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SYNTHESIS AND SPECTROSCOPIC STUDIES OF COPPER(II)/COBALT(III) CYANIDE COMPOUNDS WITH IMIDAZOLE, 1-METHYLIMIDAZOLE, AND 2-METHYLIMIDAZOLE

Year 2025, Volume: 26 Issue: 1, 1 - 13, 25.03.2025
https://doi.org/10.18038/estubtda.1541919

Abstract

New Cu(II)/Co(III) cyanide compounds, [Cu3(L)4Co2(CN)12]∙nH2O, with imidazole and methyl derivatives of imidazole have been synthesized in powder form and analyzed using elemental analyses, vibrational (FT-IR and Raman) spectroscopy, and powder X-ray diffraction (PXRD). The elemental analyses of all compounds for C, H, and N were performed and formulas of the compounds were calculated according to the results obtained. In addition, the phase purity of the compounds was confirmed through powder X-ray diffraction (PXRD) analysis. The results of PXRD patterns and vibrational spectroscopic show that the structural characteristics of Cu-Co-L [L = Imidazole(im), 1-methylimidazole(1-meim), and 2-methylimidazole(2-meim)] compounds are analogous to each other. The spectral properties of the Cu-Co-L compounds were obtained by considering the characteristic peak values of cyanide, imidazole, 1-methylimidazole, and 2-methylimidazole ligands

Ethical Statement

No

Supporting Institution

Eskişehir Osmangazi University, Scientific Research Unit (Grant No: 2022-2561).

References

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  • [2] Andrei GŞ, Andrei BF, Roxana PR. Imidazole derivatives and their antibacterial activity-a mini-review. Mini Rev Med Chem 2021; 21: 1380-1392.
  • [3] Yang H, Chen J-M, Sun J-J, Yang S-P, Yu J, Tan H, Li W. Syntheses, crystal structures and magnetic properties of three novel cobalt (II) complexes containing imidazole derivative groups. Dalton Trans 2009: 14: 2540-2551.
  • [4] Sundberg RJ, Martin RB. Interactions of histidine and other imidazole derivatives with transition metal ions in chemical and biological systems. Chem Rev 1974; 74: 471-517.
  • [5] Johnson CR, Shepherd RE, Marr B, O'Donnell S, Dressick W. Affinities of imidazolate and imidazole ligands for pentacyanoiron (III). J Am Chem Soc 1980; 102: 6227–6235.
  • [6] Fudulu A, Olar R, Maxim C, Scăeţeanu GV, Bleotu C, Matei L, Chifiriuc MC, Badea M. New cobalt (II) complexes with imidazole derivatives: antimicrobial efficiency against planktonic and adherent microbes and in vitro cytotoxicity features. Molecules 2020; 26: 55
  • [7] Abu-Dief AM, Abdel-Rahman LH, Abdelhamid AA, Marzouk AA, Shehata MR, Bakheet MA, Almaghrabi OA, Nafady A. Synthesis and characterization of new Cr(III), Fe(III) and Cu(II) complexes incorporating multi-substituted aryl imidazole ligand: Structural, DFT, DNA binding, and biological implications. Spectrochim Acta A Mol Biomol Spectrosc 2020; 228: 117700.
  • [8] Xie C, Wang W, Zou J-Z, Liu H-L, Shen X-P, Li B-L, Hu H-M, Xu Z. Template self-assembly of cyano-bridged supramolecular complexes {[Cu(en)2][KM(CN)6]}n (M = Cr(III), Fe(III), Co(III). J Coord Chem 2004; 57: 1519-1527.
  • [9] Saha MK, Lloret F, Bernal I. Inter-string arrays of bimetallic assemblies with alternative Cu2+− Cl−Cu2+ and Cu−NC−M (M = Co3+, Fe+ 3, Cr+3) bridges: syntheses, crystal structure, and magnetic properties. Inorg Chem 2004; 43: 1969-1975.
  • [10] Shiga T, Mishima A, Sugimoto K, Ōkawa H, Oshio H, Ohba M. One‐Dimensional 3d–3d–4f trimetallic assemblies consisting of CuII2LnIII trinuclear complexes and hexacyanometallate. Eur J Inorg Chem 2012; 2012: 2784-2791.
  • [11] Billa E. Synthesis and characterization of mononuclear and dinuclear copper(II) complexes containing sterically hindered polyimidazole ligands: University of Louisville; 1997.
  • [12] Machura B, Świtlicka A, Mroziński J, Kalińska B, Kruszynski R. Structural diversity and magnetic properties of thiocyanate copper (II) complexes. Polyhedron 2013; 52: 1276-1286.
  • [13] Liu M, Hu J, Wang Y. Synthesis, crystal structure and MMCT of a heterobimetallic cyanide-bridged complex trans-BrRuII(dppe)2(μ-CN)(FeIIIBr3). Polyhedron 2018; 149: 79-83.
  • [14] Černák J, Orendáč M, Potočňák I, Chomič J, Orendáčová A, Skoršepa J, Feher A. Cyanocomplexes with one-dimensional structures: preparations, crystal structures and magnetic properties. Coord Chem Rev 2002; 224: 51-66.
  • [15] Janiak C. Engineering coordination polymers towards applications. Dalton Trans 2003: 2781-2804.
  • [16] Geiss A, Vahrenkamp H. M(μ-CN)Fe(μ-CN)Mꞌ chains with phthalocyanine iron centers: preparation, structures, and isomerization. Inorg Chem 2000; 39: 4029-4036.
  • [17] Matiková Maľarová M, Černák J, Matik M, Briančin J, Varret F. Thermal properties of four Co/Fe complexes based on amine-type and cyanido ligands. J Therm Anal Calorim 2019; 136: 703-715.
  • [18] Xu H, Zhou B-Y, Yu K, Su Z-H, Zhou B-B, Su Z-M. Copper cyanide polymers with controllable dimensions modulated by rigid and flexible bis-(imidazole) ligands: synthesis, crystal structure and fluorescence properties. Crystengcomm 2019; 21: 1242-1249.
  • [19] Ismael M, Abdou A, Abdel‐Mawgoud AM. synthesis, characterization, modeling, and antimicrobial activity of FeIII, CoII, NiII, CuII, and ZnII complexes based on trisubstituted imidazole ligand. Z Anorg Allg Chem 2018; 644: 1203-1214.
  • [20] Huo J, Li H, Yu D, Arulsamy N. Three new metal complexes with imidazole-containing tripodal ligands as fluorophores for nitroaromatics-and ion-selective sensing. Inorg Chim Acta 2020; 502: 119310.
  • [21] An B, Yin F, de Voogd NJ, Chen X, Cheng W, Lin W. Chagosendines A–C, New Metal Complexes of Imidazole Alkaloids from the Calcareous Sponge Leucetta chagosensis. Chemistry & Biodiversity 2018; 15: e1700481.
  • [22] Kürkçüoğlu GS, Sayın E, Yavuz T, Şahin O. One-dimensional heteronuclear complexes with cyanide and 2-ethylimidazole ligands. Spectrosc Lett 2021; 54: 1-13.
  • [23] Karaağaç D, Kürkçüoğlu GS. Syntheses and characterizations of the cyanide-bridged heteronuclear polymeric complexes with 2-ethylimidazole. Bull Chem Soc Ethiop 2016; 30: 263-272.
  • [24] Kürkçüoğlu GS, Yeşilel OZ, Kavlak I, Kurtaran S, Büyükgüngör O. Synthesis, characterization and crystal structure of a novel three-dimensional supramolecular framework containing Ni··· π interaction heteronuclear complex: {[Cu(4(5)-Meim)4][Ni(CN)4]·H2O}n. J Inorg Organomet Polym Mater 2009; 19: 314-321.
  • [25] Kürkçüoğlu GS, Yeşilel OZ, Çaylı İ, Büyükgüngör O. One-and two-dimensional cadmium (II) tetracyanonickelate (II) coordination polymers with imidazole and 2-methylimidazole ligands. J Inorg Organomet Polym Mater 2011; 21: 306-315.
  • [26] Kürkçüoğlu GS, Gör K, Büyükgüngör O. New cyano bridged heteropolynuclear Cu(II) and Cd(II)-tetracyanopalladate (II) polymeric complexes with 2-methylimidazole ligand. Spectrochim Acta A Mol Biomol Spectrosc 2014; 124: 588-594.
  • [27] Kürkçüoğlu GS, Sayın E, Şahin O. Cyanide bridged hetero-metallic polymeric complexes: Syntheses, vibrational spectra, thermal analyses and crystal structures of complexes [M(1,2-dmi)2Ni(μ-CN)4]n (M = Zn(II) and Cd(II)). J Mol Struct 2015; 1101: 82-90.
  • [28] Mwanza T, Kürkçüoğlu GS, Ünver H, Şahin O, Yeşilel OZ. Synthesis, spectroscopic, structural characterizations, and catalytic properties of cyanide-bridged heteronuclear metal organic frameworks with imidazole. J Solid State Chem 2022; 314: 123344.
  • [29] Tchouka H. Magnetic and spectroscopic studies of iron and manganese complexes: from molecular materials to catalysis. Chemistry, University of groningen, The netherlands, 2011.
  • [30] Al Abbas A, Heinrich B, L'Her M, Couzigné E, Welter R, Douce L. Bolaamphiphilic liquid crystals based on bis-imidazolium cations. NJC 2017; 41: 2604-2613.
  • [31] Majoube M, Vergoten G. Assignment of normal modes for imidazole on the basis of 3-21G and 4-21G Ab Initio Force Fields. J Mol Struct 1992; 266: 345-352.
  • [32] Sheinker V, Movshovich DY, Osipov OA. Investigation and structure of properties of heterocyclic compounds and their complexes. IV. Calculation and interpretation of the vibrational spectra of N-methylimidazole. Zh Obshch Khim 1973; 43: 2725.
  • [33] Bellocq AM, Garrigoou-lagrange C. Vibration du méthyl-4(5) imidazole, du méthyl-4(5) imidazole (D)-1, du méthyl-4(5) imidazole (D2)-2,5(4) et du méthyl-4(5) imidazole (D3)-1,2,5(4). J Chim Phys 1969; 66: 1511-1521.
  • [34] Çaylı İ, Kürkçüoğlu GS, Yeşilel OZ, Şahin O, Büyükgüngör O. C− H⋯ Pd interactions and cyano-bridged heteronuclear polymeric complexes. Polyhedron 2012; 31: 386-394.
  • [35] Tufan Y, Karacan N, Davies JED. Vibrational spectroscopic investigations of M(imidazole)2Ni(CN)4·2C6H12 clathrates. Vib Spectros 2000; 23: 51-55.
  • [36] Tufan Y. An infrared spectroscopic study on the Hofmann Td-Type clathrates: M(imidazole)2M'(CN)4·2C6H6. J Incl Phenom Macrocycl Chem 2004; 48: 131-134.
  • [37] Nakagawa I. Far infrared and Raman spectra of K3[Co(CN)6] and [Co(NH3)6][Co(CN)6]. BCSJ 1973; 46: 3690-3693.

SYNTHESIS AND SPECTROSCOPIC STUDIES OF COPPER(II)/COBALT(III) CYANIDE COMPOUNDS WITH IMIDAZOLE, 1-METHYLIMIDAZOLE, AND 2-METHYLIMIDAZOLE

Year 2025, Volume: 26 Issue: 1, 1 - 13, 25.03.2025
https://doi.org/10.18038/estubtda.1541919

Abstract

References

  • [1] Gupta P, Gupta JK. Synthesis of bioactive imidazoles: a review. Int J Modern Chem 2015; 7: 60-80.
  • [2] Andrei GŞ, Andrei BF, Roxana PR. Imidazole derivatives and their antibacterial activity-a mini-review. Mini Rev Med Chem 2021; 21: 1380-1392.
  • [3] Yang H, Chen J-M, Sun J-J, Yang S-P, Yu J, Tan H, Li W. Syntheses, crystal structures and magnetic properties of three novel cobalt (II) complexes containing imidazole derivative groups. Dalton Trans 2009: 14: 2540-2551.
  • [4] Sundberg RJ, Martin RB. Interactions of histidine and other imidazole derivatives with transition metal ions in chemical and biological systems. Chem Rev 1974; 74: 471-517.
  • [5] Johnson CR, Shepherd RE, Marr B, O'Donnell S, Dressick W. Affinities of imidazolate and imidazole ligands for pentacyanoiron (III). J Am Chem Soc 1980; 102: 6227–6235.
  • [6] Fudulu A, Olar R, Maxim C, Scăeţeanu GV, Bleotu C, Matei L, Chifiriuc MC, Badea M. New cobalt (II) complexes with imidazole derivatives: antimicrobial efficiency against planktonic and adherent microbes and in vitro cytotoxicity features. Molecules 2020; 26: 55
  • [7] Abu-Dief AM, Abdel-Rahman LH, Abdelhamid AA, Marzouk AA, Shehata MR, Bakheet MA, Almaghrabi OA, Nafady A. Synthesis and characterization of new Cr(III), Fe(III) and Cu(II) complexes incorporating multi-substituted aryl imidazole ligand: Structural, DFT, DNA binding, and biological implications. Spectrochim Acta A Mol Biomol Spectrosc 2020; 228: 117700.
  • [8] Xie C, Wang W, Zou J-Z, Liu H-L, Shen X-P, Li B-L, Hu H-M, Xu Z. Template self-assembly of cyano-bridged supramolecular complexes {[Cu(en)2][KM(CN)6]}n (M = Cr(III), Fe(III), Co(III). J Coord Chem 2004; 57: 1519-1527.
  • [9] Saha MK, Lloret F, Bernal I. Inter-string arrays of bimetallic assemblies with alternative Cu2+− Cl−Cu2+ and Cu−NC−M (M = Co3+, Fe+ 3, Cr+3) bridges: syntheses, crystal structure, and magnetic properties. Inorg Chem 2004; 43: 1969-1975.
  • [10] Shiga T, Mishima A, Sugimoto K, Ōkawa H, Oshio H, Ohba M. One‐Dimensional 3d–3d–4f trimetallic assemblies consisting of CuII2LnIII trinuclear complexes and hexacyanometallate. Eur J Inorg Chem 2012; 2012: 2784-2791.
  • [11] Billa E. Synthesis and characterization of mononuclear and dinuclear copper(II) complexes containing sterically hindered polyimidazole ligands: University of Louisville; 1997.
  • [12] Machura B, Świtlicka A, Mroziński J, Kalińska B, Kruszynski R. Structural diversity and magnetic properties of thiocyanate copper (II) complexes. Polyhedron 2013; 52: 1276-1286.
  • [13] Liu M, Hu J, Wang Y. Synthesis, crystal structure and MMCT of a heterobimetallic cyanide-bridged complex trans-BrRuII(dppe)2(μ-CN)(FeIIIBr3). Polyhedron 2018; 149: 79-83.
  • [14] Černák J, Orendáč M, Potočňák I, Chomič J, Orendáčová A, Skoršepa J, Feher A. Cyanocomplexes with one-dimensional structures: preparations, crystal structures and magnetic properties. Coord Chem Rev 2002; 224: 51-66.
  • [15] Janiak C. Engineering coordination polymers towards applications. Dalton Trans 2003: 2781-2804.
  • [16] Geiss A, Vahrenkamp H. M(μ-CN)Fe(μ-CN)Mꞌ chains with phthalocyanine iron centers: preparation, structures, and isomerization. Inorg Chem 2000; 39: 4029-4036.
  • [17] Matiková Maľarová M, Černák J, Matik M, Briančin J, Varret F. Thermal properties of four Co/Fe complexes based on amine-type and cyanido ligands. J Therm Anal Calorim 2019; 136: 703-715.
  • [18] Xu H, Zhou B-Y, Yu K, Su Z-H, Zhou B-B, Su Z-M. Copper cyanide polymers with controllable dimensions modulated by rigid and flexible bis-(imidazole) ligands: synthesis, crystal structure and fluorescence properties. Crystengcomm 2019; 21: 1242-1249.
  • [19] Ismael M, Abdou A, Abdel‐Mawgoud AM. synthesis, characterization, modeling, and antimicrobial activity of FeIII, CoII, NiII, CuII, and ZnII complexes based on trisubstituted imidazole ligand. Z Anorg Allg Chem 2018; 644: 1203-1214.
  • [20] Huo J, Li H, Yu D, Arulsamy N. Three new metal complexes with imidazole-containing tripodal ligands as fluorophores for nitroaromatics-and ion-selective sensing. Inorg Chim Acta 2020; 502: 119310.
  • [21] An B, Yin F, de Voogd NJ, Chen X, Cheng W, Lin W. Chagosendines A–C, New Metal Complexes of Imidazole Alkaloids from the Calcareous Sponge Leucetta chagosensis. Chemistry & Biodiversity 2018; 15: e1700481.
  • [22] Kürkçüoğlu GS, Sayın E, Yavuz T, Şahin O. One-dimensional heteronuclear complexes with cyanide and 2-ethylimidazole ligands. Spectrosc Lett 2021; 54: 1-13.
  • [23] Karaağaç D, Kürkçüoğlu GS. Syntheses and characterizations of the cyanide-bridged heteronuclear polymeric complexes with 2-ethylimidazole. Bull Chem Soc Ethiop 2016; 30: 263-272.
  • [24] Kürkçüoğlu GS, Yeşilel OZ, Kavlak I, Kurtaran S, Büyükgüngör O. Synthesis, characterization and crystal structure of a novel three-dimensional supramolecular framework containing Ni··· π interaction heteronuclear complex: {[Cu(4(5)-Meim)4][Ni(CN)4]·H2O}n. J Inorg Organomet Polym Mater 2009; 19: 314-321.
  • [25] Kürkçüoğlu GS, Yeşilel OZ, Çaylı İ, Büyükgüngör O. One-and two-dimensional cadmium (II) tetracyanonickelate (II) coordination polymers with imidazole and 2-methylimidazole ligands. J Inorg Organomet Polym Mater 2011; 21: 306-315.
  • [26] Kürkçüoğlu GS, Gör K, Büyükgüngör O. New cyano bridged heteropolynuclear Cu(II) and Cd(II)-tetracyanopalladate (II) polymeric complexes with 2-methylimidazole ligand. Spectrochim Acta A Mol Biomol Spectrosc 2014; 124: 588-594.
  • [27] Kürkçüoğlu GS, Sayın E, Şahin O. Cyanide bridged hetero-metallic polymeric complexes: Syntheses, vibrational spectra, thermal analyses and crystal structures of complexes [M(1,2-dmi)2Ni(μ-CN)4]n (M = Zn(II) and Cd(II)). J Mol Struct 2015; 1101: 82-90.
  • [28] Mwanza T, Kürkçüoğlu GS, Ünver H, Şahin O, Yeşilel OZ. Synthesis, spectroscopic, structural characterizations, and catalytic properties of cyanide-bridged heteronuclear metal organic frameworks with imidazole. J Solid State Chem 2022; 314: 123344.
  • [29] Tchouka H. Magnetic and spectroscopic studies of iron and manganese complexes: from molecular materials to catalysis. Chemistry, University of groningen, The netherlands, 2011.
  • [30] Al Abbas A, Heinrich B, L'Her M, Couzigné E, Welter R, Douce L. Bolaamphiphilic liquid crystals based on bis-imidazolium cations. NJC 2017; 41: 2604-2613.
  • [31] Majoube M, Vergoten G. Assignment of normal modes for imidazole on the basis of 3-21G and 4-21G Ab Initio Force Fields. J Mol Struct 1992; 266: 345-352.
  • [32] Sheinker V, Movshovich DY, Osipov OA. Investigation and structure of properties of heterocyclic compounds and their complexes. IV. Calculation and interpretation of the vibrational spectra of N-methylimidazole. Zh Obshch Khim 1973; 43: 2725.
  • [33] Bellocq AM, Garrigoou-lagrange C. Vibration du méthyl-4(5) imidazole, du méthyl-4(5) imidazole (D)-1, du méthyl-4(5) imidazole (D2)-2,5(4) et du méthyl-4(5) imidazole (D3)-1,2,5(4). J Chim Phys 1969; 66: 1511-1521.
  • [34] Çaylı İ, Kürkçüoğlu GS, Yeşilel OZ, Şahin O, Büyükgüngör O. C− H⋯ Pd interactions and cyano-bridged heteronuclear polymeric complexes. Polyhedron 2012; 31: 386-394.
  • [35] Tufan Y, Karacan N, Davies JED. Vibrational spectroscopic investigations of M(imidazole)2Ni(CN)4·2C6H12 clathrates. Vib Spectros 2000; 23: 51-55.
  • [36] Tufan Y. An infrared spectroscopic study on the Hofmann Td-Type clathrates: M(imidazole)2M'(CN)4·2C6H6. J Incl Phenom Macrocycl Chem 2004; 48: 131-134.
  • [37] Nakagawa I. Far infrared and Raman spectra of K3[Co(CN)6] and [Co(NH3)6][Co(CN)6]. BCSJ 1973; 46: 3690-3693.
There are 37 citations in total.

Details

Primary Language English
Subjects Inorganic Green Chemistry
Journal Section Articles
Authors

Güneş Süheyla Kürkçüoğlu 0000-0003-3945-3085

Dursun Karaağaç 0000-0003-3504-6765

Seray Kekeç 0000-0001-7777-8257

Publication Date March 25, 2025
Submission Date September 1, 2024
Acceptance Date January 17, 2025
Published in Issue Year 2025 Volume: 26 Issue: 1

Cite

AMA Kürkçüoğlu GS, Karaağaç D, Kekeç S. SYNTHESIS AND SPECTROSCOPIC STUDIES OF COPPER(II)/COBALT(III) CYANIDE COMPOUNDS WITH IMIDAZOLE, 1-METHYLIMIDAZOLE, AND 2-METHYLIMIDAZOLE. Estuscience - Se. March 2025;26(1):1-13. doi:10.18038/estubtda.1541919