The kinetics of hydrolysis and aminolysis of N-acetyl-O-formylserinamide

Abstract

Kinetic data for the hydrolysis of N-Acetyl-O-formylserinamide (I) show that its enhanced reactivity relative to methyl formate originates entirely in increased entropy of activation. Imidazole acts as a general base in the catalysis of hydrolysis of compound (I) but as a nucleophile towards 2,2,2-trifluoroethyl formate. General base catalysis is more effective in aminolysis of compound (I) than in that of methyl formate, and imidazole achieves both general-acid and general-base catalysis of such reactions.