The mechanism of the hydrolysis of phenyl salicylate and catechol monobenzoate in the presence and absence of borate ions

Abstract

The mechanism of the hydrolysis of phenyl salicylate, and catechol monobenzoate in neutral and alkaline solutions has been investigated. It is concluded that in the non-buffer-catalysed part of these reactions the ionised phenolic group provides intramolecular general-base catalysis. In borate buffers ([Borate]<0·05M) the rate of hydrolysis of phenyl salicylate (but not that of catechol monobenzoate) increases with increasing borate concentration and k_Borate is 80–120-fold greater than that for the hydrolysis of phenyl o-methoxybenzoate and phenyl benzoate, owing it is thought to the formation of a complex between boric acid or borate and the transition state for the formation of the tetrahedral intermediate in the hydrolysis of phenyl salicylate.