Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Determination of Reactivities by MO Theory (XI). Nucleophilic Substitution Reactions of N-Acetylpyrrolidone

MO 理論에 依한 反應性의 決定 (XI). N-아세틸피롤리돈의 親核性 置換反應

  • 이익춘 (仁荷大學校 理科大學 化學科) ;
  • 정대형 (仁荷大學校 理科大學 化學科) ;
  • 이석기 (釜山大學校 文理科大學 化學科) ;
  • 김시준 (釜山大學校 文理科大學 化學科)
  • Published : 1977.12.30
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Abstract

The orbital mixing analysis was applied to the acid-catalyzed nucleophilic substitution reaction of N-acetylpyrrolidone. It was found that the reactivity of protonated carbonyl carbon is greatly enhanced due to increase in positive charge (for charge controlled reaction) and also increase in LUMO AO coefficient (for orbital controlled reaction) of the carbonyl carbon atom.

N-아세틸피롤리돈의 산-촉매 친핵성 치환반응을 궤도함수 혼합법을 적용 분석하였다. MO계산 결과로 전하-조절 반응에서는 카르보닐 탄소원자의 양전하의 증가가, 그리고 궤도함수 조절 반응에서는 LUMO AO 계수의 증가가 프로톤화된 카르보닐 탄소의 반응성을 크게 증가시킴을 밝혔다.

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