BibTex RIS Cite

CONVENTIONAL AND MICROWAVE-ASSISTED SYNTHESIS AND CHARACTERIZATION of Ru(III)/Cu(II) COMPLEXES CONTAINING DICARBOXYLIC ACID GROUPS

Year 2016, Volume: 3 Issue: 2, 103 - 116, 06.05.2016
https://doi.org/10.18596/jotcsa.20088

Abstract

Abstract: In this study, microwave-assisted and conventional syntheses of Ru(III) and Cu(II) complexes with 2,4-pyridinedicarboxylic acid (L1), 3,5-pyridinedicarboxylic acid (L2), and 3,5-pyrazoledicarboxylic acid (L3) have been studied. A comparative study of microwave and conventional methods was performed to determine their differences in terms of reaction time, the amount of solvent, and reaction yield. The reaction time was reduced significantly from several hours to a few minutes, and high yields were obtained by microwave method while using considerably less amount of solvent. The synthesized complexes were characterized by FT-IR, UV-Vis, AAS, 1H-NMR, elemental analyses, and magnetic susceptibility. These studies showed that copper and ruthenium complexes have square planar and octahedral geometries, respectively. The metal complexes of Cu(II) and Ru(III) were easily synthesized upon exposure to microwave irradiation.

References

  • Lan A, Han L, Yuan D, Jiang F, Hong M. A blue luminescent inorganic–organic hybrid with infinite [Cd3(μ3-OH)2(μ2-Cl)2] connectivity. Inorganic Chemistry Communications. 2007 Sep;10(9):993–6. DOI: 10.1016/j.inoche.2007.05.009.S, Swami M. Microwave-assisted synthesis, characterization and biological activities of organotin (IV) complexes with some thio Schiff bases. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2009 Mar;72(2):260–8. DOI: 10.1016/j.saa.2008.09.017.
  • Liu Y, Li Y-X, Zhang S-W, Ji H-M, Cao R-G, Liu S-X. Organic–inorganic hybrid based on the molybdenum tellurite. Journal of Molecular Structure. 2009 Mar;921(1-3):114–7. DOI: 10.1016/j.molstruc.2008.12.058.
  • Wu L, Ma H, Han Z, Li C. Synthesis, structure and property of a new inorganic–organic hybrid compound [Cu(phen)2][Cu(phen)H2O]2[Mo5P2O23]·3.5H2O. Solid State Sciences. 2009 Jan;11(1):43–8. DOI: 10.1016/j.solidstatesciences.2008.05.016.
  • Ellsworth JM, Smith MD, zur Loye H-C. Improved synthesis of 4,4′-bipyridine-2-carboxylic acid and its use in the construction of novel metal and mixed-metal coordination polymers. Solid State Sciences. 2008 Dec;10(12):1822–34. DOI: 10.1016/j.solidstatesciences.2008.03.014.
  • Wang R, Lu X, Yu X, Shi L, Sun Y. Acid-catalyzed solvent-free synthesis of 2-arylbenzimidazoles under microwave irradiation. Journal of Molecular Catalysis A: Chemical. 2007 Apr;266(1-2):198–201. DOI: 10.1016/j.molcata.2006.04.071.
  • Cortijo M, Delgado-Martínez P, González-Prieto R, Herrero S, Jiménez-Aparicio R, Perles J, et al. Microwave and solvothermal methods for the synthesis of nickel and ruthenium complexes with 9-anthracene carboxylate ligand. Inorganica Chimica Acta. 2015 Jan;424:176–85. DOI: 10.1016/j.ica.2014.07.063.
  • Bui HTB, Ha QTK, Oh WK, Vo DD, Chau YNT, Tu CTK, et al. Microwave assisted synthesis and cytotoxic activity evaluations of new benzimidazole derivatives. Tetrahedron Letters. 2016 Feb;57(8):887–91. DOI: 10.1016/j.tetlet.2016.01.042.
  • Anderson TJ, Scott JR, Millett F, Durham B. Decarboxylation of 2,2‘-Bipyridinyl-4,4‘-dicarboxylic Acid Diethyl Ester during Microwave Synthesis of the Corresponding Trichelated Ruthenium Complex. Inorganic Chemistry. 2006 May;45(10):3843–5. DOI: 10.1021/ic060008v.
  • Singh RV, Chaudhary P, Chauhan S, Swami M. Microwave-assisted synthesis, characterization and biological activities of organotin (IV) complexes with some thio Schiff bases. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2009 Mar;72(2):260–8. DOI: 10.1016/j.saa.2008.09.017.
  • Shaabani A, Maleki-Moghaddam R, Maleki A, Rezayan AH. Microwave assisted synthesis of metal-free phthalocyanine and metallophthalocyanines. Dyes and Pigments. 2007 Jan;74(2):279–82. DOI: 10.1016/j.dyepig.2006.02.005.
  • McDonald FC, Applefield RC, Halkides CJ, Reibenspies JH, Hancock RD. A thermodynamic and crystallographic study of complexes of the highly preorganized ligand 8-hydroxyquinoline-2-carboxylic acid. Inorganica Chimica Acta. 2008 May;361(7):1937–46. DOI: 10.1016/j.ica.2007.10.004.
  • Sharma K, Singh R, Fahmi N, Singh RV. Microwave assisted synthesis, characterization and biological evaluation of palladium and platinum complexes with azomethines. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2010 Jan;75(1):422–7. DOI: 10.1016/j.saa.2009.10.052.
  • Refat MS, El-Korashy SA, Kumar DN, Ahmed AS. Syntheses and characterization of Ru(III) with chelating containing ONNO donor quadridentate Schiff bases. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2008 Sep;70(4):898–906. DOI: 10.1016/j.saa.2007.10.005.
  • Chandra S, Jain D, Sharma AK. EPR, mass, electronic, IR spectroscopic and thermal studies of bimetallic copper(II) complexes with tetradentate ligand, 1,4-diformyl piperazine bis(carbohydrazone). Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2009 Jan;71(5):1712–9. DOI: 10.1016/j.saa.2008.06.028.
  • Mohanan K, Kumari BS, Rijulal G. Microwave assisted synthesis, spectroscopic, thermal, and antifungal studies of some lanthanide(III) complexes with a heterocyclic bishydrazone. Journal of Rare Earths. 2008 Feb;26(1):16–21. DOI: 10.1016/S1002-0721(08)60028-9.
  • Jolly WL. Modern inorganic chemistry. New York: McGraw-Hill; 1984. 610 p. ISBN: 978-0-07-032760-3.
  • Yıldız E, Bozkurt G. Synthesis of Ru(III) and Al(III) Complexes Containing Anthraquinone Moiety and Interactions of the UV Radiations. Asian Journal of Chemistry. 2009;5:4047–53. URL: http://search.proquest.com/openview/48f867dd7f5c02e0bb7ca95a21886989/1?pq-origsite=gscholar.
  • Dong Y-B, Smith MD, zur Loye H-C. Synthesis and characterization of a novel copper(II)-silver(I) mixed-metal coordination polymer: Ag[Cu(2-pyrazinecarboxylate)2](H2O)(NO3). Solid State Sciences. 2000 May;2(3):335–41. DOI: 10.1016/S1293-2558(00)00139-4.
  • Driessen WL, Chang L, Finazzo C, Gorter S, Rehorst D, Reedijk J, et al. Two pyrazolato-bridged, linear trinuclear Cu(II) complexes. Crystal structures and magnetic properties. Inorganica Chimica Acta. 2003 Jul;350:25–31. DOI: 10.1016/S0020-1693(02)01509-8.
  • Serbest K, Değirmencioğlu İ, Ünver Y, Er M, Kantar C, Sancak K. Microwave-assisted synthesis and characterization and theoretical calculations of the first example of free and metallophthalocyanines from salen type Schiff base derivative bearing thiophen and triazole heterocyclic rings. Journal of Organometallic Chemistry. 2007 Dec;692(25):5646–54. DOI: 10.1016/j.jorganchem.2007.09.026.
  • Kufelnicki A, Woźniczka M, Chęcińska L, Miernicka M, Budzisz E. Synthesis and structure of novel copper(II) complexes with pyrazole derived ligands and metal–ligand interaction in solution. Polyhedron. 2007 Jul;26(12):2589–96. DOI: 10.1016/j.poly.2006.12.043.
  • Mizushima K, Nakaura M, Park S-B, Nishiyama H, Monjushiro H, Harada K, et al. Ruthenium(II) complexes with the tetradentate 6,6′-bis(oxazolinyl or benzimidazolyl)-2,2′-bipyridine ligand: synthesis, electrochemical properties, and catalytic reactivities. Inorganica Chimica Acta. 1997 Sep;261(2):175–80. DOI: 10.1016/S0020-1693(97)05479-0.
Year 2016, Volume: 3 Issue: 2, 103 - 116, 06.05.2016
https://doi.org/10.18596/jotcsa.20088

Abstract

References

  • Lan A, Han L, Yuan D, Jiang F, Hong M. A blue luminescent inorganic–organic hybrid with infinite [Cd3(μ3-OH)2(μ2-Cl)2] connectivity. Inorganic Chemistry Communications. 2007 Sep;10(9):993–6. DOI: 10.1016/j.inoche.2007.05.009.S, Swami M. Microwave-assisted synthesis, characterization and biological activities of organotin (IV) complexes with some thio Schiff bases. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2009 Mar;72(2):260–8. DOI: 10.1016/j.saa.2008.09.017.
  • Liu Y, Li Y-X, Zhang S-W, Ji H-M, Cao R-G, Liu S-X. Organic–inorganic hybrid based on the molybdenum tellurite. Journal of Molecular Structure. 2009 Mar;921(1-3):114–7. DOI: 10.1016/j.molstruc.2008.12.058.
  • Wu L, Ma H, Han Z, Li C. Synthesis, structure and property of a new inorganic–organic hybrid compound [Cu(phen)2][Cu(phen)H2O]2[Mo5P2O23]·3.5H2O. Solid State Sciences. 2009 Jan;11(1):43–8. DOI: 10.1016/j.solidstatesciences.2008.05.016.
  • Ellsworth JM, Smith MD, zur Loye H-C. Improved synthesis of 4,4′-bipyridine-2-carboxylic acid and its use in the construction of novel metal and mixed-metal coordination polymers. Solid State Sciences. 2008 Dec;10(12):1822–34. DOI: 10.1016/j.solidstatesciences.2008.03.014.
  • Wang R, Lu X, Yu X, Shi L, Sun Y. Acid-catalyzed solvent-free synthesis of 2-arylbenzimidazoles under microwave irradiation. Journal of Molecular Catalysis A: Chemical. 2007 Apr;266(1-2):198–201. DOI: 10.1016/j.molcata.2006.04.071.
  • Cortijo M, Delgado-Martínez P, González-Prieto R, Herrero S, Jiménez-Aparicio R, Perles J, et al. Microwave and solvothermal methods for the synthesis of nickel and ruthenium complexes with 9-anthracene carboxylate ligand. Inorganica Chimica Acta. 2015 Jan;424:176–85. DOI: 10.1016/j.ica.2014.07.063.
  • Bui HTB, Ha QTK, Oh WK, Vo DD, Chau YNT, Tu CTK, et al. Microwave assisted synthesis and cytotoxic activity evaluations of new benzimidazole derivatives. Tetrahedron Letters. 2016 Feb;57(8):887–91. DOI: 10.1016/j.tetlet.2016.01.042.
  • Anderson TJ, Scott JR, Millett F, Durham B. Decarboxylation of 2,2‘-Bipyridinyl-4,4‘-dicarboxylic Acid Diethyl Ester during Microwave Synthesis of the Corresponding Trichelated Ruthenium Complex. Inorganic Chemistry. 2006 May;45(10):3843–5. DOI: 10.1021/ic060008v.
  • Singh RV, Chaudhary P, Chauhan S, Swami M. Microwave-assisted synthesis, characterization and biological activities of organotin (IV) complexes with some thio Schiff bases. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2009 Mar;72(2):260–8. DOI: 10.1016/j.saa.2008.09.017.
  • Shaabani A, Maleki-Moghaddam R, Maleki A, Rezayan AH. Microwave assisted synthesis of metal-free phthalocyanine and metallophthalocyanines. Dyes and Pigments. 2007 Jan;74(2):279–82. DOI: 10.1016/j.dyepig.2006.02.005.
  • McDonald FC, Applefield RC, Halkides CJ, Reibenspies JH, Hancock RD. A thermodynamic and crystallographic study of complexes of the highly preorganized ligand 8-hydroxyquinoline-2-carboxylic acid. Inorganica Chimica Acta. 2008 May;361(7):1937–46. DOI: 10.1016/j.ica.2007.10.004.
  • Sharma K, Singh R, Fahmi N, Singh RV. Microwave assisted synthesis, characterization and biological evaluation of palladium and platinum complexes with azomethines. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2010 Jan;75(1):422–7. DOI: 10.1016/j.saa.2009.10.052.
  • Refat MS, El-Korashy SA, Kumar DN, Ahmed AS. Syntheses and characterization of Ru(III) with chelating containing ONNO donor quadridentate Schiff bases. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2008 Sep;70(4):898–906. DOI: 10.1016/j.saa.2007.10.005.
  • Chandra S, Jain D, Sharma AK. EPR, mass, electronic, IR spectroscopic and thermal studies of bimetallic copper(II) complexes with tetradentate ligand, 1,4-diformyl piperazine bis(carbohydrazone). Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2009 Jan;71(5):1712–9. DOI: 10.1016/j.saa.2008.06.028.
  • Mohanan K, Kumari BS, Rijulal G. Microwave assisted synthesis, spectroscopic, thermal, and antifungal studies of some lanthanide(III) complexes with a heterocyclic bishydrazone. Journal of Rare Earths. 2008 Feb;26(1):16–21. DOI: 10.1016/S1002-0721(08)60028-9.
  • Jolly WL. Modern inorganic chemistry. New York: McGraw-Hill; 1984. 610 p. ISBN: 978-0-07-032760-3.
  • Yıldız E, Bozkurt G. Synthesis of Ru(III) and Al(III) Complexes Containing Anthraquinone Moiety and Interactions of the UV Radiations. Asian Journal of Chemistry. 2009;5:4047–53. URL: http://search.proquest.com/openview/48f867dd7f5c02e0bb7ca95a21886989/1?pq-origsite=gscholar.
  • Dong Y-B, Smith MD, zur Loye H-C. Synthesis and characterization of a novel copper(II)-silver(I) mixed-metal coordination polymer: Ag[Cu(2-pyrazinecarboxylate)2](H2O)(NO3). Solid State Sciences. 2000 May;2(3):335–41. DOI: 10.1016/S1293-2558(00)00139-4.
  • Driessen WL, Chang L, Finazzo C, Gorter S, Rehorst D, Reedijk J, et al. Two pyrazolato-bridged, linear trinuclear Cu(II) complexes. Crystal structures and magnetic properties. Inorganica Chimica Acta. 2003 Jul;350:25–31. DOI: 10.1016/S0020-1693(02)01509-8.
  • Serbest K, Değirmencioğlu İ, Ünver Y, Er M, Kantar C, Sancak K. Microwave-assisted synthesis and characterization and theoretical calculations of the first example of free and metallophthalocyanines from salen type Schiff base derivative bearing thiophen and triazole heterocyclic rings. Journal of Organometallic Chemistry. 2007 Dec;692(25):5646–54. DOI: 10.1016/j.jorganchem.2007.09.026.
  • Kufelnicki A, Woźniczka M, Chęcińska L, Miernicka M, Budzisz E. Synthesis and structure of novel copper(II) complexes with pyrazole derived ligands and metal–ligand interaction in solution. Polyhedron. 2007 Jul;26(12):2589–96. DOI: 10.1016/j.poly.2006.12.043.
  • Mizushima K, Nakaura M, Park S-B, Nishiyama H, Monjushiro H, Harada K, et al. Ruthenium(II) complexes with the tetradentate 6,6′-bis(oxazolinyl or benzimidazolyl)-2,2′-bipyridine ligand: synthesis, electrochemical properties, and catalytic reactivities. Inorganica Chimica Acta. 1997 Sep;261(2):175–80. DOI: 10.1016/S0020-1693(97)05479-0.
There are 22 citations in total.

Details

Journal Section Articles
Authors

Emel Yıldız

Burak Ay

Publication Date May 6, 2016
Submission Date February 22, 2016
Published in Issue Year 2016 Volume: 3 Issue: 2

Cite

Vancouver Yıldız E, Ay B. CONVENTIONAL AND MICROWAVE-ASSISTED SYNTHESIS AND CHARACTERIZATION of Ru(III)/Cu(II) COMPLEXES CONTAINING DICARBOXYLIC ACID GROUPS. JOTCSA. 2016;3(2):103-16.