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KMID : 1059519970410010046
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Journal of the Korean Chemical Society
1997 Volume.41 No. 1 p.46 ~ p.51
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Kinetic Studies on Nucleophilic Substitution Reaction of Phenacyl Halides with Pyridines in MeOH-MeCN Mixtures
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Koo In-Sun
Yang Ki-Yull
Park Jong-Keun
Lee Ik-Choon
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Abstract
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Kinetic studies on nucleophilic substitution reaction of phenacyl bromide and phenacyl chloride with pyridines were conducted at 25℃ and 35℃ in methanol-acetonitrile solvents mixtures. It was shown that the reaction proceeds via an SN2 reaction mechanism based on the transition state parameters, ΔH≠ and ΔS≠ and Bro nsted β values. Quantum mechanical model predicted a product-like transition state, where bond-formation is much more progressed than bond breaking, upon changing the leaving group to that with a better leaving ability.
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