Synthesis and Complexation of Functionalized Mixed Thia‐Aza‐Macrocyclic

Total Page:16

File Type:pdf, Size:1020Kb

Synthesis and Complexation of Functionalized Mixed Thia‐Aza‐Macrocyclic © 2009 WILHELM S. MALASI ALL RIGHTS RESERVED SYNTHESIS AND COMPLEXATION OF FUNCTIONALIZED MIXED THIA‐AZA‐MACROCYCLIC AND MEDIUM SIZED LIGANDS A Dissertation Presented to The Graduate Faculty of the University of Akron In Partial Fulfillment of the Requirement for the Degree Doctor of Philosophy Wilhelm Malasi May 2009 SYNTHESIS AND COMPLEXATION OF FUNCTIONALIZED MIXED THIA‐AZA‐MACROCYCLIC AND MEDIUM SIZED LIGANDS Wilhelm Malasi Dissertation Approved: Accepted: _________________________ _________________________ Advisor Department Chair Dr. Michael J. Taschner Dr. Kim C. Calvo _________________________ _________________________ Committee Member Dean of the College Dr. David Modarelli Dr. Chand Midha _________________________ _________________________ Committee Member Dean of the Graduate School Dr. Jun Hu Dr. George R. Newkome _________________________ _________________________ Committee Member Date Dr. Wiley J. Youngs _________________________ Committee Member Dr. Amy Milsted ii ABSTRACT Six ligands of mixed thia-aza donor atoms 40, 90, 100, 107, 110 and 112 have been synthesized and characterized. The metal complexes of Copper 114, Rhodium 116, and Nickel 115 with 1,8-dithia-4,11-diazacyclotetradecane 40 have been made and crystal structures grown in appropriate solvents to give good crystals suitable for X-ray crystallographic analysis. Other molecules whose crystals have been made and analyzed by X-ray crystallography are the secondary amine 82, tosylated double ligand tertiary amine 91, the seven member ring ester 100 and the perchlorate salt of the double nine member ligand tertiary amine 110. All these crystals have their analysis data in Appendix D. The seventh ligand 113 has been adapted, and complexed with rhodium and its crystal structure 117 has been analyzed. The curative activity of the rhodium complex 116 was tested against ovarian cancer cells Nutu-19 at 1.54 mM concentrations. The results showed that the cells became detached with extreme morphological changes and extreme internal vesicle formation causing the cells to die. Ovarian normal cells, tested at the same concentration, showed that the cells remain attached, with no morphological changes and only slightly vesicle formation. Table 4 in Chapter II shows 87% of the cancer cells died while only 30% of the normal ovarian cells died. If the toxicity of this complex can be further controlled and minimized, it may be very useful in the treatment of cancer in the future. iii The ligand 40 was functionalized through carboxylic acid derivatives to give rise to the new ligand 90. Also ligand 107 was functionalized in the same way to give the new ligand 110, while the liands 82 and 107 were successfully joined by a butane chain to form a new ligand 112. In an attempt to synthesize the carbon bridged functionalized fourteen membered ring, ligand 99, the functionalized seven membered ring molecule 100 was isolated instead. iv DEDICATION To my mother Delfina and memory of my father Simon Lucas who passed away July 22, 2008. Those who sow in tears shall reap rejoicing (Ps 126:5) v ACKNOWLEDGEMENTS Heartfelt appreciations to my mentor Dr. Michael J. Taschner for his commitment, fraternal assistance, constant guidance and encouragement the whole period of my course. Special thanks to my colleagues Zin Min from Dr. Tessier’s research group for her encouragement and computer data handling, Dr. Wiley Young’s group for X-ray crystallography, Dr. Wedsmiotes’s group for mass spectrometry, Jacob Weingart in Dr. Jun Hu’s group for Infrared (IR) spectra and the staff members Dr. Joe Massey, Dr. Venkat Dudipala and Simon Stakleff for NMR instruments operations and technicalities. Also, the chemistry department secretaries Nancy Homa and Jean Garcia for their constant availability to assist and direction. The chemstore provider and instructor Lisa Zickefoose for promptness and efficiency. I acknowledge my research group members and friends Swaranjali Bhide, Wenchao Qu, Tara Scheiber and Aaron Lineberry for cooperation and providing a viable environment to work smoothly. Special recognition to all my committee members and professors who made my course work, subsequent studies and research possible, and brought my dream to reality. Remarkable acknowledgement to my superiors for offering me the opportunity for studies, my family, relatives and friends at home (Tanzania) for their sacrifices and patience, especially my mother for understanding. vi TABLE OF CONTENTS Page LIST OF TABLES............................................................................................................. ix LIST OF FIGURES .............................................................................................................x LIST OF SCHEMES......................................................................................................... xii CHAPTER I. INTRODUCTION......................................................................................................1 1.1 Synthesis and Study of Supramolecular Properties .......................................1 1.2 Metal Complexes of the Macrocyclic Ligands..............................................9 1.3 Other [14] Member Ring Macrocylic Molecules ........................................18 1.4 Medium Cyclic Molecules Synthesized ......................................................20 II. RESULTS AND DISCUSSIONS ............................................................................25 2.1 Synthesis, Complexation and Characterization of the Ligands ...................25 2.2 The Macrocyclic Ligands Synthesized in This Work..................................26 III. SUMMARY .............................................................................................................51 IV. EXPERIMENTAL ...................................................................................................53 4.1 General Procedure........................................................................................53 4.2 Synthesis ......................................................................................................55 4.3 Complexing the Synthesized Ligands..........................................................79 REFERENCES ..................................................................................................................82 vii APPENDICES ...................................................................................................................90 APPENDIX A. 1H AND 13C NMR SPECTRA OF THE COMPOUNDS....................91 APPENDIX B. IR SPECTRA OF THE MOLECULES AND THE LIGANDS ........122 APPENDIX C. MASS SPECTRA OF SELECTED PRODUCTS .............................133 APPENDIX D. X-RAY CRYSTAL STRUCTURES AND DATA ANALYSIS OF THE PRODUCTS........................................................................136 viii LIST OF TABLES Table Page 1. Enthalpies and Entropies of Cu(II) Complexation with 29-37...................................6 2. Summary of Some Specific Rate Constants for Aquocopper(II) Ions Reacting with Various Protonated Amino/thia Ethers2 Quadridentate and Quinquedentate Macrocycles.....................................................................................9 3. Selected Crystallography Data for 40, 114, 116 and 115.........................................37 4. Activity of Rhodium Complex on Ovarian Cancer..................................................39 ix LIST OF FIGURES Figure Page 1. Plastocyanin6 and Rusticyanin8 as examples of blue copper protein in nature ..........3 2. A variety of ligands with mixed donor atom..............................................................4 3. Various size all tetra-aza ligands used to complex copper (II) to study enthalpies and entropies of complex formation..........................................................................5 4. Various macrocyclic ligands studied by Westerby et al.............................................8 5. Demonstrating electron transfer in Cu(II/I) redox, D1-4 represent donor atoms.......11 6. Electron transfer and geometry changes of Cu(II/I)/Fe (II/III) complexes ..............11 7. Complexes of nickel and the ligand .........................................................................12 8. Arca et al.119 synthesized ligands 121-123 and Taylor et al.120 synthesized 124,125 .....................................................................................................................14 9. The model of ligands functionalized at the bridging carbons ..................................15 10. Ball and stick X-ray structures developed from available data for rhodium complexed with [14]aneN2S2 and [14]aneNS3 .........................................................18 11. Nine member rings reported in literature .................................................................20 12. Two copper atoms complexed with [9]aneNS2 in a bridging manner......................21 13. Copper atom sandwiched between two [9]aneNS2 ligands......................................22 14. Nickel complexed with [9]aneNS2 ...........................................................................23 15. A crystal structure of rhodium complexed with a nine member ring ligand............24 16. Crystal structures of the tosylated amine 82.............................................................29 17. The crystal structure of the ligand 40 .......................................................................31 x 18. Crystal structure 114 of copper complexed with ligand 40.....................................32 19. Crystal
Recommended publications
  • First Principles Prediction of Thermodynamic Properties
    2 First Principles Prediction of Thermodynamic Properties Hélio F. Dos Santos and Wagner B. De Almeida NEQC: Núcleo de Estudos em Química Computacional, Departamento de Química, ICE Universidade Federal de Juiz de Fora (UFJF), Campus Universitário Martelos, Juiz de Fora LQC-MM: Laboratório de Química Computacional e Modelagem Molecular Departamento de Química, ICEx, Universidade Federal de Minas Gerais (UFMG) Campus Universitário, Pampulha, Belo Horizonte Brazil 1. Introduction The determination of the molecular structure is undoubtedly an important issue in chemistry. The knowledge of the tridimensional structure allows the understanding and prediction of the chemical-physics properties and the potential applications of the resulting material. Nevertheless, even for a pure substance, the structure and measured properties reflect the behavior of many distinct geometries (conformers) averaged by the Boltzmann distribution. In general, for flexible molecules, several conformers can be found and the analysis of the physical and chemical properties of these isomers is known as conformational analysis (Eliel, 1965). In most of the cases, the conformational processes are associated with small rotational barriers around single bonds, and this fact often leads to mixtures, in which many conformations may exist in equilibrium (Franklin & Feltkamp, 1965). Therefore, the determination of temperature-dependent conformational population is very much welcomed in conformational analysis studies carried out by both experimentalists and theoreticians.
    [Show full text]
  • Comparing Models for Measuring Ring Strain of Common Cycloalkanes
    The Corinthian Volume 6 Article 4 2004 Comparing Models for Measuring Ring Strain of Common Cycloalkanes Brad A. Hobbs Georgia College Follow this and additional works at: https://kb.gcsu.edu/thecorinthian Part of the Chemistry Commons Recommended Citation Hobbs, Brad A. (2004) "Comparing Models for Measuring Ring Strain of Common Cycloalkanes," The Corinthian: Vol. 6 , Article 4. Available at: https://kb.gcsu.edu/thecorinthian/vol6/iss1/4 This Article is brought to you for free and open access by the Undergraduate Research at Knowledge Box. It has been accepted for inclusion in The Corinthian by an authorized editor of Knowledge Box. Campring Models for Measuring Ring Strain of Common Cycloalkanes Comparing Models for Measuring R..ing Strain of Common Cycloalkanes Brad A. Hobbs Dr. Kenneth C. McGill Chemistry Major Faculty Sponsor Introduction The number of carbon atoms bonded in the ring of a cycloalkane has a large effect on its energy. A molecule's energy has a vast impact on its stability. Determining the most stable form of a molecule is a usefol technique in the world of chemistry. One of the major factors that influ­ ence the energy (stability) of cycloalkanes is the molecule's ring strain. Ring strain is normally viewed as being directly proportional to the insta­ bility of a molecule. It is defined as a type of potential energy within the cyclic molecule, and is determined by the level of "strain" between the bonds of cycloalkanes. For example, propane has tl1e highest ring strain of all cycloalkanes. Each of propane's carbon atoms is sp3-hybridized.
    [Show full text]
  • Text Related to Segment 5.02 ©2002 Claude E. Wintner from the Previous Segment We Have the Value of the Heat of Combustion Of
    Text Related to Segment 5.02 ©2002 Claude E. Wintner From the previous segment we have the value of the heat of combustion of an "unstrained" methylene unit as -157.4 kcal/mole. On this basis one would predict that combustion of "unstrained" cyclopropane should liberate 3 X 157.4 = 472.2 kcal/mole; however, when cyclopropane is burned, a value of 499.8 kcal/mole is measured for the actual heat of combustion. The difference of 27.6 kcal/mole is interpreted as representing the higher internal energy ("strain energy") of real cyclopropane as compared to a postulated strain-free "model." ("Model" in this usage speaks of a proposal, or postulate.) These facts are graphed conveniently on an energy diagram as follows: "Strain Energy" represents the error units: kcal/mole not to scale in the "strain-free model" real cyclopropane + 4.5 O2 27.6 "strain-free model" of cyclopropane 499.8 observed heat of combustion + 4.5 O2 472.2 3CO2 + 3H2O heat of combustion predicted for "strain-free model" Note that this estimate of the strain energy in cyclopropane amounts to 9.2 kcal/mole of strain per methylene group (dividing 27.6 by 3, because of the three carbon atoms). Comparable values in kcal/mole for other small and medium rings are given in the following table. As one might expect, in general the strain decreases as the ring is enlarged. units: kcal/mole n Total Strain Strain per CH2 3 27.6 9.2 (CH2)n 4 26.3 6.6 5 6.2 1.2 6 0.1 0.0 ! 7 6.2 0.9 8 9.7 1.2 9 12.6 1.4 10 12.4 1.2 12 4.1 0.3 15 1.9 0.1 Without entering into a discussion of the relevant bonding concepts here, and instead relying on geometry alone, interpretation of the source of the strain energy in cyclopropane and cyclobutane is to some extent self-evident.
    [Show full text]
  • The Enthalpy of Formation of Organic Compounds with “Chemical Accuracy”
    chemengineering Article Group Contribution Revisited: The Enthalpy of Formation of Organic Compounds with “Chemical Accuracy” Robert J. Meier Pro-Deo Consultant, 52525 Heinsberg, North-Rhine Westphalia, Germany; [email protected] Abstract: Group contribution (GC) methods to predict thermochemical properties are of eminent importance to process design. Compared to previous works, we present an improved group contri- bution parametrization for the heat of formation of organic molecules exhibiting chemical accuracy, i.e., a maximum 1 kcal/mol (4.2 kJ/mol) difference between the experiment and model, while, at the same time, minimizing the number of parameters. The latter is extremely important as too many parameters lead to overfitting and, therewith, to more or less serious incorrect predictions for molecules that were not within the data set used for parametrization. Moreover, it was found to be important to explicitly account for common chemical knowledge, e.g., geminal effects or ring strain. The group-related parameters were determined step-wise: first, alkanes only, and then only one additional group in the next class of molecules. This ensures unique and optimal parameter values for each chemical group. All data will be made available, enabling other researchers to extend the set to other classes of molecules. Keywords: enthalpy of formation; thermodynamics; molecular modeling; group contribution method; quantum mechanical method; chemical accuracy; process design Citation: Meier, R.J. Group Contribution Revisited: The Enthalpy of Formation of Organic Compounds with “Chemical Accuracy”. 1. Introduction ChemEngineering 2021, 5, 24. To understand chemical reactivity and/or chemical equilibria, knowledge of thermo- o https://doi.org/10.3390/ dynamic properties such as gas-phase standard enthalpy of formation DfH gas is a necessity.
    [Show full text]
  • Baeyer Strain Theory Introduction Van't Hoff and Lebel Proposed
    Baeyer Strain Theory instable cycloalkanes. The large ring systems involve negative strain hence do not exists. Introduction The bond angles in cyclohexane and higher Van’t Hoff and Lebel proposed tetrahedral cycloalkanes (cycloheptane, cyclooctane, geometry of carbon. The bond angel is of 109˚ cyclononane……..) are not larger than 109.5 28' (or 109.5˚) for carbon atom in tetrahedral because the carbon rings of those compounds geometry (methane molecule). Baeyer are not planar (flat) but they are puckered observed different bond angles for different (Wrinkled). cycloalkanes and also observed some These assumptions are helpful to understand different properties and stability .On this instability of cycloalkane ring systems. basis, he proposed angle strain theory. The theory explains reactivity and stability of Cyclopropane is more prone to cycloalkanes. Baeyer proposed that the undergo ring opening reaction than optimum overlap of atomic orbitals is cyclobutane or cyclopentane achieved for bond angel of 109.5 .In short, it is Cyclopropane is more reactive than ideal bond angle for alkane compounds. cyclobutane and cyclopentane Effective and optimum overlap of atomic orbitals produces maximum bond strength The ring of cyclopropane is triangle. hance stable molecule. All the three angles are of 60 in place of 109.5 (normal bond angle for If bond angles deviate from the ideal carbon atom) to adjust them into then ring produce strain. triangle ring system. Higher the strain higher the In same manner, cyclobutane is instability. square and the bond angles are of 90o in place of 109.5o (normal bond Higher strain increases reactivity and angle for carbon atom) to adjust them increases heat of combustion.
    [Show full text]
  • Cycloalkanes, Cycloalkenes, and Cycloalkynes
    CYCLOALKANES, CYCLOALKENES, AND CYCLOALKYNES any important hydrocarbons, known as cycloalkanes, contain rings of carbon atoms linked together by single bonds. The simple cycloalkanes of formula (CH,), make up a particularly important homologous series in which the chemical properties change in a much more dramatic way with increasing n than do those of the acyclic hydrocarbons CH,(CH,),,-,H. The cyclo- alkanes with small rings (n = 3-6) are of special interest in exhibiting chemical properties intermediate between those of alkanes and alkenes. In this chapter we will show how this behavior can be explained in terms of angle strain and steric hindrance, concepts that have been introduced previously and will be used with increasing frequency as we proceed further. We also discuss the conformations of cycloalkanes, especially cyclo- hexane, in detail because of their importance to the chemistry of many kinds of naturally occurring organic compounds. Some attention also will be paid to polycyclic compounds, substances with more than one ring, and to cyclo- alkenes and cycloalkynes. 12-1 NOMENCLATURE AND PHYSICAL PROPERTIES OF CYCLOALKANES The IUPAC system for naming cycloalkanes and cycloalkenes was presented in some detail in Sections 3-2 and 3-3, and you may wish to review that ma- terial before proceeding further. Additional procedures are required for naming 446 12 Cycloalkanes, Cycloalkenes, and Cycloalkynes Table 12-1 Physical Properties of Alkanes and Cycloalkanes Density, Compounds Bp, "C Mp, "C diO,g ml-' propane cyclopropane butane cyclobutane pentane cyclopentane hexane cyclohexane heptane cycloheptane octane cyclooctane nonane cyclononane "At -40". bUnder pressure. polycyclic compounds, which have rings with common carbons, and these will be discussed later in this chapter.
    [Show full text]
  • In This Handout, All of Our Functional Groups Are Presented As Condensed Line Formulas, 2D and 3D Formulas and with Nomenclature Prefixes and Suffixes (If Present)
    In this handout, all of our functional groups are presented as condensed line formulas, 2D and 3D formulas and with nomenclature prefixes and suffixes (if present). Organic names are built on a foundation of alkanes, alkenes and alkynes. Those examples are presented first and you need to know those rules. The strategies can be found in Chapter 4 of our textbook (alkanes: pages 93-98, cycloalkanes 102-104, alkenes: pages 104-110, alkynes: pages 112-113 and combinations of all of them 113-115). After introducing examples of alkanes, alkenes, alkynes and combinations of them, the functional groups are presented in order of priority. A few nomenclature examples are provided for each of the functional groups. Examples of the various functional groups are presented on pages 115-135 in the textbook. Two overview pages are on pages 136-137. Some functional groups have a suffix name when they are the highest priority functional group and a prefix name when they are not the highest priority group, and these are added to the skeletal names with identifying numbers and stereochemistry terms (E and Z for alkenes, R and S for chiral centers and cis and trans for rings). Several low priority functional groups only have a prefix name. A few additional special patterns are shown on pages 98-102. The only way to learn this topic is practice (over and over). The best practice approach is to actually write out the names (on an extra piece of paper or on a white board, and then do it again). The same functional groups are used throughout the entire course.
    [Show full text]
  • (12) United States Patent (10) Patent No.: US 7,560,510 B2 Wang Et Al
    US007560510B2 (12) United States Patent (10) Patent No.: US 7,560,510 B2 Wang et al. (45) Date of Patent: *Jul. 14, 2009 (54) NANO-SIZED INORGANIC METAL 4,906,695 A 3, 1990 Blizzard et al. PARTICLES, PREPARATION THEREOF, AND 4,920,160 A 4/1990 Chip et al. APPLICATION THEREOF IN IMPROVING 4.942,209 A 7, 1990 Gunesin RUBBER PROPERTIES 5,036,138 A 7, 1991 Stamhuis et al. (75) Inventors: Xiaorong Wang, Hudson, OH (US); 5,066,729 A 1 1/1991 Srayer, Jr. et al. Georg G. A. Böhm, Akron, OH (US) 5,073,498 A 12/1991 Schwartz et al. 5,075,377 A 12/1991 Kawakubo et al. (73) Assignee: Bridgestone Corporation, Tokyo (JP) 5, 120,379 A 6/1992 Noda et al. (*) Notice: Subject to any disclaimer, the term of this 5,130,377 A 7/1992 Trepka et al. patent is extended or adjusted under 35 5,169,914 A 12, 1992 Kaszas et al. U.S.C. 154(b) by 17 days. 5,194,300 A 3/1993 Cheung 5,219,945 A 6/1993 Dicker et al. This patent is Subject to a terminal dis 5,227419 A 7, 1993 Moczygemba et al. claimer. 5,237,015 A 8, 1993 Urban (21) Appl. No.: 11/642,124 5,241,008 A 8, 1993 Hall 5,247,021 A 9/1993 Fujisawa et al. (22) Filed: Dec. 20, 2006 5,256,736 A 10/1993 Trepka et al. 5,262,502 A 11/1993 Fujisawa et al. (65) Prior Publication Data 5,290,873 A 3, 1994 Noda et al.
    [Show full text]
  • Polypropylene-Based Adhesive Compositions Klebstoffzusammensetzung Auf Polypropylenbasis Compositions Adhésives À Base De Polypropylène
    (19) TZZ Z _T (11) EP 2 627 702 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C08L 23/10 (2006.01) C09J 123/10 (2006.01) 27.03.2019 Bulletin 2019/13 (86) International application number: (21) Application number: 11776952.1 PCT/US2011/055875 (22) Date of filing: 12.10.2011 (87) International publication number: WO 2012/051239 (19.04.2012 Gazette 2012/16) (54) POLYPROPYLENE-BASED ADHESIVE COMPOSITIONS KLEBSTOFFZUSAMMENSETZUNG AUF POLYPROPYLENBASIS COMPOSITIONS ADHÉSIVES À BASE DE POLYPROPYLÈNE (84) Designated Contracting States: • MITCHELL, Cynthia, A. AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Houston, TX 77008 (US) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO • DATTA, Sudhin PL PT RO RS SE SI SK SM TR Houston, TX 77007 (US) (30) Priority: 15.10.2010 US 393728 P (74) Representative: ExxonMobil Chemical Europe Inc. IP Law Europe (43) Date of publication of application: Hermeslaan 2 21.08.2013 Bulletin 2013/34 1831 Machelen (BE) (73) Proprietor: ExxonMobil Chemical Patents Inc. (56) References cited: Baytown, TX 77520 (US) EP-A2- 2 045 304 US-A- 4 178 272 US-A1- 2003 096 896 (72) Inventors: • TSE, Mun, Fu Seabrook, TX 77586 (US) Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations.
    [Show full text]
  • Industrial Hydrocarbon Processes
    Handbook of INDUSTRIAL HYDROCARBON PROCESSES JAMES G. SPEIGHT PhD, DSc AMSTERDAM • BOSTON • HEIDELBERG • LONDON NEW YORK • OXFORD • PARIS • SAN DIEGO SAN FRANCISCO • SINGAPORE • SYDNEY • TOKYO Gulf Professional Publishing is an imprint of Elsevier Gulf Professional Publishing is an imprint of Elsevier The Boulevard, Langford Lane, Kidlington, Oxford OX5 1GB, UK 30 Corporate Drive, Suite 400, Burlington, MA 01803, USA First edition 2011 Copyright Ó 2011 Elsevier Inc. All rights reserved No part of this publication may be reproduced, stored in a retrieval system or transmitted in any form or by any means electronic, mechanical, photocopying, recording or otherwise without the prior written permission of the publisher Permissions may be sought directly from Elsevier’s Science & Technology Rights Department in Oxford, UK: phone (+44) (0) 1865 843830; fax (+44) (0) 1865 853333; email: [email protected]. Alternatively you can submit your request online by visiting the Elsevier web site at http://elsevier.com/locate/ permissions, and selecting Obtaining permission to use Elsevier material Notice No responsibility is assumed by the publisher for any injury and/or damage to persons or property as a matter of products liability, negligence or otherwise, or from any use or operation of any methods, products, instructions or ideas contained in the material herein. Because of rapid advances in the medical sciences, in particular, independent verification of diagnoses and drug dosages should be made British Library Cataloguing in Publication Data
    [Show full text]
  • 1 Chapter 3: Organic Compounds: Alkanes and Cycloalkanes
    Chapter 3: Organic Compounds: Alkanes and Cycloalkanes >11 million organic compounds which are classified into families according to structure and reactivity Functional Group (FG): group of atoms which are part of a large molecule that have characteristic chemical behavior. FG’s behave similarly in every molecule they are part of. The chemistry of the organic molecule is defined by the function groups it contains 1 C C Alkanes Carbon - Carbon Multiple Bonds Carbon-heteroatom single bonds basic C N C C C X X= F, Cl, Br, I amines Alkenes Alkyl Halide H C C C O C C O Alkynes alcohols ethers acidic H H H C S C C C C S C C H sulfides C C thiols (disulfides) H H Arenes Carbonyl-oxygen double bonds (carbonyls) Carbon-nitrogen multiple bonds acidic basic O O O N H C H C O C Cl imine (Schiff base) aldehyde carboxylic acid acid chloride O O O O C C N C C C C O O C C nitrile (cyano group) ketones ester anhydrides O C N amide opsin Lys-NH2 + Lys- opsin H O H N rhodopsin H 2 Alkanes and Alkane Isomers Alkanes: organic compounds with only C-C and C-H single (s) bonds. general formula for alkanes: CnH(2n+2) Saturated hydrocarbons Hydrocarbons: contains only carbon and hydrogen Saturated" contains only single bonds Isomers: compounds with the same chemical formula, but different arrangement of atoms Constitutional isomer: have different connectivities (not limited to alkanes) C H O C4H10 C5H12 2 6 O OH butanol diethyl ether straight-chain or normal hydrocarbons branched hydrocarbons n-butane n-pentane Systematic Nomenclature (IUPAC System) Prefix-Parent-Suffix
    [Show full text]
  • Platinum Metals Review
    PLATINUM METALS REVIEW A quurterly survey of research on the platinum metuls and of dwelopments in their applications in industry ~~ VOL. 14 OCTOBER 1970 NO. 4 Contents Platinum Containers for the Growth of Single Crystal Oxides 118 Platinum Inclusions in Laser Glasses 122 Rhodium Plated Langmuir Probes for Sounding Rockets 123 Platinum and the Refractory Oxides 124 Combined Catalysts for Ammonia Oxidation 130 Absorption of Hydrogen by Palladium Alloys 131 Platinum-Carbon Catalysts with Molecular Sieve Properties 133 Platinum Metal Coatings for Stereoscan Specimens 139 The History of Matthey Bishop 140 Abstracts 147 New Patents 156 Index to Volume 14 159 Communications should be addressed to The Editor, Platinum Metals Review Johnson, Matthey & Co Limited, Hatton Garden, London ECl P 1 AE Platinum Containers for the Growth of Single Crystal Oxides By L. G. Van Uitert Bell Telephone Laboratories Incorporated, Murray Hill, Kew Jersey The growth of single crystal oxides for optical and magnetic purposes is commonly carried out using platinum containers. ilIodijications to container design have been important factors in improving growth conditions. A new composite three-layer crucible has been fabricated in platinum and iridium for growing crystals of sodium barium niobate, and a platinum container which can be drained of jlux has been de- veloped for growing rare earth iron garnets. Single crystals are of basic importance as taker design. A melt (or fused mixture of the integral parts of semiconductor devices, components of a crystal) can conveniently be oscillators, transducers, detectors, delay lines contained in a platinum crucible-susceptor and power limiters. There is also an interest that is heated by radio frequency induction.
    [Show full text]