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KMID : 1059519970410020069
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Journal of the Korean Chemical Society
1997 Volume.41 No. 2 p.69 ~ p.76
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Nucleophilic Substitution Reactions of Benzoic Anhydrides with Aniline in Methanol-Acetonitrile Mixtures
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Lee Byung-Choon
Shin Young-Kook
Lee Seung-Woo
Lee Ik-Choon
Lee Won-Heui
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Abstract
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Kinetic studies for the nucleophilic substitution reactions of the benzoic anhydrides with anilines in methanol-acetonitrile mixtures at 35.0 ℃ have been carried out in order to elucidate the reaction mechanism. Individual rate constants kXY and kXZ were decided from the ratios of the reaction products for the competitive substitution reaction at either one of the two carbonyl carbons in benzoic anhydride. Transition state structure and reaction mechanism were elucidated by the Hammett ρx, ρy and ρz values and cross interaction constant ρx, ρy and ρz values. The reaction of the benzoic anhydride has been proposed to proceed by a frontside attack SN2 mechanism with four-membered ring transition state from unusually large magnitude of the ρX, ρXY, ρXZ and positive ρY values.
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