Skip to main content
SpringerLink
Log in

Proton magnetic resonance in coumarins

  • Published:
Proceedings of the Indian Academy of Sciences - Section A Aims and scope Submit manuscript

Abstract

The high resolution proton magnetic resonance spectra of AB, ABC and ABCD systems in fourteen coumarins have been studied. Chemical shifts and spin coupling constants for the protons in various positions in the benzo-α-pyrone ring have been obtained. The spectrum of coumarin confirms the ethylenic nature of double bond between carbon atoms in positions 3 and 4. The chemical shifts for the phenyl protons are in conformity with the reactivities of the coumarins at various positions in the ring. A linear relation has been observed between the chemical shift for proton in 8 position in various 6 substituted coumarins and the Hammett’s constants (σ) for substituents in themeta position. The NMR spectra offer a very convenient method for distinguishing between 3 and 4 substituted coumarins on account of the large chemical shift for the protons in positions 3 and 4.

The results do not substantiate resonance of the naphthalene type in coumarin as suggested to explain its dipole moment.

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

References

  1. Bishop, E. O. and Richard, R. E.Mol. Phys., 1960,3, 114.

    Article  Google Scholar 

  2. Clayton, A...Jour. Chem. Soc., 1910,97, 2106.

    Google Scholar 

  3. Dharmatti, S. S., Govil, G., Kanekar, C. R. and Virmani, Y. P.Bull. AMPERE, Colloque de Pise, 1960, p. 492.

  4. Govil, G., Kanekar, C. R., Khetrapal, C. L. and Virmani, Y. P.Curr. Sci., 1961,30, 331.

    Google Scholar 

  5. Govinda Rao, M. A...Proc. Ind. Acad. Sci., 1936,4A, 695.

    Google Scholar 

  6. Jaeffe..Chem. Rev., 1953,53, 191.

    Article  Google Scholar 

  7. Jha, S. S...Proc. Ind. Acad. Sci., 1961,54 A, 13.

    Google Scholar 

  8. Lewis, C. W...Jour. Poly. Sci., 1951,6, 777.

    Article  Google Scholar 

  9. Morgan, G. T. and Micklethwait, F. M. G.Jour. Chem. Soc., 1904,85, 1233.

    Google Scholar 

  10. Pople, J. A., Schneider, W. G. and Bernstein, H. J.High Resolution Nuclear Magnetic Resonance, McGraw-Hill Publication, 1959, (a) p. 92, (b) p. 182.

  11. Sen, R. N. and Chakravarty, D.J. Ind. Chem. Soc., 1928,5, 433.

    Google Scholar 

  12. —————..Jour. Am. Chem. Soc., 1928,50, 2428.

    Article  Google Scholar 

  13. Thakore and Shah..Jour. Univ. Bombay, 1947,16 A, 38.

    Google Scholar 

  14. Waugh, J. S. and Fessenden, R. W.Jour. Am. Chem. Soc., 1957,79, 846.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Tata Institute of Fundamental Research and Atomic Energy Establishment, Trombay, Bombay-5

    S. S. Dharmatti F.A.Sc., G. Govil, C. R. Kanekar, C. L. Khetrapal & Y. P. Virmani

Authors
  1. S. S. Dharmatti F.A.Sc.
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. Govil
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. C. R. Kanekar
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. C. L. Khetrapal
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Y. P. Virmani
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dharmatti, S.S., Govil, G., Kanekar, C.R. et al. Proton magnetic resonance in coumarins. Proc. Indian Acad. Sci. 56, 71–85 (1962). https://doi.org/10.1007/BF03045815

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF03045815

Keywords

Search

Navigation