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π-Electron structures of certain carbo- and heterohelicenes

  • Physical Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    By applying the asymptotic method of Hückel π-approximation, energy characteristics have been calculated for the π-electron structures of 20 infinite helicenes, systems with a screw axis of symmetry obtained by cata-condensation of 5-, 6-, and 7-membered cycles. This procedure gives a good reproduction of the energy characteristics of macromolecules containing more than 10 cata-condensed cycles.

  2. 2.

    A forbidden band appears in the spectra of helicenes based on molecules with closed π-electron clouds. The width of this band increases in parallel with the electronegativity of the heteroatom carrying the unshared electron pair.

  3. 3.

    The infinite hydrocarbon pentalino (II), heptalino (IX), (XIII), and indenylo (XVII) helicenes and certain of their B-analogs (I), (XII), and (XVI) show metallic conduction.

  4. 4.

    The properties of the energy band structure of the spectra of the infinite catacondensed systems vary with the mode of structural unit addition, the result being that the spectrum of the infinite benzohelicene (VI) has a rather wide forbidden band while the spectra of the infinite acenes do not.

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Literature cited

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Authors and Affiliations

  1. Institute of Heteroorganic Compounds, Academy of Sciences of the USSR, Moscow

    D. A. Bochvar & E. G. Gal'pern

Authors
  1. D. A. Bochvar
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  2. E. G. Gal'pern
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2740–2745, December, 1977.

The authors want to thank N. P. Gambaryan and I. V. Stankevich for a discussion and valuable suggestions concerning this work.

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Bochvar, D.A., Gal'pern, E.G. π-Electron structures of certain carbo- and heterohelicenes. Russ Chem Bull 26, 2532–2538 (1977). https://doi.org/10.1007/BF00924559

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  • DOI: https://doi.org/10.1007/BF00924559

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