Skip to main content
SpringerLink
Log in

Intramolecular hydrogen bonding in 1-nitro-5,10-dihydrophenazine derivatives

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The formation of free radicals only for derivatives with a nitro group in the 1 position was observed in the oxidation of a number of 5-substituted 5,10-dihydrophenazines with lead dioxide. A long-wave absorption band was observed in the electronic spectra of the derivatives with a nitro group in the 1 position. The assumption of the formation of an intramolecular hydrogen bond in dihydrophenazines with a nitro group in the 1 position was confirmed by quantum-chemical modeling of the three structures of the 1,3-dinitro-5-phenyl-5,10-dihydrophenazine molecule. By comparison of the integral intensities of the bands of the stretching vibrations of the N-H bond in 5-substituted dihydrophenazines it was concluded that this bond is depolarized in derivatives with an intramolecular hydrogen bond.

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. Z. V. Pushkareva, I. N. Noskova, and V. F. Gryazev, Khim. Geterotsikl. Soedin., No. 10 1428 (1970).

    Google Scholar 

  2. I. N. Borukhova, V. F. Gryazev, Z. V. Pushkareva, and V. I. Koryakov, Khim. Geterotsikl. Soedin., No. 4, 521 (1977).

    Google Scholar 

  3. P. C. Taunk, R. P. Gupta, and R. L. Mital, J. Ann. Soc. Scient. Brux.,85, 291 (1971).

    Google Scholar 

  4. A. P. Zeif, G. N. Lipunova, N. P. Bednyagina, L. N. Shchegoleva, and L. I. Chernyavskii, Zh. Org. Khim.,6, 2590 (1970).

    Google Scholar 

  5. G. N. Lipunova, N. N. Gulemina, A. P. Zeif, and N. P. Bednyagina, Khim. Geterotsikl. Soedin., No. 4, 493 (1974).

    Google Scholar 

  6. M. D. Gordon and J. F. Neumer, J. Phys. Chem.,78, 1868 (1974).

    Google Scholar 

  7. Tablea of Interatomic Distances and Configurations in Molecules and Ions, Special Publication No. 18, London (1965).

  8. A. V. Iogansen and B. V. Rassadin, Zh. Prirodn. Soedin.,11, 828 (1969).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. S. M. Kirov Ural Polytechnic Institute, 620002, Sverdlovsk

    I. N. Borukhova, V. F. Gryazev, E. G. Kovalev & Z. V. Pushkareva

Authors
  1. I. N. Borukhova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. F. Gryazev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. G. Kovalev
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Z. V. Pushkareva
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No, 2, pp, 263–265, February, 1978.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Borukhova, I.N., Gryazev, V.F., Kovalev, E.G. et al. Intramolecular hydrogen bonding in 1-nitro-5,10-dihydrophenazine derivatives. Chem Heterocycl Compd 14, 215–217 (1978). https://doi.org/10.1007/BF00945339

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00945339

Keywords

Search

Navigation