Ester hydrolysis, general base and nucleophilic catalysis

Ester hydrolysis, general base and nucleophilic catalysis, 5,237... 

Energetic tritium and carbon atoms, reactions of, with organic compounds, 2, 201 Entropies of activation and mechanisms of reactions in solution, 1, 1 Equilibrium constants, N.M.R. measurements of, as a function of temperature, 3, 187 Ester hydrolysis, general base and nucleophilic catalysis, 5, 237... 

General base and nucleophilic catalysis of ester hydrolysis and related reactions, 5, 237... 

Gaseous carbonium ions from the decay of tritiated molecules, 8, 79 General base and nucleophilic catalysis of ester hydrolysis and related reactions, 5, The Gomberg Century Free Radicals 1900-2000, 36, 1 Gomberg and the Nobel Prize, 36, 59... 

The hydrolysis of the more reactive carboxylic esters is catalyzed by a wide range of oxyanions. The mechanism proposed for the neutral hydrolysis of esters on p. 158 involves two molecules of water, one as a nucleophile and one as a general base. In principle an oxyanion or other nucleophile can replace either of these molecules, and both general base and nucleophilic catalysis of ester hydrolysis are well-known. The detailed mechanism of nucleophilic catalysis depends, to some extent, on the type of anion concerned, but the differences occur at a relatively late stage in the reaction, and the similarities are sufficient to allow generalizations about oxyanion reactions as a class. Some of the differences are not normally kinetically significant, and are best mentioned briefly at this point. 

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