Skip to main content
SpringerLink
Log in

3,5-Dimethylpyrazole Complexes with Strong Carboxylic Acids

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

3,5-Dimethylpyrazole and halogen-containing carboxylic acids in solution give rise to equilibrium between the free molecules and 1 : 1 and 1 : 2 H-complexes. These complexes either have a ion pair-like structure with two equivalent hydrogen bonds O−⋯HN+ (1 : 1) or include homoconjugate anion with strong hydrogen bond C-O-H⋯O-C (1 : 2). At low temperatures, 2 : 1 complexes were detected. The structure and harmonic vibration frequencies of the complexes were calculated in terms of the density functional theory.

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. Bevilacqua, P.C., Biopolymers, 2004, vol. 73, no.1, p. 90.

    CAS  Google Scholar 

  2. Frey, P., J. Phys. Org. Chem., 2004, vol. 17, nos.6–7, p. 511.

    Google Scholar 

  3. Schowen, K.B., Limbach, H.-H., Denisov, G.S., and Schowen, R.L., Biochim. Biophys. Acta, 2000, vol. 1458, no.1, p. 43.

    CAS  Google Scholar 

  4. Paraschiv, V., Crego-Calama, M., Fokkens, R.H., Padberg, C.J., Timmerman, P., and Rainhourt, D.N., J. Org. Chem., 2001, vol. 66, no.25, p. 8297.

    Article  CAS  Google Scholar 

  5. Archer, E.A., Gong, H., and Krische, M.J., Tetrahedron, 2001, vol. 57, no.7, p. 1139.

    Article  CAS  Google Scholar 

  6. Desiraju, G.R., Acc. Chem. Res., 2002, vol. 35, no.7, p. 565.

    Article  CAS  Google Scholar 

  7. Klein, O., Aguilar-Parrilla, F., Lopez, J.M., Jagerovic, N., Elguero, J., and Limbach, H.-H., J. Am. Chem. Soc., 2004, vol. 126, no.37, p. 11 718.

    Article  CAS  Google Scholar 

  8. Boldog, I., Rusanov, E.B., Sieler, J., and Domasevitch, K.V., New J. Chem., 2004, vol. 28, no.6, p. 756.

    Article  CAS  Google Scholar 

  9. Claramunt, R.M., Lopez, C., Garcia, M.A., Denisov, G.S., Alkorta, I., and Elguero, J., New J. Chem., 2003, vol. 27, no.4, p. 734.

    Article  CAS  Google Scholar 

  10. Detering, K., Tolstoi, P.M., Golubev, N.S., Denisov, G.S., and Limbakh, Kh.-Kh., Dokl. Ross. Akad. Nauk, 2001, vol. 379, no.3, p. 353.

    CAS  Google Scholar 

  11. Saratikov, A.S., Prishchep, T.P., and Yavorovskaya, V.E., Protivovospalitel'nye sredstva gruppy pirazola (Antiphlogistic Agents of the Pyrazole Series), Tomsk: Tomsk. Univ., 1975.

    Google Scholar 

  12. Castaneda, J.P., Denisov, G.S., Kucherov, S.Yu., Schreiber, V.M., and Shurukhina, A.V., J. Mol. Struct., 2003, vol. 660, p. 25.

    Article  CAS  Google Scholar 

  13. Bureiko, S.F., Golubev, N.S., and Chernyshova, I.V., Khim. Fiz., 1987, vol. 6, no.2, p. 176.

    CAS  Google Scholar 

  14. Bureiko, S.F. and Chernyshova, I.V., Zh. Fiz. Khim., 1993, vol. 63, no.2, p. 319.

    Google Scholar 

  15. Bellamy, L.J., The Infra-red Spectra of Complex Molecules, London: Methuen, 1958.

    Google Scholar 

  16. Golubev, N.S. and Denisov, G.S., J. Mol. Struct., 1992, vol. 270, p. 263.

    Article  CAS  Google Scholar 

  17. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Montgomery, J.A., Stratmann, R.E., Burant, J.C., Dapprich, S., Millam, J.M., Daniels, A.D., Kudin, K.N., Strain, M.C., Farkas, O., Tomasi, J., Barone, V., Cossi, M., Cammi, R., Mennucci, B., Pomelli, C., Adamo, C., Clifford, S., Ochterski, J., Petersson, G.A., Ayala, P.Y., Cui, Q., Morokuma, K., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Cioslowski, J., Ortiz, J.V., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Gomperts, R., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Gonzalez, C., Challacombe, M., Gill, P.M.W., Johnson, B.G., Chen, W., Wong, M.W., Andres, J.L., Head-Gordon, M., Replogle, E.S., and Pople, J.A., GAUSSIAN-98. Rev. A.1, Pittsburgh: Gaussian, 1998.

    Google Scholar 

  18. Becke, A.D., J. Chem. Phys., 1993, vol. 98, no.7, p. 5648.

    Article  CAS  Google Scholar 

  19. Lee, C., Yang, W., and Parr, R.G., Phys. Rev. B: Condens. Matter Mater. Phys., 1988, vol. 37, no.2, p. 785.

    CAS  Google Scholar 

  20. Becke, A.D., Phys. Rev. A: At., Mol., Opt. Phys., 1988, vol. 38, no.6, p. 3098.

    CAS  Google Scholar 

  21. Onsager, L., J. Am. Chem. Soc., 1936, vol. 58, no.8, p. 1486.

    Article  CAS  Google Scholar 

  22. Wong, M.W., Frisch, M.J., and Wiberg, K.B., J. Am. Chem. Soc., 1991, vol. 113, no.13, p. 4776.

    Article  CAS  Google Scholar 

  23. Yan Zh. and Sebastian, J.F., Tetrahedron, 2004, vol. 60, no.48, p. 10 899.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Fok Research Institute of Physics, St. Petersburg State University, St. Petersburg, Russia

    S. F. Bureiko, N. S. Golubev, G. S. Denisov, S. Yu. Kucherov & P. M. Tolstoi

Authors
  1. S. F. Bureiko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. S. Golubev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. S. Denisov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. Yu. Kucherov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. P. M. Tolstoi
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

__________

Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 11, 2005, pp. 1907–1915.

Original Russian Text Copyright © 2005 by Bureiko, Golubev, Denisov, Kucherov, Tolstoi.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bureiko, S.F., Golubev, N.S., Denisov, G.S. et al. 3,5-Dimethylpyrazole Complexes with Strong Carboxylic Acids. Russ J Gen Chem 75, 1821–1829 (2005). https://doi.org/10.1007/s11176-005-0518-1

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11176-005-0518-1

Keywords

Search

Navigation