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Colloque
The rate sequence PhO-CO-Cl > MeO-CO-Cl > EtO-CO-Cl > i-PrO-CO-Cl for hydrolysis in pure water indicates a change of mechanism for the latter reaction. The enthalpies and entropies of activation support this conclusion. The solvent deuterium isotope effects indicate that pre-equilibrium with water is important for the hydrolyses of the first three compounds but not for isopropyl chloroformate. The heat capacities of activation (ΔCp*) have been determined and have been used in determining the operative mechanisms.
