of Academic Technology, Quinnipiac University, Hamden, CT 06518, United States

Inorganic Chemistry is often a low enrollment class. Use of audience response systems (ARS, or "clickers") has been seen as a way to increase student engagement and achieve course objectives in large classes. This pilot study was run during the Fall 2011 semester in an Inorganic Chemistry class of 14 student to measure the effectiveness of ARS in a low enrollment course. The types of questions and approaches used will be discussed along with preliminary findings, which indicate that students performed better on exams when material was covered using ARS rather than traditional lecture means. Results of student opinion surveys will also be presented.

CHED 484

Professional practices in chemistry: A course using active learning to teach important career issues

Suzanne M Ruder, [email protected], Sally S Hunnicutt.Department of Chemistry, Virginia Commonwealth University, Richmond, VA 23284-2006, United States

“Professional Practices in Chemistry” is a course developed for chemistry majors to help them gain a better understanding of career opportunities and preparation for the workforce. The course grew out of a similar plan developed for use during orientation for a summer Research Experience for Undergraduate (REU) students. Students engage in active learning to explore practices including writing resumes and personal statements and interviewing. Activities on scientific professionalism, reading a scientific paper, and plagiarism have been particularly successful at helping students gain an understanding of issues that are rarely covered in regular chemistry courses. The outline of the course will be discussed as well as some examples from the active learning activities mentioned above.

CHED 485

Fostering international collaboration, education, and training: Outcomes of the ACS GREET Program

Steven R Meyers, [email protected], Bradley D Miller.Office of International Activities, American Chemical Society, Washington, DC 20036, United States The concomitant shifting realities of international collaboration and innovation, the need to prepare the next generation, and the essentialness of problem solving on a global scale provided the rationale for the creation of the ACS Global Research Experiences, Education, and Training (GREET) program. GREET aims to provide intensive, high-impact, international research and collaboration opportunities to U.S. chemical scientists with particular focus given to the inclusion of both undergraduate and graduate students. Additionally, GREET aims to: offer a tremendous mentoring experience to the participating students, help attract and retain talented students in chemistry-related programs and careers; boost substantive undergraduate and early career graduate student research; and infuse a more global perspective into U.S. curricula.

To date the tangible outcomes of the GREET participants have ranged from obtainment of large research grants to changes in university curricula. Further details on this model program will be given and the outcomes discussed.

CHED 486

Chemistry for future presidents

David A Katz, [email protected] of Chemistry, Pima Community College, Tucson, AZ 85709, United States

The chemistry courses for non-major students, taught by this author, have been redirected over the past 20 years as constantly evolving hands-on issues-based courses examining the chemistry behind topics such as life in the universe, atmospheric chemistry, climate change, Earth and water chemistry, energy and nuclear issues, science and science fiction, nanotechnology, introductory forensics, consumer products, and food chemistry becoming the driving forces for course content. The aim of these integrated lecture-laboratory courses is to prepare the future business person or political leader to be able to understand the basics of chemistry in their everyday life and to be able to find and evaluate information on science issues of public concern. Internet links and instructor developed materials have replaced the textbook with chemical principles, structures, and nomenclature taught on a need-to-know basis in context with demonstrations, hands-on activities, and tasting sessions. Laboratory activities have been designed to go beyond the traditional tedious verification experiments to those that allow students to utilize concepts and apply them to everyday chemistry and issues discussed in these courses. This presentation will review the teaching strategies along with a number of class activities and laboratory experiments that this author is using to shape the knowledge of our future leaders.