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Complexation and Extraction of Transition Metal Cations by New Azodyes: Synthesis, Structure Elucidation and Binding Properties
Corresponding Author(s) : Naceur Hamdi
Asian Journal of Chemistry,
Vol. 30 No. 6 (2018): Vol 30 Issue 6
Abstract
A series of new 3-aryl(hetaryl)hydrazono-2,4-chromandiones (3a-c) were obtained in high yields, by coupling 4-hydroxycoumarin with derivatives diazonium salts, which were obtained by diazotization of aniline derivatives in presence of sodium nitrite and concentrated HCl. The azo dyes prepared may exist in four tautomeric forms. Structures of the synthesized compounds have been investigated by means of UV, IR, 1H NMR, 13C NMR and elemental analysis in order to elucidate their tautomeric and isomeric structures. The results of such spectral data indicated that compound 3 exist predominantly in hydrazo structure (D). The complexation and extraction of some transition metal cations have been followed by UV-visible spectrophotometry absorption. The conductivity studies have been used in order to confirm complex’s stoichiometries.
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- B. Kirkan and R. Gup, Turk. J. Chem., 32, 9 (2008).
- A.M. Metwally, S. Bondock, S.I. El-Desouky and M.M. Abdou, Am. J. Chem., 2, 347 (2012).
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- D. Hinks, H.S. Freeman, M. Nakpathom and J. Sokolowska, Dyes Pigments, 44, 199 (2000); https://doi.org/10.1016/S0143-7208(99)00078-9.
- K. Wojciechowski, A. Wyrebak and J. Gumulak, Dyes Pigments, 56, 99 (2003); https://doi.org/10.1016/S0143-7208(02)00130-4.
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- Z.H. Chohan, A.U. Shaikh, A. Rauf and C.T. Supuran, J. Enzyme Inhib. Med. Chem., 21, 741 (2006); https://doi.org/10.1080/14756360600810340.
- M. Velascovelazquez, Cancer Lett., 198, 179 (2003); https://doi.org/10.1016/S0304-3835(03)00333-1.
- A.C. Luchini, P. Rodrigues-Orsi, S.H. Cestari, L.N. Seito, A. Witaicenis, C.H. Pellizzon and L.C. Di Stasi, Biol. Pharm. Bull., 31, 1343 (2008); https://doi.org/10.1248/bpb.31.1343.
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- O.I. Aruoma and S.L. Cuppett, Arch. Ital. Sci. Farmacol., 9, 61 (1959).
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- H.K. Frensdorff, J. Am. Chem. Soc., 92, 4684 (1971); https://doi.org/10.1021/ja00748a006.
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- W.W. Coblentz, Investigation of Infrared Spectra, Comegle Institute, Washington (1905).
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References
B. Kirkan and R. Gup, Turk. J. Chem., 32, 9 (2008).
A.M. Metwally, S. Bondock, S.I. El-Desouky and M.M. Abdou, Am. J. Chem., 2, 347 (2012).
R. Medyouni, W. Elgabsi, O. Naouali, A. Romerosa, A. Sulaiman Al-Ayed, L. Baklouti and N. Hamdi, Spectrochim. Acta A Mol. Biomol. Spectrosc., 167, 165 (2016); https://doi.org/10.1016/j.saa.2016.04.045.
Y. Arfaoui, A.S. Al-Ayed, R.B. Said and A.I. Hamed, Int. J. Chem., 5, 73 (2013); https://doi.org/10.5539/ijc.v5n4p73.
I. Sviben, N. Galic, V. Tomisic and L. Frkanec, New J. Chem., 39, 6099 (2015); https://doi.org/10.1039/C5NJ00805K.
S.I. Klink, P.O. Alink, L. Grave, F.G.A. Peters, J.W. Hofstraat, F. Geurts and F.C.J.M. Van Veggel, J. Chem. Soc. Perkin Trans. II, 363 (2001); https://doi.org/10.1039/b007704f.
G. Gong, X. Gao, J. Wang, D. Zhao and H.S. Freeman, Dyes Pigments, 53, 109 (2002); https://doi.org/10.1016/S0143-7208(02)00010-4.
D. Hinks, H.S. Freeman, M. Nakpathom and J. Sokolowska, Dyes Pigments, 44, 199 (2000); https://doi.org/10.1016/S0143-7208(99)00078-9.
K. Wojciechowski, A. Wyrebak and J. Gumulak, Dyes Pigments, 56, 99 (2003); https://doi.org/10.1016/S0143-7208(02)00130-4.
H.G. Garg and C. Prakash, J. Med. Chem., 15, 435 (1972); https://doi.org/10.1021/jm00274a035.
A. Khalid, M. Arshad and D.E. Crowley, Appl. Microbiol. Biotechnol., 78, 361 (2008); https://doi.org/10.1007/s00253-007-1302-4.
Z.H. Chohan, A.U. Shaikh, A. Rauf and C.T. Supuran, J. Enzyme Inhib. Med. Chem., 21, 741 (2006); https://doi.org/10.1080/14756360600810340.
M. Velascovelazquez, Cancer Lett., 198, 179 (2003); https://doi.org/10.1016/S0304-3835(03)00333-1.
A.C. Luchini, P. Rodrigues-Orsi, S.H. Cestari, L.N. Seito, A. Witaicenis, C.H. Pellizzon and L.C. Di Stasi, Biol. Pharm. Bull., 31, 1343 (2008); https://doi.org/10.1248/bpb.31.1343.
B.S. Kirkiacharian, E. De Clercq, R. Kurkjian and C. Pannecouque, J. Pharm. Chem., 42, 265 (2008); https://doi.org/10.1007/s11094-008-0103-0.
O.I. Aruoma and S.L. Cuppett, Arch. Ital. Sci. Farmacol., 9, 61 (1959).
M.A. Metwally, S. Bondock, S.I. El-Desouky and M.M. Abdou, J. Korean Chem. Soc., 56, 82 (2012); https://doi.org/10.5012/jkcs.2012.56.1.082.
M.A. Metwally, S. Bondock, S.I. El-Desouky and M.M. Abdou, J. Korean Chem. Soc., 56, 348 (2012); https://doi.org/10.5012/jkcs.2012.56.3.348.
A. Casnati, A. Pochini, R. Ungaro, F. Ugozzoli, F. Arnaud, S. Fanni, M.-J. Schwing, R.J.M. Egberink, F. de Jong and D.N. Reinhoudt, J. Am. Chem. Soc., 117, 2767 (1995); https://doi.org/10.1021/ja00115a012.
L.G. Sillén, B. Warnqvist, V. Meisalo and P. Kelly, Acta Chem. Scand., 22, 3032 (1968); https://doi.org/10.3891/acta.chem.scand.22-3032.
C. Pedersen, J. Am. Chem. Soc., 93, 391 (1970); https://doi.org/10.1021/ja00705a606.
H.K. Frensdorff, J. Am. Chem. Soc., 92, 4684 (1971); https://doi.org/10.1021/ja00748a006.
W. Collier, T.P. Schultz and F. Kalasinsky, Holzforschung, 46, 523 (1992); https://doi.org/10.1515/hfsg.1992.46.6.523.
W.W. Coblentz, Investigation of Infrared Spectra, Comegle Institute, Washington (1905).
G.B. Bonino, Trans. Faraday Soc., 25, 876 (1929); https://doi.org/10.1039/tf9292500876.
H. Irving and R.J.P. Williams, J. Chem. Soc., 3192 (1953); https://doi.org/10.1039/jr9530003192.
O. Naouali, B. Mellah, R. Medyouni, N. Hamdi and L. Baklouti, Eur. J. Chem., 6, 337 (2015); https://doi.org/10.5155/eurjchem.6.3.337-341.1271.
R. Medyouni, O. Naouali, N. Hamdi, F. Zagrouba and L. Baklouti, J. Adv. Chem., 11, 3512 (2015).
W. Thabet, L. Baklouti, R. Zieba and S. Parola, J. Incl. Phenom. Macrocycl. Chem., 73, 135 (2012); https://doi.org/10.1007/s10847-011-0033-4.