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Synthesis, Characterization of Schiff Base Ligand from Salicylaldehyde Derivative and Investigation of Some Transition Metal Complexes

Year 2019, , 1329 - 1340, 31.12.2019
https://doi.org/10.18185/erzifbed.505339

Abstract

Schiff bases are among the widely used ligands due
to their structural and biological properties and their importance in our
practical life is increasing day by day. In this work, a Schiff base ligand                                                        
[5-methoxysalicylidene-o-aminophenol
(LH)] was synthesized from the reaction of                                                                         5-methoxysalicylaldehyde
and o-aminophenol, a salicylaldehyde
derivative. With using this ligand, complexes were prepared from
Co+2, Ni+2,
Cu+2 ve Zn+2
acetate salts. The Schiff base and complexes
were identified by using Elemental Analysis, FT-IR, 1H-NMR, 13C-NMR,
UV-Vis, Magnetic Susceptibility and TGA as techniques.

References

  • Pfeiffer P., Breith E., Lubbe E., Tsumaki T., 1933, ‘Tricyclische Orthokondenzierte Nebenvolenzringe’, Annalen Der Chemie, 503, 84-127.Tunalı, N.K. ve Özkar, S., 1999, ‘Koordinasyon Bileşikleri’, Anorganik Kimya, Ankara, 263-286.
  • Roberts D. W., Schultz T. W., Api A. M., 2017, ‘Skin Sensitization QMM for HRIPT NOEL Data: Aldehyde Schiff-Base Domain’, Chem. Res. Toxicol., 30(6), 1309-1316.
  • Sharaby C. M., Amine M. F., Hamed A. A., 2017, ‘Synthesis, structure characterization and biological activity of selected metal complexes of sulfonamide Schiff base as a primary ligand and some mixed ligand complexes with glycine as a secondary ligand’, J. Mol. Struct., 1134, 208-216.
  • Birbiçer N., 1998, ‘Suda Çözünülebilir Boyar Maddelerin Metal Komplekslerinin Sentezi ve Boyar Madde Özelliklerinin İncelenmesi’, Doktora Tezi, Çukurova Üniversitesi Fen Bilimleri Enstitüsü, Adana, 69s.
  • Serin, S., Gök, Y., 1988, ‘Hidroksi Schiff Bazı Metal Komplekslerinin Tekstil Boyamacılığında Kullanabilirliğinin İncelenmesi’, T. Kimya D.C., 12, 325-331.
  • Golcu A., Tümer M., Demirelli H., Wheatley R., 2005, ‘Cd(II) and Cu(II) complexes of polydentate Schiff base ligands: synthesis, characterization, properties and biological activity’, Inorg. Chim. Acta, 358, 1785-1797.
  • Silva da C., Silva da D., Modolo L., Alves R., 2011, ‘Schiff bases: A short review of their antimicrobial activities’, J. Ad. Res., 2, 1-8.
  • Rehman W., Baloch M. K., Muhammad B., Badshah A., Khan K. M., 2004, ‘Characteristic spectral studies and in vitro antifungal activity of some Schiff bases and their organotin (IV) complexes’, Chin. Sci. Bull., 49, 119-122.
  • Scovill J.P., Klayman D. L., Franchino F.F., 1982, ‘2-Acetylpyridine Thiosemicarbazones. 4. Complexes with Transition Metals as Antimalarial and Antileukemic Agents’, Journal of Medicinal Chemistry, 25 (10), 1261-1264.
  • West D.X., Pannell L.K., 1989, ‘Transition-Metal Ion Complexes of Thiosemicarbazones Derived from 2-Acetrypyridine N-oxide 2 the N-4- Dimethyl Derivative’, Transition Metal Chemistry, 14 (6), 457-462.
  • Tuna, S., ‘Aromatik Amin İçeren Schiff Bazı Ligandlarının Sentezi, Karakterizasyonu ve Bazı Geçiş Metal Komplekslerinin İncelenmesi’, 2010, Doktora Tezi, Fırat Üniversitesi Fen Bilimleri Enstitüsü, Elazığ.
  • Brown, J.F., 1955, ‘The Infrared Spectra of Nitro and Other Oxidized Nitrogen Compounds’, J. Am. Chem. Soc., 77, 6341-6351.
  • Hundekar, A.M. and Sen, D.N., 1984, ‘Preparation and Characterization of Metal Complexes of N-Acetyl-Aroylferrocenyl Hydrazides’, Indian J. Chem. A., 23(6), 477-479.
  • Saxena, A. And Tandon, J.P., 1984, ‘Structural Features of Some Organotin(IV) Complexes of Semi-Semicarbazone and Thio-Semicarbazones’, Polyhedron, 3(6), 681-688.
  • Nelson, S.M., Knox, C.V., McCann, M. And Drew, M.G.B., 1981, ‘Metal-Ion-Controlled Transamination in the Synthesis of Macrocyclic Schiff Base Ligands-Reactions of 2,6-Diacetylpyridine and Dicarbonyl Compounds with 3,6-Dioxaoctane-1,8-Diamine’, J. Chem. Soc. Dalton Trans., 8, 1669-1677.
  • Canpolat, E. And Kaya, M., 2003, ‘The Synthesis and Characterization of A Novel (E-E)-Dioxime and Its Mononuclear Complexes Containing 1,3-Dioxolane Moieties’, Polish J. Chem., 77, 961-968.
  • Canpolat, E., 2003, ‘İmin ve Oksim İçeren Ligandların Sentezi, Karakterizasyonu ve Bu Ligandların Bazı Metal Komplekslerinin İncelenmesi’, Doktora Tezi, Fırat Üniversitesi Fen Bilimleri Enstitüsü, Elazığ.
  • Levy, G.C. and Nelson, G.L., 1972, ‘Carbon-13 Nuclear Magnetic Resonance for Organic Chemists’, Wiley-Interscience, New York.
  • Atkins, R., Brewer, G. Kokot, E., Mockler, G.M. and Sin, E., 1985, ‘Copper(II) and Nickel(II) Complexes of Unsymmetrical Tetradentate Schiff Base Ligands’, Inorg. Chem., 24(2), 127-134.
  • Yamada, S. And Takeuchi, A., 1982, ‘The Conformation and Interconversion of Schiff Base Complexes of Nickel(II) and Copper(II)’, Coord. Chem. Rev., 43, 187-204.
  • Wagner, M.R. and Walker, F.A., 1983, ‘Spectroscopic Study of 1:1 Copper(II) Complexes with Schiff Base Ligands Derived from Salicylaldehyde and L-Histidine and Its Analogs’, Inorg. Chem., 22, 3021-3028.
  • Sharma, P.K., Sen, A.K., Singh, K. and Dubey, S.N., 1997, ‘Divalent Cobalt, Copper and Zinc Complexes of N-Salicylideneamino Acids’, J.Indian Chem. Soc., 74(6), 446-447.
  • West, B. 1952, ‘Studies on Bond Type in Certain Cobalt Complexes II Constitution of Cobalt Complexes with Salicylaldehyde Anils’, J. Chem. Soc., 3123-3129.
  • Maurya, R.C., Patel, P. and Rajput, S., 2003, ‘Synthesis and Characterization of N-(o-vanilinidene)-p-anisidine and N,N’-bis(o-vanillinidene)ethylenediamine and Their Metal Complexes’, Synth. React. Inorg. Met. Org. Chem., 33(5), 817-836.
  • Çelik, C., Tümer, M. And Serin, S., 2002, ‘Complexes of Tetradentate Schiff Base Ligands with Divalent Transition Metals’, Synth. React. Inorg. Met. Org. Chem., 32(10), 1839-1854.
  • Li, S.L., Liu, D.X., Zhang, S.Q., Wang, H. And Yang, Z.H., 1996, ‘Determinetion of Mechanism Function and Kinetic Parameters of Thermodecomposition of Complexes with the Schiff Base Derived From 3-Methoxysalicylaldehyde and Diamine with Non-Isothermal TG and DTG Curves’, Thermochim. Acta., 275(2), 215-224.

Salisilaldehit Türevinden Schiff Bazı Ligandının Sentezi, Karakterizasyonu ve Bazı Geçiş Metal Komplekslerinin İncelenmesi

Year 2019, , 1329 - 1340, 31.12.2019
https://doi.org/10.18185/erzifbed.505339

Abstract

Schiff bazları, yapısal ve biyolojik
özelliklerinden dolayı yaygın olarak kullanılan ligandlar arasında yer
almaktadır ve bunların pratik hayatımızdaki önemi de gün geçtikçe artmaktadır. Bu
çalışmada, bir salisilaldehit türevi olan 5-metoksisalisilaldehit ile o-aminofenol’ün reaksiyonundan bir
Schiff bazı ligandı                                              [5-metoksisalisiliden-o-aminofenol (LH)] sentezlendi. Bu ligand ile Co+2, Ni+2,
Cu+2 ve Zn+2 asetat tuzlarından kompleksleri hazırlandı.
Schiff bazı ve kompleksleri elementel analiz, IR, 1H-NMR, 13C-NMR,
UV-Vis, manyetik süsseptibilite ve TGA yöntemleri kullanılarak aydınlatıldı.
 

References

  • Pfeiffer P., Breith E., Lubbe E., Tsumaki T., 1933, ‘Tricyclische Orthokondenzierte Nebenvolenzringe’, Annalen Der Chemie, 503, 84-127.Tunalı, N.K. ve Özkar, S., 1999, ‘Koordinasyon Bileşikleri’, Anorganik Kimya, Ankara, 263-286.
  • Roberts D. W., Schultz T. W., Api A. M., 2017, ‘Skin Sensitization QMM for HRIPT NOEL Data: Aldehyde Schiff-Base Domain’, Chem. Res. Toxicol., 30(6), 1309-1316.
  • Sharaby C. M., Amine M. F., Hamed A. A., 2017, ‘Synthesis, structure characterization and biological activity of selected metal complexes of sulfonamide Schiff base as a primary ligand and some mixed ligand complexes with glycine as a secondary ligand’, J. Mol. Struct., 1134, 208-216.
  • Birbiçer N., 1998, ‘Suda Çözünülebilir Boyar Maddelerin Metal Komplekslerinin Sentezi ve Boyar Madde Özelliklerinin İncelenmesi’, Doktora Tezi, Çukurova Üniversitesi Fen Bilimleri Enstitüsü, Adana, 69s.
  • Serin, S., Gök, Y., 1988, ‘Hidroksi Schiff Bazı Metal Komplekslerinin Tekstil Boyamacılığında Kullanabilirliğinin İncelenmesi’, T. Kimya D.C., 12, 325-331.
  • Golcu A., Tümer M., Demirelli H., Wheatley R., 2005, ‘Cd(II) and Cu(II) complexes of polydentate Schiff base ligands: synthesis, characterization, properties and biological activity’, Inorg. Chim. Acta, 358, 1785-1797.
  • Silva da C., Silva da D., Modolo L., Alves R., 2011, ‘Schiff bases: A short review of their antimicrobial activities’, J. Ad. Res., 2, 1-8.
  • Rehman W., Baloch M. K., Muhammad B., Badshah A., Khan K. M., 2004, ‘Characteristic spectral studies and in vitro antifungal activity of some Schiff bases and their organotin (IV) complexes’, Chin. Sci. Bull., 49, 119-122.
  • Scovill J.P., Klayman D. L., Franchino F.F., 1982, ‘2-Acetylpyridine Thiosemicarbazones. 4. Complexes with Transition Metals as Antimalarial and Antileukemic Agents’, Journal of Medicinal Chemistry, 25 (10), 1261-1264.
  • West D.X., Pannell L.K., 1989, ‘Transition-Metal Ion Complexes of Thiosemicarbazones Derived from 2-Acetrypyridine N-oxide 2 the N-4- Dimethyl Derivative’, Transition Metal Chemistry, 14 (6), 457-462.
  • Tuna, S., ‘Aromatik Amin İçeren Schiff Bazı Ligandlarının Sentezi, Karakterizasyonu ve Bazı Geçiş Metal Komplekslerinin İncelenmesi’, 2010, Doktora Tezi, Fırat Üniversitesi Fen Bilimleri Enstitüsü, Elazığ.
  • Brown, J.F., 1955, ‘The Infrared Spectra of Nitro and Other Oxidized Nitrogen Compounds’, J. Am. Chem. Soc., 77, 6341-6351.
  • Hundekar, A.M. and Sen, D.N., 1984, ‘Preparation and Characterization of Metal Complexes of N-Acetyl-Aroylferrocenyl Hydrazides’, Indian J. Chem. A., 23(6), 477-479.
  • Saxena, A. And Tandon, J.P., 1984, ‘Structural Features of Some Organotin(IV) Complexes of Semi-Semicarbazone and Thio-Semicarbazones’, Polyhedron, 3(6), 681-688.
  • Nelson, S.M., Knox, C.V., McCann, M. And Drew, M.G.B., 1981, ‘Metal-Ion-Controlled Transamination in the Synthesis of Macrocyclic Schiff Base Ligands-Reactions of 2,6-Diacetylpyridine and Dicarbonyl Compounds with 3,6-Dioxaoctane-1,8-Diamine’, J. Chem. Soc. Dalton Trans., 8, 1669-1677.
  • Canpolat, E. And Kaya, M., 2003, ‘The Synthesis and Characterization of A Novel (E-E)-Dioxime and Its Mononuclear Complexes Containing 1,3-Dioxolane Moieties’, Polish J. Chem., 77, 961-968.
  • Canpolat, E., 2003, ‘İmin ve Oksim İçeren Ligandların Sentezi, Karakterizasyonu ve Bu Ligandların Bazı Metal Komplekslerinin İncelenmesi’, Doktora Tezi, Fırat Üniversitesi Fen Bilimleri Enstitüsü, Elazığ.
  • Levy, G.C. and Nelson, G.L., 1972, ‘Carbon-13 Nuclear Magnetic Resonance for Organic Chemists’, Wiley-Interscience, New York.
  • Atkins, R., Brewer, G. Kokot, E., Mockler, G.M. and Sin, E., 1985, ‘Copper(II) and Nickel(II) Complexes of Unsymmetrical Tetradentate Schiff Base Ligands’, Inorg. Chem., 24(2), 127-134.
  • Yamada, S. And Takeuchi, A., 1982, ‘The Conformation and Interconversion of Schiff Base Complexes of Nickel(II) and Copper(II)’, Coord. Chem. Rev., 43, 187-204.
  • Wagner, M.R. and Walker, F.A., 1983, ‘Spectroscopic Study of 1:1 Copper(II) Complexes with Schiff Base Ligands Derived from Salicylaldehyde and L-Histidine and Its Analogs’, Inorg. Chem., 22, 3021-3028.
  • Sharma, P.K., Sen, A.K., Singh, K. and Dubey, S.N., 1997, ‘Divalent Cobalt, Copper and Zinc Complexes of N-Salicylideneamino Acids’, J.Indian Chem. Soc., 74(6), 446-447.
  • West, B. 1952, ‘Studies on Bond Type in Certain Cobalt Complexes II Constitution of Cobalt Complexes with Salicylaldehyde Anils’, J. Chem. Soc., 3123-3129.
  • Maurya, R.C., Patel, P. and Rajput, S., 2003, ‘Synthesis and Characterization of N-(o-vanilinidene)-p-anisidine and N,N’-bis(o-vanillinidene)ethylenediamine and Their Metal Complexes’, Synth. React. Inorg. Met. Org. Chem., 33(5), 817-836.
  • Çelik, C., Tümer, M. And Serin, S., 2002, ‘Complexes of Tetradentate Schiff Base Ligands with Divalent Transition Metals’, Synth. React. Inorg. Met. Org. Chem., 32(10), 1839-1854.
  • Li, S.L., Liu, D.X., Zhang, S.Q., Wang, H. And Yang, Z.H., 1996, ‘Determinetion of Mechanism Function and Kinetic Parameters of Thermodecomposition of Complexes with the Schiff Base Derived From 3-Methoxysalicylaldehyde and Diamine with Non-Isothermal TG and DTG Curves’, Thermochim. Acta., 275(2), 215-224.
There are 26 citations in total.

Details

Primary Language Turkish
Subjects Engineering
Journal Section Makaleler
Authors

Sümeyra Tuna Yıldırım 0000-0001-5564-9630

Publication Date December 31, 2019
Published in Issue Year 2019

Cite

APA Tuna Yıldırım, S. (2019). Salisilaldehit Türevinden Schiff Bazı Ligandının Sentezi, Karakterizasyonu ve Bazı Geçiş Metal Komplekslerinin İncelenmesi. Erzincan University Journal of Science and Technology, 12(3), 1329-1340. https://doi.org/10.18185/erzifbed.505339