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Using spin labels to study molecular processes in soils: Covalent binding of aromatic amines to humic acids of soils

  • Structure of Matter and Quantum Chemistry
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Abstract

Interactions of aliphatic and aromatic amines with soil and humic acids isolated from it are studied by means of spin labels and electron paramagnetic resonance (EPR) spectroscopy. Nitroxyl radicals containing amino groups are used as spin labels. It is found experimentally that aromatic amines are instantaneously converted to the bound state. It is shown that the microareas of their incorporation are characterized by a significant delay in the reduction of the nitroxyl fragment of spin-label molecules, indicating the formation of condensed structures typical of an oxidative binding mechanism. It is concluded that aliphatic amines do not bind to humic acids. It is noted that the studied process allows elucidating the formation of bound xenobiotic residues in soils.

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References

  1. A. L. Buchachenko, Stable Radicals (Akad. Nauk SSSR, Moscow, 1963) [in Russian].

    Google Scholar 

  2. G. I. Likhtenstein, Spin Labeling Methods in Molecular Biology (Wiley, New York, 1976).

    Google Scholar 

  3. Spin Labeling: The Next Millennium, Ed. by L. J. Berliner (Plenum Press, New York, 1998).

    Google Scholar 

  4. A. N. Tikhonov, Soros. Obrazov. Zh., No. 1, 8 (1998).

    Google Scholar 

  5. M. Lucarini and E. Mezzina, Electron Paramagn. Reson. 22, 41 (2011).

    Article  CAS  Google Scholar 

  6. M. A. Voinov and A. I. Smirnov, Electron Paramagn. Reson. 22, 71 (2011).

    Article  CAS  Google Scholar 

  7. E. V. Arinushkina, Guide for Chemical Analysis of Soils (Mosk. Gos. Univ., Moscow, 1961) [in Russian].

    Google Scholar 

  8. D. S. Orlov, L. K. Sadovnikova, and N. I. Sukhanova, Soil Chemistry (Vyssh. Shkola, Moscow, 2005) [in Russian].

    Google Scholar 

  9. G. V. Dobrovol’skii and E. D. Nikitin, Ecology of Soils (Nauka, Moscow, 2006) [in Russian].

    Google Scholar 

  10. K. H. Tan, Principles of Soil Chemistry (Taylor and Francis, USA, 2011).

    Google Scholar 

  11. Chemical Processes in Soils, Ed. by M. A. Tabatabai and D. L. Sparks (Soil Science Society of America, Madison, Wiskonsin, 2005).

    Google Scholar 

  12. Molecular Environmental Soil Science, Ed. by J. Xu and D. L. Sparks (Springer, Netherlands, 2013).

    Google Scholar 

  13. M. Hutta, R. Gora, R. Halko, et al., J. Chromatogr. A 1218, 8946 (2011).

    Article  CAS  Google Scholar 

  14. N. Yu. Grechishcheva, V. A. Kholodov, I. A. Vakhrushkina, et al., Zashch. Okruzh. Sredy Neftegaz. Komplekse, No. 5, 21 (2012).

    Google Scholar 

  15. S. T. J. Droge and K.-U. Goss, Environ. Sci. Technol 47, 798 (2013).

    Article  CAS  Google Scholar 

  16. E. J. Weber, D. L. Spidle, and K. A. Thorn, Environ. Sci. Technol. 30, 2755 (1996).

    Article  CAS  Google Scholar 

  17. K. A. Thron, P. J. Pettigrew, and W. S. Goldenberg, Environ. Sci. Technol. 30, 2764 (1996).

    Article  Google Scholar 

  18. A. Gulkowska, B. Thalmann, J. Hollender, et al., Chemosphere 107, 366 (2014).

    Article  CAS  Google Scholar 

  19. A. L. N. Cruz, W. Gehling, S. Lomnick, et al., Environ. Sci. Technol. 45, 6356 (2011).

    Article  Google Scholar 

  20. K. M. Nowak, A. Miltner, M. Gehre, et al., Environ. Sci. Technol. 45, 999 (2011).

    Article  CAS  Google Scholar 

  21. C. Lattao, X. Cao, Y. Li, J. Mao, et al., Environ. Sci. Technol. 46, 12814 (2012).

    Article  CAS  Google Scholar 

  22. H. M. Bialk and J. A. Pedersen, Environ. Sci. Technol. 42, 106 (2008).

    Article  CAS  Google Scholar 

  23. M. Forster, V. Laabs, M. Lamshoft, et al., Environ. Sci. Technol. 43, 1824 (2009).

    Article  CAS  Google Scholar 

  24. K. Schauss, A. Focks, H. Heuer, et al., Trends Anal. Chem. 28, 612 (2009).

    Article  CAS  Google Scholar 

  25. Reviews of Environmental Contamination and Toxicology, Continuation of Residue Reviews, Vol. 134, Ed. by G. W. Ware (Springer, New York, 1994; Mir, Moscow, 1993).

    Google Scholar 

  26. Viable Methods of Soil and Water Pollution Monitoring, Protection and Remediation, Ed. by I. Twardowska, H. E. Allen, and M. M. Haggblom (Springer, Netherlands, 2006), p. 249.

    Google Scholar 

  27. Use of Humic Substances to Remediate Polluted Environments: From Theory to Practice, Ed. by I. V. Perminova, K. Hatfield, and N. Hertkorn (Springer, Netherlands, 2005), p. 3.

    Google Scholar 

  28. M. M. Kononova, Organic Matter of Soil (Akad. Nauk SSSR, Moscow, 1963) [in Russian].

    Google Scholar 

  29. O. N. Aleksandrova, H.-J. Steinhoff, J. Klasmeier, et al., in Proceedings of the Magnetic Resonance Conference EUROMAR 2011 (Cuvillier Verlag, Goettingen, Germany, 2011), p. 235.

    Google Scholar 

  30. O. N. Aleksandrova, J. Geochem. Explorat. 129, 6 (2013).

    Article  CAS  Google Scholar 

  31. O. N. Aleksandrova, H.-J. Steinhoff, J. Klasmeier, et al., in Proceedings of the European Geosciences Union General Assembly 2013, Geophys. Res. 15, 2013 (2013).

    Google Scholar 

  32. S. Gadanyi, T. Kalai, J. Jeki, et al., Synthesis 14, 2039 (2000).

    Article  Google Scholar 

  33. Methods of Soil Analysis, Ed. by D. L. Sparks (Soil Science Society of America, Madison, WI, 1996), Vol. 3, p. 1018.

    Google Scholar 

  34. V. A. Kholodov, A. I. Konstantinov, and I. V. Perminova, Euras. Soil Sci. 42, 1229 (2009).

    Article  Google Scholar 

  35. V. A. Kholodov, A. I. Konstantinov, E. Yu. Belyaeva, et al., Euras. Soil Sci. 42, 1095 (2009).

    Article  Google Scholar 

  36. www.humicsubstances.org

  37. A. Skrzypczak-Bonduelle, L. Binet, O. Delpoux, et al., Appl. Magn. Reson. 33, 371 (2008).

    Article  CAS  Google Scholar 

  38. A. Paul, R. Stoesser, A. Zehl, et al., Environ. Sci. Technol. 40, 5897 (2006).

    Article  CAS  Google Scholar 

  39. Supramolecular Structure and Function 8, Ed. by G. Pifat-Mrzljak, (Springer, New York, 2004), p. 157.

    Google Scholar 

  40. V. Ibrahim, N. Volkova, S.-H. Pyo, et al., J. Mol. Catal. B: Enzym. 97, 45 (2013).

    Article  CAS  Google Scholar 

  41. V. S. Nithianandam and S. Erhan, Polymer 32, 1146 (1991).

    Article  CAS  Google Scholar 

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Correspondence to O. N. Aleksandrova.

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Original Russian Text © O.N. Aleksandrova, V.A. Kholodov, I.V. Perminova, 2015, published in Zhurnal Fizicheskoi Khimii, 2015, Vol. 89, No. 8, pp. 1269–1276.

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Aleksandrova, O.N., Kholodov, V.A. & Perminova, I.V. Using spin labels to study molecular processes in soils: Covalent binding of aromatic amines to humic acids of soils. Russ. J. Phys. Chem. 89, 1407–1413 (2015). https://doi.org/10.1134/S0036024415080038

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  • DOI: https://doi.org/10.1134/S0036024415080038

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