Stereochemistry and Bonding

By Richard J. Payne
364
2026

Description

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.

About Author

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.

Table of Content

Preface
1. MOLECULAR GEOMETRY AND CHEMICAL BONDING

1.1 . Introduction
1.2 . Molecular Structure And Chemical Bonding
1.3 . Hybridisation And Chemical Bonding
1.4 . Hydrogen Bonding
1.5 . Rotation Around Bonds And Change In Dihedral Angle
1.6 . Catenanes
1.7 . Summary

2. MOLECULAR SYMMETRY AND CHIRALITY 
2.1 . Introduction
2.3 . Point Group Classification
2.4 . Molecular Symmetry And Chirality
2.5 . Point Groups And Symmetry Number
2.6 . Summary

3. STEREOISOMERISM: DEFINITIONS AND CLASSIFICATION 
3.1 . Introduction
3.2 . Molecular Representation
3.3 . Classification Of Stereoisomers
3.4 . Stereoisomerism, Conformation, And Chirality
3.5 . Racemic Modifications
3.6 . Summary

4. STEREOISOMERISM AND CENTRE OF CHIRALITY 
4.1 . Introduction
4.2 . Molecules With A Single Chiral (Stereogenic) Centre
4.3 . E And Z Nomenclature
4.4 . Molecules With A Centre Of Chirality And Simple Axes Of Symmetry (Cn)
4.5 . Molecules With Two And More Chiral Centres
4.6 . Summary

5. STEREOISOMERISM : AXIAL CHIRALITY, PLANAR CHIRALITY AND HELICITY 
5.1 . Introduction
5.2 . Principles Of Axial And Planar Chirality
5.3 . Stereochemistry Of Allenes
5.4 . Stereochemistry Of Spiranes And Analogues
5.5 . Biphenyl Derivatives And Atropisomerism
5.6 . Stereochemistry Of Molecules With Planar Chirality
5.7 . Helicity
5.8 . Cyclostereoisomerism
5.9 . Summary

6. TOPICITY AND PROSTEREOISOMERISM 
6.1 . Introduction
6.2 . Topicity Of Ligands And Faces
6.3 . Nomenclature Of Stereoheterotopic Ligands And Faces
6.4 . Prostereoisomerism And Stereoisomerism
6.5 . Summary
7. RACEMISATION AND METHODS OF RESOLUTION 
7.1 . Introduction
7.2 . Mechanisms Of Racemisation
7.3 . Asymmetric Transformation And Mutarotation
7.4 . Methods Of Resolution
7.5 . Optical Purity And Enantiomeric Excess
7.6 . Summary

8. DETERMINATION OF CONFIGURATION 
8.1 . Introduction
8.2 . Determination Of Absolute Configuration
8.3 . Correlative Methods For Configurational Assignment
8.4 . Configuration Of Molecules With Axial And Planar Chirality
8.5 . Relative Configuration Of Diastereomers
8.6 . Summary

9. CONFORMATIONS OF ACYCLIC MOLECULES 
9.1 . Introduction
9.2 . Molecular Mechanics And Conformation
9.3 . Klyne-Prelog Terminology For Torsion Angles
9.4 . Physical Methods For Conformational Analysis
9.5 . Conformations Of A Few Acyclic Molecules
9.6 . Diastereomers: Configurations, And Conformations
9.7 . Summary

10. CONFORMATIONS OF CYCLIC SYSTEMS: MONOCYCLIC COMPOUNDS 
10.1 . Introduction
10.2 . Conformations Of Cyclohexane
10.3 . Conformations Of Monosubstituted Cyclohexanes
10.4 . Conformations Of Di- And Polysubstituted Cyclohexanes
10.5 . Cyclohexane Ring With One And Two Sp2 Carbons
10.6 . Carbocycles Other Than Cyclohexane
10.7 . Summary

11. CONFORMATIONS OF CYCLIC SYSTEMS: FUSED RING AND BRIDGED RING COMPOUNDS
11.1 . Introduction
11.2 . Fused Bicyclic Systems
11.3 . Fused Polycyclic Systems
11.4 . Bridged Ring Systems
11.5 . Summary

Bibliography
Index