Abstract
The mechanism of hydrolysis of the ester group of benzoylglycolic acid in buffered aqueous solutions at 80 °C in the range where the rate is independent of pH was studied. The uptake of 18O in benzoic acid during hydrolysis in 20%18O enriched water, the interpretation of a Bronsted correlation of hydrolysis catalysed by some oxy-anions (β 0.49), and the evaluation of activation entropy brought us to the conclusion that the reaction involves the anion of the substrate, and may be interpreted in terms of intramolecular general base catalysis (kH2o8–×[H2O] 1.33 × 10–6 s–1, ΔH‡ 22.5 kcal mol–1, ΔS‡–22.2 cal mol–1 K–1).
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