Skip to main content
Log in

Mechanism of rotation around the carbon-carbon double bond in the nitroenamines, and study of the structures of these compounds in solution by1H and13C NMR methods and UV spectroscopy

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

Conclusions

  1. 1.

    Dynamic NMR spectroscopy has been used to show that the Z, E isomerization of the N-alkyl and N-acyl substitutedα-nitro-β-aminoacrylic acid esters follows a thermal mechanism involving rotation around the C=C bond.

  2. 2.

    The PMR, UV, and13C NMR spectra suggest formation of intramolecular H bonds in these compounds.

  3. 3.

    The UV spectra indicate ionization of the N-H bond of these compounds in pyridine and DMSO solution.

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. I. Bakhmutov, V. A. Burmistrov, K. K. Babievskii, V. M. Belikov, and É. I. Fedin, Izv. Akad. Nauk SSSR, Ser. Khim., 2820 (1977).

  2. V. I. Bakhmutov, V. A. Burmistrov, K. K. Babievskii, É. I. Fedin, and V. M. Belikov, Izv. Akad. Nauk SSSR, Ser. Khim., 2601 (1977).

  3. H. Kalinowski and H. Kessler, Top. Stereochem.,7, 296 (1973).

    Google Scholar 

  4. K. K. Babievskii, V. I. Bakhmutov, K. A. Kochetkov, B. A. Burmistrov, and B. M. Belikov, Izv. Akad. Nauk SSSR, Ser. Khim., 425 (1977).

  5. H. Shanan-Atidi and H. K. Bar-Eli, J. Phys. Chem.,74, 961 (1970).

    Google Scholar 

  6. E. Czerwinska, L. Kozerski, and J. Boska, J. Org. Magn. Reson.,8, 345 (1976).

    Google Scholar 

  7. Y. Shvo, E. Taylor, and J. Bartulin, Tetrahedron Lett., 3259 (1967).

  8. M. Barthelemy and Y. Bessiere, Tetrahedron,32, 1665 (1976).

    Google Scholar 

  9. G. Levy and G. Nelson, Carbon-13 Nuclear Magnetic Resonance for Organic Chemists, Wiley, New York (1972).

    Google Scholar 

  10. J. Freimanis, The Chemistry of the Enamine Ketones, Enamine Imines, and Enamine Thiones [in Russian], Zinatne, Riga (1974), p. 80.

    Google Scholar 

  11. G. Foier (editor), Chemistry of the Nitro and Nitroso Groups [Russian translation], Vol. 1, Mir (1972), p. 85.

  12. K. K. Babievskii, N. A. Tikhonova, and V. M. Belikov, Izd. Akad. Nauk SSSR, Ser. Khim., 2755 (1969).

  13. I. Riddick and W. Bunger, Organic Solvents, Wiley, New York (1970).

    Google Scholar 

  14. G. Levy and G. Nelson, Carbon-13 Nuclear Magnetic Resonance for Organic Chemists, Wiley, New York (1972).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2719–2725, December, 1978.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bakhmutov, V.I., Babievskii, K.K., Burmistrov, V.A. et al. Mechanism of rotation around the carbon-carbon double bond in the nitroenamines, and study of the structures of these compounds in solution by1H and13C NMR methods and UV spectroscopy. Russ Chem Bull 27, 2426–2432 (1978). https://doi.org/10.1007/BF00941090

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00941090

Keywords

Navigation