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

[GRAPHICS] The rate constants for the hydronium ion, hydroxide, and water-catalyzed br eakdown of N-(hydroxymethyl)benzamide (1), 4-chloro-N- (hydroxymethyl)benza mide (2), and 2,4-dichloro-N-(hydroxymethyl)benzamide (3) in H2O, at 25 deg reesC, I = 1.0 (KCl), have been determined. The reactions of 1, 2, and 3 we re found to be specific acid and specific base catalyzed with a first order dependence on hydronium and hydroxide ions. At higher hydroxide concentrat ions, the reactions were found to be pH independent for each compound studi ed.