New 5-bromo-2-hydroxybenzaldehyde S-ethylisothiosemicarbazone and its mixed-ligand Cu(II) complex with imidazole: synthesis, characterization and DFT calculation

Reza Takjoo 1 , Alireza Akbari 2 , Mehdi Ahmadi 2 , Hadi Rudbari 3 , and Giuseppe Bruno 4
  • 1 Department of Chemistry, School of Sciences, Ferdowsi University of Mashhad, Mashhad, 91775-1436, Iran
  • 2 Department of Chemistry, Payame Noor University (PNU), 19395-4697, Tehran, Iran
  • 3 Department of Chemistry, Isfahan University of Technology, Isfahan, 84156-83111, Iran
  • 4 Department of Inorganic Chemistry, Analytical Chemistry and Physical Chemistry, University of Messina, Salita Sperone, 98199, Messina, Italy

Abstract

A new Schiff base ligand of 5-bromo-2-hydroxybenzaldehyde S-ethyl-isothiosemicarbazone (H2L) was synthesized and its mixed-ligand Cu(II) complex was also prepared by reaction of Cu(NO3)2·3H2O with H2L and imidazole. Their structures were fully characterized by elemental analysis, FT-IR, molar conductivity and UV-Vis methods. The analytical data suggest that the metal, H2L and imidazole ratios in the Schiff base complex are 1:1:1. Single crystal diffraction was also used to better understand the molecular structure of the Cu(II) complex. The results of physico-chemical analyses of the Schiff base complex reveal the coordination geometry around the central atom is square planar. The H2L ligand (NNO donor) is coordinated to the metal center as a tridentate bionegatively agent. Another position of the square planar geometry is occupied by the imidazole ligand. Furthermore, computational studies of the new complex were performed by carrying out DFT calculations. Geometry optimization and natural band analysis of the complex is discussed in further detail.

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  • [1] J. Jia, Y. Tian, Z. Li, Synth. Met. 161, 1377 (2011) http://dx.doi.org/10.1016/j.synthmet.2011.05.004

  • [2] J.P. Naskar, B. Guhathakurta, L. Lu, M. Zhu, Polyhedron 43, 89 (2012) http://dx.doi.org/10.1016/j.poly.2012.06.001

  • [3] A. Aytaç, J. Mater. Sci. 45, 6812 (2010) http://dx.doi.org/10.1007/s10853-010-4779-7

  • [4] N.B. Pathan, A.M. Rahatgaonkar, M.S. Chorghade, Catal. Commun. 12, 1170 (2011) http://dx.doi.org/10.1016/j.catcom.2011.03.040

  • [5] J.J.H. Cotelesage, M.J. Pushie, P. Grochulski, I.J. Pickering, G.N. George, J. Inorg. Biochem. 115, 127 (2012) http://dx.doi.org/10.1016/j.jinorgbio.2012.06.019

  • [6] A.J. Pardey, A.D. Rojas, J.E. Yánez, P. Betancourt, C. Scott, C. Chinea, C. Urbina, D. Moronta, C. Longo, Polyhedron 24, 511 (2005) http://dx.doi.org/10.1016/j.poly.2004.12.014

  • [7] M. Hakimi, H. Vahedi, R. Takjoo, A. Rezaeifard, Inter. J. ChemTech Res. 4, 1658 (2012)

  • [8] Z. Hu, F.M. Kerton, Appl. Catal., A 413–414, 332 (2012)

  • [9] F. Heshmatpour, S. Rayati, H.M. Afghan, P. Abdolalian, B. Neumueller, Polyhedron 31, 443 (2012) http://dx.doi.org/10.1016/j.poly.2011.09.048

  • [10] S. Wang, H. Li, C. Chen, J. Zhang, S. Li, X. Qin, X. Li, K. Wang, Bioorg. Med. Chem. Lett. 22,15 6347 (2012) http://dx.doi.org/10.1016/j.bmcl.2012.08.079

  • [11] E. Farkas, E. Csapó, P. Buglyó, C.A. Damante, G.D. Natale, Chem. Biol. 362, 753 (2009)

  • [12] A. Pietrzyk, S. Suriyanarayanan, W. Kutner, R. Chitta, F. Dsouza, Anal. Chem. 81, 2633 (2009) http://dx.doi.org/10.1021/ac8025652

  • [13] D. Zampieri, M.G. Mamolo, L. Vio, E. Banfi, G. Scialino, M. Fermeglia, M. Ferrone, S. Pricl, Bioorg. Med. Chem. 15, 7444 (2007) http://dx.doi.org/10.1016/j.bmc.2007.07.023

  • [14] C.H. Shen, S. Lien-Chung Hsu, E. Bulycheva, N. Belomoina, J. Membr. Sci. 399, 11 (2012) http://dx.doi.org/10.1016/j.memsci.2012.01.016

  • [15] W.G. Lu, L. Jiang, X.L. Feng, T.B. Lu, Inorg. Chem. 48, 6997 (2009) http://dx.doi.org/10.1021/ic900506z

  • [16] T. Gu, Y. Hasebe, Biosens. Bioelectron. 21, 2121 (2006) http://dx.doi.org/10.1016/j.bios.2005.10.007

  • [17] A.H. Pathan, R.P. Bakale, G.N. Naik, C.S. Frampton, K.B. Gudasi, Polyhedron 34, 149 (2012) http://dx.doi.org/10.1016/j.poly.2011.12.033

  • [18] S.J. Franklin, C. Opin, Chem. Biol. 5, 201 (2001)

  • [19] M.A. Alvarez, E.J. Saavedra, M.S. Olivella, F.D. Suvire, M.A. Zamora, R.D. Enriz, Cent. Eur. J. Chem. 10, 248 (2012) http://dx.doi.org/10.2478/s11532-011-0136-1

  • [20] P.T. Todorov, R.N. Petrova, E.D. Naydenova, B.L. Shivachev, Cent. Eur. J. Chem. 7, 14 (2009) http://dx.doi.org/10.2478/s11532-008-0087-3

  • [21] COSMO, version 1.60 (Bruker AXS Inc., Madison, Wisconsin, 2005)

  • [22] SAINT, version 7.06A (Bruker AXS Inc., Madison, Wisconsin, 2005)

  • [23] SADABS, version 2.10 Bruker (AXS Inc., Madison, Wisconsin, 2005)

  • [24] M.C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G.L. Cascarano, L. De-Caro, C. Giacovazzo, G. Polidori, R. Spagna, SIR2004, J. Appl. Crystallogr. 38, 381 (2005) http://dx.doi.org/10.1107/S002188980403225X

  • [25] G.M. Sheldrick, SHELXL97 (University of Gottingen, Germany, 1997)

  • [26] J.M. Seminario (Ed.), Density Functional Theory, Adv. Quantum Chem, (Academic, San Diego, 1998) vol. 33

  • [27] A.D.J. Becke, Chem. Phys. 98, 5648 (1993)

  • [28] C. Lee, W. Yang, R.G. Parr, Phys. Rev. B. 37, 785 (1988) http://dx.doi.org/10.1103/PhysRevB.37.785

  • [29] M.J. Frisch et al. Gaussian 98, Revision A.7 (Gaussian, Inc., Pittsburgh, PA, 1998)

  • [30] P.J. Hay, W.R.J. Wadt, Chem. Phys. 82, 299 (1985)

  • [31] E. Reed, L.A. Curtiss, F. Weinhold, Chem. Rev. 88, 899 (1988) http://dx.doi.org/10.1021/cr00088a005

  • [32] V. Jevtovic, D. Vidovic, J. Chem. Crystallogr. 40, 794 (2010) http://dx.doi.org/10.1007/s10870-010-9746-2

  • [33] R. Takjoo, M. Ahmadi, A. Akbari, H.A. Rudbari, F. Nicolò, J. Coord. Chem. 65, 3403 (2012) http://dx.doi.org/10.1080/00958972.2012.709935

  • [34] X.R. Bu, C.R. Jackson, D.V. Derveer, X.Z. You, Q.J. Meng, R.X. Wang, Polyhedron 16, 2991 (1997) http://dx.doi.org/10.1016/S0277-5387(97)00048-X

  • [35] A. Akbari, M. Ahmadi, R. Takjoo, F.W. Heinemann. J. Coord. Chem. 65, 4115 (2012) http://dx.doi.org/10.1080/00958972.2012.733379

  • [36] A. Dehno-Khalaji, M. Weil, H. Hadadzade, M. Daryanavard, Inorg. Chim. Acta 362, 4837 (2009) http://dx.doi.org/10.1016/j.ica.2009.06.033

  • [37] R. Takjoo, A. Akbari, M. Ahmadi, H.A. Rudbari, G. Bruno, Polyhedron 55, 225 (2013) http://dx.doi.org/10.1016/j.poly.2013.02.078

  • [38] S. Chandr, R. Kumar, Spectrochim. Acta, Part A 61, 437 (2005) http://dx.doi.org/10.1016/j.saa.2004.04.018

  • [39] M. Ahmadi, J.T. Mague, A. Akbari, R. Takjoo. Polyhedron 42, 128 (2012) http://dx.doi.org/10.1016/j.poly.2012.05.004

  • [40] A.A. Khandar, B. Shaabani, F. Belaj, A. Bakhtiari, Inorg. Chim. Acta 360, 3255 (2007) http://dx.doi.org/10.1016/j.ica.2007.03.036

  • [41] B. Atasever, B. Ülküseven, T. Bal-Demirci, S. Erdem-Kuruca, Z. Solakoğlu, Invest. New Drugs 28, 421 (2010) http://dx.doi.org/10.1007/s10637-009-9272-2

  • [42] B. Neelama, M. Mannar, N. Fehmida, B. Alok, B. Sudha, A. Amir, Eur. J. Med. Chem. 35, 481 (2000) http://dx.doi.org/10.1016/S0223-5234(00)00145-8

  • [43] T. Bal Demirci, Y. Koseoglu, S. Guner, B. Ülküseven, Cent. Eur. J. Chem. 4, 149 (2006) http://dx.doi.org/10.1007/s11532-005-0011-z

  • [44] A. John, V. Katiyar, K. Pang, M. M. Shaikh, H. Nanavati, P. Ghosh, Polyhedron 26, 4033 (2007) http://dx.doi.org/10.1016/j.poly.2007.04.039

  • [45] N. Galesic, R. Trojko, V.M. Leovac, E.Z. Iveges, Z. Kristallogr. 203, 57 (1993) http://dx.doi.org/10.1524/zkri.1993.203.Part-1.57

  • [46] A.B. Ilyukhin, V.S. Sergienko, V.L. Abramenko, Kristallografiya (Russ.) (Crystallogr. Rep.) 39, 843 (1994)

  • [47] V.M. Leovac, V. Divjakovic, A.F. Petrovic, N.V. Gerbeleu, Monatsh. Chem. 120, 181 (1989) http://dx.doi.org/10.1007/BF00809272

  • [48] P.N. Bourosh, F.K. Zhovmir, Y.A. Simonov, A.A. Dvorkin, N.V. Gerbeleu, Koord. Khim. (Russ.) (Coord.Chem.) 19, 864 (1993)

  • [49] B. Machur, R. Kruszynsk, J. Mrozinski, J. Kusz, Polyhedron 27, 1739 (2008) http://dx.doi.org/10.1016/j.poly.2008.02.012

  • [50] T. Akitsu, Y. Einaga, Polyhedron 24, 1869 (2005) http://dx.doi.org/10.1016/j.poly.2005.06.019

  • [51] I. Fleming, Frontier Orbitals and Organic Chemical Reactions (John Wiley and Sons, New York, 1976)

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