EVIDENCE OF A STEPWISE ACYL-TRANSFER REACTION-MECHANISM - NONLINEAR HAMMETT-PLOTS FOR REACTIONS OF P-NITROPHENYL SUBSTITUTED BENZOATES WITHHYDROXIDE AND P-CHLOROPHENOXIDE

Authors
UM IH CHUNG EK KWON DS
Citation
Ih. Um et al., EVIDENCE OF A STEPWISE ACYL-TRANSFER REACTION-MECHANISM - NONLINEAR HAMMETT-PLOTS FOR REACTIONS OF P-NITROPHENYL SUBSTITUTED BENZOATES WITHHYDROXIDE AND P-CHLOROPHENOXIDE, Tetrahedron letters, 38(27), 1997, pp. 4787-4790
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
27
Year of publication
1997
Pages
4787 - 4790
Database
ISI
SICI code
0040-4039(1997)38:27<4787:EOASAR>2.0.ZU;2-H
Abstract
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 stepwis e mechanism for the acyl-transfer reaction. (C) 1997 Elsevier Science Ltd.