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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 39, Number 8
JKCSEZ 39(8)
April 20, 1995 

Hydrolysis Mechanism of N-(benzenesulfonyl)-C-(N-methylanilino)imidoyl Chloride Derivatives

N-(benzenesulfonyl)-C-(N-methylanilino)imidoyl Chloride 유도체의 가수분해 반응 메카니즘
Ki-Sung Kwon*, Yun-Yi Song

권기성*, 송윤이
25℃의 50%(v/v) 메탄올-물의 혼합용매 속에서 N-(benzenesulfonyl)-C-(N-methylanilino)imidoyl chloride 유도체의 가수분해 반응 속도 상수를 자외선 분광광도법으로 측정하여 반응속도식, 치환기효과, 용매효과, 염효과, 열역학적 활성화 파라미터 및 가수분해 생성물의 분석 등의 결과로부터 pH 9.0 이하의 범위에서는 azocarbonium ion 중간체를 지나는 Sn1형 반응, pH 10.0 이상의 pH에서는 사면체 중간체를 지나는 친핵성 첨가-제거반응(AdN-E)이 일어남을 제안하였다.

Rate Constants of hydrolysis of N-(benzenesulfonyl)-C-(N-methylanilino)imidoyl chlorides 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-(benzenesulfonyl)-C-(N-methylanilino)imidoyl chlorides proceed through SN1 mechanism via azocarbonium ion intermediate below pH 9.0, while aebove pH 10.0 the hydrolysis proceeds through nucleophilic addition-elimination (AdN-E) mechanism.

650 - 656
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