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

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
38
Issue
27
Identifiers
DOI: 10.1016/s0040-4039(97)01033-2

Abstract

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.

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