Proton magnetic resonance in coumarins
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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.
KeywordsCoumarin Hydroxy Coumarin Spin Coupling Constant Chemical Shift Data Phenyl Proton
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- 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.Google Scholar
- 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
- 7.Jha, S. S...Proc. Ind. Acad. Sci., 1961,54 A, 13.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.Google Scholar
- 11.Sen, R. N. and Chakravarty, D.J. Ind. Chem. Soc., 1928,5, 433.Google Scholar
- 13.Thakore and Shah..Jour. Univ. Bombay, 1947,16 A, 38.Google Scholar