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Cu(II) p-Floro-, p-Kloro- ve p-Bromobenzoatların N,N'-Dietilnikotinamid Komplekslerinin Sentezi, Spektroskopik ve Termik Özellikleri

Year 2019, Volume: 6 Issue: 2, 124 - 136, 27.12.2019

Abstract

Bu çalışmada bakır(II) p-floro-,
p-kloro- ve p-bromobenzoatların N,N'-dietilnikotinamid ligandı içeren üç yeni
karışık ligandlı metal kompleksi sentezlendi ve yapıları incelendi.
Komplekslerin yapılarının tartışılmasında elemental analiz, FT-IR ve UV-Vis
spektroskopisi, termik analiz (TGA-DTA), yöntemlerinden faydalanıldı.
Komplekslerin kapalı formülleri [Cu(p-F-C6H4COO)2(C10H14N2O)2(H2O)]
(I), [Cu(p-Cl-C6H4COO)2(C10H14N2O)2(H2O)2]
(II) ve [Cu(p-Br-C6H4COO)2(H2O)2]
(III) olarak belirlendi. Yapıda p-halojenobenzoatlar ve N,N'-dietilnikotinamid
monodentat olarak koordine olmuştur. Komplekslerin yapısında, metal atomu
çevresinde iki p-halojenobenzoat
anyonundan gelen iki oksijen atomu, iki N,N'-dietilnikotinamid ligandından
gelen iki azot atomu ve iki su molekülünden gelen iki oksijen atomu ile
oktahedral geometri meydana gelmiştir. Bakır: p-halojenobenzoat:N,N'-dietilnikotinamid oranlarının 1:2:2 olduğu
belirlenmiştir. Komplekslerin termal kararlılık sıralaması ise IIIII>I şeklindedir. Komplekslerin
termal bozunma ürünleri ise bakır (II) oksittir.

Supporting Institution

TÜBİTAK

Project Number

106T472

Thanks

Çalışma 106T472 numaralı TÜBİTAK projesi ile desteklenmiştir. Desteklerinden dolayı TÜBİTAK’a teşekkür ederim.

References

  • Abuhijleh A.L., Khalaf J. (2010). Copper (II) complexes of the anti-inflammatory drug naproxen and 3-pyridylmethanol as auxiliary ligand. Characterization, superoxide dismutase and catecholase – mimetic activities. European Journal of Medicinal Chemistry, 45(9), 3811–3817.
  • Agwara M.O., Ndifon P.T., Ndosiri N. B., Paboudam A. G., Yufanyi D.M., Mohamadou A. (2010). Synthesis, characterisation and antimicrobial activities of cobalt(II), copper(II) and zinc(II) mixed-ligand complexes containing 1,10-phenanthroline and 2,2’-bipyridine. Bulletin of the Chemical Society of Ethiopia, 24(3).
  • Amombo Noa F.M., Jacobs A. (2017). Phenylacetic acid co-crystals with acridine, caffeine, isonicotinamide and nicotinamide: Crystal structures, thermal analysis, FTIR spectroscopy and Hirshfeld surface analysis. Journal of Molecular Structure, 1139, 60–66.
  • Batool S.S., Gilani S.R., Tahir M.N., Rüffer T. (2017). Synthesis, and structural characterization of mixed ligand copper(II) complexes of N,N,N′,N’-tetramethylethylenediamine incorporating carboxylates. Journal of Molecular Structure, 1148, 7–14.
  • Bozkurt N., Tunç T., Çaylak Delibaş N., Necefoğlu H., Hökelek T. (2013). Aquabis(3-chlorobenzoato-κ O )bis( N , N -diethylnicotinamide-κ N )copper(II). Acta Crystallographica Section E Structure Reports Online, 69(8), m458–m459.
  • Bushma M. I., Zavodnik L.B., Lukienko P.I. (1989). [Effect of the diethylamide of nicotinic acid (cordiamine) on the hydroxylating function of the liver]. Farmakologiia I Toksikologiia, 52(4), 56–59.
  • Findoráková L., Győryová K., Melník M., Koman M., Nour El-Dien F.A. (2010). Preparation, thermal decomposition, and crystal structure of Zn(II) 2-chlorobenzoate complex with nicotinamide. Journal of Coordination Chemistry, 63(19), 3348–3355.
  • Fountoulaki S., Perdih F., Turel I., Kessissoglou D. P., Psomas G. (2011). Non-steroidal anti-inflammatory drug diflunisal interacting with Cu(II). Structure and biological features. Journal of Inorganic Biochemistry, 105(12), 1645–1655.
  • Halaška J., Pevec A., Strauch P., Kozlevčar B., Koman M., Moncol J. (2013). Supramolecular hydrogen-bonding networks constructed from copper(II) chlorobenzoates with nicotinamide: Structure and EPR. Polyhedron, 61, 20–26.
  • Kuchtanin V., Moncol J., Mroziński J., Kalińska B., Padělková Z., Švorec J., Seglá P., Melník M. (2013). Study of copper(II) thiophenecarboxylate complexes with N-methylnicotinamide. Polyhedron, 50(1), 546–555.
  • Lakowicz J. R. (2010). Principles of fluorescence spectroscopy (Third edition, corrected at 4. printing.). New York, NY: Springer.
  • Lever A. B. P. (1986). Inorganic electronic spectroscopy (2. ed.), 2. impression (with corr.). Amsterdam: Elsevier.
  • Lewandowski W., Kalinowska M., Lewandowska H. (2005). The influence of halogens on the electronic system of biologically important ligands: spectroscopic study of halogenobenzoic acids, halogenobenzoates and 5-halogenouracils. Inorganica Chimica Acta, 358(7), 2155–2166.
  • M. Qadir A. (2017). Copper(II) Carboxylate Containing Paddle Wheel Structure: Synthesis and Crystal Structure. Oriental Journal of Chemistry, 33(2), 968–970.
  • Mahata P., Ramya, K. V., Natarajan S. (2007). Synthesis, structure and optical properties of rare-earth benzene carboxylates. Dalton Transactions, (36), 4017.
  • Mandal A., Patel B.K. (2017). Molecular structures and fluorescence property of Zn(II), Cd(II) complexes of 3-pyridyl-5-aryl-(1 H )-1,2,4-triazoles. Polyhedron, 132, 112–122.
  • Ming C.L., Hao Z.C., Yu B.Y., Van Hecke K., Cui G.H. (2015). Synthesis, Structures, and Catalytic Properties of Three New Metal–Organic Coordination Polymers Constructed from Flexible Benzimidazole-Based and cis-1,2-Cyclohexanedicarboxylate Synthons. Journal of Inorganic and Organometallic Polymers and Materials, 25(3), 559–568.
  • Mitra A., Clark R. J., Hubley C. T., Saha S. (2014). Anion–π and CH···anion interactions in naphthalenediimide-based coordination complexes. Supramolecular Chemistry, 26(3–4), 296–301.
  • Nakamoto K. (1986). Infrared and Raman spectra of inorganic and coordination compounds (4. ed.). New York: Wiley.
  • Özbek F. E., Sertçelik M., Yüksek M., Küçüköz B., Elmali A., Şahin E. (2019). Two new potential optical materials: Co(II) and Ni(II) 3-fluorobenzoate complexes with pyridine-3-carboxamide. Journal of Coordination Chemistry, 72(5–7), 786–795.
  • Özbek F. E., Sertçelik M., Yüksek M., Necefoğlu H., Çelik R. Ç., Nayir G. Y., 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.
  • Pavia D. L., Lampman G. M., Kriz G. S. (2001). Introduction to spectroscopy: a guide for students of organic chemistry (3. ed.). South Melbourne: Brooks/Cole.
  • Perec M., Baggio R. F., Peña O., Sartoris R. P., Calvo R. (2011). Synthesis and structures of four new compounds of the copper(II)–carboxylate–pyridinecarboxamide system. Inorganica Chimica Acta, 373(1), 117–123. https://doi.org/10.1016/j.ica.2011.03.065
  • Puchoňová M., Repická Z., Moncol J., Růžičková Z., Mazúr M., Valigura D. (2015). Supramolecular structure formation of molecular copper(II)methylsalicylate complexes with nicotinamide or methylnicotinamide – Crystal structure and spectral properties. Journal of Molecular Structure, 1092, 1–8.
  • Sertçelik M., Çaylak Delibaş N., Necefoğlu H., Hökelek T. (2012). Diaquabis(4-formylbenzoato-κO1)bis(nicotinamide-κN1)copper(II). Acta Crystallographica Section E Structure Reports Online, 68(7), m1010–m1011.
  • Sertçelik M., Çaylak Delibaş N., Necefoğlu H., Hökelek T. (2013). Bis( -4-formylbenzoato- 2O:O')bis[(4-formylbenzoato- 2O,O')bis(isonicotinamide- N1)copper(II)]. Acta Crystallographica Section E Structure Reports Online, 69, m290–m291.
  • Sertçelik M., Özbek F.E., Sugeçti S., Necefoğlu H. (2018). Synthesis of Izonicotınamide Complexes Of 4-Formilbenzoate with Co (II), Cu (II) And Zn (II); Investigation of Spectroscopic, Thermal Properties and Antibacterial Activıties. Journal of the Institute of Science and Technology, 189–195.
  • Silverstein R.M., Webster F.X., Kiemle D.J., Bryce, D.L. (Eds.). (2015). Spectrometric identification of organic compounds (8. ed.). Hoboken, NJ: Wiley.
  • Solomons, T.W.G., Fryhle C.B., Snyder S.A. (2016). Solomons´ organic chemistry ([12th edition], global edition.). Hoboken, New Jersey: John Wiley & Sons, Inc.
  • Sorenson J. R. J. (1976). Copper chelates as possible active forms of the antiarthritic agents. Journal of Medicinal Chemistry, 19(1), 135–148.
  • Stachová P., Melník M., Korabik M., Mrozinski J., Koman M., Glowiak T., Valigura D. (2007). Synthesis, spectral and magnetical characterization of monomeric [Cu(2-NO2bz)2(nia)2(H2O)2] and structural analysis of similar [Cu(RCOO)2(L–N)2(H2O)2] complexes. Inorganica Chimica Acta, 360(5), 1517–1522.
  • Tarushi A., Perontsis S., Hatzidimitriou A. G., Papadopoulos A. N., Kessissoglou D. P., Psomas G. (2015). Copper(II) complexes with the non-steroidal anti-inflammatory drug tolfenamic acid: Structure and biological features. Journal of Inorganic Biochemistry, 149, 68–79.
  • Wang D.W., Wang T., Du L., Zhou J., Yan T., Zhao, Q.H. (2018). Four supramolecular transition metal(II) complexes based on triazole-benzoic acid derivatives: crystal structure, Hirshfeld surface analysis, and spectroscopic and thermal properties. Structural Chemistry.
  • Xia C.K., Wu F., Yang K., Sun W., Min Y.Y., Wu Y.L., Lu, X.J. (2016). Zn(II) and Cd(II) complexes assembled from versatile 1,2,3,5-benzenetetracarboxylic acid and chelating N-donor auxiliary coligands. Polyhedron, 117, 637–643.
  • Zhang Q., Yue C., Zhang Y., Lü Y., Hao Y., Miao Y., Li J., Liu Z. (2018). Six metal-organic frameworks assembled from asymmetric triazole carboxylate ligands: Synthesis, crystal structures, photoluminescence properties and antibacterial activities. Inorganica Chimica Acta, 473, 112–120.

Synthesis and Spectroscopic and Thermal Properties of N,N'-Diethylnicotinamide Complexes of Cu(II) p-Fluoro-, p-Chloro- and p-Bromobenzoates

Year 2019, Volume: 6 Issue: 2, 124 - 136, 27.12.2019

Abstract

In this
study, three new mixed ligand metal complexes containing N,N'-diethylnicotinamide
ligand of copper (II) p-fluoro-, p-chloro- and p-bromobenzoates were synthesized and their structures were
investigated. Elemental analysis, FT-IR and UV-Vis spectroscopy, thermal
analysis (TGA-DTA) methods were used to evaluate the structures of the
complexes. The general formulas of
the complexes were determined as [Cu(p-F-C6H4COO)2(C10H14N2O)2(H2O)]
(I), [Cu(p-Cl-C6H4COO)2(C10H14N2O)2(H2O)2]
(II) ve [Cu(p-Br-C6H4COO)2(H2O)2]
(III). In all complexes, p-halogenobenzoates and
N,N'-diethylnicotinamide behave as monodentate ligand. In the complexes, each
metal ion possesses an octahedral geometry with two oxygen atoms of two p-halogenobenzoate anions, two nitrogen
atoms from two N,N'-diethylnicotinamide ligands and two oxygen atoms of two
water molecules. Copper: p-halogenobenzoate: N, N'-diethylnicotinamide ratios
were determined to be 1: 2: 2. The thermal stability of the complexes is
III≥II> I. The thermal decomposition product of the complexes was determined
as copper (II) oxide.

Project Number

106T472

References

  • Abuhijleh A.L., Khalaf J. (2010). Copper (II) complexes of the anti-inflammatory drug naproxen and 3-pyridylmethanol as auxiliary ligand. Characterization, superoxide dismutase and catecholase – mimetic activities. European Journal of Medicinal Chemistry, 45(9), 3811–3817.
  • Agwara M.O., Ndifon P.T., Ndosiri N. B., Paboudam A. G., Yufanyi D.M., Mohamadou A. (2010). Synthesis, characterisation and antimicrobial activities of cobalt(II), copper(II) and zinc(II) mixed-ligand complexes containing 1,10-phenanthroline and 2,2’-bipyridine. Bulletin of the Chemical Society of Ethiopia, 24(3).
  • Amombo Noa F.M., Jacobs A. (2017). Phenylacetic acid co-crystals with acridine, caffeine, isonicotinamide and nicotinamide: Crystal structures, thermal analysis, FTIR spectroscopy and Hirshfeld surface analysis. Journal of Molecular Structure, 1139, 60–66.
  • Batool S.S., Gilani S.R., Tahir M.N., Rüffer T. (2017). Synthesis, and structural characterization of mixed ligand copper(II) complexes of N,N,N′,N’-tetramethylethylenediamine incorporating carboxylates. Journal of Molecular Structure, 1148, 7–14.
  • Bozkurt N., Tunç T., Çaylak Delibaş N., Necefoğlu H., Hökelek T. (2013). Aquabis(3-chlorobenzoato-κ O )bis( N , N -diethylnicotinamide-κ N )copper(II). Acta Crystallographica Section E Structure Reports Online, 69(8), m458–m459.
  • Bushma M. I., Zavodnik L.B., Lukienko P.I. (1989). [Effect of the diethylamide of nicotinic acid (cordiamine) on the hydroxylating function of the liver]. Farmakologiia I Toksikologiia, 52(4), 56–59.
  • Findoráková L., Győryová K., Melník M., Koman M., Nour El-Dien F.A. (2010). Preparation, thermal decomposition, and crystal structure of Zn(II) 2-chlorobenzoate complex with nicotinamide. Journal of Coordination Chemistry, 63(19), 3348–3355.
  • Fountoulaki S., Perdih F., Turel I., Kessissoglou D. P., Psomas G. (2011). Non-steroidal anti-inflammatory drug diflunisal interacting with Cu(II). Structure and biological features. Journal of Inorganic Biochemistry, 105(12), 1645–1655.
  • Halaška J., Pevec A., Strauch P., Kozlevčar B., Koman M., Moncol J. (2013). Supramolecular hydrogen-bonding networks constructed from copper(II) chlorobenzoates with nicotinamide: Structure and EPR. Polyhedron, 61, 20–26.
  • Kuchtanin V., Moncol J., Mroziński J., Kalińska B., Padělková Z., Švorec J., Seglá P., Melník M. (2013). Study of copper(II) thiophenecarboxylate complexes with N-methylnicotinamide. Polyhedron, 50(1), 546–555.
  • Lakowicz J. R. (2010). Principles of fluorescence spectroscopy (Third edition, corrected at 4. printing.). New York, NY: Springer.
  • Lever A. B. P. (1986). Inorganic electronic spectroscopy (2. ed.), 2. impression (with corr.). Amsterdam: Elsevier.
  • Lewandowski W., Kalinowska M., Lewandowska H. (2005). The influence of halogens on the electronic system of biologically important ligands: spectroscopic study of halogenobenzoic acids, halogenobenzoates and 5-halogenouracils. Inorganica Chimica Acta, 358(7), 2155–2166.
  • M. Qadir A. (2017). Copper(II) Carboxylate Containing Paddle Wheel Structure: Synthesis and Crystal Structure. Oriental Journal of Chemistry, 33(2), 968–970.
  • Mahata P., Ramya, K. V., Natarajan S. (2007). Synthesis, structure and optical properties of rare-earth benzene carboxylates. Dalton Transactions, (36), 4017.
  • Mandal A., Patel B.K. (2017). Molecular structures and fluorescence property of Zn(II), Cd(II) complexes of 3-pyridyl-5-aryl-(1 H )-1,2,4-triazoles. Polyhedron, 132, 112–122.
  • Ming C.L., Hao Z.C., Yu B.Y., Van Hecke K., Cui G.H. (2015). Synthesis, Structures, and Catalytic Properties of Three New Metal–Organic Coordination Polymers Constructed from Flexible Benzimidazole-Based and cis-1,2-Cyclohexanedicarboxylate Synthons. Journal of Inorganic and Organometallic Polymers and Materials, 25(3), 559–568.
  • Mitra A., Clark R. J., Hubley C. T., Saha S. (2014). Anion–π and CH···anion interactions in naphthalenediimide-based coordination complexes. Supramolecular Chemistry, 26(3–4), 296–301.
  • Nakamoto K. (1986). Infrared and Raman spectra of inorganic and coordination compounds (4. ed.). New York: Wiley.
  • Özbek F. E., Sertçelik M., Yüksek M., Küçüköz B., Elmali A., Şahin E. (2019). Two new potential optical materials: Co(II) and Ni(II) 3-fluorobenzoate complexes with pyridine-3-carboxamide. Journal of Coordination Chemistry, 72(5–7), 786–795.
  • Özbek F. E., Sertçelik M., Yüksek M., Necefoğlu H., Çelik R. Ç., Nayir G. Y., 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.
  • Pavia D. L., Lampman G. M., Kriz G. S. (2001). Introduction to spectroscopy: a guide for students of organic chemistry (3. ed.). South Melbourne: Brooks/Cole.
  • Perec M., Baggio R. F., Peña O., Sartoris R. P., Calvo R. (2011). Synthesis and structures of four new compounds of the copper(II)–carboxylate–pyridinecarboxamide system. Inorganica Chimica Acta, 373(1), 117–123. https://doi.org/10.1016/j.ica.2011.03.065
  • Puchoňová M., Repická Z., Moncol J., Růžičková Z., Mazúr M., Valigura D. (2015). Supramolecular structure formation of molecular copper(II)methylsalicylate complexes with nicotinamide or methylnicotinamide – Crystal structure and spectral properties. Journal of Molecular Structure, 1092, 1–8.
  • Sertçelik M., Çaylak Delibaş N., Necefoğlu H., Hökelek T. (2012). Diaquabis(4-formylbenzoato-κO1)bis(nicotinamide-κN1)copper(II). Acta Crystallographica Section E Structure Reports Online, 68(7), m1010–m1011.
  • Sertçelik M., Çaylak Delibaş N., Necefoğlu H., Hökelek T. (2013). Bis( -4-formylbenzoato- 2O:O')bis[(4-formylbenzoato- 2O,O')bis(isonicotinamide- N1)copper(II)]. Acta Crystallographica Section E Structure Reports Online, 69, m290–m291.
  • Sertçelik M., Özbek F.E., Sugeçti S., Necefoğlu H. (2018). Synthesis of Izonicotınamide Complexes Of 4-Formilbenzoate with Co (II), Cu (II) And Zn (II); Investigation of Spectroscopic, Thermal Properties and Antibacterial Activıties. Journal of the Institute of Science and Technology, 189–195.
  • Silverstein R.M., Webster F.X., Kiemle D.J., Bryce, D.L. (Eds.). (2015). Spectrometric identification of organic compounds (8. ed.). Hoboken, NJ: Wiley.
  • Solomons, T.W.G., Fryhle C.B., Snyder S.A. (2016). Solomons´ organic chemistry ([12th edition], global edition.). Hoboken, New Jersey: John Wiley & Sons, Inc.
  • Sorenson J. R. J. (1976). Copper chelates as possible active forms of the antiarthritic agents. Journal of Medicinal Chemistry, 19(1), 135–148.
  • Stachová P., Melník M., Korabik M., Mrozinski J., Koman M., Glowiak T., Valigura D. (2007). Synthesis, spectral and magnetical characterization of monomeric [Cu(2-NO2bz)2(nia)2(H2O)2] and structural analysis of similar [Cu(RCOO)2(L–N)2(H2O)2] complexes. Inorganica Chimica Acta, 360(5), 1517–1522.
  • Tarushi A., Perontsis S., Hatzidimitriou A. G., Papadopoulos A. N., Kessissoglou D. P., Psomas G. (2015). Copper(II) complexes with the non-steroidal anti-inflammatory drug tolfenamic acid: Structure and biological features. Journal of Inorganic Biochemistry, 149, 68–79.
  • Wang D.W., Wang T., Du L., Zhou J., Yan T., Zhao, Q.H. (2018). Four supramolecular transition metal(II) complexes based on triazole-benzoic acid derivatives: crystal structure, Hirshfeld surface analysis, and spectroscopic and thermal properties. Structural Chemistry.
  • Xia C.K., Wu F., Yang K., Sun W., Min Y.Y., Wu Y.L., Lu, X.J. (2016). Zn(II) and Cd(II) complexes assembled from versatile 1,2,3,5-benzenetetracarboxylic acid and chelating N-donor auxiliary coligands. Polyhedron, 117, 637–643.
  • Zhang Q., Yue C., Zhang Y., Lü Y., Hao Y., Miao Y., Li J., Liu Z. (2018). Six metal-organic frameworks assembled from asymmetric triazole carboxylate ligands: Synthesis, crystal structures, photoluminescence properties and antibacterial activities. Inorganica Chimica Acta, 473, 112–120.
There are 35 citations in total.

Details

Primary Language Turkish
Subjects Environmental Sciences
Journal Section Articles
Authors

Füreya Elif Özbek This is me 0000-0001-6376-4161

Project Number 106T472
Publication Date December 27, 2019
Submission Date November 18, 2019
Acceptance Date December 7, 2019
Published in Issue Year 2019 Volume: 6 Issue: 2

Cite

APA Özbek, F. E. (2019). Cu(II) p-Floro-, p-Kloro- ve p-Bromobenzoatların N,N’-Dietilnikotinamid Komplekslerinin Sentezi, Spektroskopik ve Termik Özellikleri. Caucasian Journal of Science, 6(2), 124-136.

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