Abstract
The condensation of 2-hydroxybenzaldehyde or 2,4-dihydroxybenzaldehyde with 4,4′-diaminobiphenyl in absolute EtOH in a molar ratio 2:1 gave, respectively, the Schiff base ligands H2L1 or H2L2. The bases served as tetradentate ligands to coordinate CoII, NiII and CdII chlorides, leading to complexes where the metal:ligand ratio is 2:1. All of the compounds were characterized by elemental analysis, infrared, electronic and mass spectroscopy, 1H-n.m.r. and d.s.c. The cyclic voltammograms of the ligands and their complexes in DMF are discussed.
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Garnovskii, A.D., Nivorozhkin, A.L., Minkin, V.I.: Ligand environment and the structure of Schiff base adducts and tetracoordinated metal-chelates. Coord. Chem. Rev. 126, 1–69 (1993)
Cozzi, P.G.: Metal-Salen Schiff base complexes in catalysis: practical aspects. Chem. Soc. Rev. 33, 410–421 (2004)
Ziessel, R.: Schiff-based bipyridine ligands. Unusual coordination features and mesomorphic behaviour. Coord. Chem. Rev. 216–217, 195–223 (2001)
Aubert, P.-H., Audebert, P., Roche, M., Capdevielle, P., Maumy, M.: Synthesis and electrochemical investigation of bis(Salen) complex precursors allowing the formation of a ladder-type polymer. Chem. Mater. 13, 2223–2230 (2001)
Frausto da Silva, J.J.R., Williams, R.J.P.: The Biological Chemistry of the Elements. Clarendon Press, Oxford (1991)
Kaim, W., Schwederski, B.: Bioinorganic Chemistry, Inorganic Elements in the Chemistry of Life. Wiley, New York (1996)
Coughlin, P.K., Lippard, S.J.: Copper(II) chemistry in hexaaza binucleating macrocycles: hydroxide and acetate derivatives. J. Am. Chem. Soc. 106, 2328–2336 (1984)
Zanello, P., Tamburini, S., Vigato, P.A., Mazzochim, G.A.: Syntheses, structure and electrochemical characterization of homo- and heterodinuclear copper complexes with compartmental ligands. Coord. Chem. Rev. 77, 165–273 (1987)
Vigato, P.A., Tamburini, S., Fenton, D.E.: The activation of small molecules by dinuclear complexes of copper and other metals. Coord. Chem. Rev. 106, 25–170 (1990)
Katsuki, T.: Catalytic asymmetric oxidations using optically active (Salen) manganese(III) complexes as catalysts. Coord. Chem. Rev. 140, 189–214 (1995)
Samsel, E.G., Srinivasan, K., Kochi, J.K.: Mechanism of the chromium-catalyzed epoxidation of olefins. Role of oxochromium(V) cations. J. Am. Chem. Soc. 107, 7606–7617 (1985)
Elmorsi, M.A., Gabor, M., Barendrecht, E.: Cathodic reduction of oxygen at new iron complexes. J. Appl. Electrochem. 21, 1005–1012 (1991)
Bermejo, M.R., Castineiras, A., Garcia-Monteagudo, J.C., Rey, M., Sousa, A., Watkinson, M., McAuliffe, C.A., Pritchard, R.G., Beddose, R.L.: Electronic and steric effects in manganese Schiff-base complexes as models for the water oxidation complex phitosystem. II. The isolation of manganese-(II) and -(III) complexes of 3- and 3,5-substituted N,N′-bis(salicylidene)ethane-1,2-diamine (H2Salen) ligands. J. Chem. Soc., Dalton Trans. 2935–2944 (1996)
Watkinson, M., Fonda, M., Bermejo, M.R., Sousa, A., McAuliffe, C.A., Pritchard, R.G., Jaiboon, N., Aurangzeb, N., Naeem, M.: Further attempts to rationalise the co-ordination chemistry of manganese with Schiff base ligands and supplementary carboxylate donors. J. Chem. Soc., Dalton Trans. 31–42 (1999)
Briley, N.A., Rodriguez de Barbarin, C.O., Fenton, D.E., Hellier, P.C., Hempstead, M., Danezato, P.D., Leeson, P.B.: Attempted functionalization of a mononuclear barium complex of a 24-membered bibracchial tetraimine Schiff-base macrocycle derived from tris(2-aminoethyl)amine using salicylaldehyde. J. Chem. Soc., Dalton Trans. 765–770 (1995)
Ngwenya, M.P., Chen, D., Martell, A.E., Reibenspies, J.: Oxygenation of a copper(I) complex of a binucleating macrocyclic Schiff base ligand derived from 1,4,7-triazaheptane and furan-2,5-dicarboxaldehyde. J. Inorg. Chem. 30, 2732–2736 (1991)
Fenton, D.E.: Tetraimine Schiff base macrocycles derived from heterocyclic dicarbonyles. Pure Appl. Chem. 58, 1437–1444 (1986)
Jacobson, K.B., Turner, J.E.: The interaction of cadmium and certain other metal ions with proteins and nucleic acids. Toxicology 16, 1–37 (1980)
Hidalgo, H.A., Koppa, V., Bryan, E.S.: Effects of cadmium on RNA—polymerase and protein synthesis in rat liver. FEBS Lett. 64, 159–162 (1976)
Dakternieks, D.: Zinc and cadmium. Coord. Chem. Rev. 98, 279–294 (1990)
Cai, Y.P., Su, C.Y., Xu, A.W., Kang, B.S., Tong, Y.X., Liu, H.Q., Jie, S.: Syntheses and characterization of copper(II) complexes of bis(acetylacetone)trimethylenediimine. Polyhedron 20, 657–662 (2001)
Reddy, K.H., Reddy, M.R., Raju, K.M.: Syntheses, characterization, electrochemistry and axial ligation properties of macrocyclic divalent metal complexes of acetylacetone buckled with different diamines. Polyhedron 16, 2673–2679 (1997)
Boucher, L.J., Herrington, D.R.: Manganese Schiff base complexes. III. Circular dichroism of tetradentate chelates of manganese III. Inorg. Chem. 13, 1105–1108 (1974)
Matsushita, T., Kono, H., Shono, T.: The preparation and characterization of dichloromanganese(IV) Schiff base complexes. Bull. Chem. Soc. Jpn. 54, 2646–2651 (1981)
Khandar, A.A., Hosseini-Yazdi, S.A., Zarei, S.A.: Syntheses, characterization and X-ray crystal structures of copper(II) and nickel(II) complexes with potentially hexadentate Schiff-base ligands. Inorg. Chim. Acta 358, 3211–3217 (2005)
Kessissoglou, D.P., Kirk, M.L., Lah, M.S., Li, X., Raptopoulou, C., Hatfield, W.E., Pecoraro, V.L.: Structural and magnetic characterization of trinuclear mixed-valence manganese acetates. Inorg. Chem. 31, 5424–5432 (1992)
Saydam, S., Alakn, C.: Synthesis and characterization of a new thiazole Schiff base 5-bromo-2-hydroxybenzylidene-2-aminobenzothiazole and its complexes with Co(II), Cu(II) and Ni(II). Polish J. Chem. 75, 29–33 (2001)
Gili, P., Martin-Reyes, M.G., Martin-Zarza, P., Machado, I.L.F., Guedes da Silva, M.F.C., Lemos, M.A.D.A., Pombiero, A.J.L.: Syntheses, spectroscopic, magnetic and electrochemical properties of Cu(II) and Fe(III) complexes with the new ligand N,N′-[1,1′-dithiobis(phenyl)]bis (5′-methoxysalicylaldimine). Inorg. Chim. Acta 244, 25–36 (1996)
Gili, P., Martin-Reyes, M.G., Martin-Zarza, P., Machado, I.L.F., Guedes da Silva, M.F.C., Tong, Y.Y., Pombiero, A.J.L.: Complexes of Mn(II) and Mn(III) with the Schiff base N-[2-(3-ethylindole)]pyridoxaldimine. Electrochemical study of these and related Ni(II) and Cu(II) complexes. Inorg. Chim. Acta 255, 279–288 (1997)
Vogt, A., Wolowiec, S., Prasad, R.L., Gupta, A., Sharzewski, J.: Syntheses and characterization of nickel(II), copper(II), manganese(III) and iron(III) complexes with new chiral Salen-type ligand N,N′-bis(3,5-di-tert-butylsalicylidene)-(1R,3S)-1,3-diamine-1,2,2-trimethylcyclopentane. Polyhedron 17, 1231–1240 (1998)
Cimerman, Z., Galic, N., Bosner, B.: The Schiff bases of salicylaldehyde and aminopyridines as highly sensitive analytical reagents. Anal. Chim. Acta 343, 145–153 (1997)
Lalia-Kantouri, M., Hartophylles, M., Jannakoudakis, P.D., Voutsas, G.P.: Spectral and electrochemical features of some substituted bis(2-hydroxyaryloximato) Co(II), Ni(II), Pd(II) and Cu(II) chelates. Crystal and molecular structure of trans-bis(propanone,1-[2-hydroxyphenyl]-oximato)Ni(II). Z. Anorg. Allg. Chem. 621, 645–653 (1995)
Hassaan, A.M., Khalifa, M.A.: Metal chelates of some transition and non-transition metal ions with Schiff base derived from isatin with o-phenylenediamine. Monatsh. Chem. 124, 803–808 (1993)
Ali, M.A., Mirza, A.H., Butcher, R.J.: Synthesis and characterization of copper(II) complexes of the methylpyruvate Schiff base of S-methyldithiocarbazate (Hmpsme) and the X-crystal structures of Hmpsme and [Cu(mpsme)Cl]. Polyhedron 20, 1037–1043 (2001)
Felicio, R.C., Da Silva, G.A., Ceridorio, L.F., Dockal, E.R.: Tetradentate Schiff base copper(II) complexes. Synth. React. Inorg. Met.-Org. Chem. 29, 171–192 (1999)
Abu-El-Wafa, S.M., Issa, R.M., McAuliffe, C.A.: Unusual Cu(III) Schiff’s base complexes. Inorg. Chim. Acta 99, 103–106 (1985)
Lechat, S., Khan, M.A., Bouet, G.M., Vierling, F.: Spectrophotometric study of cobalt(II) chloride complexes in ethanol and propan-2-ol. Inorg. Chim. Acta 211, 33–36 (1993)
Lever, A.B.P.: Inorganic Electronic Spectroscopy, 1st edn. Elsevier, Amsterdam (1968)
Abd-Elzaher, M.M.: Spectroscopic characterization of some tetradentate Schiff bases and their complexes with nickel, copper and zinc. J. Chin. Chem. Soc. 48, 153–160 (2001)
Gulloti, M., Casella, L., Pasini, A., Ugo, R.: Optically active complexes of Schiff base. Part 3. Complexes of iron(III) with quadridentate Schiff-bases derived from salicylaldehyde. J. Chem. Soc., Dalton Trans. 339–345 (1977)
Anthonysamy, A., Balasubramanian, S.: Synthesis, spectral, thermal and electrochemical studies of nickel(II) complexes with N2O2 ligands. Inorg. Chem. Commun. 8, 908–911 (2005)
Kaabi, I., Douadi, T., Haffar, D., Chafaa, S., Allain, M., Khan, M.A., Bouet, G.M.: Crystal structure of a new pentadentate symmetrical: di[4-(phenylimino)penta-2-one] ether. Structural and electrochemical studies of its CoII, NiII, CuII and CdII complexes. Transit. Met. Chem. 32, 666–673 (2007)
Cavalheiro, E.T.G., Lemos, F.C.D., Zukerman Schpector, J., Dockal, E.R.: The thermal behaviour of nickel, copper and zinc complexes with the Schiff bases cis- and trans-N,N′-bis(salicylidene)-1,2-cyclohexadiamine (Salen). Thermochim. Acta 370, 129–133 (2001)
Chavan, M.Y., Meade, T.J., Busch, D.H., Kuwana, T.: Structural dependence of an electron-transfer process: nature of the product of one-electron oxidation of the lacunar cyclidene complexes of nickel(II) and cobalt(II). Inorg. Chem. 25, 314–321 (1986)
Beloglazkina, E.K., Majouga, A.G., Romashkina, R.B., Moiseeva, A.A., Zyk, N.V.: The preparation, crystal structure and electrochemistry of (5Z,5′Z)-2,2′-(alkane-α,ω-diylsulfanyldiyl)bis (5-(3-pyridylmethylene)-3,5-dihydro-4-imidazol-4-ones) and their complexes with cobalt(II) chloride. Polyhedron 26, 797–802 (2007)
Lintvedt, R.L., Ranger, G., Kramer, L.S.: Cyclic voltammetric study of a series of related mono- and binuclear nickel complexes of beta di- and triketonates and their diamine Schiff bases. Inorg. Chem. 25, 2635–2637 (1986)
Ourari, A., Ouari, K., Moumeni, W., Sibous, L., Bouet, G.M., Khan, M.A.: Unsymmetrical tetradentate Schiff base complexes derived from 2,3-diaminophenol and salicylaldehyde or 5-bromosalicylaldehyde. Transit. Met. Chem. 31, 169–175 (2006)
Lever, A.B.P.: Inorganic Electronic Spectroscopy, 2nd edn. Elsevier, Amsterdam (1984)
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Sibous, L., Bentouhami, E., Maïza, A. et al. Synthesis, Characterization and Electrochemical Behavior of CoII, NiII and CdII Complexes with N2O2 Donor Ligands Derived from 4,4′-Diaminobiphenyl and 2-Hydroxybenzaldehyde or 2,4-Dihydroxybenzaldehyde. J Solution Chem 39, 511–521 (2010). https://doi.org/10.1007/s10953-010-9512-2
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DOI: https://doi.org/10.1007/s10953-010-9512-2