Kinetic dependence of the aqueous reaction of N-(hydroxymethyl)benzamide derivatives upon addition of electron-withdrawing groups.

[figure: see text] The rate constants for the hydronium ion, hydroxide, and water-catalyzed breakdown of N-(hydroxymethyl)benzamide (1), 4-chloro-N-(hydroxymethyl)benzamide (2), and 2,4-dichloro-N-(hydroxymethyl)benzamide (3) in H2O, at 25 degrees C, I = 1.0 (KCl), have been determined. The reactions of 1, 2, and 3 were found to be specific acid and specific base catalyzed with a first-order dependence on hydronium and hydroxide ions. At higher hydroxide concentrations, the reactions were found to be pH independent for each compound studied.