Tetrahedron Letters

Rate of formation of N-(hydroxymethyl) benzamide derivatives in water as a function of pH and their equilibrium constants

RV Ankem, JL Murphy, RW Nagorski

Index: Ankem, Ramana V.; Murphy, John L.; Nagorski, Richard W. Tetrahedron Letters, 2008 , vol. 49, # 46 p. 6547 - 6549

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Citation Number: 6

Abstract

The third-order rate constants for the pH-dependent formation of the carbinolamides generated from the reaction of formaldehyde and benzamide, 4-chloro, 4-nitro, 4-methyl and 4-methoxybenzamide, are reported. The acid-catalyzed reaction was found to occur via rate- limiting proton transfer, whereas the hydroxide-dependent reaction occurred via a specific- base process. Coupling the rate constants for carbinolamide formation reported herein ...