Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Hydrolysis Mechanism of N-(benzoyl)-C-(N-methylanilino)imidoylchloride Derivatives

N-(benzoyl)-C-(N-methylanilino)imidoylchloride 유도체의 가수분해 반응메카니즘

  • 권기성 (충남대학교 자연과학대학 화학과) ;
  • 이용구 (충남대학교 자연과학대학 화학과) ;
  • 성낙도 (충남대학교 농과대학 농화학과) ;
  • 김천석 (한국인삼연초연구소)
  • Published : 1993.06.20
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Abstract

Rate constants of hydrolysis of N-(benzoyl)-C-(N-methylanilino)imidoylchlorides were determined by UV spectrophotometry in 50% (v/v) aqueous methanol at 25$^{\circ}C$. On the basis of rate equation, substituent effect, solvent effect, salt effect, thermodynamic parameters and hydrolysis product analysis, it may be concluded that the hydrolysis of N-(benzoyl)-C-(N-methylanilino)imidoylchlorides proceed through $S_N$1 mechanism via azocarbonium ion intermediate in the range of from pH 3.0 to pH 10.0, while above pH 10.0 and below pH 3.0 the hydrolysis proceeds through nucleophilic addition-elimination (A$d_{N-E}$) mechanism.

25$^{\circ}C$의 50%(v/v) 메탄올-물의 혼합용액 속에서 pH 변화에 따른 X-치환된 N-(benzoyl)-C-(N-methylanilino)imidoylchloride(s)들의 가수분해 반응속도상수를 측정하여 반응속도식, 치환기효과, 용매효과, 염효과, 열역학적 활성화 파라미터 및 가수분해반응 생성물 분석 등의 결과로부터 pH 3.0~10.0까지의 사이에서는 azocarbonium ion 중간체를 지나는 $S_N$1형 반응, pH 3.0 이하의 pH 10.0 이상의 pH에서는 사면체 중간체를 지나는 친핵성 첨가-제거반응(A$d_{N-E}$)이 일어남을 제안하였다.

Keywords

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