Research Article
BibTex RIS Cite

SYNTHESIS and CHARACTERIZATION of a NOVEL BENZIMIDAZOLE-OXIME LIGAND and ITS Fe(II), Co(II), Ni(II), Cu(II) and Zn(II) COMPLEXES

Year 2022, Issue: 049, 1 - 11, 30.06.2022

Abstract

(1E, 2Z)-2-(1H-benzoimidazol-1-yl)-2-(hydroxyimino)acetaldehyde oxime (H2L) and its metal(II) complexes (1-5) (Fe, Co, Ni, Cu and Zn) were obtained using anti-monochloroglyoxime (glyox) and 1H-benzimidazole (HBI) in absolute ethanol for the first time. The H2L was characterized by 1H-NMR, elemental analysis, IR, and UV-Vis methods while IR, elemental analysis, UV-Vis, ICP-OES, TGA, molar conductivity and magnetic susceptibility techniques were applied to analyse of metal complexes (1-5).

Thanks

This work was supported by Dumlupınar University Research Foundation (Grant No: 2010-02) and was carried out at the Chemistry Department of same University. In addition, the author would like to thank Prof. Dr. Cengiz YENİKAYA.

References

  • [1] Coban, B., Eser, N., Babahan, I., (2017), DNA binding by copper (II) complexes of semithiocarbazone containing ligands, Bulgarian Chemical Communications, 49(4), 908-913.
  • [2] Deveci, P., Taner B., (2013), Synthesis, spectroscopic, and cyclic voltammetric studies of ferrocene containing vic-dioxime ligand and its complexes with Ni(II), Cu(II), Co(II), Cd(II) and Zn(II), Inorganica Chimica Acta, 405, 326-330.
  • [3] Motaleb, M. A., Selim, A. A. (2019), Dioximes: Synthesis and biomedical applications, Bioorganic Chemistry, 82, 145-155.
  • [4] Tuyun, A. F., Bayrak, N., Yıldırım, H., Yıldız, M., Kara, E. M. Celik, B. O., (2021), Bis(Substituted Phenylamino)Glyoxime derivatives: Synthesis, characterization, and antimicrobial evaluation, Journal of Molecular Structure, 1242, 130812.
  • [5] Findik, M., Ucar, A., Türkkan E., Pehlivanoglu, S., Ozcan E., (2021), Synthesis of anti-4-phenoxyphenylaminoglyoxime and its some transition metal complexes: Spectral, DFT, electrochemical and anticancer activity studies, Journal of Molecular Structure, 1215, 128190.
  • [6] Deveci, P., Taner, B., Kılıç, Z., Solak, A.O. and Özcan, E., (2012), Synthesis and structural and electrochemical characterization of novel macrocyclic vic-dioxime ligand and its mononuclear transition and nontransition metal complexes, Turkish Journal Of Chemistry, 36, 25-36.
  • [7] Yenikaya, C., Kaya, M. and Demir, İ., (2008), Synthesis of a imine vic-dioxime ligand and its Ni(II), Co(II), Cu(II) complexes, Asian Journal of Chemistry, 20(7), 5651-5657.
  • [8] Kaya, M., Demir, İ. and Yenikaya, C., (2008), Synthesis and characterization of complexes of vic-dioxime derivatives with transition metal. Asian Journal of Chemistry, 20(3), 2221-2228.
  • [9] Kaya, M., Yenikaya, C., Demir, İ. and Kalfa, O.M., (2008), Synthesis and characteristics of N-(glyoxyldioxime)-N′-(2-hydroxybenzylidene)-1,4-diaminonaphthalene and its metal complexes, Russian Journal of General Chemistry, 78(5), 939-945.
  • [10] Kaya, M., Yenikay,a C., Çolak, A.T. and Çolak, F., (2008), Synthesis, spectral, thermal and biological studies of Co(III) and binuclear Ni(II) complexes with a novel amine-imine-oxime ligand, Russian Journal of General Chemistry, 78(9), 1808-1815.
  • [11] Canpolat, E., Yazıcı, A., Kaya, M. (2004), Synthesis and Characterization of Co(II), Ni(II), Cu(II), and Zn(II) Complexes with a new vic-dioxime (E,E)-N′-hydroxy-2-(hydroxyimino)-N-(4-{[(2-phenyl-1,3-dioxolan-4yl)methyl]amino}butyl)ethanimidamide. Russian Journal of Coordination Chemistry, 30(2), 87-93.
  • [12] Poyraz, M., Yenikaya, C. and Çolak, A.T., (2008), Synthesis and Structural Studies of Bidentate Schiff Bases and Their Complexes with Cu(II), Ni(II), Co(II), Cd(II) and Zn(II), Asian Journal of Chemistry, 20(5), 3515-3524.
  • [13] Gök, Y. and Demirbas, A., (1989), The Synthesis and Complex Formation of Dibenzo [e,k]-2,3-Bis(Hydroxyimino)-1,4-Diaza-7,10-Dithia-2,3,8,9-Tetrahydrocyclododecine, Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 19(5), 681-689.
  • [14] Gül, A. and Bekaroglu, O., (1983), Syntheses of NN′-bis(4′-benzo[15-crown-5])diaminoglyoxime and its complexes with copper(II), nickel(II), cobalt(II), cobalt(III), palladium(II), platinum(II), and uranyl(VI), Journal of the Chemical Society, Dalton Transactions, 12, 2537-2541.
  • [15] Kurtoğlu, M and Serin, S., (2002), Syntheses and characterization of 4-(11-chloro-3,6,9-trioxaundecyloxy) phenylamino-glyoxime and its complexes with copper(II), nickel(II), and cobalt(II), Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 32(3), 629-637.
  • [16] Durmus, M., Ahsen, V., Luneau, D. and Pécaut, J., (2004), Synthesis and structures of morpholine substituted new vic-dioxime ligand and its Ni(II) complexes, Inorganica Chimica Acta, 357(2), 588-594.
  • [17] Atilla, D., Asma, S. and Gurek, A., (2009), Highly soluble Ni(II) vic-dioxime complexes containing branched thioether with alkyl chains of different lengths:synthesis and characterization, Journal of Coordination Chemistry, 62(18), 3050–3059.
  • [18] Walia, R., Md, H., Naaz, S.F., Iqbal, K. and Lamba H.S., (2011), Benzimidazole derivatives – an overview, International Journal Of Research In Pharmacy and Chemistry, 1(3):565-573.
  • [19] Téllez, F., López-Sandoval, H., Castillo-Blum, S.E. and Barba-Behrens, N., (2008), Coordination behavior of benzimidazole, 2-substituted benzimidazoles and benzothiazoles, towards transition metal ions, Arkivoc, (v), 245-275.
  • [20] Pawar, N.S., Dalal, D.S., Shimpi, S.R. and Mahulikar, P.P., (2004), Studies of antimicrobial activity of N-alkyl and N-acyl 2-(4-thiazolyl)-1H-benzimidazoles, European Journal Of Pharmaceutical Sciences, 21, 115-118.
  • [21] Özden, S., Atabey, D., Yildiz S. and Göker, H., (2005), Synthesis and potent antimicrobial activity of some novel methyl or ethyl 1H-benzimidazole-5-carboxylates derivatives carrying amide or amidine groups, Bioorganic & Medicinal Chemistry, 13(5), 1587-1597.
  • [22] Ören, I., Temiz, Ö., Yalcin, I., Sener, E. and Altanlar, N., (1998), Synthesis and antimicrobial activity of some novel 2, 5-and/or 6-substituted benzoxazole and benzimidazole derivatives, European Journal Of Pharmaceutical Sciences, 7, 153-160.
  • [23] He, Y., Ww, B., Yang, J., Robinson, D., Risen, L., Ranken, R., Blyn, L., Sheng, S. and Swayze, E.E., (2003), 2-Piperidin-4-yl-benzimidazoles with broad spectrum antibacterial activities, Bioorganic & Medicinal Chemistry Letters, 13(19): 3253-3256.
  • [24] Varhelyi, Cs. Jr., Kovacs, A., Nemcsok, D., Nemeth, Z., Kuzmann, E., Vertes, A., Vekey, K., Varhelyi, Cs., Pokol, G., (2007), Spectroscopic and thermal studies of [Fe(dioximato) (amine)]mixed chelates, Journal of Coordination Chemistry 60(4), 379-392.
  • [25] Gok, Y., Ertepinar, H., (1992), Synthesis and Characterization of Novel Polyamidoxime Transition Metal Complexes. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 22(10), 1495–1505.
  • [26] Ertepinar, H., Gök, Y., Küçükislamoğlu, M. (1995), Synthesis and characterizations of new polyamidoximes and their crosslinking by metal ions. European Polymer Journal, 31(6), 603–608.
  • [27] Kraska, J., Czajkowski, W.,(1982), Metal complex pigments, Poland, PL123437 B2
  • [28] Zsako, J., Varhelyi, C., Demeter-Vodnar, J., Liptay, G., (1992), On the dioxime complexes of transition metals. XCV. New iodo-amino-bis-dimethylglyoximatocobalt(III)-nonelectrolytes, Periodica Polytechnica, Chemical Engineering, 36(4), 271-278.
  • [29] Zsako, J., Varhelyi, C., Sarvari, T., (1989), On the dioximine complexes of transition metals. LXXIX. Some new chelates of iron with nioxime and trioxime, Studia Universitatis Babes-Bolyai, Chemia, 34(2), 10-15.
  • [30] Houben, J. and Kaufman, H., (1913), Über Chlor-glyoxime, Oxim-Derivate des Oxalylchlorids und Oxalsäure-halbchlorids und über Cyan-formyl-chloridoxim, Berichte der deutschen chemischen Gesellschaft, 46, 2821-2835.
  • [31] March, J., (1977), Advanced Organic Chemistry: Reaction, Mechanisms, Structure, 609.
  • [32] Phillips, M.A., (1931), CCCXVII.—The formation of 2-substituted benziminazoles, Journal of the Chemical Society, 1143-1153.
  • [33] Ueno, K. and Martell, A.E., (1956), Infrared studies on synthetic oxygen carriers, The Journal of Physical Chemistry, 60, 1270-1275.
  • [34] Nakamoto, K. and Martell, A.E., (1960), Infrared Spectra of Metal Chelate Compounds. VI. A Normal Coordinate Treatment of Oxalato Metal Complexes, The Journal of Chemical Physics, 32, 588-588.
  • [35] Coleman, W.M. and Taylor, L.T., (1971), Pentadentate ligands. I. Nickel(II) complexes of the linear Schiff base ligands derived from substituted salicylaldehydes and diethylenetriamine and 2,2'-bis(aminopropyl)amine, Inorganic Chemistry, 10, 2195-2199.
  • [36] Geary, W.J., (1971), The Use of Conductivity Measurements in Organic Solvents for the Characterisation of Coordination Compounds. Coordination Chemistry Reviews, 7, 81-122.
Year 2022, Issue: 049, 1 - 11, 30.06.2022

Abstract

References

  • [1] Coban, B., Eser, N., Babahan, I., (2017), DNA binding by copper (II) complexes of semithiocarbazone containing ligands, Bulgarian Chemical Communications, 49(4), 908-913.
  • [2] Deveci, P., Taner B., (2013), Synthesis, spectroscopic, and cyclic voltammetric studies of ferrocene containing vic-dioxime ligand and its complexes with Ni(II), Cu(II), Co(II), Cd(II) and Zn(II), Inorganica Chimica Acta, 405, 326-330.
  • [3] Motaleb, M. A., Selim, A. A. (2019), Dioximes: Synthesis and biomedical applications, Bioorganic Chemistry, 82, 145-155.
  • [4] Tuyun, A. F., Bayrak, N., Yıldırım, H., Yıldız, M., Kara, E. M. Celik, B. O., (2021), Bis(Substituted Phenylamino)Glyoxime derivatives: Synthesis, characterization, and antimicrobial evaluation, Journal of Molecular Structure, 1242, 130812.
  • [5] Findik, M., Ucar, A., Türkkan E., Pehlivanoglu, S., Ozcan E., (2021), Synthesis of anti-4-phenoxyphenylaminoglyoxime and its some transition metal complexes: Spectral, DFT, electrochemical and anticancer activity studies, Journal of Molecular Structure, 1215, 128190.
  • [6] Deveci, P., Taner, B., Kılıç, Z., Solak, A.O. and Özcan, E., (2012), Synthesis and structural and electrochemical characterization of novel macrocyclic vic-dioxime ligand and its mononuclear transition and nontransition metal complexes, Turkish Journal Of Chemistry, 36, 25-36.
  • [7] Yenikaya, C., Kaya, M. and Demir, İ., (2008), Synthesis of a imine vic-dioxime ligand and its Ni(II), Co(II), Cu(II) complexes, Asian Journal of Chemistry, 20(7), 5651-5657.
  • [8] Kaya, M., Demir, İ. and Yenikaya, C., (2008), Synthesis and characterization of complexes of vic-dioxime derivatives with transition metal. Asian Journal of Chemistry, 20(3), 2221-2228.
  • [9] Kaya, M., Yenikaya, C., Demir, İ. and Kalfa, O.M., (2008), Synthesis and characteristics of N-(glyoxyldioxime)-N′-(2-hydroxybenzylidene)-1,4-diaminonaphthalene and its metal complexes, Russian Journal of General Chemistry, 78(5), 939-945.
  • [10] Kaya, M., Yenikay,a C., Çolak, A.T. and Çolak, F., (2008), Synthesis, spectral, thermal and biological studies of Co(III) and binuclear Ni(II) complexes with a novel amine-imine-oxime ligand, Russian Journal of General Chemistry, 78(9), 1808-1815.
  • [11] Canpolat, E., Yazıcı, A., Kaya, M. (2004), Synthesis and Characterization of Co(II), Ni(II), Cu(II), and Zn(II) Complexes with a new vic-dioxime (E,E)-N′-hydroxy-2-(hydroxyimino)-N-(4-{[(2-phenyl-1,3-dioxolan-4yl)methyl]amino}butyl)ethanimidamide. Russian Journal of Coordination Chemistry, 30(2), 87-93.
  • [12] Poyraz, M., Yenikaya, C. and Çolak, A.T., (2008), Synthesis and Structural Studies of Bidentate Schiff Bases and Their Complexes with Cu(II), Ni(II), Co(II), Cd(II) and Zn(II), Asian Journal of Chemistry, 20(5), 3515-3524.
  • [13] Gök, Y. and Demirbas, A., (1989), The Synthesis and Complex Formation of Dibenzo [e,k]-2,3-Bis(Hydroxyimino)-1,4-Diaza-7,10-Dithia-2,3,8,9-Tetrahydrocyclododecine, Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 19(5), 681-689.
  • [14] Gül, A. and Bekaroglu, O., (1983), Syntheses of NN′-bis(4′-benzo[15-crown-5])diaminoglyoxime and its complexes with copper(II), nickel(II), cobalt(II), cobalt(III), palladium(II), platinum(II), and uranyl(VI), Journal of the Chemical Society, Dalton Transactions, 12, 2537-2541.
  • [15] Kurtoğlu, M and Serin, S., (2002), Syntheses and characterization of 4-(11-chloro-3,6,9-trioxaundecyloxy) phenylamino-glyoxime and its complexes with copper(II), nickel(II), and cobalt(II), Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 32(3), 629-637.
  • [16] Durmus, M., Ahsen, V., Luneau, D. and Pécaut, J., (2004), Synthesis and structures of morpholine substituted new vic-dioxime ligand and its Ni(II) complexes, Inorganica Chimica Acta, 357(2), 588-594.
  • [17] Atilla, D., Asma, S. and Gurek, A., (2009), Highly soluble Ni(II) vic-dioxime complexes containing branched thioether with alkyl chains of different lengths:synthesis and characterization, Journal of Coordination Chemistry, 62(18), 3050–3059.
  • [18] Walia, R., Md, H., Naaz, S.F., Iqbal, K. and Lamba H.S., (2011), Benzimidazole derivatives – an overview, International Journal Of Research In Pharmacy and Chemistry, 1(3):565-573.
  • [19] Téllez, F., López-Sandoval, H., Castillo-Blum, S.E. and Barba-Behrens, N., (2008), Coordination behavior of benzimidazole, 2-substituted benzimidazoles and benzothiazoles, towards transition metal ions, Arkivoc, (v), 245-275.
  • [20] Pawar, N.S., Dalal, D.S., Shimpi, S.R. and Mahulikar, P.P., (2004), Studies of antimicrobial activity of N-alkyl and N-acyl 2-(4-thiazolyl)-1H-benzimidazoles, European Journal Of Pharmaceutical Sciences, 21, 115-118.
  • [21] Özden, S., Atabey, D., Yildiz S. and Göker, H., (2005), Synthesis and potent antimicrobial activity of some novel methyl or ethyl 1H-benzimidazole-5-carboxylates derivatives carrying amide or amidine groups, Bioorganic & Medicinal Chemistry, 13(5), 1587-1597.
  • [22] Ören, I., Temiz, Ö., Yalcin, I., Sener, E. and Altanlar, N., (1998), Synthesis and antimicrobial activity of some novel 2, 5-and/or 6-substituted benzoxazole and benzimidazole derivatives, European Journal Of Pharmaceutical Sciences, 7, 153-160.
  • [23] He, Y., Ww, B., Yang, J., Robinson, D., Risen, L., Ranken, R., Blyn, L., Sheng, S. and Swayze, E.E., (2003), 2-Piperidin-4-yl-benzimidazoles with broad spectrum antibacterial activities, Bioorganic & Medicinal Chemistry Letters, 13(19): 3253-3256.
  • [24] Varhelyi, Cs. Jr., Kovacs, A., Nemcsok, D., Nemeth, Z., Kuzmann, E., Vertes, A., Vekey, K., Varhelyi, Cs., Pokol, G., (2007), Spectroscopic and thermal studies of [Fe(dioximato) (amine)]mixed chelates, Journal of Coordination Chemistry 60(4), 379-392.
  • [25] Gok, Y., Ertepinar, H., (1992), Synthesis and Characterization of Novel Polyamidoxime Transition Metal Complexes. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 22(10), 1495–1505.
  • [26] Ertepinar, H., Gök, Y., Küçükislamoğlu, M. (1995), Synthesis and characterizations of new polyamidoximes and their crosslinking by metal ions. European Polymer Journal, 31(6), 603–608.
  • [27] Kraska, J., Czajkowski, W.,(1982), Metal complex pigments, Poland, PL123437 B2
  • [28] Zsako, J., Varhelyi, C., Demeter-Vodnar, J., Liptay, G., (1992), On the dioxime complexes of transition metals. XCV. New iodo-amino-bis-dimethylglyoximatocobalt(III)-nonelectrolytes, Periodica Polytechnica, Chemical Engineering, 36(4), 271-278.
  • [29] Zsako, J., Varhelyi, C., Sarvari, T., (1989), On the dioximine complexes of transition metals. LXXIX. Some new chelates of iron with nioxime and trioxime, Studia Universitatis Babes-Bolyai, Chemia, 34(2), 10-15.
  • [30] Houben, J. and Kaufman, H., (1913), Über Chlor-glyoxime, Oxim-Derivate des Oxalylchlorids und Oxalsäure-halbchlorids und über Cyan-formyl-chloridoxim, Berichte der deutschen chemischen Gesellschaft, 46, 2821-2835.
  • [31] March, J., (1977), Advanced Organic Chemistry: Reaction, Mechanisms, Structure, 609.
  • [32] Phillips, M.A., (1931), CCCXVII.—The formation of 2-substituted benziminazoles, Journal of the Chemical Society, 1143-1153.
  • [33] Ueno, K. and Martell, A.E., (1956), Infrared studies on synthetic oxygen carriers, The Journal of Physical Chemistry, 60, 1270-1275.
  • [34] Nakamoto, K. and Martell, A.E., (1960), Infrared Spectra of Metal Chelate Compounds. VI. A Normal Coordinate Treatment of Oxalato Metal Complexes, The Journal of Chemical Physics, 32, 588-588.
  • [35] Coleman, W.M. and Taylor, L.T., (1971), Pentadentate ligands. I. Nickel(II) complexes of the linear Schiff base ligands derived from substituted salicylaldehydes and diethylenetriamine and 2,2'-bis(aminopropyl)amine, Inorganic Chemistry, 10, 2195-2199.
  • [36] Geary, W.J., (1971), The Use of Conductivity Measurements in Organic Solvents for the Characterisation of Coordination Compounds. Coordination Chemistry Reviews, 7, 81-122.
There are 36 citations in total.

Details

Primary Language English
Journal Section Research Articles
Authors

Halil İlkimen 0000-0003-1747-159X

Publication Date June 30, 2022
Submission Date September 30, 2021
Published in Issue Year 2022 Issue: 049

Cite

IEEE H. İlkimen, “SYNTHESIS and CHARACTERIZATION of a NOVEL BENZIMIDAZOLE-OXIME LIGAND and ITS Fe(II), Co(II), Ni(II), Cu(II) and Zn(II) COMPLEXES”, JSR-A, no. 049, pp. 1–11, June 2022.