Computational studies of the aminolysis of oxoesters and thioesters in aqueous solution

Authors
Yang, W Drueckhammer, DG
Citation
W. Yang et Dg. Drueckhammer, Computational studies of the aminolysis of oxoesters and thioesters in aqueous solution, ORG LETT, 2(26), 2000, pp. 4133-4136
Citations number
22
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
26
Year of publication
2000
Pages
4133 - 4136
Database
ISI
SICI code
1523-7060(200012)2:26<4133:CSOTAO>2.0.ZU;2-L
Abstract
[GRAPHICS] Transition state structures and energies have been investigated for concert ed and stepwise mechanisms for the acyltransfer reactions of ethyl acetate and ethyl thioacetate with ammonia. Specific and general solvent effects ha ve been evaluated. The results predict stepwise mechanisms involving water- catalyzed proton transfer for both reactions and indicate that the thioeste r is more reactive than the oxoester in both the addition and elimination s teps.