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13C NMR spectra and azoquinone hydrazone tautomerism of azo-2-naphthols and azo-1-naphthols

  • Physical Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

The13C NMR spectra of 1-phenylazo-2-naphthols and 2-phenylazo-1-naphthols have been investigated. For both classes the azoquinone hydrazone tautomeric equilibrium is shifted as a result of the nature of the substituent in the benzene ring and a qualitative series of effects has been established. A quantitative measurement of the tautomer composition has been obtained for the arylazo-2-naphthols.

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Literature cited

  1. G. Tsollinger, Chemistry of Azodyes, GCI, Leningrad (1960).

    Google Scholar 

  2. I. U. Bershtein and O. F. Ginzburg, Usp. Khim.,41, 177 (1972).

    Google Scholar 

  3. A. Burawoy, A. G. Salem, and A. R. Thompson, J. Chem. Soc., 4793 (1952).

  4. L. W. Reeves, Can. J. Chem.,38, 748 (1960).

    Google Scholar 

  5. L. A. Fedorov, NMR Spectroscopy of Organic Analytical Reagents and Their Metal Ion Complexes [in Russian], Nauka, Moscow (1987).

    Google Scholar 

  6. A. Lycka, D. Snobl. V. Machacek, and M. Vecera, Org. Magn. Reson.,15, 390 (1981).

    Google Scholar 

  7. J. Kelemen, J. Moss, H. Sauter, and T. Winkler, Dyes Pigm.,3, 27 (1982).

    Google Scholar 

  8. A. Lycka and P. E. Hansen, Org. Magn. Reson.,22, 569 (1984).

    Google Scholar 

  9. L. A. Fedorov, M. S. Zhukov, N. V. Korsakova, et al., Izv. Akad. Nauk SSSR, Ser. Khim., 1763 (1984).

  10. L. A. Fedorov, M. S. Zhukov, and A. N. Ermakov, Zh. Anal. Khim.,39, 1568 (1984).

    Google Scholar 

  11. P. E. Hansen and A. Lycka, Magn. Reson. Chem.,24, 772 (1986).

    Google Scholar 

  12. A. H. Berrie, P. Hampson, S. W. Longworth, and A. Mathias, J. Chem. Soc. B, 1308 (1968).

    Google Scholar 

  13. A. Lycka, Coll. Czech. Chem. Commun.,47, 1112 (1982).

    Google Scholar 

  14. A. J. Klaus and P. Rys, Helv. Chim. Acta,64, 1452 (1981).

    Google Scholar 

  15. R. Haessner, H. Mustroph, and R. Borsdorf, J. Prakt. Chem.,327, 555 (1985).

    Google Scholar 

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2271–2277, October, 1988.

The authors thank M. V. Gorelika for submitting samples for investigation and for an interesting discussion.

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Fedorov, L.A., Sokolovskii, S.A. 13C NMR spectra and azoquinone hydrazone tautomerism of azo-2-naphthols and azo-1-naphthols. Russ Chem Bull 37, 2043–2048 (1988). https://doi.org/10.1007/BF00953401

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  • DOI: https://doi.org/10.1007/BF00953401

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