Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Kinetic Studies on Nucleophilic Substitution Reaction for Naphthalene Carbonyl Chloride

염화나프탈렌카르보닐의 친핵성 치환반응에 관한 연구

  • 윤상기 (東亞大學校 理科大學 化學科) ;
  • 엄태섭 (東亞大學校 理科大學 化學科) ;
  • 성대동 (東亞大學校 理科大學 化學科)
  • Published : 1980.10.30
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Abstract

The rate constants for the reaction of ${\alpha}$-naphthalene carbonyl chloride and ${\beta}$-naphthalene carbonyl chloride have been determined in methanol-acetonitrile and methanol-acetone. The rate constant of ${\alpha}$-naphtalene carbonyl chloride is higher than that of ${\beta}$-naphthalene carbonyl chloride. This behavior is consistent with Dewar's number, Nr and also Streitwieser's value ${\sigma}^+$. Since in the transition state carbonyl carbon is transformed to$sp^3$, no peri-hydrogen effect was observed.

${\alpha}$- 및 ${\beta}$-염화나프탈렌카르보닐의 가메탄올 분해반응속도를 메탄올-아세톤, 메탄올-아세토니트릴 혼합용매 속에서 측정하였다. 각 혼합용매마다 공통적으로 ${\alpha}$-염화나프탈렌카르보닐이 ${\beta}$-염화나프탈렌카르보닐보다 반응속도 상수가 크게 관측되었다. 이것은 Dewar수 Nr과 Streitwieser의 ${\sigma}^+$값과도 일치하였다. 카르보닐탄소가 천이상태에서 $sp^3$로 바뀌어 인접수소에 의한 입체장애가 없어지는 것을 알 수 있었다.

Keywords

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