General-buffer catalysis of the reaction of N-(hydroxymethyl)benzamide: a new pathway for the aqueous reaction of carbinolamides

The second-order rate constants for the general-buffer catalyzed breakdown of N-(hydroxymethyl)benzamide (1) in water at 25 °C, I = 1.0 (KCl) by pivalic, acetic, chloroacetic, and dichloroacetic acid were determined by initial rates. The observed rate increased with increasing amounts of the acidic form of the buffer and a Brønsted correlation of α = 0.35 was determined. The results presented here, represent the first evidence for a general-buffer catalytic mechanism for the aqueous reaction of 1 and for carbinolamides in general.