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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 37, Number 12
JKCSEZ 37(12)
December 20, 1993 

Synthesis and Hydrolysis Mechanism of N-[1-(benzotriazol-1-yl)benzyl]aniline Aniline Derivatives

N-[1-(benzotriazol-1-yl)benzyl]aniline 유도체의 합성과 가수분해 반응 메카니즘
Ki-sung Kwon, Cheon-Kyu Park, Nack-Do Sung, Tae-rin Kim

권기성, 박천규, 성낙도, 김태린
일련의 새로운 N-[1-(benzotriazol-1-yl)-X-치환-benzyl]-Y-치환-aniline 유도체(S)를 합성하고 25℃의 25%(v/v) methanol-물의 혼합용액속에서 pH 변화에 따른 가수분해 반응속도 상수를 측정하여 용매효과(m ≪ 1, n ≤ 3 및 m ≪ l), 염 효과, 일반염기 촉매 효과, 치환기 효과(ρxy > 0), 가수분해 반응생성물의 분석 및 반응속도식 등의 결과로부터 pH 12.0 이하에서는 주로 "A-SN2형" 반응, 그리고 pH 13.0 이상에서는 전형적인 "Sn2형"의 반응으로 진행하는 가수분해 반응 메카니즘을 제안하였다.

A series of New N-[1-(benzotriazol-1-yl)-X-substituted benzyl]-Y-substituted aniline derivaties (S) have been synthesized. And the rate of hydrolysis was investigated kinetically in 25% (v/v) aqueous methanol at 25℃. On the basis of rate equations, solvent effect m ≪ 1, n ≤ 3 and m ≪ l), salt effect, general base catalysis, substituent effect (ρxy > 0), and hydrolysis products analysis, it may be concluded that the hydrolysis of N-[1-(benzotriazol-1-yl)benzyl]aniline proceeds the "A-SN2" mechanism below pH 12.0, while above pH 13.0, the hydrolysis proceeds through a typical "SN2" mechanism.

1060 - 1067
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