Abstract
Electrochemical method for the evaluation of antioxidative activity of compounds based on their reaction with the stable radical, 2,2-diphenyl-1-picrylhydrazyl, was suggested with monitoring of the reaction by cyclic voltammetry (CVA). Antioxidative properties of new ferrocene derivatives Fc(L)R (where Fc is the ferrocenyl, R is the fragment of 2,6-di-tert-butylphenol or its aromatic analog, L is the spacer) were studied. Anodic oxidation of the compounds Fc(L)R, which contain azomethine and 2,6-di-tert-butylphenol moities, proceeds in three steps, that suggests a possibility of intramolecular proton-coupled electron transfer process. Conjugates of ferrocene and 2,6-di-tert-butylphenol are efficient antioxidants.
Similar content being viewed by others
References
Methods in Molecular Biology, Vol. 196, Oxidants and Antioxidatives: Ultrastructure and Molecular Biology Protocols, Ed. D. Armstrong, Humana Press, Inc., Totowa (NJ), 2002, 348 pp.
R. Apak, K. Guclu, B. Demirata, M. Ozyurek, S. E. Celik, B. Bektasoglu, K. I. Berker, D. Ozyurt, Molecules, 2007, 12, 1496.
G. Litwinenko, K. U. Ingold, J. Org. Chem., 2003, 68, 3433.
E. Baciocchi, A. Calcagni, O. Lanzalinga, J. Org. Chem., 2008, 73, 4110.
R. Scherer, H. T. Godoy, Food Chem., 2009, 112, 654.
E. Solon, A. J. Bard, J. Am. Chem. Soc., 1964, 86, 1926.
E. Solon, A. J. Bard, J. Phys. Chem., 1964, 68, 1144.
Z. Galus, Teoretyczne Podstawy Electroanalizy Chemicznej, Panstwowe Wydawnictwo Naukowe, Warszawa, 1971.
C. Constentin, Chem. Rev., 2008, 108, 2145.
M. H. V. Hyunn, T. J. Meyer, Chem. Rev., 2007, 107, 5004.
C. Constentin, C. Louault, M. Robert, J.-M. Saveant, J. Am. Chem. Soc., 2008, 130, 15817.
C. Constentin, M. Robert, J.-M. Saveant, J. Electroanal. Chem., 2006, 588, 197.
C. Constentin, D. H. Evans, M. Robert, J.-M. Saveant, P. S. Singh, J. Am. Chem. Soc., 2005, 127, 12490.
C. Constentin, M. Robert, J.-M. Saveant, J. Am. Chem. Soc., 2006, 128, 4552.
C. Constentin, M. Robert, J.-M. Saveant, J. Am. Chem. Soc., 2007, 129, 5870.
M. W. Lehmann, D. H. Evans, J. Phys. Chem. B., 2001, 105, 8877.
S. Chevion, M. A. Roberts, M. Chevion, Free Radical Biol. Med., 2000, 28, 860.
B. H. Kipp, C. Faraj, G. Li, D. Njus, Bioelectrochem., 2004, 64, 7.
D. R. van Staveren, N. Metzler-Nolte, Chem. Rev., 2004, 104, 5931.
N. A. Antonova, V. P. Osipova, M. N. Kolyada, I. V. Smolninov, N. T. Berberova, V. Yu. Tyurin, U Yaokhuań, E. R. Milaeva, Dokl. Akad. Nauk, 2010, 432, 629 [Dokl. Chem. (Engl. Transl.), 2010, 432, 165].
S. Toma, Chem. Zwesti, 1965, 19, 703.
Weygand-Hilgetag, Organisch-chemische Experimentierkunst, Johann Ambrosius Barth, Leipzig, 1964, 1142 pp.
N. N. Meleshonkova, D. B. Shpakovsky, A. V. Fionov, A. V. Dolganov, T. V. Magdesieva, E. R. Milaeva, J. Organomet. Chem., 2007, 692, 5339.
Organic Electrochemistry, Eds M. Beizer, H. Lund, Marcel Dekker, New York, 1983, 1166 pp.
P. Zanello, Inorganic Electrochemistry: Theory, Practice and Application, RCS Publ., Cambridge, 2003, p. 579.
M. V. Nekhoroshev, E. P. Ivakhnenko, O. Yu. Okhlobystin, Zh. Org. Khim., 1974, 13, 662 [J. Org. Chem. USSR (Engl. Transl.), 1974, 13, 605].
A. J. Gordon, R. A. Ford, The Chemist’s Companion: a Handbook of Practical Data, Techniques and References, Wiley, New York, 1972, p. 422.
C. K. Mann, K. K. Barnes, Electrochemical Reactions in Nonaqueous Systems, Marcel Dekker, New York, 1970, 560 pp.
E. R. Milaeva, S. I. Filimonova, N. N. Meleshonkova, L. G. Dubova, E. F. Shevtsova, S. O. Bachurin, N. S. Zefirov, Bioinorg. Chem. Appl., 2010, ID 165482, doi: 10. 1155/2010/165482.
E. G. Perevalova, K. I. Grandberg, N. A. Zharikova, S. P. Gubin, A. N. Nesmeyanov, Izv. Akad. Nauk SSSR, Ser. Khim., 1966, 832 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1966, 15, 796].
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 633–641, April, 2011.
Rights and permissions
About this article
Cite this article
Tyurin, V.Y., Meleshonkova, N.N., Dolganov, A.V. et al. Electrochemical method in determination of antioxidative activity using ferrocene derivatives as examples. Russ Chem Bull 60, 647–655 (2011). https://doi.org/10.1007/s11172-011-0100-4
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-011-0100-4