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KMID : 1059519920360020287
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Journal of the Korean Chemical Society
1992 Volume.36 No. 2 p.287 ~ p.292
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Solvent Effects on the Nucleophilc Addition (Ⅰ) Effect of Solvent Polarity on the Nucleophilic Addition of Amine to Phenylvinylketone
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Shin Gap-Cheol
Kim Tae-Rin
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Abstract
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The rate constants of the nucleophilic addition reaction of amines (piperidine and diethylamine) to phenylvinylketone in various solvents have been determined by UV spectrophotometry at 25℃. On the basis of the high sensitivity of the rate to the polarity of the medium, it may be concluded that the reaction intermediate has zwitterionic character. The effect of the solvents on the rate of the bimolecular nucleophilic addition reaction is described well by the Kirkwood equation: The transition state of the reaction has a cyclic structure formed through an intramolecular hydrogen bond. The addition reaction of primary and secondary amines to phenylvinylketone in all solvents take place considerably faster than that of tertiary amine and this results also can be explained by the intermediate products in the reaction have a cyclic structure formed through an intramolecular hydrogen bond for the primary and secondary amines but not for the tertiary amine.
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