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KMID : 1059519880320060581
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Journal of the Korean Chemical Society
1988 Volume.32 No. 6 p.581 ~ p.587
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Solvolysis of Substituted Benzyl Bromides
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Yoh Soo-Dong
Kim Hye-Ryung
Kim Sung-Hong
Park Byung-Soo
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Abstract
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The solvolysis of substituted benzyl bromides was studied in binary solvent mixtures of acetone-water and ethanol-water at 25℃ and 45℃. The rate constants increase with electron-donating substituents in benzene ring and increasing of water contents in both of solvent mixtures. The sensitivity parameter (m) of the solvolysis of substituted benzyl bromides to solvent ionizing power (Y) was decreased in going from the electron-donating group to electron-withdrawing one, whereas their nucleophilic sensitivity increased continuously in going to above same substituents. It was shown that electron-donating (electron-withdrawing) groups make the transition state looser (tighter). The above results were consisted with the account for the potential energy surface model and the quantum mechanical approach.
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KEYWORD
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