The Proton: Applications to Organic Chemistry

Preface1 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 References2 Strengths of Neutral Organic Acids I. Introduction II. Oxygen Acids III. Sulfur Acids IV. Carbon and Nitrogen Acids References3 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 References4 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 References5 Alternative Sites of Protonation and Deprotonation I. Introduction II. Alternative Sites of Protonation III. Alternative Sites of Deprotonation IV. Amphiprotic Systems That Form Zwitterions References6 Acidity and Basicity of Unstable and Metastable Organic Species I. Introduction II. Organic Free Radicals III. Electronically Excited States IV. Tetrahedral Intermediates References7 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 ReferencesIndex