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Yeni Bir Ligand ve Pd(II), Ru(II), Fe(II), Co(II) Komplekslerinin Sentezi, Karakterizasyonu ve Antimikrobiyal Özellikleri

Year 2018, Volume:6 No:2 (2018) (Special Issue: IMCOFE 2017), 433 - 443, 06.04.2018

Abstract

Schiff bazları ve kompleksleri, karbonil bileşikleri ile bir amino bileşiğinin kondenzasyonundan sentezlenen ve endüstriyel amaçlı yaygın olarak kullanılan ve ayrıca geniş bir aralıkta antifungal, antibakteriyel, antimalarial, antiproliferatif, antiviral ve antipiretik özellikler sergileyen çok yönlü bileşiklerdir. Bu çalışmada, (E)-2-(3,5-ditert-bütil-2-hidroksibenzilidenamino)-6-metil 4,5,6,7-tetrahidrobenzo[b]tiyofen-3-karbonitril (L) ile Co(II), Fe(II), Pd(II) ve Ru(II) kompleksleri başarıyla hazırlandı. Elde edilen Schiff bazı ve metal komplekslerinin yapıları FT-IR, 1H-NMR, 13C-NMR, UV-vis, manyetik süsseptibilite, kütle spektroskopisi ve element analiz yöntemleri ile belirlendi. Sentezlenen Schiff bazı ve metal komplekslerinin antimikrobiyal aktiviteleri çalışıldı.Antimikrobiyal aktivitelere bakıldığında en düşük aktiviteyi ligandın gösterdiği, en yüksek aktiviteyi ise Co(II) ve Pd(II) komplekslerinin gösterdiği görüldü. Maddelerimizin hiçbirinin antifungal aktivite göstermedikleri tespit edilmiştir.

References

  • [1] P. Chaudhuri, K. Wieghardt, “Phenoxyl radical complexes,’’ Prog. Inorg. Chem., vol. 50, pp. 151-216, 2001.
  • [2] A. D. Garnovski, A. P. Sadimenko, M. C. Sadimenko, D. A. Garnovski, “Common and less-common coordination modes of the typical chelating and heteroaromatic ligands,’’ Coord. Chem Rev., vol. 173, pp. 31-77, 1998.
  • [3] H. Keypour, M. Shayesteh, M. Rezaeivala, F. Chalabian, Y. Elerman, O. Buyukgungor, “Synthesis, spectral characterization, structural investigation and antimicrobial studies of mononuclear Cu(II), Ni(II), Co(II), Zn(II) and Cd(II) complexes of a new potentially hexadentate N2O4 Schiff base ligand derived from salicylaldehyde,’’ J. Mol. Struct., Vol. 1032, pp. 62-68, 2013.
  • [4] A. D. Tiwari, A. K. Mishra, S. B. Mishra, B. B. Mamba, B. Maji, S. Bhattacharya, “Synthesis and DNA binding studies of Ni(II), Co(II), Cu(II) and Zn(II) metalcomplexes of N1,N5-bis[pyridine-2-methylene]-thiocarbohydrazone Schiff-base ligand,’’ Spectrochim. Acta A, vol. 79, pp. 1050-1056, 2011.
  • [5] M. Hanif, Z. H. Chohan, “Design, spectral characterization and biological studies of transition metal(II) complexes with triazole Schiff bases,’’ Spectrochim. Acta Part A, vol. 104, pp. 468-476, 2013.
  • [6] K. H. Kumar, S. Selvaraj, N. Naik, “Metal complexes of ONO donor Schiff base ligand as a new class of bioactive compounds; Synthesis, characterization and biological evolution,’’ Spectrochim. Acta Part A, vol.131, pp. 599-605, 2014.
  • [7] J. M. Gichumbi, H. B. Friedrich, B. Omondi, “Synthesis and characterization of piano-stool ruthenium complexes with N,N′-pyridine imine bidentate ligands and their application in styrene oxidation,’’ J. Organomet. Chem., vol. 808, pp. 87-96, 2016.
  • [8] R. K. Rath, M. Nethaji, A. R. Chakravarty, “Transfer hydrogenation of acetophenone promoted by (arene)ruthenium(II) reduced Schiff base complexes: an X-ray structure of [(eta(6)-p-cymene)RuCl(OC6H4-2-CH2NHC6H4-p-Me)],’’ Polyhedron, vol. 20, pp. 2735, 2001.
  • [9] E. A. Enyedy, G. M. Bognar, T. Kiss, M. Hanif, C.G. Hartinger, “Solution equilibrium studies on anticancer ruthenium(II)eh6-p-cymene complexes of 3-hydroxy-2(1H)-pyridones,’’ J. Organomet. Chem., vol. 734, pp. 38, 2013.
  • [10] L. C. Matsinh, S. F. Mapolie, G. S. Smith, “Synthesis and characterization of mono- and binuclear iminopyridyl and salicylaldimine Ru(II)–arene complexes,’’ Polyhedron, vol.53, pp. 56-61, 2013.
  • [11] Z. Weiqun, Y. Wen, X. Liqun, C. Xianchen, N-Benzoyl-N’-dialkylthiourea derivatives and their Co(III) complexes: Structure, and antifungal,’’ J. Inorg. Biochem., vol. 99, pp. 1314-1319, 2005.
  • [12] J. Lv, T. Liu, S. Cai, X. Wang, L. Liu, Y. Wang, “Synthesis, structure and biological activity of cobalt(II) and copper(II) complexes of valine-derived Schiff bases,’’ J. Inorg. Biochem., vol. 100, pp. 1888-1896, 2006.
  • [13] F. Dimiza, A. N. Papadopoulos, V. Tangoulis, V. Psycharis, C. P: Raptopoulou, D. P. Kessissoglou, G. Psomas, “Biological evaluation of cobalt(II) complexes with non-steroidal anti-inflammatory drug naproxen,’’ J Inorg Biochem., vol. 107, pp. 54–64, 2012.
  • [14] L. H. Abdel-Rahman, N. M. Ismail, M. Ismael, A. M. Abu-Dief, E. Abdel-Hameed Ahmed, “Synthesis, characterization, DFT calculations and biological studies of Mn(II), Fe(II), Co(II) and Cd(II) complexes based on a tetradentate ONNO donor Schiff base ligand,’’ J. Mol. Struct., vol. 1134, pp. 851-862, 2017.
  • [15] M. A. Neelakantana, M. Sundarama, M. S. Nair, “Synthesis, spectral and thermal studies of some transition metal mixed ligand complexes: Modeling of equilibrium composition and biological activity,’’ Spectrochim. Acta Part A, vol. 79, pp. 1693-1703, 2011.
  • [16] A. A. A. Aziz, “Microwave-Assisted Synthesis of Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) Complexes of Tridentate Schiff Base N-(2-hydroxyphenyl) 2-hydroxy-5- bromobenzaldimine: Characterization, DNA Interaction, Antioxidant, and In Vitro Antimicrobial Studies,’’ Synth. React. Inorga. Met-Org. Chem., vol. 44, pp. 1137-1153, 2014.
  • [17] W. B. Williams, M. Cuvelier, C. Berset “Use of a free radical method to evaluate antioxidant activity,’’ Lebensm–Wiss Technol., vol. 28, pp. 25-30, 1995.
  • [18] B. M. Lue, N. S. Nielsen, C. Jacobsen, L. Hellgren, Z. Guo, X. Xu, “Antioxidant properties of modified rutin esters by DPPH, reducing power, iron chelation and human low density lipoprotein assays,’’ Food Chem., vol. 123, pp. 221-230, 2010.
  • [19] D. Pandiarajan, R. Ramesh, “Ruthenium(II) half-sandwich complexes containing thioamides: Synthesis,structures and catalytic transfer hydrogenation of ketones,’’ J. Organo. Chem., vol. 723, pp. 26-35, 2013.
  • [20] A. A. Alshaheri, A. A. Alshaheri, M. I. M. Tahir, M. B. A. Rahman,T. Begum, T. A. Saleh, “Synthesis, characterisation and catalytic activity of dithiocarbazate Synthesis, characterisation and catalytic activity of dithiocarbazate Schiff base complexes in oxidation of cyclohexane,’’ J. Mol. Lıq., vol. 240, pp. 486-496, 2017.
  • [21] P. K. Suganthy, R. N. Prabhu, V. S. Sridevi, “Synthesis, structural characterization and catalytic transfer hydrogenation of ruthenium(II) carbonyl complexes bearing N,N,O pincer type benzoylhydrazone ligands,’’ Polyhedron, vol. 88, pp. 57-62, 2015.
  • [22] V. T. Kasumov, I. Uçar, A. Bulut, “Synthesis, structural, spectroscopic and reactivity properties of a newN-2,3,4-trifluorophenyl-3,5-di-tert-butylsalicylaldimine ligand and its Cu(II) and Pd(II) complexes,’’ J. Fluorine Chem., vol. 131, pp. 59-65, 2010.
  • [23] T.A. Mohamed, “Synthesis, antimicrobial activity, structural and spectral characterization and DFT calculations of Co(II), Ni(II), Cu(II) and Pd(II) complexes of 4-amino-5-pyrimidinecarbonitrile,’’ Spectrochim. Acta Part A, vol. 135, pp. 417-427, 2015.

Synthesis, Characterization, and Antimicrobial Properties of a New Ligand and Its Pd(II), Ru(II), Fe(II), Co(II) Complexes

Year 2018, Volume:6 No:2 (2018) (Special Issue: IMCOFE 2017), 433 - 443, 06.04.2018

Abstract

Schiff bases and their complexes are versatile compounds synthesized from the condensation of an amino compound with carbonyl compounds and widely used for industrial purposes and also exhibit a broad range of biological activities including antifungal, antibacterial, antimalarial, antiproliferative, antiviral, and antipyretic properties. In this study, the complexes of (E)-2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-6-methyl4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile (L) with Co(II), Fe(II), Pd(II) and Ru(II) were successfully prepared. Structures of Schiff base and its metal complexes obtained were confirmed by FT-IR, 1H-NMR, 13CNMR, UV–vis, magnetic susceptibility, mass spectroscopy and elemental analysis. Antimicrobial activity of the synthesized Schiff base and its metal complexes have been studied. When the antimicrobial activities of the compounds were examined, it was observed that the lowest activity was exhibited by the ligand, and the highest activity was exhibited by the Co(II) and Pd(II) complexes. None of our compounds were been found to exhibit antifungal activity.

References

  • [1] P. Chaudhuri, K. Wieghardt, “Phenoxyl radical complexes,’’ Prog. Inorg. Chem., vol. 50, pp. 151-216, 2001.
  • [2] A. D. Garnovski, A. P. Sadimenko, M. C. Sadimenko, D. A. Garnovski, “Common and less-common coordination modes of the typical chelating and heteroaromatic ligands,’’ Coord. Chem Rev., vol. 173, pp. 31-77, 1998.
  • [3] H. Keypour, M. Shayesteh, M. Rezaeivala, F. Chalabian, Y. Elerman, O. Buyukgungor, “Synthesis, spectral characterization, structural investigation and antimicrobial studies of mononuclear Cu(II), Ni(II), Co(II), Zn(II) and Cd(II) complexes of a new potentially hexadentate N2O4 Schiff base ligand derived from salicylaldehyde,’’ J. Mol. Struct., Vol. 1032, pp. 62-68, 2013.
  • [4] A. D. Tiwari, A. K. Mishra, S. B. Mishra, B. B. Mamba, B. Maji, S. Bhattacharya, “Synthesis and DNA binding studies of Ni(II), Co(II), Cu(II) and Zn(II) metalcomplexes of N1,N5-bis[pyridine-2-methylene]-thiocarbohydrazone Schiff-base ligand,’’ Spectrochim. Acta A, vol. 79, pp. 1050-1056, 2011.
  • [5] M. Hanif, Z. H. Chohan, “Design, spectral characterization and biological studies of transition metal(II) complexes with triazole Schiff bases,’’ Spectrochim. Acta Part A, vol. 104, pp. 468-476, 2013.
  • [6] K. H. Kumar, S. Selvaraj, N. Naik, “Metal complexes of ONO donor Schiff base ligand as a new class of bioactive compounds; Synthesis, characterization and biological evolution,’’ Spectrochim. Acta Part A, vol.131, pp. 599-605, 2014.
  • [7] J. M. Gichumbi, H. B. Friedrich, B. Omondi, “Synthesis and characterization of piano-stool ruthenium complexes with N,N′-pyridine imine bidentate ligands and their application in styrene oxidation,’’ J. Organomet. Chem., vol. 808, pp. 87-96, 2016.
  • [8] R. K. Rath, M. Nethaji, A. R. Chakravarty, “Transfer hydrogenation of acetophenone promoted by (arene)ruthenium(II) reduced Schiff base complexes: an X-ray structure of [(eta(6)-p-cymene)RuCl(OC6H4-2-CH2NHC6H4-p-Me)],’’ Polyhedron, vol. 20, pp. 2735, 2001.
  • [9] E. A. Enyedy, G. M. Bognar, T. Kiss, M. Hanif, C.G. Hartinger, “Solution equilibrium studies on anticancer ruthenium(II)eh6-p-cymene complexes of 3-hydroxy-2(1H)-pyridones,’’ J. Organomet. Chem., vol. 734, pp. 38, 2013.
  • [10] L. C. Matsinh, S. F. Mapolie, G. S. Smith, “Synthesis and characterization of mono- and binuclear iminopyridyl and salicylaldimine Ru(II)–arene complexes,’’ Polyhedron, vol.53, pp. 56-61, 2013.
  • [11] Z. Weiqun, Y. Wen, X. Liqun, C. Xianchen, N-Benzoyl-N’-dialkylthiourea derivatives and their Co(III) complexes: Structure, and antifungal,’’ J. Inorg. Biochem., vol. 99, pp. 1314-1319, 2005.
  • [12] J. Lv, T. Liu, S. Cai, X. Wang, L. Liu, Y. Wang, “Synthesis, structure and biological activity of cobalt(II) and copper(II) complexes of valine-derived Schiff bases,’’ J. Inorg. Biochem., vol. 100, pp. 1888-1896, 2006.
  • [13] F. Dimiza, A. N. Papadopoulos, V. Tangoulis, V. Psycharis, C. P: Raptopoulou, D. P. Kessissoglou, G. Psomas, “Biological evaluation of cobalt(II) complexes with non-steroidal anti-inflammatory drug naproxen,’’ J Inorg Biochem., vol. 107, pp. 54–64, 2012.
  • [14] L. H. Abdel-Rahman, N. M. Ismail, M. Ismael, A. M. Abu-Dief, E. Abdel-Hameed Ahmed, “Synthesis, characterization, DFT calculations and biological studies of Mn(II), Fe(II), Co(II) and Cd(II) complexes based on a tetradentate ONNO donor Schiff base ligand,’’ J. Mol. Struct., vol. 1134, pp. 851-862, 2017.
  • [15] M. A. Neelakantana, M. Sundarama, M. S. Nair, “Synthesis, spectral and thermal studies of some transition metal mixed ligand complexes: Modeling of equilibrium composition and biological activity,’’ Spectrochim. Acta Part A, vol. 79, pp. 1693-1703, 2011.
  • [16] A. A. A. Aziz, “Microwave-Assisted Synthesis of Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) Complexes of Tridentate Schiff Base N-(2-hydroxyphenyl) 2-hydroxy-5- bromobenzaldimine: Characterization, DNA Interaction, Antioxidant, and In Vitro Antimicrobial Studies,’’ Synth. React. Inorga. Met-Org. Chem., vol. 44, pp. 1137-1153, 2014.
  • [17] W. B. Williams, M. Cuvelier, C. Berset “Use of a free radical method to evaluate antioxidant activity,’’ Lebensm–Wiss Technol., vol. 28, pp. 25-30, 1995.
  • [18] B. M. Lue, N. S. Nielsen, C. Jacobsen, L. Hellgren, Z. Guo, X. Xu, “Antioxidant properties of modified rutin esters by DPPH, reducing power, iron chelation and human low density lipoprotein assays,’’ Food Chem., vol. 123, pp. 221-230, 2010.
  • [19] D. Pandiarajan, R. Ramesh, “Ruthenium(II) half-sandwich complexes containing thioamides: Synthesis,structures and catalytic transfer hydrogenation of ketones,’’ J. Organo. Chem., vol. 723, pp. 26-35, 2013.
  • [20] A. A. Alshaheri, A. A. Alshaheri, M. I. M. Tahir, M. B. A. Rahman,T. Begum, T. A. Saleh, “Synthesis, characterisation and catalytic activity of dithiocarbazate Synthesis, characterisation and catalytic activity of dithiocarbazate Schiff base complexes in oxidation of cyclohexane,’’ J. Mol. Lıq., vol. 240, pp. 486-496, 2017.
  • [21] P. K. Suganthy, R. N. Prabhu, V. S. Sridevi, “Synthesis, structural characterization and catalytic transfer hydrogenation of ruthenium(II) carbonyl complexes bearing N,N,O pincer type benzoylhydrazone ligands,’’ Polyhedron, vol. 88, pp. 57-62, 2015.
  • [22] V. T. Kasumov, I. Uçar, A. Bulut, “Synthesis, structural, spectroscopic and reactivity properties of a newN-2,3,4-trifluorophenyl-3,5-di-tert-butylsalicylaldimine ligand and its Cu(II) and Pd(II) complexes,’’ J. Fluorine Chem., vol. 131, pp. 59-65, 2010.
  • [23] T.A. Mohamed, “Synthesis, antimicrobial activity, structural and spectral characterization and DFT calculations of Co(II), Ni(II), Cu(II) and Pd(II) complexes of 4-amino-5-pyrimidinecarbonitrile,’’ Spectrochim. Acta Part A, vol. 135, pp. 417-427, 2015.
There are 23 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Articles
Authors

Kenan Buldurun

Nevin Turan

Yusuf Alan

Naki Çolak

Publication Date April 6, 2018
Published in Issue Year 2018 Volume:6 No:2 (2018) (Special Issue: IMCOFE 2017)

Cite

APA Buldurun, K., Turan, N., Alan, Y., Çolak, N. (2018). Synthesis, Characterization, and Antimicrobial Properties of a New Ligand and Its Pd(II), Ru(II), Fe(II), Co(II) Complexes. Duzce University Journal of Science and Technology, 6(2), 433-443.
AMA Buldurun K, Turan N, Alan Y, Çolak N. Synthesis, Characterization, and Antimicrobial Properties of a New Ligand and Its Pd(II), Ru(II), Fe(II), Co(II) Complexes. DUBİTED. April 2018;6(2):433-443.
Chicago Buldurun, Kenan, Nevin Turan, Yusuf Alan, and Naki Çolak. “Synthesis, Characterization, and Antimicrobial Properties of a New Ligand and Its Pd(II), Ru(II), Fe(II), Co(II) Complexes”. Duzce University Journal of Science and Technology 6, no. 2 (April 2018): 433-43.
EndNote Buldurun K, Turan N, Alan Y, Çolak N (April 1, 2018) Synthesis, Characterization, and Antimicrobial Properties of a New Ligand and Its Pd(II), Ru(II), Fe(II), Co(II) Complexes. Duzce University Journal of Science and Technology 6 2 433–443.
IEEE K. Buldurun, N. Turan, Y. Alan, and N. Çolak, “Synthesis, Characterization, and Antimicrobial Properties of a New Ligand and Its Pd(II), Ru(II), Fe(II), Co(II) Complexes”, DUBİTED, vol. 6, no. 2, pp. 433–443, 2018.
ISNAD Buldurun, Kenan et al. “Synthesis, Characterization, and Antimicrobial Properties of a New Ligand and Its Pd(II), Ru(II), Fe(II), Co(II) Complexes”. Duzce University Journal of Science and Technology 6/2 (April 2018), 433-443.
JAMA Buldurun K, Turan N, Alan Y, Çolak N. Synthesis, Characterization, and Antimicrobial Properties of a New Ligand and Its Pd(II), Ru(II), Fe(II), Co(II) Complexes. DUBİTED. 2018;6:433–443.
MLA Buldurun, Kenan et al. “Synthesis, Characterization, and Antimicrobial Properties of a New Ligand and Its Pd(II), Ru(II), Fe(II), Co(II) Complexes”. Duzce University Journal of Science and Technology, vol. 6, no. 2, 2018, pp. 433-4.
Vancouver Buldurun K, Turan N, Alan Y, Çolak N. Synthesis, Characterization, and Antimicrobial Properties of a New Ligand and Its Pd(II), Ru(II), Fe(II), Co(II) Complexes. DUBİTED. 2018;6(2):433-4.