Abstract
This study describes the effects of the substituents on electrochemical behavior and antioxidant activity of the six tetradentate Schiff bases, containing ethane-1,2-diamine or propane-1,2-diamine as the amine part and pentane-2,4-dione and/or 1-phenylbutane-1,3-dione as β-diketone, and corresponding copper(II) complexes. Cyclic voltammograms of these compounds were recorded in dimethylsulfoxide and 0.1 M sodium perchlorate as supporting electrolyte with glassy carbon as working electrode at different scan rates. The voltammograms of Schiff bases alone showed only one irreversible peak. Voltammograms recorded for complexes showed the presence of quasi-reversible processes taking place at the metal center and reversible process at the ligand part. Both steric and inductive effects of substituents and structure of imine bridge of Schiff base ligands as well as complexes were discussed. These effects appear relevant for the antioxidant activity. Antioxidant activity of the investigated compounds expressed as Trolox equivalent antioxidant capacity is also discussed. The electrochemical behavior showed a high correlation with the antioxidant activity for investigated compounds.
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References
R. Jones, D. Summerville, F. Basolo, Chem. Rev. 79, 139 (1979)
M. Dolaz, V. McKee, S. Urus, N. Demir, A.E. Sabik, A. Golcu, M. Tümer, Spectrochim. Acta A 76, 174 (2010)
G.H. Oliv, S. Olive, The Chemistry of the Catalyzes Hydrogenation of Carbon Monoxide (Springer, Berlin, 1984), p. 152
K.S. Alleman, D.G. Peters, J. Electroanal. Chem. 460, 207 (1999)
H. Dugas, C. Penney, Bioorganic Chemistry (Springer, New York, 1981), p. 435
N. Raman, A. Kulandaisamy, A. Shunmugasundaram, Transit. Metal Chem. 26, 131 (2001)
S. Kumar, D. Nath Dhar, P. Saxena, J. Sci. Ind. Res. India 68, 181 (2009)
M. Tümer, D. Ekinci, F.A. Tümer, Spectrochim. Acta A 67, 916 (2007)
K.P. Balasubramanian, K. Parameswari, V. Chinnusamy, R. Prabhakaran, K. Natarajan, Spectrochim. Acta A 65, 678 (2006)
R. Baošić, A. Radojević, M. Radulović, S. Miletić, M. Natić, Ž. Tešić, Biomed. Chromatogr. 22, 379 (2008)
Z.Y. Huang, S.H. Qu, Y. Feng, Thermochim. Acta 320, 121 (1998)
A.K. Jain, R.K. Singh, S. Jain, J. Raisoni, Transit. Metal Chem. 33, 243 (2008)
T.R.L. Dadamos, M.F.S. Teixeira, Electrochim. Acta 54, 4552 (2009)
T.L. Yang, W.W. Qin, Spectrochim. Acta A 67, 568 (2007)
L.J. Klein, K.S. Alleman, D.G. Peters, J.A. Karty, J.P. Reilly, J. Electroanal. Chem. 481, 24 (2000)
D. Pletcher, H. Thomson, J. Electroanal. Chem. 464, 168 (1999)
S. Zolezzi, E. Spodine, A. Decinti, Polyhedron 21, 55 (2002)
S. Ershad, L.-A. Sagathforoush, G. Karim-nezhad, S. Kangari, Int. J. Electrochem. Sci. 4, 846 (2009)
H.H. Hussain, G. Babic, T. Durst, J. Wright, M. Flueraru, A. Chichirau, L.L. Chepelev, J. Org. Chem. 68, 7023 (2003)
B. Lapornik, A. Golc Wondra, M. Prošek, J. Planar Chromatogr. 17, 207 (2004)
D.D. Perrin, W.L.F. Amarego, D.R. Perrin, Purification of Laboratory Chemicals, 2nd edn. (Pergamon, New York, 1988), p. 69
R.M. Baošić, ŽLj Tešić, J. Serb. Chem. Soc. 60(10), 903 (1995)
M. Ulusoy, H. Karabiyik, R. Kilincarslan, M. Aygun, B. Cetinkaya, S. Garcia-Granda, Struct. Chem. 19, 749 (2008)
A.H. Kianfar, S. Zargari, H.R. Khavasi, J. Iran. Chem. Soc. 7, 908 (2010)
H.H. Monfared, Z. Kalantari, M.-A. Kamyabi, C. Janiak, Z. Anorg. Allg. Chem. 633, 1945 (2007)
G.A. Al-Hazmi, M.S. El-Shahawi, A.A. El-Asmy, Transit. Met. Chem. 30, 464 (2005)
S. Rayati, A. Ghaemi, N. Sadeghzadeh, Catal. Commun. 11, 792 (2010)
J. Losada, I. del Peso, L. Beyer, Inorg. Chim. Acta 321, 107 (2001)
A.J. Blasco, M.C. Gonzalez, A. Escarpa, Anal. Chim. Acta 511, 71 (2004)
R. Abreu, S. Falcão, R.C. Calhelha, I.C.F.R. Ferreira, M.R.P. Queiroz, M. Vilas-Boas, J. Electroanal. Chem. 628, 43 (2009)
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This work was performed within the framework of the research project No 172017 supported by the Ministry of Education and Science of Serbia.
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Aburas, N., Lolić, A., Stevanović, N. et al. Electrochemical behavior and antioxidant activity of tetradentate Schiff bases and their copper(II) complexes. J IRAN CHEM SOC 9, 859–864 (2012). https://doi.org/10.1007/s13738-012-0102-7
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DOI: https://doi.org/10.1007/s13738-012-0102-7