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New supramolecular compounds: the complexes of nickel(II), copper(II), cobalt(II), cadmium(II) and zinc(II) with anti- [N-(4-aminophenyl)aza-15-crown-5]-4-(phenoxy)phenylglyoxime ligand

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Abstract

A new vic-dioxime ligand (1), bearing pendant an azacrown ether moiety and its soluble mononuclear cadmium(II), zinc(II), nickel(II), copper(II) and cobalt(II) complexes were obtained with the metal: ligand ratios of 1:2 and 1:1. The structures of the ligand and its complexes were verified using Fourier transform infrared (FT-IR), ultraviolet–visible (UV–Vis), mass spectrometry (MS), 1H and 13C NMR techniques. More detailed information about the structure of the 1 was provided by the two-dimensional (2D) heteronuclear single quantum coherence and heteronuclear multiple bond correlation techniques. The complexation properties of the ligand 1 were studied in the presence of different cations such as Pb2+, Zn2+,Cu2+, Cr3+, Hg2+, Zn2+, Fe3+ and Al3+ by UV–Vis spectroscopy and 1H NMR titration methods. All experimental results indicated that the new ligand acts as a selective compound only for Hg+2 cation. The redox behaviour of the complexes, were investigated by cyclic voltammetry at the glassy carbon electrode in 0.1 M tetrabutylamoniumtetrafluoroborate in dimethyl sulfoxide.

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References

  1. Rani, S., Kumar, S., Chandra, S.: Spectroscopic and biological approach in the characterization of a novel 14-membered [N4] macrocyclic ligand and its Palladium(II), Platinum(II), Ruthenium(III) and Iridium(III) complexes. Spectrochim. Acta Part B 118, 244–250 (2014)

    Article  CAS  Google Scholar 

  2. Huang, J., Li, S.A., Li, D.F., Yang, D.X., Sun, W.Y., Tang, W.X.: The interaction of glycine, aspartic acid, and lysine by the protonated macrocyclic ligand 6,19-bis(2-hydroxypropyl)-3,6,9,16,19,22-hexaaza-tricyclo-[22.2.2.211,14]triaconta-11,13,24,26,27,29-hexaene. Bioorg. Med. Chem. 12, 529–535 (2004)

    Article  Google Scholar 

  3. Qiu, L.G., Jiang, X., Gu, L.N., Hu, G.: Gemini metallomicellar catalysis: hydrolysis of p-nitrophenyl picolinate catalyzed by Cu(II) and Ni(II) complexes of macrocyclic ligands in gemini surfactant micelles. J. Mol. Catal. A 277, 15–20 (2007)

    Article  CAS  Google Scholar 

  4. Singh, P., Singh, A.K., Jain, A.K.: Electrochemical sensors for the determination of Zn2+ ions based on pendant armed macrocyclic ligand. Electrochim. Acta 56, 5386–5395 (2011)

    Article  CAS  Google Scholar 

  5. Tschugaeff, L.: Zur Kenntniss der Dioximine und ähnlicher Verbindungen. Berichte Der Deytschen Chemischen Gesellschaft. 39, 3382–3389 (1906)

    Article  CAS  Google Scholar 

  6. Babahan, I., Ozmen, A., Orhan, N., Kazar, D., Değirmenci, E.H.: Synthesis, characterization, and in vitro anti-neoplastic activity of novel vic-dioximes bearing thiosemicarbazone side groups and their mononuclear complexes. Bioorg. Chem. 53, 92–98 (2014)

    Article  CAS  Google Scholar 

  7. Babahan, I., Eyduran, F., Poyrazoglu Coban, E., Orhan, N., Kazar, D., Biyik, H.: Spectroscopic and biological approach of Ni(II), Cu(II) and Co(II) complexes of 4-methoxy/ethoxybenzaldehyde thiosemicarbazone glyoxime. Spectrochim. Acta Part A 121, 205–215 (2014)

    Article  CAS  Google Scholar 

  8. Sellman, D., Utz, J., Heinemann, F.W.: Transition-metal complexes with sulfur ligands. 132.1 electron-rich Fe and Ru complexes with [MN2S3] cores containing the new pentadentate ligand ‘N2H2S3 2−’ (=2,2′-bis(2-mercaptophenylamino)diethyl Sulfide(2−)). Inorg. Chem. 38, 459–466 (1999)

    Article  Google Scholar 

  9. Luis, S.V., Burguete, M.I., Salvador, R.V.: Coamplexation of mercury(II) compounds by crown ethers in organic media. J. Incl. Phenom. Macrocycl. Chem. 10, 341–353 (1991)

    Article  CAS  Google Scholar 

  10. Bilgin, A., Ertem, B., Dinç Ağın, F., Gök, Y., Karslıoğlu, S.: Synthesis, characterization and extraction studies of a new vic-dioxime and its complexes containing bis(diazacrown ether) moieties. Polyhedron 25, 3165 (2006)

    Article  CAS  Google Scholar 

  11. Wen, F., Yang, F., Zong, X., Ma, B., Wang, D., Li, C.: Photocatalytic H2 production on hybrid catalyst system composed of inorganic semiconductor and cobaloximes catalysts. J. Catal. 281, 318 (2011)

    Article  CAS  Google Scholar 

  12. Demetgül, C., Serin, S.: Synthesis and characterization of a new vic-dioxime derivative of chitosan and its transition metal complexes. Carbohydr. Polym. 72, 506 (2008)

    Article  Google Scholar 

  13. Özer, M., Kandaz, M., Özkaya, A.R., Bulut, M., Güney, O.: Fluorescent vic-dioxime-type ligand and its mono- and dinuclear complexes: the preparation, spectroscopy, and electrochemistry of its various complexes. Dyes Pigments 76, 125 (2008)

    Article  Google Scholar 

  14. Lu, X.X., Qin, S.Y., Zhou, Z.Y., Yam, V.W.W.: Synthesis, structure, and ion-binding studies of cobalt(II) complexes with aza-crown substituted salicylaldimine Schiff base ligand. Inorg. Chim. Acta 346, 49 (2003)

    Article  CAS  Google Scholar 

  15. Cavallini, G., Massarani, E., Nardi, D., Mauri, L., Tenconi, F., Pacchiano, F., Mantegazza, P.: Antibacterial agents. Some new halomethyl aryl ketones. J. Med. Chem. 6, 573 (1963)

    Article  CAS  Google Scholar 

  16. Coşkun, A., Yılmaz, F., Akgemci, E.G.: Synthesis, characterization and electrochemical investigation of a novel vic-dioxime ligand and its some transition metal complexes. J. Incl. Phenom. Macrocycl. Chem. 60, 393–400 (2008)

    Article  Google Scholar 

  17. Gök, Y., Kantekin, H.: The synthesis and characterization of new (E, E)- dioxime and its mono and heteronuclear complexes containing 14-membered tetraaza macrocyclic moiety. Polyhedron 16, 2413–2420 (1997)

    Article  Google Scholar 

  18. Gök, Y., Karaböcek, S., Mısır, M.N.: A novel vicinal dioxime and its homo- and heterotrinuclear complexes. Transit Met. Chem. 23, 333–336 (1998)

    Article  Google Scholar 

  19. Sengottuvelan, N., Manonmani, J., Kandaswamy, M.: Synthesis of unsymmetrical compartmental oxime nickel(II) and copper(II) complexes: spectral, electrochemical and magnetic studies. Polyhedron 21, 2767–2772 (2002)

    Article  CAS  Google Scholar 

  20. Suksai, C., Pakawatchai, C., Thipyapong, K.: Unexpected Schiff-base complex formation from the oxidation reaction of a nickel(II) complex with the meso-HMPAO ligand by molecular oxygen. Polyhedron 27, 759–764 (2008)

    Article  CAS  Google Scholar 

  21. Deveci, P., Taner, B.: Synthesis, spectroscopic, and cyclic voltammetric studies of ferrocene containing vic-dioxime ligand and its complexes with Ni(II), Cu(II), Co(II), Cd(II) and Zn(II) Inorg. Chim. Acta 405, 326–330 (2013)

    CAS  Google Scholar 

  22. Kılıç, A., Taş, E., Gümgüm, B., Yılmaz, İ.: The synthesis, spectroscopic and voltametric studies of new metal complexes containing three different vic-dioximes. J. Coord. Chem. 60, 1233–1246 (2007)

    Article  Google Scholar 

  23. Deveci, P., Taner, B., Kılıc, Z., Solak, A.O., Arslan, U., Ozcan, E.: Synthesis of novel ferrocene containing vic-dioxime ligands and their Ni(II), Cu(II) and Co(II) complexes: Spectral, electrochemical and biological activity studies. Polyhedron 30, 1726–1731 (2011)

    Article  CAS  Google Scholar 

  24. Isse, A.A., Gennaro, A., Vianello, E.: Electrochemical reduction of Schiff base ligands H2 salen and H2 salophen. Electrochim. Acta 42, 2065–2071 (1997)

    Article  CAS  Google Scholar 

  25. Chandra, S., Kumar, R.: Spectroscopic studies, cyclic voltammetry and synthesis of nickel(II) complexes with N(4), N(2)O(2) and N(4)S(2) donor macrocyclic ligands. Spectrochim. Acta A 62, 518–525 (2005)

    Article  Google Scholar 

  26. Franco, E., López-Torres, E., Mendiola, M.A., Sevilla, M.T.: Synthesis, spectroscopic and cyclic voltammetry studies of copper(II) complexes with open chain, cyclic and a new macrocyclic thiosemicarbazones. Polyhedron 19, 441–451 (2000)

    Article  CAS  Google Scholar 

  27. Kılıç, A., Durgun, M., Tas, E., Yılmaz, İ.: The Novel vic-dioxime ligands and their poly-metal complexes bearing 1,8-diamino-3,6-dioxaoctane: synthesis, characterization, spectroscopy and electrochemistry. Trans. Met. Chem. 33, 29–37 (2008)

    Article  Google Scholar 

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Acknowledgments

This work was supported by TUBITAK (Scientific and Technological Research Council of Turkey) with project numbers of 111T970, and the Research Fund of Selcuk University Project Number 13401023.

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Correspondence to Pervin Deveci.

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Özpınar, K., Deveci, P., Kılınç, M. et al. New supramolecular compounds: the complexes of nickel(II), copper(II), cobalt(II), cadmium(II) and zinc(II) with anti- [N-(4-aminophenyl)aza-15-crown-5]-4-(phenoxy)phenylglyoxime ligand. J Incl Phenom Macrocycl Chem 82, 407–415 (2015). https://doi.org/10.1007/s10847-015-0503-1

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