Strained Organic Molecules - 1st Edition - ISBN: 9780122995507, 9781483217956

Strained Organic Molecules

1st Edition

Organic Chemistry: A Series of Monographs, Vol. 38

Authors: Arthur Greenberg Joel F. Liebman
Editors: Harry H. Wasserman
eBook ISBN: 9781483217956
Imprint: Academic Press
Published Date: 28th November 1978
Page Count: 422
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Description

Strained Organic Molecule, Volume 38 considers the vast field of strained organic molecules. The book discusses energy and entropy; cyclopropane and cyclobutane; and unique strained groupings or building blocks. The text also describes the aesthetics, rearrangements, and topology of polycycles; kinetic and thermodynamic stability; and tetrahedral tetracoordinate carbon. The inverted tetrahedra, propellanes, buttaflanes, and paddlanes; planar methane and its derivatives; and five- and six-coordinaste carbon are also considered. Chemists will find the book invaluable.

Table of Contents


Preface

Chapter 1 Energy and Entropy

l.A Reference States and Reference Books

l.B Origin of Molecular Strain

l.C Thermodynamics and Symmetry

l.D Potential Energy Curves and Zero-Point Energy

Chapter 2 Cyclopropane and Cyclobutane

2.A Conceptual Models for the Bonding in Cyclopropane

2.B Selected Reactions of Cyclopropanes

2.C Cyclobutane

Chapter 3 Unique Strained Groupings or Building Blocks

3.A Cycloalkanes

3.B Bicyclic, Spirocyclic, and Bridged Hydrocarbons

3.C Tetrahedrane

3.D Strained Alkenes: Molecules Lacking Torsional Strain

3.E Torsionally Distorted ð Bonds

3.F "Bredt Compounds" and Cyclic Alienes

3.G Cycloalkynes, Benzyne, and Cyclocumulenes

3.H Distorted Aromatic Rings

Chapter 4 Polycycles: Aesthetics, Rearrangements, and Topology

4.A Adamantanes and Higher Homologues

4.B Iceane

4.C Miscellaneous Acid-Catalyzed Rearrangements

4.D Strained Molecules of Formula (CH)n

4.E Additional Polycyclic Molecules

4.F Molecular Topology

Chapter 5 Kinetic and Thermodynamic Stability

5.A Introduction

5.B Orbital Symmetry and Stabilities of Benzene Valence Isomers

5.C Transition Metals and Strained Carbocyclic Molecules

5.D Strained Heterocyclic Molecules

5.E Substituted Derivatives of Strained Molecules

Chapter 6 A Potpourri of Pathologies

6. A When is Tetracoordinate Carbon Tetrahedral?

6.B Inverted Tetrahedra, Propellanes, Buttaflanes, and Paddlanes

6.C Planar Methane and Its Derivatives

6.D Five- and Six-Coordinate Carbon

Addendum

Index


Details

No. of pages:
422
Language:
English
Copyright:
© Academic Press 1978
Published:
Imprint:
Academic Press
eBook ISBN:
9781483217956

About the Author

Arthur Greenberg

Affiliations and Expertise

Duke University, Durham, North Carolina, U.S.A.

Joel F. Liebman

About the Editor

Harry H. Wasserman