ol006691l_si_001.pdf (383.96 kB)
Computational Studies of the Aminolysis of Oxoesters and Thioesters in Aqueous Solution
journal contribution
posted on 2000-12-08, 00:00 authored by Wei Yang, Dale G. DrueckhammerTransition state structures and energies have been investigated for concerted and stepwise mechanisms for the acyltransfer reactions of ethyl
acetate and ethyl thioacetate with ammonia. Specific and general solvent effects have been evaluated. The results predict stepwise mechanisms
involving water-catalyzed proton transfer for both reactions and indicate that the thioester is more reactive than the oxoester in both the
addition and elimination steps.