Some Transition Metal Complexes of NO Type Schiff Base: Preparation and Characterization

Year 2016, Volume: 37 Issue: 1, 65 - 73, 19.01.2016

Erdal Canpolat , Ayşe Ağlamış Hakan Şahal Mehmet Kaya

https://doi.org/10.17776/csj.38701

Abstract

Abstract. Metal complexes of Schiff base ligand (5-bromo-3-methoxysalicyliden-p-iminoacetophenone oxime) derived from 5-bromo-3-methoxsalicylaldehyde and p-aminoacetophenoneoxime is reported. Schiff base was found to be bidentate ligand involving the imino nitrogen and carboxyl oxygen atoms in the complexes. Metal to ligand ratio were found to be 1:2 for all of the complexes. Co(II), Ni(II), and Zn(II) complexes have been found tetrahedral geometry and Cu(II) complex has been found four coordinated geometry. The complexes are found to have the formulae [M(L)2]. The compounds obtained have been characterized by their elemental analyses, IR, 1H-NMR, 13C-NMR, UV spectra, magnetic susceptibility and thermogravimetric analyses (TGA).

Keywords: Schiff base, transition metal complexes

 

Özet. Bu çalışmada, 5-brom-3-metoksi salisilaldehit ve p-aminoasetofenon oksimden türetilmiş Schiff bazı ligandı (5-brom-3-metoksisalisiliden-p-iminoasetofenon oksim) nın metal kompleksleri rapor edildi. Bütün komplekslerde Schiff bazlarının metal iyonuna imin azotu ve fenolik oksijeninden bağlanarak iki dişli şelat olarak davrandığı ve yine bütün komplekslerde M:L oranının 1:2 olduğu görüldü. Co+2, Ni+2 ve Zn+2 komplekslerinin tetrahedral ve Cu+2 kompleksinin ise dört koordinasyonlu yapıya sahip olduğu belirlendi. Komplekslerin [M(L)2] formülüne sahip oldukları bulunmuştur. Elde edilen bileşiklerin yapıları, elementel analiz, IR, 1H-NMR, 13C-NMR, Uv, manyetik süsseptibilite ve termogravimetrik analiz ile karakterize edilmiştir.

Anahtar Kelimeler: Schiff bazı, geçiş metal kompleksleri

N,O Tipi Schiff Bazının Bazı Geçiş Metal Kompleksleri: Hazırlanması ve Karakterizasyonu

Abstract

Bu çalışmada, 5-brom-3-metoksi salisilaldehit ve p-aminoasetofenon oksimden türetilmiş Schiff bazı ligandı (5-brom-3- metoksisalisiliden-p-iminoasetofenon oksim) nın metal kompleksleri rapor edildi. Bütün komplekslerde Schiff bazlarının metal iyonuna imin azotu ve fenolik oksijeninden bağlanarak iki dişli şelat olarak davrandığı ve yine bütün komplekslerde M:L oranının 1:2 olduğu görüldü. Co+2, Ni+2 ve Zn+2 komplekslerinin tetrahedral ve Cu+2 kompleksinin ise dört koordinasyonlu yapıya sahip olduğu belirlendi. Komplekslerin [M(L)2] formülüne sahip oldukları bulunmuştur. Elde edilen bileşiklerin yapıları, elementel analiz, IR, 1H-NMR, 13C-NMR, Uv, manyetik süsseptibilite ve termogravimetrik analiz ile karakterize edilmiştir

Keywords

Schiff bazı, geçiş metal kompleksleri

References

• Alexander A., Design and synthesis of macrocyclic ligands and their complexes of lanthanides and actinides. Chem Rev 1995; 95: 273-342
• Vigato P.A., Tamburini S., Bertolo L., The development of compartmental macrocyclic Schiff bases and related polyamine derivatives. Coord Chem Rev 2007; 251: 1311-1492
• Quiruga A.G., Ranninger C.N., Contribution to the SAR field of metallated and coordination complexes: Studies of the palladium and platinum derivatives with selected thiosemicarbazones as antitumoral drugs. Coord Chem Rev 2004; 248: 119-133.
• West D.X., Liberta A.E., Padhye S.B., Chikate R.C., Sonawane P.B., Kumbhar A.S., Yerande R.G., Thiosemicarbazone complexes of copper(II): structural and biological studies. Coord Chem Rev 1993; 123: 49-71.
• Rai B.K., Kumari R., Synthesis, structural, spectroscopic and antibacterial studies of schiff base ligands and their metal complexes containing nitrogen and sulphur donor atomantixancer. Oriental J Chem 2013; 29: 1163-1167.
• Lobana T.S., Sharma R., Bawa G., Khanna S., Bonding and structure trends of thiosemicarbazone derivatives of metals-an overview. Coord Chem Rev 2009; 253: 977-1055.
• Ugras H.I., Basaran I., Kilic T., Cakir U., Synthesis, complexation and antifungal, antibacterial activity studies of a new macrocyclic schiff base. J Het Chem 2006; 43: 1679-1684.
• Shi L., Ge Hui-M., Tan Shu-H., Li Huan-Qiu., Song Yong-C., Zhu Hai-L., Synthesis and antimicrobial activities of Schiff bases derived from 5-chloro-salicylaldehyde. Eur J Med Chem 2007; 42: 558-564.
• Dilmaghani K.A., Jazani N.H., Behrouz A., Fakhraee F.M., Synthesis, characterization and antibacterial activity of some schiff bases derived from 4-aminobenzoic acid. Asian J Chem 2009; 21: 5947-5954.
• Hearn M.J., Cynamon, M.H., Chen M.F., Coppins R., Davis J., Kang HJ-On., Noble A., Tu-Sekine B., Terrot M.S., Trombino D., Thai M., Webster E.R., Wilson R., Preparation and antitubercular activities in vitro and in vivo of novel schiff bases of isoniazid. Eur J Med Chem 2009; 44: 4169- 4178.
• Saghatforoush L.A., Chalabian F., Aminkhani A., Karimnezhad G., Ershad S., Synthesis, spectroscopic characterization and antibacterial activity of new cobalt(II) complexes of unsymmetrical tetradentate (OSN2) schiff base ligands. Eur Med Chem 2009; 44: 4490-4495.
• Yaftian M.R., Rayati S., Safarbali R., Torabi N., Khavasi H.R., A new tetradentate N2O2-type Schiff base ligand. Synthesis, extractive properties towards transition metal ions and X-ray crystal structure of its nickel complex. Trans Met Chem 2007; 32: 374-378.
• Salehzadeh S., Golbedaghi R., Khavasi., H.R., Synthesis, characterization, and crystal structure of a Ni(II) complex of an acyclic pentadentate schiff base; an agreement between the experimental and theoretical results. J Coord Chem 2009; 62: 2532-2539.
• Zhang Chen-X., Cui C., Lu M., Yu L., Zhan Yue-X., In situ synthesis, characterization and crystal structure of a novel cobalt(III) complex with tridentate schiff base. Synth React Inorg Met-Org Nano-Met Chem 2009; 39: 136-138.
• Ramesh R., Sivagamasundari M., Synthesis, spectral and antifungal activity of Ru(II) mixed‐ligand complexes. Synth React Inorg Met-Org Nano-Met Chem 2003; 33: 899-910.
• Tuna S., Canpolat E., Kaya M., Synthesis and characterization of a new 4-methoxysalicyliden-p- aminoacetophenoneoxime and its complexes with Co(II), Ni(II), Cu(II) and Zn(II). Polish J Chem 2006; 80: 1651-1656.
• Canpolat E., Şahal H., Kaya M., Gür S., Synthesis, characterization antibacterial and antifungal activities studies of copper(II), cobalt(II) and zinc(II) complexes of the schiff base ligand derived from 4,4-diaminodiphenylether. J Chem Soc Pakistan 2014; 36: 106-112.
• Saxena A., Tandon J.P., Structural features of some organotin(IV) complexes of semi-and thio- semicarbazones. Polyhedron 1984; 3: 681-688.
• Kukushkin Y.N., Krylov V.K., Kaplan S.F., Calligaris M., Zangrando E., Pombeiro A.J.L., Kukushkin V.Y., Different chlorination modes of oximes: chlorination of salicylaldoxime coordinated to platinum. Inorg Chim Acta 1999; 285: 116-121.
• Bakırdere E.G., Canpolat E., Kaya M., Gür N., Synthesis, antibacterial and antifungal activity of a new 2-{(e)-[(4-aminophenyl) ımino]methyl}-6-methoxy-4-nitrophenol and its complexes with Co(II), Ni(II), Cu(II) and Zn(II). J Chem Soc Pakistan 2012; 34: 1186-1190.
• Satapathy S., Sahoo B., Salicylaldazinate metal chelates and their I.R. spectra. J lnorg Nucl Chem 1970; 32: 2223-2227.
• Canpolat E., Studies on mononuclear chelates derived from substituted schiff bases ligands (part 8): synthesis and characterization of a new 5-chlorosalicyliden-p-aminoacetophenoneoxime and its complexes with Co(II), Ni(II), Cu(II) and Zn(II). Polish J Chem 2005; 79: 619-625.
• Khera B., Sharma A.K., Kaushik N.K., Bis(indenyl)titanium(IV) and zirconium(IV) complexes of monofunctional bidentate salicylidimines. Polyhedron 1983; 2: 1177-1180.
• Maurya R.C., Patel P., Rajput S., Synthesis and characterization of n‐(o‐vanillinidene)‐p‐anisidine and N,N′‐bis(o‐vanillinidene)ethylenediamine and their metal complexes. Synth React Inorg Met- Org Nano-Met Chem 2003; 33: 817-836.
• Bamfield P., The reaction of cobalt halides with N-arylsalicylideneimines. J Chem Soc A: Inorg Phys Theor 1967; 804-808.
• Canpolat E., Kaya M., Studies on mononuclear chelates derived from substituted schiff bases ligands: synthesis and characterization of a new 5-methoxysalicyliden-p-aminoacetophenoneoxime and its complexes with Co(II), Ni(II), Cu(II) and Zn(II). Russian J Coord Chem 2005; 31: 790-794.
• Boucher L.J., Manganese schiff's base complexes—II: Synthesis and spectroscopy of chloro- complexes of some derivatives of (salicylaldehydeethylenediimato) manganese(III). J lnorg Nucl Chem 1974; 36: 531-536.
• Canpolat E., Kaya M., Studies on mononuclear chelates derived from substituted schiff bases ligands (part 4): synthesis and characterization of a new 5-hydroxysalicyliden-p- aminoacetophenoneoxime and its complexes with Co(II), Ni(II), Cu(II) and Zn(II). Turkish J Chem 2005; 29: 409-415.
• Nour E.M., Taha A.A., Alnaimi I.S., Infrared and Raman studies of [UO2(salen)(L)] (L=H2O and CH3OH). Inorg Chem Acta 1988; 141: 139-144.
• Agarwala B.V., Hingorani S., Puri V., Khetrapal C.L., Naganagowda G.A., Physicochemical studies of (o-vanillin thiosemicarbazonato)-nickel(II) chelate. Trans Met Chem 1994; 19: 25-27.
• Canpolat E., Yazıcı A., Kaya M., Studies on mononuclear chelates derived from substituted schiff- base ligands (part 10): synthesis and characterization of a new 4-hydroxysalicyliden-p- aminoacetophenoneoxime and its complexes with Co(II) Ni(II), Cu(II) and Zn(II). J Coord Chem 2007; 60: 473-480.
• Panda P.K., Mishra S.B., Mohapatra B.K. Complexes of cobalt(II), nickel(II), copper(II) and zinc(II) with dicyanadiamide. J lnorg Nucl Chem 1980; 42: 497-499.
• West D.X., Nassar A.A., El-Saied F.A., Ayad M.I., Copper(II) complexes of 2-aminoacetophenone N(4)-substituted thiosemicarbazones. Trans Met Chem 1998; 23: 321-325.
• Aboaly M.M., Khalil M.M.H., Synthesis and spectroscopic study of Cu(II), Ni(II), and Co(II) complexes of the ligand salicylidene-2-amino thiophenol. Spectr Lett 2001; 34: 495-504.
• Yamada S., Takeuchi A., The conformation and interconversion of schiff base complexes of nickel(II) and copper(II). Coord Chem Rev 1982; 43: 187-204.
• Wagner M.R., Walker F.A., Spectroscopic study of 1:1 copper(II) complexes with schiff base ligands derived from salicylaldehyde and L-histidine and its analogs. lnorg Chem 1983; 22: 3021- 3028.
• Atkins R., Brewer G., Kokot E., Mockler G.M., Sinn E., Copper(II) and nickel(II) complexes of unsymmetrical tetradentate schiff base ligands. lnorg Chem 1985;. 24: 127-134.
• Brzyska W., Krol A., Properties and thermal decomposition in air atmosphere of Co(II), Ni(II), Cu(II) and Zn(II) benzene-1,2-dioxyacetates. Therm Acta 1993; 223: 241-249.
• Li S-Lan., Liu D-Xin., Zhang S-Qiang., Wang H., Yang Z-He., Determination of mechanism functions and kinetic parameters of thermodecomposition of complexes with the schiff base derived from 3-methoxysalicylaldehyde and diamine with non-isothermal TG and DTG curves. Therm Acta 1996;. 275: 215-224.
• El-Bindary A.A, El-Sonbati A.Z., Synthesis and properties of complexes of copper(II), nickel(II), cobalt(II) and uranyl ions with 3-(p-tolylsulphonamido)rhodanine. Polish J Chem 2000; 74: 615- 620.