Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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The Reaction of Benzyl Arenesulfonate with N,N-Dimethylanilines (III). Substituent Effects of Leaving Group for Benzyl Arenesulfonate

Benzyl Arenesulfonate와 N,N-디메틸아닐린과의 反應 (第3報). Benzyl Arenesulfonate의 難脫基의 置換基 效果

  • Soo-Dong Yoh (Department of Chemistry, Teacher's College, Kyungpook National University)
  • 여수동 (慶北大學敎 師範大學 化學科)
  • Published : 1975.12.30
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Abstract

Substituent effect of the leaving groups of the reaction of benzyl arenesulfonate with dimethylanilines in acetone at $35^{\circ}C$ was obtained with the following results. 1. Substituent effect of the leaving groups was not variable when changed from pyridine to N,N-dimethylaniline in nucleophile 2.In acetone, the Hammett ${\sigma}$ constant of p-MeO of the leaving group was -0.35. 3. The weaker the nucleophilicity in dimethylaniline, the stronger the movement of electron from N to C, and the cleavage of the C${\ldots}$0 bond in transition state proceeds.

Benzyl arenesulfonate와 디메틸아닐린을 아세톤 중에서 $35^{\circ}C$로 반응시켜 離脫基의 置換基效果를 硏究한 結果 다음과 같은 結論을 얻었다. (1) 親核試藥이 피리딘에서 N,N-디메틸아닐린으로 바뀌어도 離脫基의 치환기效果는 변화가 없다. (2) p-MeO의 치환기정수는 아세톤에서 -0.35가 적당했다. (3) 치환 디메틸아닐린의 ) 親核力이 弱할 수록 전이상태에서는 N에서 C로 電子移動이 보다 크며 C${\ldots}$O結合 開裂은 보다 진행된 상태라고 생각된다.

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