The Proton: Applications to Organic Chemistry

The Proton: Applications to Organic Chemistry

1st Edition - January 28, 1985

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  • Author: Ross Stewart
  • eBook ISBN: 9780323155878

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Description

The Proton: Applications to Organic Chemistry deals with several aspects of the proton drawn from organic chemistry. This book begins with an introductory chapter, followed by discussions on the strengths of neutral organic acids and neutral organic bases. The mode of transfer of hydrogen in its three forms—H+, H•, and H-, alternative sites of protonation or deprotonation of organic compounds, and acid-base chemistry of unstable and metastable species are also elaborated. This text concludes with a presentation of the activation induced in organic molecules by proton addition or removal and its catalytic effects. This publication is intended for practicing organic chemists and researchers conducting work on protons.

Table of Contents


  • Preface

    1 Introduction

    I. Water and the Reference State

    II. Acid-Base Equilibria: Terms and Symbols

    III. Limitations on Water as a Medium for Acid-Base Measurements

    References

    2 Strengths of Neutral Organic Acids

    I. Introduction

    II. Oxygen Acids

    III. Sulfur Acids

    IV. Carbon and Nitrogen Acids

    References

    3 Strengths of Neutral Organic Bases

    I. Introduction

    II. Amidines and Guanidines

    III. Amines

    IV. Amides

    V. Oxygen Bases

    VI. Carbon Bases

    VII. Sulfur Compounds

    VIII. Effect of Oxidation State on Basicity

    References

    4 Proton Transfer, Hydrogen Atom Transfer, and Hydride Transfer

    I. Introduction

    II. The Geometry of Hydrogen Transfer

    III. Hydrogen Isotope Effects as a Criterion of Mechanism in Proton and Hydride Transfer

    IV. Competition Among Proton, Hydrogen Atom, and Hydride Transfer Processes

    References

    5 Alternative Sites of Protonation and Deprotonation

    I. Introduction

    II. Alternative Sites of Protonation

    III. Alternative Sites of Deprotonation

    IV. Amphiprotic Systems That Form Zwitterions

    References

    6 Acidity and Basicity of Unstable and Metastable Organic Species

    I. Introduction

    II. Organic Free Radicals

    III. Electronically Excited States

    IV. Tetrahedral Intermediates

    References

    7 Activation of Organic Molecules by Acids and Bases

    I. Introduction

    II. Specific Acid and Specific Base Catalysis

    III. General Acid and General Base Catalysis

    IV. Reactions Conducted under Strongly Acidic or Strongly Basic Conditions

    References

    Index

Product details

  • No. of pages: 324
  • Language: English
  • Copyright: © Academic Press 1985
  • Published: January 28, 1985
  • Imprint: Academic Press
  • eBook ISBN: 9780323155878

About the Author

Ross Stewart

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