Evidence of a stepwise acyl-transfer reaction mechanism: Nonlinear Hammett plots for reactions of p-nitrophenyl substituted benzoates with hydroxide and p-chlorophenoxide

被引:19
|
作者
Um, IH
Chung, EK
Kwon, DS
机构
[1] Department of Chemistry, Ewha Womans University, Seoul
关键词
D O I
10.1016/S0040-4039(97)01033-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Hammett plots obtained for the title reactions exhibit a break, i.e. rho(acyl) values decrease from 2.21 similar to 2.44 to 1.45 similar to 1.52 as the acyl substituent becomes a strong electron withdrawing group (sigma > 0.6). Such a break in the Hammett plots is suggestive of a change in the reaction mechanism and strong evidence of a stepwise mechanism for the acyl-transfer reaction. (C) 1997 Elsevier Science Ltd.
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页码:4787 / 4790
页数:4
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