Principles and Applications of Stereochemistry: 1st Edition (Paperback) book cover

Principles and Applications of Stereochemistry

1st Edition

By Michael North

CRC Press

262 pages

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Paperback: 9780748739943
pub: 1998-10-23
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Description

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.

Table of Contents

MOLECULAR STRUCTURE AND BONDING

Isomerism

Drawing Three Dimensional Chemical Stuctures

VSEPR and the Shape of Molecules

Structure and Bonding

Clasification of Stereoisomers

CIS-TRANS ISOMERISM

Cis-Trans Isomerism in Alkenes

Cis-Trans Isomerism in Other Systems Which Contain a double Bond

Cis-Trans Isomerism in Cyclic Systems

Cis-Trans Isomerism in Square Planar and Octohedral Metal Complexes

Cis-Trans Isomerism about Single Bonds (Conformational Diastereomers)

Methods for Distinguishing Cis-Trans Isomers

ENANTIOMERS

Structure of Enantiomers

Nomenclature for Enantiomers (Speciation of Absolute Configuration)

Chemical Properties of Enantiomers

Physical Properties of Enantiomers

Enantiomeric Excess

Biological Properties of Enantiomers

Chirality Due to Stereocentres at Atoms Other than Carbon

Other Stereogenic Elements Which Can Produce Molecular Chirality

COMPOUNDS WITH TWO OR MORE STEREOCENTRES

Compounds with Two Stereocentres

Compounds with More Than Two Stereocentres

Polymer Stereochemistry

Relative Stereochemistry Nomenclature

Diastereomeric Excess

INTERCONVERSION AND ANALYSIS OF STEREOISOMERS

Racemization

Epimerization

Resolution

Methods for Determining Enantiomeric Excess

Determination of Absolute Configuration

Determination of Relative Configuration

MOLECULAR SYMMETRY

Introduction

Symmetry Elements and Symmetry Operations

Symmetry of Molecules with Multiple Conformations

Point Groups

Symmetry and Chirality

TOPISM AND PROSTEREOGENICITY

Homotopic, Enantiopic and Diastereotopic Groups

Homotopic, Enantiopic and Diastereotopic Faces

Nomenclature for Heterotopic Groups and Faces

CONFORMATION OF ACYLIC AND CYCLIC MOLECULES

Introduction

Conformations of Acyclic Molecules

Conformations of Cyclic Alkanes and their Derivatives

Cyclopropane

Cyclobutane

Cyclohexane

Medium and Large Rings

Conformation of Inorganic and Organometallic Compounds

Conformation of Biopolymers

Methods for Determining Molecular Conformation

STEREOCHEMISTRY OF CHEMICAL REACTIONS

Introduction

Substitution Reactions

Elimination Reactions

Addition Reactions to Alkenes

Addition of Nucleophiles to Aldehydes and Ketones

Pericyclic Reactions

ASYMMETRIC SYNTHESIS

Introduction

Use of Chiral Auxiliaries

Use of Enantiomerically Pure Reagents

Index

Subject Categories

BISAC Subject Codes/Headings:
MED008000
MEDICAL / Biochemistry
SCI013040
SCIENCE / Chemistry / Organic