Skip to main content
Log in

Mass spectra of isomeric thieno [2,3-b]- and thieno[3,2-b]pyridines

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The mass spectra of six isomeric thieno- and thionaphthenopyridines were studied for the first time, and the pathways of fragmentation of the molecular ions, which made it possible to isolate the peaks of the fragment ions that characterize the destruction of the pyridine and thiophene rings, were traced. It is shown that the character and type of conjugation of the heterorings can be distinguished by analyzing the mass-spectral data. The relationship between the intensity of the peak of the doubly charged molecular ion and the number of π electrons in the system and the π -donor character of the heteroring was illustrated by means of the literature data on the mass spectrometry of heteroaromatic systems with one heteroatom.

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

Access this article

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. V. G. Zhiryakov and P. I. Abramenko, Zh. Vsesoyuzn. Khim. Obshchestva, 5, 707 (1960); Khim. Geterotsikl. Soedin., No. 3, 334 (1965).

    Google Scholar 

  2. P. I. Abramenko, Khim. Geterotsikl. Soedin., No. 2, 368 (1967); No. 4, 468 (1971).

    Google Scholar 

  3. A. A. Polyakova and R. A. Khmel'nitskii, Mass Spectrometry in Organic Chemistry [in Russian], Khimiya, Moscow (1972), p. 85.

    Google Scholar 

  4. W. G. Cole, D. H. Williams, and A. N. H. Yeo, J. Chem. Soc., B, 1284 (1968).

  5. S. Meyerson and E. K. Fields, Org. Mass Spectrom., 2, No. 3, 241 (1969).

    Google Scholar 

  6. P. I. Abramenko and V. A. Kosobutskii, Khim. Geterotsikl. Soedin., No. 9, 1202 (1976).

    Google Scholar 

  7. Q. N. Porter and J. Baldas, Mass Spectrometry of Heterocyclic Compounds, Wiley-Interscience, New York-London (1972), p. 419.

    Google Scholar 

  8. E. I. Reed (editor), Recent Topics in Mass Spectrometry, Gordon and Breach, New York-London (1971), p. 73.

    Google Scholar 

  9. A. Streitwieser, in: Modern Problems of Physical Organic Chemistry [Russian translation], Mir, Moscow (1967), p. 28.

    Google Scholar 

  10. A. F. Pozharskii, Khim. Geterotsikl. Soedin., No. 6, 726 (1977).

    Google Scholar 

  11. N. A. Klyuev, A. F. Pozharskii, A. B. Belikov, and V. M. Adanin, Khim. Geterotsikl. Soedin., No. 5, 684 (1980).

    Google Scholar 

  12. Catalog of Mass-Spectral Data, Amer. Petrol. Inst. Res. Project 44, Pittsburg: a) No. 616; b) No. 638; c) No. 158; d) No. 917; e) No. 448; f) No. 633; g) No. 617; h) No. 625; i) No. 639.

  13. E. Stenhagen, S. Abramsson, and F. W. McLafferty (editors), Atlas of Mass Spectral Data, Interscience, New York-London, a) p. 442; b) p. 51.

  14. Atlas of Spectral Data and Physical Constants of Organic Compounds, Vol. 3, CRC Press, Cleveland, Ohio (1975), p. 187, d. 251.

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 758–761, June, 1982.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Klyuev, N.A., Abramenko, P.I., Shpileva, I.S. et al. Mass spectra of isomeric thieno [2,3-b]- and thieno[3,2-b]pyridines. Chem Heterocycl Compd 18, 572–575 (1982). https://doi.org/10.1007/BF00506144

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00506144

Keywords

Navigation