Correlation between electron capture response and chemical structure for aryl halides

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  • SATOUCHI Masaru
    Department of Industrial Chemistry, Shiga Prefectural Junior Colleage
  • KOJIMA Tsugio
    Department of Industrial Chemistry, Faculty of Enginieering, Kyoto University

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Other Title
  • ハロゲン化アリルに対する電子捕獲型検出器の応答と分子構造の関係
  • ハロゲンカ アリル ニ タイスル デンシ ホカクガタ ケンシュツキ ノ オウト

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Electron capture coefficients (K) for halobenzenes were calculated at various temperatures from data obtained by using electron capture techniques. The electron affinity(EA) of halobenzenes through a non-dissociative process and the activation energy(E) for a dissociative process were calculated from a plot of K vs. 1/T. The dissociative electron capture reaction for halobenzenes probably proceeds through anion radical intermidiates and the reaction mechanism is similar to the SN 2 displacement for aromatic compounds. In the cases of chlorinated benzonitriles and acetophenones, the electron affinity increases. The increase is probably due to the stabilization of the anion radical by the inductive effect of chlorine atom. The values of E for halobenzenes substituted with electron-accepting groups(cyano-, acetyl- and nitro-) were lower than for the non-substituted analogues. These groups appear to contribute to the resonance stabilization of the anion radical. An increase in the value of E for the methyl halobenzenes and a decrease in E for the chlorinated halobenzenes were observed.

Journal

  • BUNSEKI KAGAKU

    BUNSEKI KAGAKU 25 (11), 764-769, 1976

    The Japan Society for Analytical Chemistry

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