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

被引：82

作者：

Yang, W ^{[1
]}

Drueckhammer, DG ^{[1
]}

机构：

[1] SUNY Stony Brook, Dept Chem, Stony Brook, NY 11794 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 26期

关键词：

D O I：

10.1021/ol006691l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Transition 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.

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页码：4133 / 4136

页数：4

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