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

Title
Evidence of a stepwise acyl-transfer reaction mechanism: Nonlinear hammett plots for reactions of p-nitrophenyl substituted benzoates with hydroxide and p-chlorophenoxide
Authors
Um I.-H.Chung E.-K.Kwon D.-S.
Ewha Authors
권동숙엄익환
SCOPUS Author ID
권동숙scopusscopus; 엄익환scopusscopus
Issue Date
1997
Journal Title
Tetrahedron Letters
ISSN
0040-4039JCR Link
Citation
vol. 38, no. 27, pp. 4787 - 4790
Indexed
SCI; SCIE; SCOPUS scopus
Abstract
The Hammett plots obtained for the title-reactions exhibit a break, i.e. ρ acyl values decrease from 2.21 ~ 2.44 to 1.45 ~ 1.52 as the acyl substituent becomes a strong electron withdrawing group (σ > 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.
DOI
10.1016/S0040-4039(97)01033-2
Appears in Collections:
자연과학대학 > 화학·나노과학전공 > Journal papers
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