Skip to main content
Log in

Molecular dynamics of (Z)-1-(2-hydroxy-5-methyl-3-nitrophenyl)ethanone oxime and (E)-2-hydroxy-5-methylacetophenone thiosemicarbazone in solution studied by NMR spectroscopy

  • Research Article
  • Published:
Central European Journal of Chemistry

Abstract

The formation of hydrogen bonds and the molecular dynamics for molecules (Z)-1-(2-hydroxy-5-methyl-3-nitrophenyl)ethanone oxime and (E)-2-hydroxy-5-methylacetophenone thiosemicarbazone, (E)-4-bromoacetophenone thiosemicarbazone have been investigated in solution using NMR. The results confirm the formation of different O-H…O type intramolecular hydrogen bonds in the oxime molecule. The rotational barrier energy and energy of intramolecular hydrogen bonds have been determined.

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

References

  1. N.D. Sokolov, Hydrogen bond (Nauka, Moscow, 1981) (In Russian)

    Google Scholar 

  2. T. Yamaguchi, N. Matubayasi, M. Nakahara, J. Mol. Liquids 119, 119 (2005)

    Article  CAS  Google Scholar 

  3. S. Chelmieniecka, E. Grech, Z. Rozwadowski, T. Dziembowska, W. Schilf, B. Kamienski, J. Mol. Struct. 125, 565 (2001)

    Google Scholar 

  4. A.J. Horsewill, A. Aibout, J. Phys. Cond. Matter. 1, 9609 (1989)

    Article  CAS  Google Scholar 

  5. A. Robert, H. Bernheim, H. Gutowsky, J. Lawrenson, J. Chem. Phys. 34, 565 (1961)

    Article  Google Scholar 

  6. I.G. Mamedov, U. Eichhoff, A.M. Maharramov, M.R. Bayramov, Y.V. Mamedova, Magn. Reson. Chem. 48, 671 (2010)

    Article  CAS  Google Scholar 

  7. I.G. Mamedov, U. Eichhoff, A.M. Maharramov, N.D. Sokolov, Hydrogen bond (Nauka, Moscow, 1981) (In Russian)

    Google Scholar 

  8. T. Yamaguchi, N. Matubayasi, M. Nakahara, J. Mol. Liquids 119, 119 (2005)

    Article  CAS  Google Scholar 

  9. S. Chelmieniecka, E. Grech, Z. Rozwadowski, T. Dziembowska, W. Schilf, B. Kamienski, J. Mol. Struct. 125, 565 (2001)

    Google Scholar 

  10. A.J. Horsewill, A. Aibout, J. Phys. Cond. Matter. 1, 9609 (1989)

    Article  CAS  Google Scholar 

  11. A. Robert, H. Bernheim, H. Gutowsky, J. Lawrenson, J. Chem. Phys. 34, 565 (1961)

    Article  Google Scholar 

  12. I.G. Mamedov, U. Eichhoff, A.M. Maharramov, M.R. Bayramov, Y.V. Mamedova, Magn. Reson. Chem. 48, 671 (2010)

    Article  CAS  Google Scholar 

  13. I.G. Mamedov, U. Eichhoff, A.M. Maharramov, M.R. Bayramov, Y.V. Mamedova, Appl. Magn. Reson. 3, 257 (2010)

    Article  Google Scholar 

  14. I.G. Mamedov, A.M. Maharramov, M.R. Bairamov, Y.V. Mamedova, Russ. J. Phys. Chem. 12, 2182 (2010)

    Article  Google Scholar 

  15. I.G. Mamedov, A.M. Maharramov, M.R. Bairamov, Russ. J. Phys. Chem. 7, 1382 (2008)

    Google Scholar 

  16. E.P. Robert, O.O. Omer, J. Org. Chem. 10, 1186 (1956)

    Google Scholar 

  17. A.N. Petrov, G.A. Sofronov, S.P. Nechiporenko, I.N. Somin, Russ. Chem. J. 2, 110 (2004)

    Google Scholar 

  18. G.Y. Yang, J.H. Yoon, C.M. Seong, N.S. Park, Y.S. Jung, Bull. Korean Chem. Soc. 9, 1368 (2003)

    Google Scholar 

  19. M. Stojilkovic, M. Jokanovic, Arh. Hig. Rada Toksikol. 57, 435 (2006) (In Croatian)

    Google Scholar 

  20. V.M. Peshkova, V.M. Savostina, Y.K. Ivanova, Oximes (Nauka, Moscow, 1977) (In Russian)

    Google Scholar 

  21. G. Domagk, An. Rev. Tubreit. 16, 8 (1950)

    Google Scholar 

  22. W.L. Nobles, J. Am. Chem. Soc. 77, 6675 (1955)

    Article  CAS  Google Scholar 

  23. H.H. Fox, J. Org. Chem. 17, 555 (1952)

    Article  CAS  Google Scholar 

  24. Z.G. Jiang, M.S. Lebowitz, H.A. Ghanbari, CNS Drug Rev. 12, 77 (2006)

    Article  CAS  Google Scholar 

  25. T. Schaefer, J. Phys. Chem. 17, 1888 (1975)

    Article  Google Scholar 

  26. L.F. Tietze, Th. Eicher, Reaktionen und Synthesen im Organisch-Chemischen Praktikum und Forschungslaboratorium (Georg Thieme Verlag, Stuttgart, New York, 1991) (In German)

    Book  Google Scholar 

  27. S. Jha, R.P. Verma, Asian J. Chem. 15, 1719 (2003)

    CAS  Google Scholar 

  28. J.V. Martines, M. Rubio, R.C. Rosado, J.S. Loaiza, R.A. Toscano, G.E. Perez, S.H. Ortega, K. Ebert, J. Chem. Crystal. 11, 627 (1997)

    Article  Google Scholar 

  29. L. Fieser, Organic Experiments (D.C. Heath and Company, USA, 1992)

    Google Scholar 

  30. L.I. Chmelnitskiy, S.S. Novikov, T.I. Godovikova, Chemistry of furoxans (Nauka, Moscow, 1996) (In Russian)

    Google Scholar 

  31. N.D. Silva, T.V. Albu, Cent. Eur. J. Chem. 5, 396 (2007)

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ibrahim G. Mamedov.

About this article

Cite this article

Mamedov, I.G., Eichhoff, U., Maharramov, A.M. et al. Molecular dynamics of (Z)-1-(2-hydroxy-5-methyl-3-nitrophenyl)ethanone oxime and (E)-2-hydroxy-5-methylacetophenone thiosemicarbazone in solution studied by NMR spectroscopy. cent.eur.j.chem. 10, 241–247 (2012). https://doi.org/10.2478/s11532-011-0135-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.2478/s11532-011-0135-2

Keywords

Navigation