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KMID : 1059519930370060618
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Journal of the Korean Chemical Society
1993 Volume.37 No. 6 p.618 ~ p.625
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Hydrolysis Mechanism of N-(benzoyl)-C-(N-methylanilino)imidoylchloride Derivatives
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Kwon Ki-Sung
Lee Yong-Gu
Sung Nack-Do
Kim Cheon-Suk
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Abstract
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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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