Principles and Applications of Stereochemistry

About this book

A thorough understanding of stereochemistry is essential for the comprehension of almost all aspects of modern organic chemistry. It is also of great significance in many biochemical and medicinal disciplines, since the stereoisomers of a compound can have dramatically different biological properties. This text explains how the different properties of stereoisomers of a compound arise, and what processes can be used to prepare and analyze stereoisomerically pure compounds. It also presents prominent coverage of the stereochemistry of inorganic and organometallic compounds, which is likely to increase in importance, as these compounds are used as symmetric catalysts in asymmetric synthesis. Modern stereochemical terminology is used throughout, although reference is also made to older terms which are still widely used. A set of problems at the end of each chapter aims to further the reader's understanding of how the content can be applied. The book is designed mainly as a textbook for undergraduate students and as a reference source for more advanced levels, but is also intended for academic and professional organic chemists.

Contents

MOLECULAR STRUCTURE AND BONDINGIsomerismDrawing Three Dimensional Chemical StucturesVSEPR and the Shape of MoleculesStructure and BondingClasification of StereoisomersCIS-TRANS ISOMERISMCis-Trans Isomerism in AlkenesCis-Trans Isomerism in Other Systems Which Contain a double BondCis-Trans Isomerism in Cyclic SystemsCis-Trans Isomerism in Square Planar and Octohedral Metal ComplexesCis-Trans Isomerism about Single Bonds (Conformational Diastereomers)Methods for Distinguishing Cis-Trans IsomersENANTIOMERSStructure of EnantiomersNomenclature for Enantiomers (Speciation of Absolute Configuration)Chemical Properties of EnantiomersPhysical Properties of EnantiomersEnantiomeric ExcessBiological Properties of EnantiomersChirality Due to Stereocentres at Atoms Other than CarbonOther Stereogenic Elements Which Can Produce Molecular ChiralityCOMPOUNDS WITH TWO OR MORE STEREOCENTRESCompounds with Two StereocentresCompounds with More Than Two StereocentresPolymer StereochemistryRelative Stereochemistry NomenclatureDiastereomeric ExcessINTERCONVERSION AND ANALYSIS OF STEREOISOMERSRacemizationEpimerizationResolutionMethods for Determining Enantiomeric ExcessDetermination of Absolute ConfigurationDetermination of Relative ConfigurationMOLECULAR SYMMETRYIntroductionSymmetry Elements and Symmetry OperationsSymmetry of Molecules with Multiple ConformationsPoint GroupsSymmetry and ChiralityTOPISM AND PROSTEREOGENICITYHomotopic, Enantiopic and Diastereotopic GroupsHomotopic, Enantiopic and Diastereotopic FacesNomenclature for Heterotopic Groups and FacesCONFORMATION OF ACYLIC AND CYCLIC MOLECULESIntroductionConformations of Acyclic MoleculesConformations of Cyclic Alkanes and their DerivativesCyclopropaneCyclobutaneCyclohexaneMedium and Large RingsConformation of Inorganic and Organometallic CompoundsConformation of BiopolymersMethods for Determining Molecular ConformationSTEREOCHEMISTRY OF CHEMICAL REACTIONSIntroductionSubstitution ReactionsElimination ReactionsAddition Reactions to AlkenesAddition of Nucleophiles to Aldehydes and KetonesPericyclic ReactionsASYMMETRIC SYNTHESISIntroductionUse of Chiral AuxiliariesUse of Enantiomerically Pure ReagentsIndex

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