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Electronic structure and reactivity of organofluorine compounds

1. Electronic structure of fluoroethylenes on the basis of quantum-chemical calculations by the MNDO and STO-3G methods

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

Abstract

It was established on the basis of MNDO and STO-3G quantum-chemical calculations of fluoroethylenes that the fluorine atom at the vinylic position greatly stabilizes all theσ-MOs of the molecule on account of the accepting induction effect. The absence of additional stabilization of theπ-MO is due to the antiphase overlap of the free pair of the fluorine atom and theπ-MO. The concept of the “electronic depletion of the double bond” in fluorinated olefins is not confirmed by the calculations.

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Literature cited

  1. R. E. Banks (ed.), Organofluorine Chemicals and Their Industrial Application, Horwood, Chichester (1979), p. 29.

    Google Scholar 

  2. W. A. Sheppard and C. M. Sharts, Organic Fluorine Chemistry, W. A. Benjamin, New York (1969).

    Google Scholar 

  3. H. E. O'Neal and S. W. Benson, J. Phys. Chem.,72, 1866 (1968).

    Google Scholar 

  4. E. W. Schlag and E. W. Kaiser, J. Am. Chem. Soc.,87, 1171 (1965).

    Google Scholar 

  5. J. M. Tedder, J. C. Walton, and L. T. Vertommen, J. Chem. Soc. Faraday Trans. I, No. 5, 177 (1979).

    Google Scholar 

  6. D. A. Dixon and T. Fukunaga, J. Am. Chem. Soc.,108, 1585 (1986).

    Google Scholar 

  7. J. K. Carlos, R. R. Karl, and S. H. Bauer, J. Chem. Soc., Faraday Trans. II, No. 1, 177 (1974).

    Google Scholar 

  8. J. A. Sell and A. Kuppermann, J. Chem. Phys.,71, 4703 (1979).

    Google Scholar 

  9. C. N. R. Rao and P. K. Basu, Appl. Spectrosc. Rev.,15, 1 (1979).

    Google Scholar 

  10. C. R. Brundle, M. B. Robin, N. A. Kuebler, and H. Basch, J. Am. Chem. Soc.,94, 1451 (1972).

    Google Scholar 

  11. N. S. Chiu, P. D. Burrow, and K. D. Jordan, Chem. Phys. Lett.,68, 121 (1979).

    Google Scholar 

  12. N. M. Paddon-Row, N. G. Rondan, K. N. Houk, and K. D. Jordan, J. Am. Chem. Soc.,104, 1143 (1982).

    Google Scholar 

  13. R. D. Bach and G. J. Wolber, J. Am. Chem. Soc.,106, 1401 (1984).

    Google Scholar 

  14. J. Mirik and A. Buda, Z. Naturforsch. A,39A, (4), 386 (1984).

    Google Scholar 

  15. M. J. S. Dewar and H. S. Rzepa, J. Am. Chem. Soc.,100, 784 (1978).

    Google Scholar 

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Authors and Affiliations

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

    I. N. Rozhkov & Yu. A. Borisov

Authors
  1. I. N. Rozhkov
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  2. Yu. A. Borisov
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1801–1805, August, 1989.

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Rozhkov, I.N., Borisov, Y.A. Electronic structure and reactivity of organofluorine compounds. Russ Chem Bull 38, 1649–1653 (1989). https://doi.org/10.1007/BF00956949

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  • DOI: https://doi.org/10.1007/BF00956949

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