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KMID : 1059519930370080695
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Journal of the Korean Chemical Society
1993 Volume.37 No. 8 p.695 ~ p.701
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Solvolysis of 2-Thiophenesulfonyl Chloride
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Choi Jin-Chel
Oh Ji-Eun
Kang Dae-Ho
Koo In-Sun
Lee Ik-Choon
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Abstract
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Rate constants of solvolysis of 2-thiophenesulfonyl chloride were determined in aqueous binary mixtures with methanol, ethanol, acetone in water and in methanol. These data are interpreted using the equation of Grunwald-Winstein and Kivinen relationship. Also, kinetic solvent isotope effects in water and in methanol and product selectivities in alcohol-water mixtures were determined. Kinetic solvent isotope effect for hydrolysis of 2-thiopenesulfonyl chloride was 2.24 and 1.47 for methanol and water, respectively. Selectivity values for formation of ester relative to acid in ethanol-water mixtures show maximum S value. From kinetic solvent isotope effect in methanol and water, selectivity data in aqueous alcoholic solvents and solvent effects, it is proposed that the reaction channel favoured in low polarity solvents is general-base catalysis and/or is possibly addition elimination (SAN) reaction pathway and in high polarity solvents iS SN2 reaction mechanism.
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KEYWORD
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