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KMID : 1059519860300030265
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Journal of the Korean Chemical Society
1986 Volume.30 No. 3 p.265 ~ p.272
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Cooperative Effects of Solvatochromic Parameters on the Ionizations of tert-Butyl Halides in MeOH-1,1,2,2-Tetrachloroethane Mixtures
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Sakong Yeol
Kim Shi-Choon
Choo Jae-Bum
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Abstract
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Kinetic studies for the methanolysis of tert-butyl halides (t-BuCl, t-BuBr, t-BuI) were carried out in MeOH-1,1,2,2-tetrachloroethane mixtures. The solvatochromic comparison method was used with six indicators to analyze solvent effects on the ionizations of tert-butyl halides. It was shown that the cooperative effect of solvent polarity-polarizability was the most important factor influenced on the methanolysis rates of tert-butyl halides, but the electrophilic assistance for halide leaving group and the nucleophilic assistance for tert-butylium ion were considerably influential, too. And it was found that the electrophilic assistance caused by hydrogen bonding and the nucleophilic assistance for carbon center were stronger for more basic leaving group (I- < Br- < Cl-) and more polarizable leaving group(t-BuCl < t-BuBr < t-BuI), respectively.
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