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Synthesis, Spectroscopic and Antibacterial Properties of Pyrazine Complexes of Co (II), Cu (II) and Ni (II) 4-carboxybenzaldehyde

Yıl 2019, Cilt: 6 Sayı: 2, 170 - 181, 27.12.2019

Öz

In this study, three complexes of Co(II),
Cu(II) and Ni(II) metals with 4-carboxybenzaldehyde and pyrazine were
synthesized. The structure of the complexes having the formula [M(C8H5O3)2(C4H4N2)(H2O)2]n
(Co(II), Cu(II), Ni(II)) was characterized by elemental analysis and FT-IR
spectroscopy. The antibacterial properties of complexes characterized in their
structures against bacterial species Pseudomonas
aeruginosa
(ATCC 27853), Klebsiella
pneumoniae
(ATCC 4352), ve Escherichia
coli
(ATCC 25922), gram positive Staphylococcus
aureus
(ATCC) 6538) were investigated.

Kaynakça

  • Al-Majidi S. M. H. (2014). Synthesis of some new 4-oxo-thiazolidines, tetrazole and triazole derived from 2-SH-benzothiazole and antimicrobial screening of some synthesized. Journal of Saudi Chemical Society, 18, 893–901.
  • Arora S., Talwar D., Singh M., Sahoo S. C. and Sharma R. (2020). Second sphere coordination in orthonitrophenolate binding: Synthesis, biological, cytotoxic and X-ray structural studies of [Co(bpy)2CO3](C6H4NO3)•3H2O. Journal of Molecular Structure, 1199, 127017.
  • Askin G. S., Celik F., Dilek N., Necefoglu H. and Hokelek T. (2015). Crystal structure of catena-poly[[diaquabis(4-formylbenzoato- kappaO-1)cobalt(II)]-mu-pyrazine-kappa N-2:N’]. Acta Crystallogr. Sect. E.-Crystallogr. Commun., 71, 339-340.
  • Çelik F., Dilek N., Çaylak Delibaş N., Necefoğlu H. and Hökelek T. (2014a). catena -Poly[[diaquabis(4-formylbenzoato-κO1)copper(II)]-μ-pyrazine-κ2N :N′]. Acta Crystallographica Section E Structure Reports, Online, 70, 4–5.
  • Çelik F., Dilek N., Çaylak Delibaş N., Necefoğlu H. and Hökelek T. (2014b). catena -Poly[[diaquabis(4-formylbenzoato-κO1)nickel(II)]-μ-pyrazine-κ2N :N′]. Acta Crystallographica Section E Structure Reports, Online, 70, 65–66.
  • Çınarlı M., Çınarlı E., Ataol Ç. Y., İdil Ö. and Kariptaş E. (2019). Synthesis, structural characterization, Hirshfeld surface analysis, antimicrobial activity, and DNA cleavage studies of (Z)-4-methyl-N’-(phenyl(pyridin-2-yl)methylene)benzenesulfonohydrazide and its Co(II), Ni(II) and Zn(II) complexes. Journal of Molecular Structure, 1196, 760–770.
  • Desiraju G. R. (1989). Crystal engineering: the design of organic solids., Elsevier, Amsterdam; New York.
  • Dolezal M. and Zitko J. (2015). Pyrazine derivatives: a patent review (June 2012 – present). Expert Opinion on Therapeutic Patents, 25, 33–47.
  • Ferreira S. B. and Kaiser C. R. (2012). Pyrazine derivatives: a patent review (2008 – present). Expert Opinion on Therapeutic Patents, 22, 1033–1051.
  • Heine J., Wehner T., Bertermann R., Steffen A. and Müller-Buschbaum K. (2014). 2∞[Bi2Cl6(pyz)4]: a 2D-pyrazine coordination polymer as soft host lattice for the luminescence of the lanthanide ions Sm3+, Eu3+, Tb3+, and Dy3+. Inorg Chem., 53, 7197–7203.
  • Ishak N. N. M., Jamsari J., Ismail A. Z., Tahir M. I. M., Tiekink E. R. T., Veerakumarasivam A. and Ravoof T. B. S. A. (2019). Synthesis, characterisation and biological studies of mixed-ligand nickel (II) complexes containing imidazole derivatives and thiosemicarbazide Schiff bases. Journal of Molecular Structure, 1198, 126888.Janovská D., Kubíková K. and Kokoška L. (2011). Screening for antimicrobial activity of some medicinal plants species of traditional Chinese medicine. Czech Journal of Food Sciences, 21, 107–110.Keypour H., Aidi M., Mahmoudabadi M., Karamian R., Asadbegy M. and Gable R. W. (2019). Synthesis, X-ray crystal structural, antioxidant and antibacterial studies of new Cu(II) macroacyclic Schiff base complex with a ligand containing homopiperazine moiety. Journal of Molecular Structure, 1198, 126666.
  • Lode H. M. (2009). Clinical impact of antibiotic-resistant Gram-positive pathogens. Clinical Microbiology and Infection, 15, 212–217.
  • Miniyar P. B., Murumkar P. R., Patil P. S. and Bothara M. A. B. and K. G. (2013). Unequivocal Role of Pyrazine Ring in Medicinally Important Compounds: A Review. Mini-Reviews in Medicinal Chemistry, Available at: http://www.eurekaselect.com/114639/article [Accessed June 21, 2019].
  • Nakamoto K. (2006). Infrared and Raman Spectra of Inorganic and Coordination Compounds. In Handbook of Vibrational Spectroscopy American Cancer Society, Available at: https://onlinelibrary.wiley.com/doi/abs/10.1002/0470027320.s4104 [Accessed August 6, 2019].
  • Özbek F. E., Sertçelik M., Yüksek M., Necefoğlu H., Çelik R. Ç., Nayir G. Y. and Hökelek T. (2017). Cu(II) and Ni(II) 4-cyanobenzoate complexes with nicotinamide: Synthesis, spectral, structural and optical characterization and thermal behavior. Journal of Molecular Structure, 1150, 112–117.
  • Rambabu A., Ganji N., Daravath S., Venkateswarlu K., Rangan K. and Shivaraj (2020). Mononuclear Co(II), Ni(II) and Cu(II) complexes of the Schiff base, 2-(((4-trifluoromethoxy)phenylimino)methyl)-6-tert-butylphenol: Synthesis, spectroscopic characterization, X-ray study and biological evaluation. Journal of Molecular Structure, 1199, 127006.
  • Saha S., Mishra M. K., Reddy C. M. and Desiraju G. R. (2018). From Molecules to Interactions to Crystal Engineering: Mechanical Properties of Organic Solids. Accounts Chem. Res., 51, 2957–2967.
  • Sertçeli̇k M., Özbek F. E., Sugeçti̇ S. and Necefoğlu H. (2018). 4-Formilbenzoat’ın Co(II), Cu(II) ve Zn(II) ile İzonikotinamid Komplekslerinin Sentezi; Spektroskopik, Termik Özelliklerinin ve Antibakteriyel Etkinliklerinin İncelenmesi. Journal of the Institute of Science & Technology / Fen Bilimleri Estitüsü Dergisi, 8, 189–195.
  • Sertçelik M., Özbek F. E., Sugeçti̇ S. and Necefoğlu H. (2018). 4-Formilbenzoat’ın Co(II), Cu(II) ve Zn(II) ile İzonikotinamid Komplekslerinin Sentezi; Spektroskopik, Termik Özelliklerinin ve Antibakteriyel Etkinliklerinin İncelenmesi. Iğdır Üniversitesi Fen Bilimleri Enstitüsü Dergis,i 8, 189–195.
  • Venkateswarlu K., Ganji N., Daravath S., Kanneboina K., Rangan K. and Shivaraj (2019). Crystal structure, DNA interactions, antioxidant and antitumor activity of thermally stable Cu(II), Ni(II) and Co(III) complexes of an N,O donor Schiff base ligand. Polyhedron 171, 86–97.
  • Yildiz S., Yilmaz A. and Can Z. (2017). In Vitro Bioactive Properties of Some Wild Mushrooms Collected from Kastamonu Province. Kastamonu Üniversitesi Orman Fakültesi Dergisi 17, 523–530.
  • Yıldırım T., Köse D. A., Avcı E., Özer D. and Şahin O. (2019). Novel mixed ligand complexes of acesulfame / nicotinamide with some transition metals. Synthesis, crystal structural characterization, and biological properties. Journal of Molecular Structure 1176, 576–582.
  • Yousef T. A., Abu El-Reash G. M., Abu AL-Zahab M. and Safaan M. A. A. (2019). Physicochemical investigations, biological studies of the Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II), Cd(II), Hg(II) and UO2(VI) complexes of picolinic acid hydrazide derivative: A combined experimental and computational approach. Journal of Molecular Structure 1197, 564–575.
  • Z. Laczkowski K., Biernasiuk A., Baranowska-Laczkowska A., Misiura K., Malm A., Plech T. and Paneth A. (2016). Synthesis, Antibacterial Activity, Interaction with Nucleobase and Molecular Docking Studies of 4-Formylbenzoic Acid Based Thiazoles. Available at: https://www.ingentaconnect.com/contentone/ben/mc/2016/00000012/00000006/art00009 [Accessed June 8, 2019].
  • Zülfikaroğlu A., Yüksektepe Ataol Ç., Çelikoğlu E., Çelikoğlu U. and İdil Ö. (2020). New Cu(II), Co(III) and Ni(II) metal complexes based on ONO donor tridentate hydrazone: Synthesis, structural characterization, and investigation of some biological properties. Journal of Molecular Structure 1199, 127012.

Co(II), Cu(II) ve Ni(II) 4-karboksibenzaldehit’in Pirazin Komplekslerinin Sentezi, Spektroskopik ve Antibakteriyel Özellikleri

Yıl 2019, Cilt: 6 Sayı: 2, 170 - 181, 27.12.2019

Öz

Bu çalışmada Co(II), Cu(II) ve Ni(II) metallerinin
4-karboksibenzaldehit ve pirazin ile üç adet kompleksi sentezlendi. [M(C8H5O3)2(C4H4N2)(H2O)2]n
(Co(II), Cu(II), Ni(II)) kapalı formülüne sahip eş yapılı olan
komplekslerin yapısı elementel analiz ve FT-IR spektroskopisi sonucunda karakterize
edildi. Yapıları karakterize edilen komplekslerin Pseudomonas aeruginosa (ATCC 27853), Klebsiella pneumoniae (ATCC 4352), ve Escherichia coli (ATCC 25922), gram pozitif Staphylococcus aureus (ATCC) 6538) bakteri türlerine karşı
antibakteriyel özellikleri araştırılmıştır.

Kaynakça

  • Al-Majidi S. M. H. (2014). Synthesis of some new 4-oxo-thiazolidines, tetrazole and triazole derived from 2-SH-benzothiazole and antimicrobial screening of some synthesized. Journal of Saudi Chemical Society, 18, 893–901.
  • Arora S., Talwar D., Singh M., Sahoo S. C. and Sharma R. (2020). Second sphere coordination in orthonitrophenolate binding: Synthesis, biological, cytotoxic and X-ray structural studies of [Co(bpy)2CO3](C6H4NO3)•3H2O. Journal of Molecular Structure, 1199, 127017.
  • Askin G. S., Celik F., Dilek N., Necefoglu H. and Hokelek T. (2015). Crystal structure of catena-poly[[diaquabis(4-formylbenzoato- kappaO-1)cobalt(II)]-mu-pyrazine-kappa N-2:N’]. Acta Crystallogr. Sect. E.-Crystallogr. Commun., 71, 339-340.
  • Çelik F., Dilek N., Çaylak Delibaş N., Necefoğlu H. and Hökelek T. (2014a). catena -Poly[[diaquabis(4-formylbenzoato-κO1)copper(II)]-μ-pyrazine-κ2N :N′]. Acta Crystallographica Section E Structure Reports, Online, 70, 4–5.
  • Çelik F., Dilek N., Çaylak Delibaş N., Necefoğlu H. and Hökelek T. (2014b). catena -Poly[[diaquabis(4-formylbenzoato-κO1)nickel(II)]-μ-pyrazine-κ2N :N′]. Acta Crystallographica Section E Structure Reports, Online, 70, 65–66.
  • Çınarlı M., Çınarlı E., Ataol Ç. Y., İdil Ö. and Kariptaş E. (2019). Synthesis, structural characterization, Hirshfeld surface analysis, antimicrobial activity, and DNA cleavage studies of (Z)-4-methyl-N’-(phenyl(pyridin-2-yl)methylene)benzenesulfonohydrazide and its Co(II), Ni(II) and Zn(II) complexes. Journal of Molecular Structure, 1196, 760–770.
  • Desiraju G. R. (1989). Crystal engineering: the design of organic solids., Elsevier, Amsterdam; New York.
  • Dolezal M. and Zitko J. (2015). Pyrazine derivatives: a patent review (June 2012 – present). Expert Opinion on Therapeutic Patents, 25, 33–47.
  • Ferreira S. B. and Kaiser C. R. (2012). Pyrazine derivatives: a patent review (2008 – present). Expert Opinion on Therapeutic Patents, 22, 1033–1051.
  • Heine J., Wehner T., Bertermann R., Steffen A. and Müller-Buschbaum K. (2014). 2∞[Bi2Cl6(pyz)4]: a 2D-pyrazine coordination polymer as soft host lattice for the luminescence of the lanthanide ions Sm3+, Eu3+, Tb3+, and Dy3+. Inorg Chem., 53, 7197–7203.
  • Ishak N. N. M., Jamsari J., Ismail A. Z., Tahir M. I. M., Tiekink E. R. T., Veerakumarasivam A. and Ravoof T. B. S. A. (2019). Synthesis, characterisation and biological studies of mixed-ligand nickel (II) complexes containing imidazole derivatives and thiosemicarbazide Schiff bases. Journal of Molecular Structure, 1198, 126888.Janovská D., Kubíková K. and Kokoška L. (2011). Screening for antimicrobial activity of some medicinal plants species of traditional Chinese medicine. Czech Journal of Food Sciences, 21, 107–110.Keypour H., Aidi M., Mahmoudabadi M., Karamian R., Asadbegy M. and Gable R. W. (2019). Synthesis, X-ray crystal structural, antioxidant and antibacterial studies of new Cu(II) macroacyclic Schiff base complex with a ligand containing homopiperazine moiety. Journal of Molecular Structure, 1198, 126666.
  • Lode H. M. (2009). Clinical impact of antibiotic-resistant Gram-positive pathogens. Clinical Microbiology and Infection, 15, 212–217.
  • Miniyar P. B., Murumkar P. R., Patil P. S. and Bothara M. A. B. and K. G. (2013). Unequivocal Role of Pyrazine Ring in Medicinally Important Compounds: A Review. Mini-Reviews in Medicinal Chemistry, Available at: http://www.eurekaselect.com/114639/article [Accessed June 21, 2019].
  • Nakamoto K. (2006). Infrared and Raman Spectra of Inorganic and Coordination Compounds. In Handbook of Vibrational Spectroscopy American Cancer Society, Available at: https://onlinelibrary.wiley.com/doi/abs/10.1002/0470027320.s4104 [Accessed August 6, 2019].
  • Özbek F. E., Sertçelik M., Yüksek M., Necefoğlu H., Çelik R. Ç., Nayir G. Y. and Hökelek T. (2017). Cu(II) and Ni(II) 4-cyanobenzoate complexes with nicotinamide: Synthesis, spectral, structural and optical characterization and thermal behavior. Journal of Molecular Structure, 1150, 112–117.
  • Rambabu A., Ganji N., Daravath S., Venkateswarlu K., Rangan K. and Shivaraj (2020). Mononuclear Co(II), Ni(II) and Cu(II) complexes of the Schiff base, 2-(((4-trifluoromethoxy)phenylimino)methyl)-6-tert-butylphenol: Synthesis, spectroscopic characterization, X-ray study and biological evaluation. Journal of Molecular Structure, 1199, 127006.
  • Saha S., Mishra M. K., Reddy C. M. and Desiraju G. R. (2018). From Molecules to Interactions to Crystal Engineering: Mechanical Properties of Organic Solids. Accounts Chem. Res., 51, 2957–2967.
  • Sertçeli̇k M., Özbek F. E., Sugeçti̇ S. and Necefoğlu H. (2018). 4-Formilbenzoat’ın Co(II), Cu(II) ve Zn(II) ile İzonikotinamid Komplekslerinin Sentezi; Spektroskopik, Termik Özelliklerinin ve Antibakteriyel Etkinliklerinin İncelenmesi. Journal of the Institute of Science & Technology / Fen Bilimleri Estitüsü Dergisi, 8, 189–195.
  • Sertçelik M., Özbek F. E., Sugeçti̇ S. and Necefoğlu H. (2018). 4-Formilbenzoat’ın Co(II), Cu(II) ve Zn(II) ile İzonikotinamid Komplekslerinin Sentezi; Spektroskopik, Termik Özelliklerinin ve Antibakteriyel Etkinliklerinin İncelenmesi. Iğdır Üniversitesi Fen Bilimleri Enstitüsü Dergis,i 8, 189–195.
  • Venkateswarlu K., Ganji N., Daravath S., Kanneboina K., Rangan K. and Shivaraj (2019). Crystal structure, DNA interactions, antioxidant and antitumor activity of thermally stable Cu(II), Ni(II) and Co(III) complexes of an N,O donor Schiff base ligand. Polyhedron 171, 86–97.
  • Yildiz S., Yilmaz A. and Can Z. (2017). In Vitro Bioactive Properties of Some Wild Mushrooms Collected from Kastamonu Province. Kastamonu Üniversitesi Orman Fakültesi Dergisi 17, 523–530.
  • Yıldırım T., Köse D. A., Avcı E., Özer D. and Şahin O. (2019). Novel mixed ligand complexes of acesulfame / nicotinamide with some transition metals. Synthesis, crystal structural characterization, and biological properties. Journal of Molecular Structure 1176, 576–582.
  • Yousef T. A., Abu El-Reash G. M., Abu AL-Zahab M. and Safaan M. A. A. (2019). Physicochemical investigations, biological studies of the Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II), Cd(II), Hg(II) and UO2(VI) complexes of picolinic acid hydrazide derivative: A combined experimental and computational approach. Journal of Molecular Structure 1197, 564–575.
  • Z. Laczkowski K., Biernasiuk A., Baranowska-Laczkowska A., Misiura K., Malm A., Plech T. and Paneth A. (2016). Synthesis, Antibacterial Activity, Interaction with Nucleobase and Molecular Docking Studies of 4-Formylbenzoic Acid Based Thiazoles. Available at: https://www.ingentaconnect.com/contentone/ben/mc/2016/00000012/00000006/art00009 [Accessed June 8, 2019].
  • Zülfikaroğlu A., Yüksektepe Ataol Ç., Çelikoğlu E., Çelikoğlu U. and İdil Ö. (2020). New Cu(II), Co(III) and Ni(II) metal complexes based on ONO donor tridentate hydrazone: Synthesis, structural characterization, and investigation of some biological properties. Journal of Molecular Structure 1199, 127012.
Toplam 25 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Konular Çevre Bilimleri
Bölüm Makaleler
Yazarlar

Mustafa Sertçelik 0000-0001-7919-7907

Füreya Elif Özbek Bu kişi benim 0000-0001-6376-4161

Fatih Çelik Bu kişi benim 0000-0002-3802-7984

Yayımlanma Tarihi 27 Aralık 2019
Gönderilme Tarihi 13 Kasım 2019
Kabul Tarihi 25 Aralık 2019
Yayımlandığı Sayı Yıl 2019 Cilt: 6 Sayı: 2

Kaynak Göster

APA Sertçelik, M., Özbek, F. E., & Çelik, F. (2019). Co(II), Cu(II) ve Ni(II) 4-karboksibenzaldehit’in Pirazin Komplekslerinin Sentezi, Spektroskopik ve Antibakteriyel Özellikleri. Caucasian Journal of Science, 6(2), 170-181.

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