Strained Organic Molecules

Strained Organic Molecules

Organic Chemistry: A Series of Monographs, Vol. 38

1st Edition - November 28, 1978

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  • Authors: Arthur Greenberg, Joel F. Liebman
  • eBook ISBN: 9781483217956

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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



Product details

  • No. of pages: 422
  • Language: English
  • Copyright: © Academic Press 1978
  • Published: November 28, 1978
  • Imprint: Academic Press
  • eBook ISBN: 9781483217956

About the Authors

Arthur Greenberg

Dr. Arthur Greenberg is a Professor of Chemistry at the University of New Hampshire. His research interests include physical organic chemistry and environmental organic chemistry. Emphases include strained organic molecules such as bridgehead bicyclic lactams, having twisted amide linkages, and epoxyoxepins of possible relevance to benzene metabolism. Interests include airborne carcinogens such as polycyclic aromatic hydrocarbons (PAH) and their derivatives.

Affiliations and Expertise

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

Joel F. Liebman

Dr. Joel Liebman is Professor of Chemistry and Biochemistry at the University of Maryland. His research is interdisicplinary — it overlaps computational/theory, organic chemistry and physical/inorganic chemistry. It is international and it is eclectic — it spans the periodic table as well as the gas and condensed phases. He has investigated the energetics of neutrals and related ions; species stabilized by aromaticity and/or those destabilized by antiaromaticity and strained rings; compounds containing novel functionalities and their energetics. Not merely organic compounds, but also those of the nonmetals and metalloids, he has especially explored species containing fluorine, the noble gases and boron.

Affiliations and Expertise

University of Maryland, College Park, Maryland, USA

About the Editor

Harry H. Wasserman

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