Hydrolysis Mechanism of N-(benzoyl)-C-(N-methylanilino)imidoylchloride Derivatives 


Vol. 37,  No. 6, pp. 618-625, Dec.  1993


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  Abstract

25℃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 Sn1형 반응, pH 3.0 이하의 pH 10.0 이상의 pH에서는 사면체 중간체를 지나는 친핵성 첨가-제거반응(AdN-E)이 일어남을 제안하였다. Rate constants of hydrolysis of N-(benzoyl)-C-(N-methylanilino)imidoylchlorides were determined by UV spectrophotometry in 50% (v/v) aqueous methanol at 25℃. 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 SN1 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 (AdN-E) mechanism.

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  Cite this article

[IEEE Style]

K. Kwon, Y. Lee, N. Sung, C. Kim, "Hydrolysis Mechanism of N-(benzoyl)-C-(N-methylanilino)imidoylchloride Derivatives," Journal of the Korean Chemical Society, vol. 37, no. 6, pp. 618-625, 1993. DOI: .

[ACM Style]

Ki-Sung Kwon, Yong-Gu Lee, Nack-Do Sung, and Chon-Suk Kim. 1993. Hydrolysis Mechanism of N-(benzoyl)-C-(N-methylanilino)imidoylchloride Derivatives. Journal of the Korean Chemical Society, 37, 6, (1993), 618-625. DOI: .

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ISSN(Print) 1017-2548
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