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KMID : 1059519890330040413
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Journal of the Korean Chemical Society
1989 Volume.33 No. 4 p.413 ~ p.418
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Substituent Effects for the Menschutkin-Type Reaction of Substituted 2-Phenylethyl arenesulfonates with Substituted Pyridines
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Yoh Soo-Dong
Kim Joong-Hyup
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Abstract
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The rates for the reaction of substituted 2-phenylethyl tosylates with substituted pyridines were measured in acetonitrile and that of 2-PNS with substituted pyridines were investigated in both acetonitrile and methanol. The substitutent effect was accelerated by an electron-donating substituent on both substrate and nucleophile. Results showed that More O'Ferrall and quantum mechanical model of predicting transition state structure suggest the reaction proceeds via an SN2 mechanism, in which bond-breaking is more advanced than bond-formation. Transition state variation predicted with the quantum mechanical model is consistent with the experimental results, whereas the predictions provided by the More O'Ferrall plots is found to be inconsistent in leaving group. In the reaction of 2-PNS, the rate constants in acetonitrile were larger than that in methanol.
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