Oxovanadium(IV) complexes of bromo-and methoxy substituted N1,N4-diarylidene-S-methylthiosemicarbazones

• Authors: Tülay. Demirci , Yüksel Köseoğlu , Sadik Güner , Bahri Ülküseven
• Languages of publication: EN

Abstracts

EN

Four new oxovanadium(IV) compounds were prepared by template reaction of salicyl-, 5-bromosalicyl-and 3-methoxysalicyl-aldehyde S-methylthiosemicarbazones with 2-hydroxy-, 5-bromo-2-hydroxy-and 3-methoxy-2-hydroxy-benzaldehyde in various combinations. The compounds were isolated as stable solid compounds with general formula [VO(L)] and characterized by elemental analysis, conductivity and magnetic measurements, electronic, IR and EPR spectroscopy. The X-band EPR signals recorded from powder forms of all samples have a single asymmetric line shape and theoretical fit studies proved the presence of axial symmetry around the paramagnetic vanadium ions. The anisotropic Lande splitting factors take values of g‖ < g⊥ < ge = 2.0023. Orbital energy levels for magnetic electrons were determined from theoretically well fitted Spin Hamiltonian parameters. The EPR spectra recorded from solution forms almost have isotropic character.

Keywords

EN

Thiosemicarbazone; S-methylthiosemicarbazone; template condensation; EPR; Vanadium

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2006
• Volume: 4
• Issue: 1
• Pages: 149-159

Dates

published

1 - 3 - 2006

online

1 - 3 - 2006

Contributors

author

Tülay. Demirci

• Department of Chemistry, Istanbul University, 34320, Avcilar Istanbul, Turkey

author

Yüksel Köseoğlu

• Department of Physics, Fatih University, 34500, Buyukcekmece Istanbul, Turkey

author

Sadik Güner

• Department of Physics, Fatih University, 34500, Buyukcekmece Istanbul, Turkey

author

Bahri Ülküseven

• Department of Chemistry, Istanbul University, 34320, Avcilar Istanbul, Turkey

References

• [1] D.X. West, A.E. Liberta, S.B. Padhye, R.C. Chikate, P.B. Sonawane, A.S. Kumbhar and R.G. Yerande: “Thiosemicarbazone Complexes of Copper(II): Structural and Biological Studies”, Coord. Chem. Rev. Vol. 123, (1993), pp. 49–57. http://dx.doi.org/10.1016/0010-8545(93)85052-6[Crossref]
• [2] M.J.M. Campbell: “Transition Metal Complexes of Thiosemicarbazide and Thiosemicarbazones”, Coord. Chem. Rev., Vol. 15, (1975), pp. 279–285. http://dx.doi.org/10.1016/S0010-8545(00)80276-3[Crossref]
• [3] A.R. Cowley, J.R. Dilworth, P.S. Donnelly, E. Labisbal and A. Sousa: “An unusual dimeric structure of a Cu(I) bis(thiosemicarbazone) complex: implications for the mechanism of hypoxic selectivity of the Cu(II) derivatives”, J. Am. Chem. Soc., Vol. 124, (2002), pp. 5270–5275. http://dx.doi.org/10.1021/ja012668z[Crossref]
• [4] D.R. Richardson: “Iron chelators as therapeutic agents for the treatment of cancer”, Critical Reviews in Oncology/Hematology, Vol. 42, (2002), pp. 267–281. http://dx.doi.org/10.1016/S1040-8428(01)00218-9[Crossref]
• [5] S.E. Asis, A.M. Bruno, A.R. Martinez, M.V. Sevilla, C.H. Gaozza, A.M. Romano, J.D. Coussio and G. Ciccia: “Diarylsemicarbazones; synthesis, antineoplastic activity and topoisomerase I inhibition assay”, II Farmaco, Vol. 54, (1999), pp. 517–525. http://dx.doi.org/10.1016/S0014-827X(99)00050-6[Crossref]
• [6] K. Nomiya, K. Sekino, M. Ishikawa, A. Honda, M. Yokoyama, N.C. Kasuga, H. Yokoyama, S. Nakano and K. Onodera: “Syntheses, crystal structures and antimicrobial activities of monomeric 8-coordinate, and dimeric and monomeric 7-coordinate bismuth(III) complexes with tridentate and pentadentate thiosemicarbazones and pentadentate semicarbazone ligands”, J. Inorg. Biochem. Vol. 98, (2004), pp. 601–615. http://dx.doi.org/10.1016/j.jinorgbio.2004.01.011
• [7] P. Ghosh, O.J. D'Cruz, R.K. Narla and F.M. Uckun: “Apoptosis-inducing vanadocene compounds against human testicular cancer”, Clin. Canc. Res., Vol. 6, (2000), pp. 1536–1545.
• [8] L.S. Chin, S.F. Murray, D.H. Harter, P.F. Doherty and S.K. Singh: “Sodium vanadate inhibits apoptosis in malignant glioma cells: a role for Akt/PKB”, J. Biomed. Sci., Vol. 6, (1999), pp. 213–220. [Crossref]
• [9] M.R. Maurya, S.K. Shailendra, A. Azam, W. Zhang and D. Rehder: “Biological and medicinal aspects of vanadium”, Eur. J. Inorg. Chem., Vol. 24, (2003), pp. 4397–4402.
• [10] M.T. Pope and A. Müller (Eds.): Polyoxometalates: From Platonic Solids to Anti-Retroviral Activity, Kluwer Academic Publishers, Dordrecht, 1994.
• [11] P.J. Stankiewicz, A.S. Tracey, D.C. Crans, H. Sigel and A. Sigel (Eds.): Vanadium and its Role in Life, Metal Ions in Biological Systems, vanadyl 31, Marcel Dekker, New York, 1995.
• [12] R.M. Brand and F.G. Hamel: “Transdermally delivered peroxovanadium can lower blood glucose levels in dibetic rats”, Int. J. Pharm., Vol. 183, (1999), pp. 117–124. http://dx.doi.org/10.1016/S0378-5173(99)00071-X[Crossref]
• [13] D.C. Crans: “Chemistry and insulin-like properties of vanadium(IV) and vanadium(V) compounds”, J. Inorg. Biochem. Vol. 80, (2000), pp. 123–129. http://dx.doi.org/10.1016/S0162-0134(00)00048-9[Crossref]
• [14] A.K. Srivastava: “Anti-diabetic and toxic effects of vanadium compounds”, Mol. Cell. Biochem., Vol. 206, (2000), pp. 177–184. http://dx.doi.org/10.1023/A:1007075204494[Crossref]
• [15] R. Yanardag, S. Bolkent, Ö. Karabulut-Bulan and S. Tunal≀: “Effects of Vanadyl Sulfate on Kidney in Experimental Diabetes”, Biol. Trace Element Research, Vol. 95, (2003), pp. 73–80. http://dx.doi.org/10.1385/BTER:95:1:73[Crossref]
• [16] H. Sakurai, Y. Kojima, Y. Yoshikawa, K. Kawabe and H. Yasui: “Antidiabetic vanadium(IV) and zinc(II) complexes”, Coord. Chem. Rev., Vol. 226, (2002), pp. 187–195. http://dx.doi.org/10.1016/S0010-8545(01)00447-7[Crossref]
• [17] T. S. Smith, R. LoBrutto and V.L. Pecoraro: “Paramagnetic spectroscopy of vanadyl complexes and its applications to biological systems”, Coord. Chem. Rev., Vol. 228, (2002), pp. 1–9. http://dx.doi.org/10.1016/S0010-8545(01)00437-4[Crossref]
• [18] C.J. Carrano, C.M. Nunn, R. Quan, J.A. Bonadies and V.L. Pecoraro: “Monomeric and Dimeric Vanadium(IV) and (V) Complexes of N-(hydroxyalkyl)salicylideneamines: Structures, Magnetochemistry and Reactivity”, Inorg. Chem. Vol. 29, (1990), pp. 941–949.
• [19] D. Wang, M. Ebel, C. Schulzke, C. Grüning, S.K.S. Hazari and D. Rehder: “Vanadium(IV and V) Complexes Containing SNO (Dithiocarbonylhydrazone; Thiosemicarbazone) Donor Sets”, Eur. J. Inorg. Chem., (2001), pp. 935-944.
• [20] R.L. Farmer and F.L. Urbach: “Stereochemistry and electronic structure of oxovanadium(IV) chelates with tetradentate Schi. base ligands derived from 1,3-diamines”, Inorg. Chem., Vol. 13, (1974), pp. 587–592. http://dx.doi.org/10.1021/ic50133a017[Crossref]
• [21] H.J. Stoklosa, J.R. Wasson and B.J. McCormick: “Electronic spectral band maxima and ligand field parameters of oxovanadium(lV) complexes with salicylidene methyl anthranilates”, Inorg. Chem., Vol. 13, (1974), pp. 592–601. http://dx.doi.org/10.1021/ic50133a018[Crossref]
• [22] C.J. Ballhausen and H.B. Gray: “The electronic structure of the vanadyl ion”, Inorg. Chem., Vol. 25, (1962), pp. 111–122. http://dx.doi.org/10.1021/ic50001a022[Crossref]
• [23] V.B. Arion, V.Ch. Kravtsov, R. Goddard, E. Bill, J.I. Gradinaru, N.V. Gerbeleu, V. Levitschi, H. Vezin, Y.A. Simonov, J. Lipkowski and V.K. Bel'skii: “Oxovanadium(IV) and oxovanadium(IV)-barium(II) complexes with heterotopic macrocyclic ligands based on isothiosemicarbazide”, Inorg. Chim. Acta, Vol. 317, (2001), pp. 33–44. http://dx.doi.org/10.1016/S0164-1212(00)00107-2[Crossref]
• [24] Ramazan Öztürk and Ahmet Gül: “Construction of nonanuclear supramolecular structures from simple modular units”, Tetrahed. Lett., Vol. 45, (2004), pp. 947–949. http://dx.doi.org/10.1016/j.tetlet.2003.11.097[Crossref]
• [25] R. Öztürk, S. Güner, B. Aktaş and A. Gül “Synthesis, characterization and EPR studies of supramolecular porphyrazine”, Supramol. Chem., Vol. 17, (2005), pp. 233–239.
• [26] J.A. Weil, J.E. Wertz and J.R. Bolton: Electron Spin Resonance-Elementary Theory and Practical Applications, McGraw-Hill, New York, 1972.
• [27] U.B. Gangadharmath, V.K. Revankar and V.B. Mahale: “Synthesis and spectroscopic characterization of cationic mononuclear oxovanadium(IV) complexes with tetradentate Schi. bases as ligands”, Spectrochimica Acta A., Vol. 58, (2002), pp. 2651–2657. http://dx.doi.org/10.1016/S1386-1425(02)00011-2[Crossref]
• [28] U.B. Gangadharmath, S.M. Annigeri, A.D. Naik, V.K. Revankar and V.B. Mahale: “Synthesis, characterisation and evaluation of molecular-orbital parameters, spinorbit, dipolar and fermi-contact terms of VO2+ ion in thiosemicarbazone complexes”, J. Mol. Struct. (Theochem), Vol. 572, (2001), pp. 61–71. http://dx.doi.org/10.1016/S0166-1280(01)00564-4[Crossref]
• [29] E. Gonca, Y. Köseoĝlu, B. Aktaş and A. Gül: “Octakis(1-naphthylmethylthio) substituted porphyrazine derivatives”, Polyhedron, Vol. 23, (2004), pp. 1845–49. http://dx.doi.org/10.1016/j.poly.2004.05.001[Crossref]
• [30] R. Heucher, G.V.R. Chandramouli and P.T. Manoharan: “Magnetic and spectroscopic investigations of tetra(4-t-butyl)phthalocyano complexes of cobalt(II) and-copper(II)”, J. Porphyrins Phthalocyanines, Vol. 2, (1998), pp. 423–29. http://dx.doi.org/10.1002/(SICI)1099-1409(199807/10)2:4/5<423::AID-JPP116>3.0.CO;2-T[Crossref]
• [31] T.S. West: Complexometry with EDTA and Related Reagents, 3rd ed., BDH, Poole, 1969, pp. 213–214.

Identifiers

DOI

10.1007/s11532-005-0011-z