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KMID : 1059519840280030155
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Journal of the Korean Chemical Society
1984 Volume.28 No. 3 p.155 ~ p.162
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Nucleophilic Substitution Reactions of Benzyl Bromides and Benzyl Iodide with Anilines in MeOH-MeCN Mixtures
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Lee Ik-Choon
Sohn Se-Chul
Song Ho-Bong
Lee Byung-Choon
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Abstract
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Kinetic studies for the nucleophilic substitution reactions of para-substituted benzyl bromides and benzyl iodide with anilines were carried out in MeOH-MeCN mixtures at 35.0℃. Hammett ρN, ρC, Brψnsted β and solvatochromic correlation coefficient a, s values were determined in order to clarify the transition state variations caused by changing nucleophiles, substituents, leaving group and solvents. The results of solvatochromic equation showed that π*effect was a dominant factor for the reaction systems studied. It was shown that the reaction proceeds via the dissociative SN2 mechanism using the potential energy surface model approach. The potential energy surface model approach however failed to account for the transition state variation due to leaving group changes. The quatum mechanical approach showed that kinetic results were consistent with proposed dissociative SN2 mechanism.
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KEYWORD
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