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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 20, Number 1
JKCSEZ 20(1)
February 20, 1976 

 
Title
Kinetics and Mechanism of the Hydrolysis of Imidoyl Halides

Imidoyl Halide의 가수분해 반응메카니즘과 그의 반응속도론적 연구
Author
Tae-Rin Kim, Jin-Hee Kim, Byung-Doo Chang, Kwang-Il Lee, Ung-Cho Kim

김태린, 김진희, 장병두, 이광일, 김응조
Keywords
Abstract
N-(2,4-dinitrophenyl)-benzimidoyl chloride의 여러가지 유도체의 가수분해 속도상수를 측정하여 넓은 pH 범위에서 잘 맞는 반응속도식을 구하였다. 이 식에 의하면 아직 잘 알려져 있지 않은 산성과 염기성 용액속에서 가수분해 반응메카니즘을 정량적으로 잘 설명할 수 있었다. 즉 pH 7.0 이하에서는 carbonium ion 중간체를 거쳐 반응이 진행되는 Sn1 반응과정이며, pH 8.5 이상에서는 hydroxide ion과 imidoyl chloride 농도에 비례하는 Sn2 반응메카니즘에 의해 가수분해가 진행되며, pH 7.0∼8.5 사이에서는 이 두 반응이 경쟁적으로 일어남을 알았다.

The rate constants of the derivatives of N-(2,4-dinitrophenyl)-benzimidoyl chloride were determined at various pH and a rate equation which can be applied over wide pH range was obtained. The reaction mechanism of hydrolysis of N-(2,4-dinitrophenyl)-benzimidoyl chloride which has not been studied carefully earlier in acidic and basic solution can be fullly explained by the rate equation obtained. The rate equation reveals that, beow pH 7.00, the hydrolysis of benzimidoyl chloride proceeds through SN2 reaction to form a carbonium ion intermediate.Above pH 8.5, however, the hydrolysis proceeds through the SN2 type reaction which depends on hydroxide ion and imidoyl chloride concentration. At pH 7.0∼8.5, two reactions occur competitively.

Page
48 - 55
Full Text
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