The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Hydroxyl group catalysis. V. Imidazole catalysis. X. General base catalysis of ester hydrolysis by imidazole and the influence of a neighboring hydroxyl group》. Authors are Bruice, Thomas C.; Fife, Thomas H.; Bruno, John J.; Benkovic, Patricia.The article about the compound:2-Chloroethyl acetatecas:542-58-5,SMILESS:CC(OCCCl)=O).Reference of 2-Chloroethyl acetate. Through the article, more information about this compound (cas:542-58-5) is conveyed.
cf. CA 57, 7102e, 7101e. Imidazole has been found to be a catalyst for the hydrolysis of alkyl acetates (AcOR’) in which the pKa’ of HOR’ is less than pKw. The catalytic coefficient for imidazole catalysis in these cases has been found to be associated with a deuterium solvent kinetic isotope effect (i.e., kH/kD) of 2 to 4. The mechanism represents an imidazole general base- or general acid-catalyzed hydrolysis. The rate of alk. hydrolysis of the cyclopentyl ester of dichloroacetic acid has been shown to be only about half as sensitive to facilitation by a neighboring hydroxyl group as previously found for the corresponding acetate. In addition, the rate of imidazole general base-catalyzed hydrolysis of cyclopentyl dichloroacetate has been found to be completely insensitive to the presence of a neighboring hydroxyl group.
Different reactions of this compound(2-Chloroethyl acetate)Reference of 2-Chloroethyl acetate require different conditions, so the reaction conditions are very important.