Template Synthesis, Structural Characterization and Antibacterial Activity of an Unsymmetrical Tridentate Schiff Base Nickel(II) Complex

Document Type : Research Article

Authors

Department of Inorganic Chemistry , University of Mazandaran, Babolsar, I.R. IRAN

Abstract

Nickel(II) complex of [NiL2](ClO4)2, where L is an unsymmetrical tridentate ligand of 2-(2-aminoethyl)imino-3-butanone oximehas been synthesized by a template condensation reaction. The complex was characterized on the basis of microanalytical, spectroscopic, and other physicochemical properties. X-ray diffraction study of the complex reveals nickel(II) center in a distorted octahedral environment through two amine nitrogen donors, two imine donors,and two nitrogen atoms of the oxime moieties of the ligand. The antibacterial activity of the complex has been tested against Gram(+) and Gram(-) bacteria. The results of the antibacterial screening indicated that the complex is effective against bacterial growth retardation activity to some extent and its effectiveness is higher for Gram(+) bacteria.

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References

[1] Tschugaeff L., Ueber Ein Neues, Empfindliches Reagens auf Nickel., Chent. Ber., 38: 2520 (1905).
[2] Gümüş G., Ahsen V., Synthesis and Complexation of a New Soluble Multidentatediaminoglyoxime and Its Ni (II) and Pd (II) Complexes,  Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 32(7): 1281-1288 (2002).
[3] Kantekin H., Ocak Ü., Gök Y., Synthesis and Characterization of a Novel Macrocyclic vic‐Dioxime and Some of its Mono and Trinuclear Complexes, Zeitschriftfüranorganische und allgemeine Chemie, 627(5): 1095-1102 (2001).
[4]  Karapinar 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), Journal of Inclusion Phenomena and Macrocyclic Chemistry, 47(1-2): 59-63 (2003).
[5] 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, Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 31(7): 1129-1139 (2001).
[6] Kantekin H., Ocak Ü., Gök Y., Synthesis and Characterization of a Novel (E, E)-Dioxime and Its Mono and Heterotrinuclear Complexes Containing a 15-Membered Dioxatrithiamacrocycle Ligand with Transition Metals, Journal of Coordination Chemistry, 57(4):265-273 (2004).
[7] Kurtoğlu M., İspir E., Kurtoğlu N., Toroğlu S., Serin, S., New Soluble Coordination Chain Polymers of Nickel (II) and Copper (II) Ions and Their Biological Activity, Transition Metal Chemistry, 30(6): 765-770 (2005).
[8] Kumagai H., Endo M., Kondo M., Kawata S., Kitagawa S., Reactions of di-2-pyridylketone Oxime in the Presence of Vanadium (III): Crystal Structures of the Coordination Products, Coordination Chemistry Reviews, 237(1): 197-203 (2003).
[9] Kukushkin V.Y., Tudela D., Pombeiro A.J., Metal-Ion Assisted Reactions of Oximes and Reactivity of Oxime-Containing Metal Complexes, Coordination Chemistry Reviews, 156: 333-362 (1996).
[10] Chakravorty A., Structural Chemistry of Transition Metal Complexes of Oximes, Coordination Chemistry Reviews, 13(1): 1-46 (1974).
[11] Kukushkin V.Y., Pombeiro A.J., Oxime and Oximate Metal Complexes: Unconventional Synthesis and Reactivity, Coordination Chemistry Reviews, 181(1): 147-175 (1999).
[12] Lockwood M.A., Blubaugh T.J., Collier A.M., Lovell S., Mayer J.M., Oxidations of C− H and O−H Bonds by Isolated Copper (III) Complexes, Angewandte Chemie, International Edition, 38(1‐2): 225-227 (1999).
[13] Özer M., Kandaz M., RızaÖzkaya A., Bulut M., Güney O., Fluorescentvic-Dioxime-Type Ligand and Its Mono-and Dinuclear Complexes: The Preparation, Spectroscopy, and Electrochemistry of Its Various Complexes, Dyes and Pigments, 76(1): 125-132 (2008).
[14] Karipcin F., Dede B., Caglar Y., Hür D., Ilican S., Caglar M., Şahin Y., A New Dioxime Ligand and Its Trinuclear Copper (II) Complex: Synthesis, Characterization and Optical properties, Optics communications, 272(1): 131-137 (2007).
[15] Cheng W.D., Wu D.S., Shen J., Huang S.P., Xie Z., Zhang H., Gong Y.J., From Molecule to Bulk Material: Optical Properties of Hydrogen‐Bonded Dimers [C12H12N4O2AgPF6]2 and [C28H28N6O3AgPF6]2 Depend on the Arrangement of the Oxime Moieties, Chemistry-A European Journal, 13(18): 5151-5159 (2007).
[16] Dilworth J., Parrott SThe biomedical Chemistry of Technetium and Rhenium, Chemical Society Reviews, 27(1): 43-55 (1998).
[17] Blower P.J., Small Coordination Complexes as Radiopharmaceuticals for Cancer Targeting, Transition metal chemistry, 23(1): 109-112 (1997).
[18] Green M.A., The Potential for Generator-Based PET Perfusion Tracers, Journal of Nuclear Medicine, 31(10): 1641-1645 (1990).
[19] John E.K., Bott A.J., Green M.A., Preparation and Biodistribution of Copper‐67 Complexes with Tetradentate schiff‐ Base Ligands, Journal of Pharmaceutical Sciences, 83(4): 587-590 (1994).
[21] Wey S.P., Mohamed Ibrahim A., Green M.A., Fanwick P.E., Synthesis and Crystal Structure of a Copper (II) Complex with a Tetradentatedithiadioxime Ligand, Polyhedron, 14(8): 1097-1100 (2006).
[21] Yari A., Azizi S., Kakanejadifard A., An Electrochemical Ni (II)-Selective Sensor-Based on a Newly Synthesized Dioxime Derivative as a Neutral Ionophore, Sensors and Actuators B: Chemical, 119(1): 167-173 (2006).
[22]  Kilic A., Tas E., Gumgum B., Yilmaz I., Synthesis, Spectral Characterization and Electrochemical Properties of New Vic-Dioxime Complexes Bearing Carboxylate, Transition Metal Chemistry, 31(5): 645-652 (2006).
[23] Rezvani AR, Hadadzadeh H., The Study of Electrochemical Behavior of Mono and Dinuclear Co(II) Complexes, Trans-[PYCO((DO) (DOH)PN) (L)] PF6 and [{PYCO((DO)(DOH)PN)}2 (M-DICYD)](PF6), Iran. J. Chem. Chem. Eng. (IJCCE), 21(1): 21-27 (2002).
[24] Ghasemi J, ShokrElahi APotentiometric Study of Binary and Mixed Complexes of Imidazole, Histamine, Histidine and Diacetylmonooxime with some Transition Metal Ions in Aqueous Solution, Iran. J. Chem. Chem. Eng. (IJCCE), 21(1): 22-28 (2001).
[25] Çolak A.T., Taş M., Irez G., Yeşilel O.Z., Büyükgüngör O., Syntheses, Spectral, Thermal and Structural Characterization of 2‐Phenyl‐2‐(1‐hydroxyiminoethyl)‐1, 2, 3, 4‐Tetrahydroquinazoline and Its Novel Nickel (II) Complex, Zeitschriftfüranorganische und AllgemeineChemie, 633(3): 504-508 (2007).
[26] Díaz T.G., Guiberteau A., Lopez Soto M.D., Ortiz J.M., Determination of Copper with 5, 5-Dimethylcyclohexane-1, 2, 3-Trione 1, 2-Dioxime 3-Thiosemicarbazone in Olive Oils by Adsorptive Stripping Square Wave Voltammetry, Food Chemistry, 96(1): 156-162 (2006).
[27] Bilgin A., Ertem B., Ağın F.D., Gök Y., Karslıoğlu S., Synthesis, Characterization and Extraction Studies of a New Vic-Dioxime and Its Complexes Containing Bis (Diazacrown Ether) Moieties, Polyhedron, 25(16): 3165-3172 (2006).
[28] Sharma G.D., Sangodkar S.G.,  Roy M.S., Study on Electrical and Photoelectrical Behaviour of Undoped and Doped Furazano [3, 4- b] Piperazine (FP) Thin-Film Devices, Synthetic Metals, 75(3): 201-207 (1995).
[29] Maity D., Mukherjee P., Ghosh A., Drew M.G., Mukhopadhyay G., A Novel Trinuclear Nickel (II) Complex of an Unsymmetrical Tetradentate Ligand Involving Bridging Oxime and Acetylacetone Functions, Inorganica Chimica Acta, 361(5): 1515-1519 (2008).
[30] Maity D., Chattopadhyay S., Ghosh A., Drew M.G., Mukhopadhyay G., Syntheses, Characterization and X-Ray Crystal Structures of Ni(II) Complexes of Tridentate Monocondensed and Tetradentatedicondensed Schiff Bases, Polyhedron, 28(4): 812-818 (2009).
[31] Kanderal O.M., Kozłowski H., Dobosz A., Swiatek-Kozlowska J., Meyer F., Fritsky I.O., Effect of Metal Ionic Radius and Chelate Ring Alternation Motif on Stabilization of Trivalent Nickel and Copper in Binuclear Complexes with Double Cis-Oximato Bridges, Dalton Transactions, 8: 1428-1437 (2005).
[32] Costes JP, Dahan F, Dupuis A, Laurent JP, Bridging Ability of a Novel Polydentate Ligand (H2L) Comprising an Oxime Function, Structures of a Mononuclear Precursor [NiL] and a Dinuclear CuII2 Complex. Magnetic Properties of Mononuclear (NiII and CuII), Dinuclear (CuII)2, NiII2, NiIICuII and CuIICrIII) and Trinuclear (CuII3, CuIIMnIICuII and CuIIZnIICuII) Complexes, J Chem. Soc. Dalton Trans: 1307-1314 (1998)
[33] Hussain M.S., Almohdhar H.M., Alarfaj A.R., Template Reactions: Axial-Ligation and Macrocyclization of Alpha-Furilglyoximates and Alpha-Aminedioximates of Cobalt (III) and Rhodium (III), J CoordChem, 18(4): 339-349 (1988).
[34] Korvenranta J., Saarinen H., Nasakkala E., The Crystal Structure of a Complex Containing Nickel in the Formal Oxidation State IV: Bis [2-(2-aminoethyl) imino-3-butanone oximato] nickel (IV) Diperchlorate, Finn. Chem. Lett, 81: 443-448 (1979).
[35] Saarinen H., Korvenranta J., Nasakkala E., The Crystal Structure of a Complex Containing Nickel in the Formal Oxidation State IV: Bis [2-(2-aminoethyl) imino-3-butanone oximato] nickel (IV) Diperchlorate, Acta Chem. Scandinavica A, 34: 443-448 (1980).
[36] Nonius B.V., Kappa C.C.D., "Operation Manual"; Nonius BV: Delft, The Netherlands (1997).
[37]  Sheldrick G.M., SHELXL-97, Program for Crystal Structure Refinement; University of Göttingen: Göttingen, Germany, 1997. There is no Corresponding Record for This Reference (2006).
[38] Smejkal C.W., Vallaeys T., Seymour F.A., Burton S.K., Lappin‐Scott H.M., Characterization of (R/S)‐Mecoprop [2‐(2‐Methyl‐4‐Chlorophenoxy) Propionic Acid]‐Degrading Alcaligenes sp. CS1 and Ralstonia sp. CS2 Isolated from Agricultural Soils, Environmental Microbiology, 3(4): 288-293 (2001).
[39] Geary W.J., The use of Conductivity Measurements in Organic solvents for the Characterisation of Coordination Compounds. Coordination Chemistry Reviews, 7(1): 81-122 (1971).
[40] Nakamoto K., "Infrared and Raman Spectra of Inorganic and Coordination Compounds", John Wiley & Sons, Ltd (1978).
[41] Raman N., Esthar S., Thangaraja C., A New Mannich Base and Its Transition Metal (II) Complexes—Synthesis, Structural Characterization and Electrochemical Study, Journal of Chemical Sciences, 116(4): 209-213 (2004).
[42] Drummond J., Wood J.S., Crystal and Molecular Structure of Tetraphenylarsoniumtetranitratomanganate (II) and X-ray study of other M (NO3) 42–ions (M= Ni, Cu, or Zn), J. Chem. Soc. A, 226-232 (1970).
[43]  Cabort A., Michel A., Therrien B., Stoeckli-Evans H., Bernauer K., Süss-Fink G., Stupka G., Iron, ., Iron, Cobalt, Nickel and Ruthenium Complexes of 2, 6-bis (3, 4-Dihydro-2H-Pyrrol-5-yl) pyridine, A Pybox Analogue, Inorganica Chimica Acta, 350: 193-200 (2003).

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