Reexamination of Tris(hydroxymethyl)aminomethane-Catalyzed Hydrolysis of p-Nitrotrifluoroacetanilide

摘要

The tris(hydroxymethyl)aminomethane (Tris)-catalyzed hydrolysis of p-nitrotrifluoroacetanilide was kinetically studied. On the contrary to the previously reported results (R. M. Pollack and T. C.Dumsha, J. Am. Chem. Soc., 1973, 95, 4463), the dependence of the rate on [Tris] consists of an initial curve portion and a subsequent linear increase. This indicates that erroneous conclusions were made in the reported work due to the insufficient amount of data. The initial portions of the rate[Tris] profiles are attributed to the catalyzed breakdown of the tetrahedral intermediate, and the linear portions to the general base-catalyzed water attack at the substrate.