Exalted Resonance Effect in the Aryl-Assisted Solvolyses of 2-Aryl-2-(trifluoromethyl)ethyl m-Nitrobenzenesulfonates
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The substituent effects on solvolysis of 2-aryl-2-(trifluoromethyl)ethyl <I>m</I>-nitrobenzenesulfonates, in acetic acid and in 80% aqueous trifluoroethanol, were analyzed by Yukawa-Tsuno equation. The resonance demands (<I>r</I> = 0.77 in acetic acid) were larger than that of standard aryl-assisted solvolysis by 0.2. This enlargement should depend on a destabilization of aryl-assisted transition-state by an electron-withdrawing trifluoromethyl group.
- Chemistry Letters
Chemistry Letters 1997(10), 973-974, 1997-10
The Chemical Society of Japan