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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

✍ Scribed by Ik-Hwan Um; Eun-Kyung Chung; Dong-Sook Kwon

Book ID: 104257390
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 225 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)01033-2

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✦ Synopsis

The Hammett plots obtained for the title reactions exhibit a break, £e. P~rl values decrease from 2.21~2.44 to 1.45-1.52 as the acyl substituent becomes a s~ong elecffon withdrawing group ( a >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-tl'ansfer reaction.

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