Skip to main content
SpringerLink
Log in

Quantum-chemical investigation of the electronic structure and geometry of 1-vinylpyrazole derivatives

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

Conclusions

  1. 1.

    The three-dimensional structure and the distribution of the electronic charges in the molecules of substituted 1-vinyl-pyrazoles were calculated by the MNDO method. It was established that the dipole moment is a good criterion for quantitative determination of the stereochemical position of the vinyl group.

  2. 2.

    The electronic effect of the CH3 groups corresponds to their positive inductive effect. The NO2 group suppresses the strong negative mesomeric effect and the weaker negative inductive effect. A positive mesomeric effect is characteristic of the Br atom.

  3. 3.

    In the substituted 1-vinylpyrazoles their electron-donating characteristics are determined by the ionization potentials of the unshared electron pair of the N2 atom.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature cited

  1. D. K. Danovich, V. K. Voronov, V. G. Zakzhevskii, and E. S. Domnina, Zh. Strukt. Khim., No. 4, (1986).

  2. D. K. Danovich, V. K. Voronov, V. G. Zakzhevskii, and L. V. Baikalova, Izv. Akad. Nauk SSSR., Ser. Khim., (1987), p. 2001.

  3. M. J. S. Dewar and W. Thiel, J. Am. Chem. Soc.,99, 4899 (1977).

    Google Scholar 

  4. W. C. Davidon, Comput. J.,10, 406 (1968).

    Google Scholar 

  5. M. J. S. Dewar and E. Healy, J. Comput. Chem.,4, 542 (1983).

    Google Scholar 

  6. M. J. S. Dewar and W. Thiel, Theor. Chim. Acta,46, 89 (1977).

    Google Scholar 

  7. M. J. S. Dewar and N. L. Sabelly, J. Phys. Chem.,66, 2310 (1962).

    Google Scholar 

  8. C. L. Habraken, P. C. M. Woerkom, H. W. Wind, and C. J. M. Kalunberg, Rec. Trav. Chim.,85, 1191 (1966).

    Google Scholar 

  9. H. Becker, Introduction to Electronic Theory of Organic Reactions [Russian translation], Mir, Moscow (1977), p. 72.

    Google Scholar 

  10. J. Elguero, E. Gonzales, and R. Jacquier, Bull. Soc. Chim. France, (1968), p. 5009.

  11. M. L. Castellanos, S. Olivella, and N. Roca, Can. J. Chem.,62, 687 (1984).

    Google Scholar 

  12. M. J. S. Dewar, Molecular Orbital Theory for Organic Chemists, McGraw-Hill, New York (1969).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Irkutsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR, USSR

    D. K. Danovich, V. K. Voronov & L. A. Es'kova

Authors
  1. D. K. Danovich
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. K. Voronov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. L. A. Es'kova
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 354–360, February, 1988.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Danovich, D.K., Voronov, V.K. & Es'kova, L.A. Quantum-chemical investigation of the electronic structure and geometry of 1-vinylpyrazole derivatives. Russ Chem Bull 37, 278–283 (1988). https://doi.org/10.1007/BF00957426

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00957426

Keywords

Search

Navigation