Hydrogen Bonds and the Reactivity of Organic Compounds in Proton Transfer and Nucleophilic Substitution Reactions

Recent data on various relations between the characteristics (spectroscopic and thermodynamic) of hydrogen bonds in different classes of organic compounds and the acid–base properties of the latter are examined. The principal approaches to the study of the influence of hydrogen bonds on acid–base equilibria in various solvents are demonstrated. Fundamentally new results, obtained in combined studies of proton transfer reactions in the gas phase and in solution, are analysed and approaches to allowance for the influence of hydrogen bonds on the reactants and the transition state in nucleophilic substitution reactions as well as the role of hydrogen bonds in the alteration of the rates and modes of chemical reactions are discussed.
The bibliography includes 152 references.