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KMID : 1059519870310050419
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Journal of the Korean Chemical Society
1987 Volume.31 No. 5 p.419 ~ p.424
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Solvation in Mixed Solvents (Part 6). Solvolysis of Benzyl Nitrates in Binary Aqueous Solvent Mixtures
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Lee Ik-Choon
Sohn Se-Chul
Lee Hai-Whang
Kim In-Chul
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Abstract
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Kinetic studies on the solvolysis of para-methyl benzyl nitrate and benzyl nitrate were carried out in aqueous methanol, ethanol, acetonitrile, acetone, tetrahydrofuran and dioxane mixtures at 60℃. The rates were faster in protic solvent mixtures than in aprotic solvent mixtures. This was considered in the light of transition state stabilization by hydrogen bonding solvation of protic solvent mixtures. Grunwald-Winstein equation, extended Grunwald-Winstein equation and correlation between ET(30) and rate constant were applied in order to discuss the transition state variations caused by changing benzyl substituents and solvents. The results showed that strong electrophilic assistance of solvent is operative in the the water-rich solvents.
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