Carboxylic Acids
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Chapter 21 the Chemistry of Carboxylic Acid Derivatives
Instructor Supplemental Solutions to Problems © 2010 Roberts and Company Publishers Chapter 21 The Chemistry of Carboxylic Acid Derivatives Solutions to In-Text Problems 21.1 (b) (d) (e) (h) 21.2 (a) butanenitrile (common: butyronitrile) (c) isopentyl 3-methylbutanoate (common: isoamyl isovalerate) The isoamyl group is the same as an isopentyl or 3-methylbutyl group: (d) N,N-dimethylbenzamide 21.3 The E and Z conformations of N-acetylproline: 21.5 As shown by the data above the problem, a carboxylic acid has a higher boiling point than an ester because it can both donate and accept hydrogen bonds within its liquid state; hydrogen bonding does not occur in the ester. Consequently, pentanoic acid (valeric acid) has a higher boiling point than methyl butanoate. Here are the actual data: INSTRUCTOR SUPPLEMENTAL SOLUTIONS TO PROBLEMS • CHAPTER 21 2 21.7 (a) The carbonyl absorption of the ester occurs at higher frequency, and only the carboxylic acid has the characteristic strong, broad O—H stretching absorption in 2400–3600 cm–1 region. (d) In N-methylpropanamide, the N-methyl group is a doublet at about d 3. N-Ethylacetamide has no doublet resonances. In N-methylpropanamide, the a-protons are a quartet near d 2.5. In N-ethylacetamide, the a- protons are a singlet at d 2. The NMR spectrum of N-methylpropanamide has no singlets. 21.9 (a) The first ester is more basic because its conjugate acid is stabilized not only by resonance interaction with the ester oxygen, but also by resonance interaction with the double bond; that is, the conjugate acid of the first ester has one more important resonance structure than the conjugate acid of the second. -
Oxalic Acid As a Heterogeneous Ice Nucleus in the Upper Troposphere and Its Indirect Aerosol Effect” by B
Atmos. Chem. Phys. Discuss., 6, S1765–S1768, 2006 Atmospheric www.atmos-chem-phys-discuss.net/6/S1765/2006/ Chemistry ACPD c Author(s) 2006. This work is licensed and Physics 6, S1765–S1768, 2006 under a Creative Commons License. Discussions Interactive Comment Interactive comment on “Oxalic acid as a heterogeneous ice nucleus in the upper troposphere and its indirect aerosol effect” by B. Zobrist et al. B. Zobrist et al. Received and published: 13 July 2006 The authors would like to thank anonymous referee #1 for his/her constructive comments. We have addressed the referee’s concerns point-by-point below. Full Screen / Esc Succinic and Adipic acid as immersion IN: The solubility of these dicarboxylic acids is very low at temperatures of about 235 K, Printer-friendly Version as supported by the deliquescence measurements of Parsons et al. (JGR 109, D06212, 2004) which are close to 100 % RH. In our experiments, the droplets of Interactive Discussion these acids are completely liquid in the first cooling cycle with concentrations of Discussion Paper 7.3 wt% for succinic acid and 1.6 wt% for adipic acid, which is why they nucleate ice S1765 EGU homogeneously at temperatures below that of pure water. When the acids precipitate, the concentration of the remaining liquid corresponds to the equilibrium solubility at ACPD each temperature when the samples are cooled in the second cycle. Because of the 6, S1765–S1768, 2006 low solubility at lower temperatures we expect the observed rise in the homogeneous ice nucleation temperature when compared to the first cooling run. In fact, if we use the measured freezing temperatures and assume they are due to homogeneous ice Interactive nucleation, we can use water-activity-based ice nucleation theory to deduce the water Comment activity of the liquid part of the samples. -
Malonic Acid
SIGMA-ALDRICH sigma-aldrich.com Material Safety Data Sheet Version 4.1 Revision Date 09/20/2012 Print Date 03/13/2014 1. PRODUCT AND COMPANY IDENTIFICATION Product name : Malonic acid Product Number : M1296 Brand : Sigma-Aldrich Supplier : Sigma-Aldrich 3050 Spruce Street SAINT LOUIS MO 63103 USA Telephone : +1 800-325-5832 Fax : +1 800-325-5052 Emergency Phone # (For : (314) 776-6555 both supplier and manufacturer) Preparation Information : Sigma-Aldrich Corporation Product Safety - Americas Region 1-800-521-8956 2. HAZARDS IDENTIFICATION Emergency Overview OSHA Hazards Toxic by inhalation., Harmful by ingestion., Irritant GHS Classification Acute toxicity, Inhalation (Category 5) Acute toxicity, Oral (Category 4) Skin irritation (Category 3) Serious eye damage (Category 1) GHS Label elements, including precautionary statements Pictogram Signal word Danger Hazard statement(s) H302 Harmful if swallowed. H316 Causes mild skin irritation. H318 Causes serious eye damage. H333 May be harmful if inhaled. Precautionary statement(s) P280 Wear protective gloves/ eye protection/ face protection. P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. HMIS Classification Health hazard: 2 Flammability: 1 Physical hazards: 0 NFPA Rating Health hazard: 2 Fire: 1 Sigma-Aldrich - M1296 Page 1 of 7 Reactivity Hazard: 0 Potential Health Effects Inhalation Toxic if inhaled. Causes respiratory tract irritation. Skin Harmful if absorbed through skin. Causes skin irritation. Eyes Causes eye irritation. Ingestion Harmful if swallowed. 3. COMPOSITION/INFORMATION ON INGREDIENTS Synonyms : Propanedioic acid Formula : C3H4O4 Molecular Weight : 104.06 g/mol Component Concentration Malonic acid CAS-No. -
Step Formation Constants of Some Malonato Lanthanide Chelate Species Marvin Lee Adolphson Iowa State University
Iowa State University Capstones, Theses and Retrospective Theses and Dissertations Dissertations 1969 Step formation constants of some malonato lanthanide chelate species Marvin Lee Adolphson Iowa State University Follow this and additional works at: https://lib.dr.iastate.edu/rtd Part of the Physical Chemistry Commons Recommended Citation Adolphson, Marvin Lee, "Step formation constants of some malonato lanthanide chelate species " (1969). Retrospective Theses and Dissertations. 3809. https://lib.dr.iastate.edu/rtd/3809 This Dissertation is brought to you for free and open access by the Iowa State University Capstones, Theses and Dissertations at Iowa State University Digital Repository. It has been accepted for inclusion in Retrospective Theses and Dissertations by an authorized administrator of Iowa State University Digital Repository. For more information, please contact [email protected]. 70-13,563 ADOLPHSON, Marvin Lee, 1941- STEP FORMATION CONSTANTS OF SOME MÀLONATO LANTHANIDE CHELATE SPECIES. Iowa State University, Ph.D., 1969 Chemistiy, physical University Microfilms, Inc., Ann Arbor, Michigan THIS DISSERTATION HAS BEEN MICROFILMED EXACTLY AS RECEIVED STEP FORMATION CONSTANTS OF SOME MALONATO LANTHANIDE CHELATE SPECIES by Marvin Lee Adolphson A Dissertation Submitted to the Graduate Faculty in Partial Fulfillment of The Requirements for the Degree of DOCTOR OF PHILOSOPHY Major Subject: Physical Chemistry Approved; Signature was redacted for privacy. In/Charge of Major Work Signature was redacted for privacy. Signature was redacted for privacy. Iowa State University Ames, Iowa 1969 ii TABLE OF CONTENTS Page INTRODUCTION 1 COMPUTATIONS 4 EXPERIMENTAL DETAILS 15 EXPERIMENTAL RESULTS 35 DISCUSSION 56 SUMMARY 88 BIBLIOGRAPHY 89 ACKNOWLEDGMENT S 94 APPENDIX 95 1 INTRODUCTION The motivations for this research were fourfold. -
Crystallization of Malonic and Succinic Acids on Sams: Toward the General Mechanism of Oriented Nucleation on Organic Monolayers†
pubs.acs.org/Langmuir © 2009 American Chemical Society Crystallization of Malonic and Succinic Acids on SAMs: Toward the General Mechanism of Oriented Nucleation on Organic Monolayers† Boaz Pokroy,‡ Victoria Fay Chernow, and Joanna Aizenberg* School of Engineering and Applied Sciences, Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138. ‡ Current address: Department of Materials Engineering, Israel Institute of Technology, Haifa 32000, Israel. Received July 25, 2009. Revised Manuscript Received September 2, 2009 Self-assembled monolayers (SAMs) were shown to induce very specific oriented growth of simple organic and inorganic crystals. Here we present a detailed study of the mechanism by which SAMs control the oriented nucleation by examining a more complex case of crystallization of bifunctional organic molecules. Malonic and succinic acids were grown on the SAMs of HS(CH2)10CO2H and HS(CH2)11CO2H supported on gold films. Each SAM induced a very controlled, specific orientation of the crystals. The preferred nucleating planes always exhibited an alignment of one of the carboxylic acid groups in the molecules of the growing crystal with the carboxylic acid groups on the surface of the SAMs. These results suggest that the translation of the structural information through the interface occurs by stereochemical registry such that the functional groups in the SAM play the role of an oriented surrogate layer for the nucleating crystal. These findings are very important to the understanding of the underlying principles by which various organic surfaces;and most probably also biological templates;control the crystallization process. Introduction templates to control the formation of both organic and inorganic An understanding of crystal nucleation and growth and the materials. -
Study on Accurate Determination of Volatile Fatty Acids in Rumen Fluid
5th International Conference on Information Engineering for Mechanics and Materials (ICIMM 2015) Study on Accurate Determination of Volatile Fatty Acids in Rumen Fluid by Capillary Gas Chromatography Cheng LUOa, Suyi CAI, Linyan JIA, Xiang TANG, Ruinan ZHANG, Gang JIA, Hua LI, Jiayong TANG, Guangmang LIU, Caimei WU*b Institute of Animal Nutrition, Key Laboratory for Animal Disease-Resistance Nutrition of Sichuan Province, Key Laboratory for Animal Disease-Resistance Nutrition and Feedstuffs of China Ministry of Agriculture, Sichuan Agricultural University, cheng’du 611130, China aemail: [email protected], *bemail:[email protected] Key Words: Capillary gas chromatography; Rumen fluid; Volatile fatty acids; Internal standard method Abstract. In order to obtain accurate results of volatile fatty acids (VFAs) in rumen fluid by capillary gas chromatography (GC), a pretreatment method was firstly conducted by dissolving VFAs in the methanol. An internal standard method (ISM) with crotonic acid as the internal standard was adopted in the detection. The results showed that the reproducibility of VFA (acetic acid, propanoic acid and butyric acid) was enhanced remarkably with methanol added as the solvent. The reproducibility was dependent on both of the VFA concentration and methanol amount. In conclusion, methanol solvent was more suitable than aqueous solvent for VFA accurate detection with ISM by capillary GC. Introduction Volatile fatty acids (VFAs) got through rumen fermentation were important energy sources for ruminant animals [1]. The acetic acid, propanoic acid, butyric acid accounted for about 95% of the total VFAs. Therefore, it was significant to determine acetic acid, propanoic acid and butyric accurately for the rumen fermentation study. In recent years, acetic acid, propanoic acid and butyric acid were detected by GC with packed column or capillary column [1-12]and ion chromatography (IC) [13]. -
Metabolomics of Metformin's Cardioprotective Effect in Acute
Sys Rev Pharm 2021;12(3):100-109 A multifaceted revieMw jouernatl ian thbe fioeld lofophamrmaciycs Of Metformin's Cardioprotective Effect In Acute Doxorubicin Induced- Cardiotoxicity In Rats Lubna Zuhair Abdul Karim *, Inam Sameh Arif **, Fouad A. Al Saady *** *Pharmacist, Department of Pharmacology and Toxicology, College of Pharmacy, Mustansiriyah University, M.Sc. program, Iraq. **Assist.Prof., Department of Pharmacology and Toxicology, College of Pharmacy, Mustansiriyah University, Iraq. *** Assist. Prof., Department of pharmaceutical chemistry, College of Pharmacy, Mustansiriyah University, Iraq. Corresponding author: Lubna Zuhair Abdul Karim *e-mail: [email protected] ABSTRACT Doxorubicin (DOX) is a powerful anticancer agent with sever cardiotoxic side Keywords: metabolomics, cardiotoxicity, doxorubicin, cardioprotection, effect which limits the clinical use. Metformin (MET) is antihyperglycemic drug metformin. with potential cardioprotective effect via AMP-activated protein kinase (AMPK) (increases fatty acid oxidation, decreases the production of ROS, maintaining Correspondence: energy homeostasis and apoptosis). Metabolomics technology deals with Lubna Zuhair Abdul Karim systematic study of chemical fingerprints of metabolite profiles. Different *Pharmacist, Department of Pharmacology and Toxicology, College of Pharmacy, metabolic processes can be identified which will give information of any change Mustansiriyah University, M.Sc. program, Iraq. in the metabolic profile of tissues as well as of biofluids after drug -
Green Chemistry Accepted Manuscript
Green Chemistry Accepted Manuscript This is an Accepted Manuscript, which has been through the Royal Society of Chemistry peer review process and has been accepted for publication. Accepted Manuscripts are published online shortly after acceptance, before technical editing, formatting and proof reading. Using this free service, authors can make their results available to the community, in citable form, before we publish the edited article. We will replace this Accepted Manuscript with the edited and formatted Advance Article as soon as it is available. You can find more information about Accepted Manuscripts in the Information for Authors. Please note that technical editing may introduce minor changes to the text and/or graphics, which may alter content. The journal’s standard Terms & Conditions and the Ethical guidelines still apply. In no event shall the Royal Society of Chemistry be held responsible for any errors or omissions in this Accepted Manuscript or any consequences arising from the use of any information it contains. www.rsc.org/greenchem Page 1 of 21 Green Chemistry Green Chemistry RSCPublishing CRITICAL REVIEW Catalytic Routes towards Acrylic Acid, Adipic Acid and ε-Caprolactam starting from Biorenewables Cite this: DOI: 10.1039/x0xx00000x Rolf Beerthuis, Gadi Rothenberg and N. Raveendran Shiju* Received 00th January 2012, The majority of bulk chemicals are derived from crude oil, but the move to biorenewable resources is Accepted 00th January 2012 gaining both societal and commercial interest. Reviewing this transition, we first summarise the types of today’s biomass sources and their economical relevance. Then, we assess the biobased productions DOI: 10.1039/x0xx00000x of three important bulk chemicals: acrylic acid, adipic acid and ε-caprolactam. -
APPENDIX G Acid Dissociation Constants
harxxxxx_App-G.qxd 3/8/10 1:34 PM Page AP11 APPENDIX G Acid Dissociation Constants § ϭ 0.1 M 0 ؍ (Ionic strength ( † ‡ † Name Structure* pKa Ka pKa ϫ Ϫ5 Acetic acid CH3CO2H 4.756 1.75 10 4.56 (ethanoic acid) N ϩ H3 ϫ Ϫ3 Alanine CHCH3 2.344 (CO2H) 4.53 10 2.33 ϫ Ϫ10 9.868 (NH3) 1.36 10 9.71 CO2H ϩ Ϫ5 Aminobenzene NH3 4.601 2.51 ϫ 10 4.64 (aniline) ϪO SNϩ Ϫ4 4-Aminobenzenesulfonic acid 3 H3 3.232 5.86 ϫ 10 3.01 (sulfanilic acid) ϩ NH3 ϫ Ϫ3 2-Aminobenzoic acid 2.08 (CO2H) 8.3 10 2.01 ϫ Ϫ5 (anthranilic acid) 4.96 (NH3) 1.10 10 4.78 CO2H ϩ 2-Aminoethanethiol HSCH2CH2NH3 —— 8.21 (SH) (2-mercaptoethylamine) —— 10.73 (NH3) ϩ ϫ Ϫ10 2-Aminoethanol HOCH2CH2NH3 9.498 3.18 10 9.52 (ethanolamine) O H ϫ Ϫ5 4.70 (NH3) (20°) 2.0 10 4.74 2-Aminophenol Ϫ 9.97 (OH) (20°) 1.05 ϫ 10 10 9.87 ϩ NH3 ϩ ϫ Ϫ10 Ammonia NH4 9.245 5.69 10 9.26 N ϩ H3 N ϩ H2 ϫ Ϫ2 1.823 (CO2H) 1.50 10 2.03 CHCH CH CH NHC ϫ Ϫ9 Arginine 2 2 2 8.991 (NH3) 1.02 10 9.00 NH —— (NH2) —— (12.1) CO2H 2 O Ϫ 2.24 5.8 ϫ 10 3 2.15 Ϫ Arsenic acid HO As OH 6.96 1.10 ϫ 10 7 6.65 Ϫ (hydrogen arsenate) (11.50) 3.2 ϫ 10 12 (11.18) OH ϫ Ϫ10 Arsenious acid As(OH)3 9.29 5.1 10 9.14 (hydrogen arsenite) N ϩ O H3 Asparagine CHCH2CNH2 —— —— 2.16 (CO2H) —— —— 8.73 (NH3) CO2H *Each acid is written in its protonated form. -
Production of Adipic Acid from Mixtures of Cyclohexanol-Cyclohexanone Using Polyoxometalate Catalysts
Makara J. Sci. 19/2 (2015), 85-90 doi: 10.7454/mss.v19i2.4778 Production of Adipic Acid from Mixtures of Cyclohexanol-Cyclohexanone using Polyoxometalate Catalysts Aldes Lesbani 1*, Sumiati 1, Mardiyanto 2, Najma Annuria Fithri 2, and Risfidian Mohadi 1 1. Department of Chemistry, Faculty of Mathematic and Natural Sciences, Universitas Sriwijaya, Indralaya (OI), Sumatera Selatan 30662, Indonesia 2. Department of Pharmacy, Faculty of Mathematic and Natural Sciences, Universitas Sriwijaya, Indralaya (OI), Sumatera Selatan 30662, Indonesia *E-mail: [email protected] Abstract Adipic acid production through catalytic conversion of cyclohexanol-cyclohexanone using polyoxometalate H 5[α-BW 12 O40 ] and H 4[α-SiW 12 O40 ] as catalysts was carried out systematically. Polyoxometalates H 5[α-BW 12 O40 ] and H 4[α-SiW 12 O40 ] were synthesized using an inorganic synthesis method and were characterized using Fourier transform infrared spectroscopy (FTIR). Adipic acid was formed from conversion of cyclohexanol-cyclohexanone and was characterized by using melting point measurement, identification of functional group using FTIR spectrophotometer, analysis of gas chromatography-mass spectrometry (GC-MS), and 1H and 13 C NMR (nuclear magnetic resonance) spectrophotometer. This research investigated the influence of reaction time and temperature on conversion. The results showed that adipic acid was formed successfully with a yield of 68% by using H 5[α-BW 12 O40 ] as catalyst at the melting point of 150-152 °C after optimization. In contrast, using H 4[α-SiW 12 O40 ] as catalyst, formation of adipic acid was only 3.7%. Investigation of time and temperature showed 9 h as the optimum reaction time and 90 °C as the optimum temperature for conversion of up to 68% adipic acid. -
A Previously Undescribed Pathway for Pyrimidine Catabolism
A previously undescribed pathway for pyrimidine catabolism Kevin D. Loh*†, Prasad Gyaneshwar*‡, Eirene Markenscoff Papadimitriou*§, Rebecca Fong*, Kwang-Seo Kim*, Rebecca Parales¶, Zhongrui Zhouʈ, William Inwood*, and Sydney Kustu*,** *Department of Plant and Microbial Biology, 111 Koshland Hall, University of California, Berkeley, CA 94720-3102; ¶Section of Microbiology, 1 Shields Avenue, University of California, Davis, CA 95616; and ʈCollege of Chemistry, 8 Lewis Hall, University of California, Berkeley, CA 94720-1460 Contributed by Sydney Kustu, January 19, 2006 The b1012 operon of Escherichia coli K-12, which is composed of tive N sources. Here we present evidence that the b1012 operon seven unidentified ORFs, is one of the most highly expressed codes for proteins that constitute a previously undescribed operons under control of nitrogen regulatory protein C. Examina- pathway for pyrimidine degradation and thereby confirm the tion of strains with lesions in this operon on Biolog Phenotype view of Simaga and Kos (8, 9) that E. coli K-12 does not use either MicroArray (PM3) plates and subsequent growth tests indicated of the known pathways. that they failed to use uridine or uracil as the sole nitrogen source and that the parental strain could use them at room temperature Results but not at 37°C. A strain carrying an ntrB(Con) mutation, which Behavior on Biolog Phenotype MicroArray Plates. We tested our elevates transcription of genes under nitrogen regulatory protein parental strain NCM3722 and strains with mini Tn5 insertions in C control, could also grow on thymidine as the sole nitrogen several genes of the b1012 operon on Biolog (Hayward, CA) source, whereas strains with lesions in the b1012 operon could not. -
Experiment 2: Two Step Synthesis of Ethyl 4-Methoxycinnamate
Experiment 2: Two step synthesis of ethyl 4-methoxycinnamate Background Why is ethyl 4-methoxycinnamate (1) interesting? First, it is the analog of octyl 4-methoxycinnamate (2), a UV light blocker found in Bain de Soleil All Day Sunblock and Coppertone Sport. The derivatives of 4-methoxycinnamic acid absorb UVB radiation due to their high level of conjugation. They are also oil soluble. UVB radiation promotes dermal cell DNA damage causing skin cancer. Octyl 4-methoxycinnamate is used in sunscreen over ethyl 4-methoxycinnamate because of its higher molar absorptivity ε and its greater lipophilicity. O R O O R = -CH3CH3 ethyl 4-methoxycinnamate (1) R = octyl 4-methoxycinnamate (2) Figure 1: Derivatives of 4-methoxycinnamic acid Second, a two step synthesis is put forth so that you can practice multi-step synthesis using a variety of laboratory techniques before diving into Honors Cup. Step 1 is the Verley-Doebner modification of the Knoevenagel condensation.1 The Knoevenagel condensation reaction dates from 1896 and is a facile one-step method of forming new carbon- carbon bonds under mild reaction conditions. It utilizes a weak amine base such as piperidine to initially form an enolate anion derived from a 1,3-dicarbonyl compound. The enolate subsequently acts as a nucleophile in the condensation with another carbonyl compound. This carbonyl is often an aldehyde and the reaction mechanism bears striking similarity to that of the aldol condensation. The isolated product is generally an α,β-conjugated carboxylic acid, formed via ready dehydration of the intermediate β-hydroxydicarbonyl compound and subsequent saponification and decarboxylation.