Skip to main content
SpringerLink
Log in

Mass-spectrometric behavior of polynuclear derivatives of benzo[f]quinoline

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

It was established on the basis of a study of the mass spectra of benzo[f]quinoline derivatives that contain a methyl group or an aromatic or heterocyclic ring in the 1 position and various quinolyl groups (2-, 4-, and 6-quinolyl) in the 3 position that the geometry of the molecule has a decisive effect on the strength of the chemical bond between the substituents and the benzoquinoline ring. The degree of coplanarity of the heterocyclic rings determines the strength of interannular conjugation and consequently the strength of the bond between the rings. For the investigated polyheterocyclic systems the coplanarity increases in the order 2-quinolyl < 6-quinolyl < 4-quinolyl. This fact in turn has a strong effect on the pathway of mass-spectrometric fragmentation for each series of derivatives, and this makes it possible to reliably distinguish the 2-, 4-, and 6-quinolyl derivatives from their mass spectra.

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.

Similar content being viewed by others

Literature cited

  1. N. A. Klyuev, R. A. Khmel'nitskii, G. A. Mal'tseva, A. K. Sheinkman, V. A. Ivanov, and B. M. Zolotarev, Khim, Geterotsikl. Soedin., No. 7, 979 (1973).

    Google Scholar 

  2. P. B. Teret'ev, N. P. Lomakina, and A. N. Kost, Org. Mass Spectrom., 11, 281 (1976).

    Google Scholar 

  3. C. N. R. Rao, Electronic Spectra in Chemistry [Russian translation], Mir, Moscow (1964), p. 264.

    Google Scholar 

  4. F. Andreani, R. Andrisano, G. Salvadory, and M. Tramontini, J. Chem. Soc., C, No. 5, 1007 (1971).

    Google Scholar 

  5. V. I. Minkin, O. A. Osipov, and Yu. A. Zhdanov, Dipole Moments in Organic Chemistry [in Russian], Khimiya, Leningrad (1968), p. 248.

    Google Scholar 

  6. R. Taylor, J. Chem. Soc., B, 2382 (1971).

    Google Scholar 

  7. G. T. Pilyugin, Ya. O. Gorichok, B. M. Gutsulyak, and S. I. Gorichok, Khim. Geterotsikl. Soedin., No. 6, 889 (1965).

    Google Scholar 

  8. N. S. Kozlov, L. K. Slobodchikova, and G. S. Shmanai, Dokl. Akad. Nauk SSSR, 187, 803 (1969).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Physical Organic Chemistry, Academy of Sciences of the Belorussian SSR, 220603, Minsk

    N. S. Kozlov, G. S. Shmanai, V. P. Suboch & V. I. Vil'chinskaya

  2. Institute of Physics, Academy of Sciences of the Belorussian SSR, 220603, Minsk

    N. S. Kozlov, G. S. Shmanai, V. P. Suboch & V. I. Vil'chinskaya

Authors
  1. N. S. Kozlov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. S. Shmanai
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. P. Suboch
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. I. Vil'chinskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Here and subsequently, the numbers that characterize the ion are the mass-to-charge ratios.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 520–526, April, 1979.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kozlov, N.S., Shmanai, G.S., Suboch, V.P. et al. Mass-spectrometric behavior of polynuclear derivatives of benzo[f]quinoline. Chem Heterocycl Compd 15, 424–429 (1979). https://doi.org/10.1007/BF00471779

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00471779

Keywords

Search

Navigation