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The orienting effect of the oxonium group

Conclusions

  1. 1.

    The distribution of electron density for the phenyloxonium ion as well as the energy of localization for electrophilic substitution in the o-, m-, and p-position of the benzene ring, were calculated by the CNDO/2 method, considering all the valence electrons.

  2. 2.

    In the system under consideration, the +M effect of the oxonium oxygen can be neglected, while the direction of electrophilic attack, just as for the anilinium ion, is determined by the inductive effect of the onium substituent, determining meta-para-orientation.

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Literature cited

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 36–39, January, 1974.

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Belen'kii, L.I., Zhidomirov, G.M. & Abronin, I.A. The orienting effect of the oxonium group. Russ Chem Bull 23, 28–31 (1974). https://doi.org/10.1007/BF00922305

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Keywords

  • Oxygen
  • Benzene
  • Anilinium
  • Benzene Ring
  • Valence Electron