Differentiation of Chiral Compounds Using NMR Spectroscopy

Thomas J. Wenzel 지음

Wiley 2018년 05월 24일 출간

작품소개

책소개

An updated guide to the most current information available for determining how to use NMR spectroscopy to differentiate chiral compounds Differentiation of Chiral Compounds Using NMR Spectroscopy offers a thoroughly revised second edition to the essential volume that puts the focus on the chiral systems that are commercially available and have been widely vetted for use in NMR spectroscopy. The text covers a broad range of reagents that make it possible to determine the enantiomeric purity and assign the absolute configuration of many classes of compounds. Comprehensive in scope, the text describes the chiral NMR differentiating agents as derivatizing agents, solvating agents, metal-based reagents and liquid crystals and gels, and explains the range and types of compounds for which they can be used for analysis. New to this edition are the most recent findings in the field as well as the development of advanced NMR measurement techniques that allow for the simplification of complex spectra resulting in more readily identified enantiodifferentiation. This important resource: Includes the most recent coverage of a large range of compounds that can be analyzed using chiral NMR reagents Explores the use of chiral NMR reagents and explains their relationship to the stereochemistry of the analyzed molecules Offers the essential information needed to help decide which method is the best NMR method to apply to a class or molecules Contains experimental strategies for using the reagents that are likely to improve the quality of the results Differentiation of Chiral Compounds Using NMR Spectroscopy is a comprehensive guide designed for investigators planning to use NMR spectroscopy to determine enantiomeric purity or assign the absolute configuration of a compound.

목차

Preface Acknowledgements Chapter 1. Introduction 1.1. Chiral derivatizing agents (CDAs) 1.2. Chiral solvating agents (CSAs) 1.3. NMR methods to improve the quality of data with CSAs and CDAs 1.4. Overview of chiral reagents and methodologies Chapter 2. Aryl-containing Carboxylic Acids 2.1 Introduction 2.2. ??-Methoxy-??-trifluoromethylphenylacetic acid (MTPA - Mosher’s reagent) 2.2.1. Analysis of secondary alcohols 2.2.2. Analysis of secondary diols and polyols 2.2.3. Analysis of primary alcohols 2.2.4. Analysis of tertiary alcohols 2.2.5. Analysis of secondary amines 2.2.6. Analysis of primary amines 2.2.7. Use as a chiral solvating agent 2.2.8. Preparation of MTPA derivatives 2.3. ??-Methoxy-??-trifluoromethylphenylacetic thioic acid 2.4. ??-Methoxyphenylacetic acid (MPA) 2.4.1. Analysis of secondary alcohols 2.4.1.1. Variable temperature method for assigning absolute stereochemistry 2.4.1.2. Barium(II) method for assigning absolute stereochemistry 2.4.2. Analysis of diols 2.4.3. Analysis of 1,2,3-primary,secondary,secondary-triols 2.4.4. Analysis of primary alcohols 2.4.5. Analysis of amines 2.4.5.1. Barium(II) method for assigning absolute stereochemistry 2.4.6. Analysis of amino alcohols 2.4.7. Analysis of sulfoxides 2.4.8. Polymer bound CDAs the “mix and shake” method 2.5. Mandelic acid (2-hydroxy-2-phenyl acetic acid) - (MA) 2.6. O-Acetyl mandelic acid (2-acetoxy-2-phenyl acetic acid) (O-AMA) 2.7. Other O-derivatized mandelic acids 2.8. 2-Phenylpropionic acid (2-PPA) 2.9. 2-Phenylselenopropionic acid 2.10. 2-methoxy-2-phenylpent-3-ynoic acid 2.11. 3-Phenylbutanoic acid (3-PBA)/2-phenylbutanoic acid (2-PBA) 2.12. ??-Cyano-??-fluorophenylacetic acid (CFPA)/??-cyano-??-fluoronaphthy

작가정보

저자(글) Thomas J. Wenzel

Thomas J. Wenzel, PHD, is the Charles A. Dana Professor of Chemistry at Bates College in Lewiston, Maine. He has served terms as chair of the Science Division, Chemistry Department, Biochemistry Program and the interdisciplinary Environmental Studies Program.