Bulletin of the Korean Chemical Society

  • 제18권2호
  • /
  • Pages.161-164
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  • 1997
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Nucleophilic Substitution Reactions of 1- and 2-Naphtylmethyl Arenesulfonates with Anilines

  • 발행 : 1997.02.20
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초록

Kinetic studies are carried out on the reactions of 1- and 2-naphthylmethyl arenesulfonates with anilines in acetonitrile at 25.0 ℃. The rates are faster for the 2-naphthylmethyl series than for the corresponding 1-naphthylmethyl series suggesting that there is a greater stabilization of positive charge development in the TS at the arylmethyl reaction center carbon for the former. The sign and magnitude of ρxz (=-0.12) are similar to those of the benzylic series. Thus, benzyl, 1- and 2-naphthylmethyl derivatives belong to a class of compounds which react with aniline nucleophiles through a relatively loose SN2 TS. Kinetic secondary deuterium isotope effects indicated that a stronger nucleophile and nucleofuge lead to a later TS as the definition of ρxz requires.

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참고문헌

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