Skip to main content
SpringerLink
Log in

Supernucleophilic systems based on functionalized surfactants in the decomposition of 4-nitrophenyl esters derived from phosphorus and sulfur acids: I. Reactivity of a hydroxyimino derivative of gemini imidazolium surfactant

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

Abstract

A new functionalized gemini surfactant, 3,3′-[2-(hydroxyimino)propane-1,3-diyl]bis(1-dodecyl-1H-imidazol-3-ium) dichloride, and its non-micelle-forming methyl analog, were synthesized. Nucleophilicity of the oximate group in these compounds in the decomposition of 4-nitrophenyl esters derived from phosphorus and sulfur acids follows Brønsted relations for monomeric functionalized surfactants and non-micelle-forming oximes. As compared to the single-chained analog, the gemini surfactant ensured the same observed rate of substrate decomposition at lower concentration and lower pH. Micellar effects of the gemini surfactant in these reactions attain a value of ∼103 and are determined mainly by substrate concentration in the micellar pseudophase.

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. Popov, A.F., Pure Appl. Chem., 2008, vol. 80, p. 1381.

    Article  CAS  Google Scholar 

  2. Morales-Rojas, H. and Moss, R.A., Chem. Rev., 2002, vol. 102, p. 2497.

    Article  CAS  Google Scholar 

  3. Kivala, M., Cibulka, R., and Hampl, F., Collect. Czech. Chem. Commun., 2006, vol. 71, p. 1642.

    Article  CAS  Google Scholar 

  4. Simanenko, Yu.S., Karpichev, E.A., Prokop’eva, T.M., Latt, A., Popov, A.F., Savelova, V.A., and Belousova, I.A., Russ. J. Org. Chem., 2004, vol. 40, p. 206.

    Article  CAS  Google Scholar 

  5. Kapitanov, I.V., Belousova, I.A., Turovskaya, M.K., Karpichev, E.A., Prokop’eva, T.M., and Popov, A.F., Russ. J. Org. Chem., 2012, vol. 48, p. 651.

    Article  CAS  Google Scholar 

  6. Prokop’eva, T.M., Karpichev, E.A., Belousova, I.A., Turovskaya, M.K., Shumeiko, A.E., Kostrykin, M.L., Razumova, N.G., Kapitanov, I.V., and Popov, A.F., Theor. Exp. Chem., 2010, vol. 46, p. 94.

    Article  Google Scholar 

  7. Terrier, F., Rodriguez-Dafonte, P., Le Guevel, E., and Moutiers, G., Org. Biomol. Chem., 2006, vol. 4, p. 4352; Buncel, E., Um I.-H., and Terrier, F., The Chemistry of Hydroxylamines, Oximes, and Hydroxamic Acids, Rappoport, Z. and Liebman, J.F., Eds., Chichester, Wiley, 2009, vol. 2, chap. 17, p. 818.

    Article  CAS  Google Scholar 

  8. Prokop’eva, T.M., Simanenko, Yu.S., Suprun, I.P., Savelova, V.A., Zubareva, T.M., and Karpichev, E.A., Russ. J. Org. Chem., 2001, vol. 37, p. 655.

    Article  Google Scholar 

  9. Belousova, I.A., Kapitanov, I.V., Shumeiko, A.E., Anikeev, A.V., Turovskaya, M.K., Zubareva, T.M., Panchenko, B.V., Prokop’eva, T.M., and Popov, A.F., Theor. Exp. Chem., 2010, vol. 46, p. 225.

    Article  CAS  Google Scholar 

  10. Welton, T., Chem. Rev., 1999, vol. 99, p. 2071; Kustov, L.M., Vasina, T.V., and Ksenofontov, V.A., Ross. Khim. Zh., 2004, vol. 48, no. 6, p. 13; Kamboj, R., Singh, S., Bhadani, A., Kataria, H., and Kaur, G., Langmuir, 2012, vol. 28, p. 11 969.

    Article  CAS  Google Scholar 

  11. Ao, M., Huang, P., Xu, G., Yang, X., and Wang, Ya., Colloid Polymer Sci., 2009, vol. 287, p. 395; Ao, M., Xu, G., Zhu, Y., and Bai, Y., J. Colloid Interface Sci., 2008, vol. 326, p. 490; Sadovskii, Yu.S., Solomoichenko, T.N., Turovskaya, M.K., Kapitanov, I.V., Piskunova, Zh.P., Kostrikin, M.L., Prokop’eva, T.M., and Popov, A.F., Theor. Exp. Chem., 2012, vol. 48, p. 122; Bhattacharya, S. and Kumar, V.P., Langmuir, 2005, vol. 21, p. 71.

    Article  CAS  Google Scholar 

  12. Gemini Surfactants: Synthesis, Interfacial and Solution-Phase Behavior, and Applications, Zana, R. and Xia, J., Eds., New York: Marcel Dekker, 2004.

    Google Scholar 

  13. Martinek, K., Yatsimirski, A.K., Osipov, A.P., and Berezin, I.V., Tetrahedron, 1973, vol. 29, p. 963.

    Article  CAS  Google Scholar 

  14. Pal, A., Datta, S., Aswal, V.K., and Bhattacharya, S., J. Phys. Chem. B, 2012, vol. 116, p. 13 239.

    Article  CAS  Google Scholar 

  15. Wetting, S.D., Nowak, P., and Verrall, R.E., Langmuir, 2002, vol. 18, p. 5354.

    Article  Google Scholar 

  16. Handbook of Applied Surface and Colloid Chemistry, Holmberg, K., Ed., Weinheim: Wiley-VCH, 2001.

    Google Scholar 

  17. Baker, D.R. and Gutman, A.D., US Patent no. 4 441 916, 1984; Chem. Abstr., 1984, vol. 101, no. 50 147 c.

  18. Albert, A. and Serjeant, E.P., Ionization Constants of Acids and Bases, New York: Willey, 1962; Epstein, J., Kaminski, J.J., Bodor, N., Enever, R., Sowa, J., and Higuchi, T., J. Org. Chem., 1978, vol. 43, p. 2816; Tiwari, S., Ghosh, K.K., Marek, J., and Kuca, K., J. Phys. Org. Chem., 2010, vol. 23, p. 519.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, ul. R. Lyuksemburg 70, Donetsk, 83114, Ukraine

    I. V. Kapitanov, I. A. Belousova, A. E. Shumeiko, M. L. Kostrikin, T. M. Prokop’eva & A. F. Popov

Authors
  1. I. V. Kapitanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. A. Belousova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. E. Shumeiko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. L. Kostrikin
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. T. M. Prokop’eva
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. F. Popov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. V. Kapitanov.

Additional information

Original Russian Text © I.V. Kapitanov, I.A. Belousova, A.E. Shumeiko, M.L. Kostrikin, T.M. Prokop’eva, A.F. Popov, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 9, pp. 1308–1316.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kapitanov, I.V., Belousova, I.A., Shumeiko, A.E. et al. Supernucleophilic systems based on functionalized surfactants in the decomposition of 4-nitrophenyl esters derived from phosphorus and sulfur acids: I. Reactivity of a hydroxyimino derivative of gemini imidazolium surfactant. Russ J Org Chem 49, 1291–1299 (2013). https://doi.org/10.1134/S1070428013090091

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428013090091

Keywords

Search

Navigation