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KMID : 1059519900340020184
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Journal of the Korean Chemical Society
1990 Volume.34 No. 2 p.184 ~ p.188
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Kinetics of Reactions of Phenacyl Bromides with Imidazoles
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Im Tong-Soon
Kwun Jong-Woo
Kim Chang-Suk
Hong Soon-Yung
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Abstract
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Rates for reactions of substituted phenacyl bromides with imidazole and those of substituted imidazoles with phenacyl bromide were measured by an electric conductivity method. The rates were accelerated by electron-withdrawing substituents of phenacyl bromide and these reactions obeyed well both the linear free energy relationship and the isokinetic relationship. The relation between pKa's of substituted imidazoles and reaction constants fit the Brφnsted rule. However, the case of 2-methylimidazole deviated far from this rule exerting steric hindrance. The reaction proceeded much faster in acetonitrile than in methanol and the observed ratio, k2 (acetonitrile)/k2 (methanol), was considerably larger than the value calculated from the Kirkwood equation.
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