Abstract: The rates of enolization of 1 catalyzed by a series of oxyanions are compared with the reactions of esters in which the oxyanions function as nucleophiles involved in rate- determining attack. The similarity in curvature of these two plots is demonstrated. The cause of the curvature for nucleophilic reactions of PNPA and PNTPA is suggested to arise from a perturbation due to solvation similar to that proposed for 1. The value of p,,, for phenoxides ...
