An Investigation into the Mechanism of Acid-Catalyzed Hydrolysis of N-Benzylbenzohydroxamic Acid

Article abstract of DOI:10.1246/bcsj.62.1304

The catalytic effects of hydrochloric, perchloric, and sulfuric acids on the hydrolysis of N-benzylbenzohydroxamic acid (BBHA) have been examined in 10percent (v/v) dioxane-water at 55 deg C.Plots of the pseudo-first-order rate constants k_Φ against +> show maxima which arise from extensive protonation of the substrate.Analyses of the kinetic data by Bunnett and Bunnett-Olsen criteria, solvent deuterium isotope effects, salt effects and entropies of activation are consistent with a bimolecular mechanism.