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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 9, Number 3
March 20, 1988 

Kinetics and Mechanism of the Hydrolysis of N-(Benzenesulfonyl) benzimidoyl Chlorides
Tae-Rin Kim*, Hyo-Shik Kwon
The rates of hydrolysis of N-(benzenesulfonyl) benzimidoyl chlorides (p-H, p-CH3, p-CH3, p-NO2 and m-NO2) have been measured by UV spectrometry in 60% methanol-water at 25℃ and a rate equation which can be applied over wide pH range was obtained. Below pH 7.00, the substituent effect on the hydrolysis rate of N-(benzenesulfonyl) benzimidoyl chloride was found to conform to the Hammett σ constant with ρ = -0.91, whereas above pH 9.00, with ρ = 0.94. On the basis of the rate equation obtained and the effect of solvent, substituents and salt, the following reaction mechanism were proposed; below pH 7.00, the hydrolysis of N-(benzenesulfonyl) benzimidoyl chloride proceeds by SN1 mechanism, however, above pH 9.00, the hydrolysis is initiated by the attack of the hydroxide ion and in the range of pH 7.00-9.00, these two reactions occur competitively.
157 - 160
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