Author Profile

Richard J. Payne is a world-renowned chemist, academic, and author who has made pioneering contributions to the fields of organic chemistry and chemical biology. He serves as a Professor of Organic Chemistry and Chemical Biology at the University of Sydney, where his groundbreaking research focuses on peptide and protein synthesis, drug discovery, and molecular structure. Professor Payne completed his PhD at the University of Cambridge as a Gates Cambridge Scholar, followed by post-doctoral studies at the Scripps Research Institute. Over his distinguished career, he has been recognized with numerous prestigious awards, including the Malcolm McIntosh Prize for Physical Scientist of the Year (Prime Minister's Prizes for Science) and the H.G. Smith Memorial Medal from the Royal Australian Chemical Institute.

About The Book

Stereochemistry and Bonding stands as a definitive, master class text that bridges the gap between fundamental molecular architecture and advanced chemical reactivity. Designed for students, researchers, and professional chemists alike, this comprehensive volume offers an immersive exploration into the three-dimensional world of molecules, untangling the complex relationship between how atoms bond and how they are arranged in space. At the heart of this book is a singular, powerful premise: a molecule's three-dimensional shape dictates its physical properties, biological behavior, and chemical destiny. By seamlessly weaving together the principles of quantum mechanics, molecular orbital theory, and spatial geometry, the text provides readers with a rigorous framework to predict, visualize, and manipulate molecular structures. It transforms abstract theoretical models into intuitive, actionable chemical insights. This text is an indispensable companion for advanced undergraduate and graduate students specializing in organic, inorganic, or physical chemistry. It also serves as a vital reference manual for medicinal chemists and materials scientists who require a flawless command of spatial architecture to design the molecules of tomorrow.

Table of Contents

Contents
Preface
1. MOLECULAR GEOMETRY AND CHEMICAL BONDING
Introduction
Molecular Structure And Chemical Bonding
Hybridisation And Chemical Bonding
Hydrogen Bonding
Rotation Around Bonds And Change In Dihedral Angle
Catenae’s
Summary
2. MOLECULAR SYMMETRY AND CHIRALITY
Introduction
Point Group Classification
Molecular Symmetry And Chirality
Point Groups And Symmetry Number
Summary
3. STEREOISOMERISM: DEFINITIONS AND CLASSIFICATION
Introduction
Molecular Representation
Classification Of Stereoisomers
Stereoisomerism, Conformation, And Chirality
Racemic Modifications
Summary
4. STEREOISOMERISM AND CENTRE OF CHIRALITY
Introduction
Molecules With A Single Chiral (Stereogenic) Centre
E And Z Nomenclature
Molecules With A Centre Of Chirality And Simple Axes Of Symmetry (Cn)
Molecules With Two And More Chiral Centres
Summary


1. STEREOISOMERISM : AXIAL CHIRALITY, PLANAR CHIRALITY AND HELICITY
Introduction
Principles Of Axial And Planar Chirality
Stereochemistry Of Allenes
Stereochemistry Of Spiranes And Analogues
Biphenyl Derivatives And Atropisomerism
Stereochemistry Of Molecules With Planar Chirality
Helicity
Cyclostereoisomerism
Summary
2. TOPICITY AND PROSTEREOISOMERISM
Introduction
Topicity Of Ligands And Faces
Nomenclature Of Stereoheterotopic Ligands And Faces
Prostereoisomerism And Stereoisomerism
Summary
3. RACEMISATION AND METHODS OF RESOLUTION
Introduction
Mechanisms Of Racemisation
Asymmetric Transformation And Mutarotation
Methods Of Resolution
Optical Purity And Enantiomeric Excess
Summary
4. DETERMINATION OF CONFIGURATION
Introduction
Determination Of Absolute Configuration
Correlative Methods For Configurational Assignment
Configuration Of Molecules With Axial And Planar Chirality
Relative Configuration Of Diastereomers
Summary
5. CONFORMATIONS OF ACYCLIC MOLECULES
Introduction
Molecular Mechanics And Conformation
Klyne-Prelog Terminology For Torsion Angles
Physical Methods For Conformational Analysis


Conformations Of A Few Acyclic Molecules
Diastereomers: Configurations, And Conformations
Summary
10. CONFORMATIONS OF CYCLIC SYSTEMS: MONOCYCLIC COMPOUNDS
Introduction
Conformations Of Cyclohexane
Conformations Of Monosubstituted Cyclohexanes
Conformations Of Di- And Polysubstituted Cyclohexanes
Cyclohexane Ring With One And Two Sp2 Carbons
Carbocycles Other Than Cyclohexane
Summary
11. CONFORMATIONS OF CYCLIC SYSTEMS: FUSED RING AND BRIDGED RING COMPOUNDS
Introduction
Fused Bicyclic Systems
Fused Polycyclic Systems
Bridged Ring Systems
Summary
Bibliography
Index