Abstract
In this study, the novel vic-dioxime ligand (3) and its Ni(II), Cu(II), Co(II), Cd(II) and Zn(II) complexes (4–8) were synthesized for the first time by condensation reactions of N-(4-aminophenyl)aza-15-crown-5 (1) and anti-chlorophenylchloroglyoxime (2). All of these new compounds were characterized by the elemental analysis, Fourier transform infrared, ultraviolet–visible, mass spectrometry, 1H NMR, 13C NMR and magnetic susceptibility measurements. The electrochemical properties of the ligand and its complexes have been investigated by cyclic voltammetry at the glassy carbon electrode in 0.1 M TBATFB in DMSO.
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Dutta, G., Kumar, K., Gupta, B.D.: Cobaloximes with bis(thiophenyl)glyoxime: synthesis and structure-property relationship study. Organometallics 28, 3485–3491 (2009)
Yılmaz, A., Taner, B., Deveci, P., Obalı, A.Y., Arslan, U., Şahin, E., Uçan, Hİ., Özcan, E.: Novel bioactive vic-dioxime ligand containing piperazine moiety: synthesis, X-ray crystallographic studies, 2D NMR applications and complexation with Ni(II). Polyhedron 29, 2991–2998 (2010)
Bilgin, A., Ertem, B., Ağın, D.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, 3165–3172 (2006)
Alp, H., Ocak, M., Özdemir, M., Ocak, Ü.: Evaluation of a (E,E)-dioxime containing two 15-membered dioxatrithiamacrocycles and its mononuclear Ni(II) complex as Ag extractants. Sep. Sci. Technol. 41, 3039–3046 (2006)
Husáková, L., Bobrowski, A., Šármková, J., Królicka, A., Vytřasa, K.: Catalytic adsorptive stripping voltammetry versus electrothermal atomic absorption spectrometry in the determination of trace cobalt and chromium in human urine. Talanta 66, 999–1004 (2005)
Thorpe, J.M., Beddoes, R.L., Collison, D., Garner, C.D., Helliwell, M., Holmes, J.M., Tasker, P.A.: Surface coordination chemistry: corrosion inhibition by tetranuclear cluster formation of iron with salicylaldoxime. Angew. Chem. Int. Ed. 38, 1119–1121 (1999)
Smith, A.G., Tasker, P.A., White, D.J.: The structures of phenolic oximes and their complexes. Coord. Chem. Rev. 241, 61–85 (2003)
Chaudhuri, P., Winter, M., Fleischhauer, P., Haase, W., Flörke, U., Hans-Jürgen Haup, H.J.: Synthesis, structure and magnetism of a tetranuclear Fe(III) complex containing an [Fe4(μ3-O)2]8+ core. Inorg. Chim. Acta 212, 241–249 (1993)
Lucić Vrdoljak, A., Čalić, M., Radić, B., Berend, S., Jun, D., Kuča, K., Kovarik, Z.: Pretreatment with pyridinium oximes improves antidotal therapy against tabun poisoning. Toxicology 228, 41–50 (2006)
Mokhir, A., Krämer, R., Voloshin, Y.Z., Varzatskii, O.A.: Synthesis and DNA binding properties of dioxime–peptide nucleic acids. Bioorg. Med. Chem. Lett. 14, 2927–2930 (2004)
Nawrot, E., Jończyk, A.: Reaction of difluorocarbene with anions from amides and oximes: synthesis of N-difluoromethyl substituted amides, O-difluoromethylimidates or O-difluoromethyl substituted oximes under phase-transfer catalysis conditions. J. Fluorine Chem. 127, 943–947 (2006)
Meshram, H.M., Eeshwaraiah, B., Sreenivas, M., Aravind, D., Syama Sundar, B., Yadav, J.S.: Convenient and efficient triton B–mediated synthesis of functionalized oxime ethers. Synth. Commun. 39, 1857–1863 (2009)
Wua, H., Yang, J., Maa, J.F., Li, J.Y., Xie, T.F.: Syntheses, structures and photoelectronic properties of a series of tri- and tetra-nuclear metal complexes based on a 36-membered tetraphenol macrocyclic ligand. Polyhedron 31, 136–142 (2012)
Huczyński, A., Janczak, J., Brzezinski, B.: Structural, spectroscopic and semiempirical characterisation of the calcium cation complexes with 14-membered macrocyclic ligand of cyclic oxaalkyl diamide of O-phthalic acid. Inorg. Chim. Acta 370, 353–362 (2011)
Sharma, S.K., Gupta, R.: Studies on the structure and properties of nickel complexes in a set of amide-based 13-membered macrocyclic ligands. Inorg. Chim. Acta 376, 95–104 (2011)
Deveci, P., Taner, B., Kılıç, Z., Solak, A.O., Özcan, E.: Synthesis and structural and electrochemical characterization of novel macrocyclic vic-dioxime ligand and its mononuclear transition and nontransition metal complexes. Turk. J. Chem. 36, 25–36 (2012)
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, 49–56 (2003)
Uçan, H.I., Mirzaoglu, R.: Synthesis and complex formation of six new unsymmetrical vic-dioximes. Synth. React. Inorg. Met. Org. Chem. 20, 437–449 (1990)
Taş, E., Kara, H., Durgun, M., Kılıç, A., Yılmaz, İ.: Synthesis, spectral characterization and electrochemical investigations of mononuclear Cu(II), Ni(II) and Co(II) metal complexes containing different new vic-dioxime groups. Synth. React. Inorg. Met. Org. Chem. 39, 379–387 (2009)
Bilgin, A., Serbest, K., Gök, Y.: A novel tetraoxime and its dinuclear and tetranuclear transition metal complexes. Transit. Metal Chem. 25, 63–68 (2000)
Taş, E., Ulusoy, M., Güler, M.: Synthesis, characterization and redox properties of a new vic-dioxime and its transition metal complexes. Transit. Metal Chem. 29, 180–184 (2004)
Ünver, H., Hayvalı, Z.: Synthesis, spectroscopic studies and structures of square-planar nickel(II) and copper(II) complexes derived from 2-{(Z)-[furan-2-ylmethyl]imino]methyl}-6-methoxyphenol. Spectrochim. Acta A 75, 782–788 (2010)
Ahsen, V., Gökceli, F., Bekaroglu, Ö.: Synthesis of SS′-bis(4′-benzo[15-crown-5])dithioglyoxime and its complexes with copper(II) nickel(II), cobalt(II), cobalt(III), palladium(II), platinum(II), and platinum(IV). J. Chem. Soc. Dalton Trans. 8, 1827–1831 (1987)
Karapınar, E.: Synthesis and characterization of a new (E,E)-dioxime and its homonuclear complexes. J. Incl. Phenom. Macro. Chem. 53, 171–175 (2005)
Coşkun, A., Karapınar, E.: Synthesis of N-(4-benzo[15-crown-5]) thiophenoxyphenylaminoglyoxime and its complexes with some transition metals. J. Incl. Phenom. Macro. Chem. 60, 59–64 (2008)
Karapınar, E., Özcan, E.: Synthesis of N-[4-benzo(15-crown-5)]-4-tolylaminoglyoxime and N-[4-benzo(15-crown-5)]-4-chlorophenylaminoglyoxime and their complexes with copper(II), nickel(II) and cobalt(II). J. Incl. Phenom. Macro. Chem. 47, 59–63 (2003)
Kurtoğlu, M., Serin, S.: Template synthesis of two new glyoxime derivatives. Characterization and investigation of their complexes with Ni(II), Cu(II), and Co(II) metal ions. Synth. React. Inorg. Met. Org. Chem. 31, 1129–1139 (2001)
Ben-Saber, S.M., Maihub, A.A., Hudere, S.S., El-Ajaily, M.M.: Complexation behavior of Schiff base toward transition metal ions. Microchem. J. 81, 191–194 (2005)
Gök, Y., Karaböcek, S., Mısır, M.N.: A novel vicinal dioxime and its homo- and heterotrinuclear complexes. Transit. Metal. Chem. 23, 333–336 (1998)
Leovac, V.M., Jovanovic, L.S., Jevtovic, V.S., Pelosi, G., Bisceglie, F.: Transition metal complexes with thiosemicarbazide-based ligand—Part LV: synthesis and X-ray structural study of novel Ni(II) complexes with pyridoxal semicarbazone and pyridoxal thiosemicarbazone. Polyhedron 26, 2971–2978 (2007)
Karipcin, F., Dede, B., Percin-Ozkorucuklu, S., Kabalcilar, E.: Mn(II), Co(II) and Ni(II) complexes of 4-(2-thiazolylazo)resorcinol: syntheses, characterization, catalase-like activity, thermal and electrochemical behaviour. Dyes Pigments 84, 14–18 (2010)
Pedersen, S.B., Larsen, E.: anti-Amphi and cis–trans isomerisms in some bis(dioximato)nickel(II) complexes. Acta Chem. Scand. 27, 3291–3301 (1973)
Kurtoğlu, M., İspir, E., Kurtoğlu, N., Serin, S.: Novel vic-dioximes: synthesis, complexation with transition metal ions, spectral studies and biological activity. Dyes Pigments 77, 75–80 (2008)
Chandra, S., Kumar, R.: Spectroscopic studies, cyclic voltammetry and synthesis of nickel(II) complexes with N4, N2O2 and N4S2 donor macrocyclic ligands. Spectrochim. Acta A 62, 518–525 (2005)
Franco, E., López, T.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)
Chandra, S., Kumar, G.L., Sangeetika, : Spectroscopic, cyclic voltammetric and biological studies of transition metal complexes with mixed nitrogen–sulphur (NS) donor macrocyclic ligand derived from thiosemicarbazide. Spectrochim. Acta A 62, 453–460 (2005)
Isse, A.A., Gennaro, A., Vianello, E.: Electrochemical reduction of Schiff base ligands H2 salen and H2 salophen. Electrochim. Acta 42, 2065–2071 (1997)
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Deveci, P. Synthesis, spectroscopic and cyclic voltammetry studies of novel azacrown ether containing vic-dioxime ligand and its Ni(II), Cu(II), Co(II), Cd(II) and Zn(II) complexes. J Incl Phenom Macrocycl Chem 77, 319–325 (2013). https://doi.org/10.1007/s10847-012-0249-y
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DOI: https://doi.org/10.1007/s10847-012-0249-y