Kinetics of reaction of triethylammonium carboxylates with α-halogenocarbonyl compounds in organic solvents : Reaction of benzoates and phenoxyacetates with phenacyl bromide in acetone

Abstract The kinetics of the reaction of phenacyl bromide with triethylammonium p-substituted benzoates and phenoxyacetates at 25°, 30° and 35° in acetone suggest a rigid cyclic transition state involving a hydrogen bonded ion-pair as the active nucleophile. The effect of addition of water on the rate constant is rationalized. Regression analysis on single parameter treatment on benzoates shows that the reaction obeys the Hammett equation (ϱ value + 0.37, with r = 0.993).