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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.
Acid dissociation constants of 10 substituted phenols have been measured by a kinetic method together with second-order rate constants for the reactions of aryl benzoates (X-C 6 H 4 CO-OC 6 H 4 -Y) with Z-substituted phenoxide (Z-C 6 H 4 O - ) and EtO - in absolute ethanol at 25.0±0.1°C. The kinetic results support a stepwise mechanism...
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