Proton inventory study of the general base-catalyzed hydrolyses of trifluoroacetanilides by imidazole

The hydrolyses of substituted trifluoroacetanilides were catalyzed by neutral imidazole. The effect of five phenyl substitutents (H, m-Cl, p-Cl, m-NO₂, and p-NO₂) on the hydrolyses was examined and proton inventory studies were carried out. Catalyses by neutral imidazole exhibited a positive ?(+0.84) and multiproton transfer in the transition state. This reaction involves general base-catalyzed formation of the tetrahedral intermediate by neutral imidazole followed by its breakdown catalyzed by water.