Principles and Applications of Stereochemistry

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Content: Cover Half Title Title Page Copyright Page Table of Contents Foreword Preface 1: Molecular structure and bonding 1.1 Isomerism 1.2 Drawing three dimensional chemical structures 1.2.1 Fischer projections 1.2.2 Newman projections 1.3 VSEPR and the shape of molecules 1.4 Structure and bonding 1.5 Classification of stereoisomers 1.5.1 Enantiomers and diastereomers 1.5.2 Conformations and configurations 1.6 Further reading 1.7 Problems 2: Cis-trans isomerism 2.1 Cis-trans isomerism in alkenes 2.2 Cis-trans isomerism in other systems which contain a double bond. 2.3 Cis-trans isomerism in cyclic systems2.4 Cis-trans isomerism in square planar and octahedral metal complexes 2.5 Cis-trans isomerism about single bonds (conformational diastereomers) 2.6 Methods for distinguishing cis-trans isomers 2.6.1 NMR spectroscopy 2.6.2 X-ray crystallography 2.6.3 Dipole moments 2.7 Further reading 2.8 Problems 3: Enantiomers 3.1 Structure of enantiomers 3.2 Nomenclature for enantiomers (specification of absolute configuration) 3.2.1 The d/l-nomenclature system 3.2.2 The R/S nomenclature system 3.3 Chemical properties of enantiomers. 3.4 Physical properties of enantiomers3.4.1 Optical rotation 3.4.2 Other chiroptical methods (optical rotary dispersion and circular dichroism) 3.5 Enantiomeric excess 3.6 Biological properties of enantiomers 3.6.1 Origin of enantiomerically pure compounds in nature 3.7 Chirality due to stereocentres at atoms other than carbon 3.7.1 Sulphur 3.7.2 Phosphorus 3.7.3 Nitrogen 3.7.4 Metal complexes 3.8 Other stereogenic elements which can produce molecular chirality 3.8.1 Stereogenic axis 3.8.2 Stereoplane 3.8.3 Helical molecules 3.9 Further reading 3.10 Problems. 4: Compounds with two or more stereocentres4.1 Compounds with two stereocentres 4.2 Compounds with more than two stereocentres 4.3 Polymer stereochemistry 4.3.1 Stereochemical consequences of backbone stereocentres 4.3.2 Helical polymers 4.4 Relative stereochemistry nomenclature 4.5 Diastereomeric excess 4.6 Further reading 4.7 Problems 5: Interconversion and analysis of stereoisomers 5.1 Racemization 5.1.1 Thermal racemization 5.1.2 Base induced racemization 5.1.3 Acid induced racemization 5.2 Epimerization 5.3 Resolution 5.3.1 Resolution by crystallization. 5.3.2 Resolution by formation of diastereomers5.3.3 Kinetic resolution 5.3.4 Resolution by preferential absorption 5.4 Methods for determining enantiomeric excess 5.4.1 Chromatography using a chiral stationary phase 5.4.2 NMR 5.4.3 Conversion to diastereomers 5.4.4 Polarimetry 5.5 Determination of absolute configuration 5.5.1 Chiroptical methods 5.5.2 X-ray crystallography 5.5.3 Conversion to a compound of known absolute configuration 5.6 Determination of relative configuration 5.7 Further reading 5.8 Problems 6: Molecular symmetry 6.1 Introduction.