Exalted Resonance Effect in the Aryl-Assisted Solvolyses of 2-Aryl-2-(trifluoromethyl)ethyl <i>m</i>-Nitrobenzenesulfonates

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  • Mutsuo Okamura
    Graduate School of Science and Technology, Niigata University
  • Ken Hazama
    Department of Chemistry, Faculty of Science, Niigata University
  • Mie Ohta
    Department of Chemistry, Faculty of Science, Niigata University
  • Keiko Kato
    Department of Chemistry, Faculty of Science, Niigata University
  • Takaaki Horaguchi
    Department of Chemistry, Faculty of Science, Niigata University
  • Atsuyoshi Ohno
    Institute for Chemical Research, Kyoto University

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Abstract

<jats:title>Abstract</jats:title> <jats:p>The substituent effects on solvolysis of 2-aryl-2-(trifluoromethyl)ethyl m-nitrobenzenesulfonates, in acetic acid and in 80% aqueous trifluoroethanol, were analyzed by Yukawa-Tsuno equation. The resonance demands (r = 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.</jats:p>

Journal

  • Chemistry Letters

    Chemistry Letters 26 (10), 973-974, 1997-10-01

    Oxford University Press (OUP)

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