Abstract
As a model for acetyl-α-chymotrypsin, 2-(2'-benzimidazolyl)phenyl acetate was synthesized in a good yield and its hydrolytic kinetics has been studied in buffer solutions at 45'C within a wide pH range (0.65–8.80). The measured pseudo-first-order rate constants (kobs) at different pH values conform well with the data derived from the proposed theoretical model. It is shown that in an acidic solution of medium strength (pH = 2.0–3.0), the ester is hydrolyzed via intramolecular general acid catalysis by benzimidazolium cation; while at pH values near neutrality (pH = 5.5–7.0), this ester is hydrolyzed via intramolecular general base catalysis by neutral benzimidazole. These findings are discussed and the activation parameters of the hydrolysis reaction were also determined.
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