Journal of Organic Chemistry p. 1216 - 1218 (1987)
Update date:2022-08-17
Topics:
Brown, R.S.
Clewley, R.G
Intramolecular general-base catalysis of the hydrolysis of an acetylimidazole by imidazole is assessed by studying the hydrolysis of 2-(imidazol-2-ylmethyl)-N-acetylimidazole (3).The pH vs. log kobsd profile exhibits three major domains that consist of H2O attack on the protonated acetylimidazolium unit,OH- attack on the neutral material, and an intramolecular general-base catalysis of H2O on the neutral species.Consistent with the latter is a plateau observed in the pH profile (k3 = 1.02*10-3 s-1) at neutrality and a solvent kinetic isotope effect of kH2O/kD2O = 2.8 in that region.The effective molarity of the intramolecular imidazole in 3 can be assessed by comparing the value of k3 with the second-order rate constant for 2-methylimidazole catalyzing the hydrolysis of 2-methyl-N-acetylimidazole (4).After the difference in the imidazole pKa values is corrected for, the effective molarity of the intramolecular catalyst is 3 M.
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