Research Article
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Year 2021, Volume: 8 Issue: 2, 659 - 676, 31.05.2021
https://doi.org/10.18596/jotcsa.912967

Abstract

Project Number

Project No. FEF19004.18.001

References

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Novel Mixed Ligand Complexes of Alkaline Earth Metals with Coumarilic Acid and Nicotinamide

Year 2021, Volume: 8 Issue: 2, 659 - 676, 31.05.2021
https://doi.org/10.18596/jotcsa.912967

Abstract

Coordination compounds with mixed ligands were synthesized with 2A group (Mg2+, Ca2+, Ba2+, Sr2+) alkaline earth metal cations of coumarilic acid and nicotinamide ligands. Afterward, the structural properties of these new molecules were investigated by melting point, elemental analysis, infrared spectroscopy, thermal analysis (TGA / DTA) curves, powder X-ray diffraction (P-XRD) spectroscopy. It has been suggested that the complex structure with the Mg2+ metal center is different from the other three structures. In this structure, it was determined that four aqua and two nicotinamide ligands were located in the coordination sphere, and the coordination number was six, as expected. With two monoanionic coumarilic acids located outside the coordination sphere, complex charge equivalence was achieved. The other three molecules, Sr2+ and Ba2+, have iso-structural properties, and it is suggested that both structures contain a dinuclear metal center, and two aqua ligands are located in the bridging position between metal centers. Besides, the two coumarilate ligands involved in coordination are thought to coordinate with the primary metal cation through carbonyl and acidic oxygens while coordinating with the secondary metal cation through furan oxygen, providing the third bridge connection between metal centers. Metal cations with nine coordination numbers complete the coordination sphere with two terminal aqua and one nicotinamide ligands, each included in the structure. In the molecule with Ca2+ cation, which differs little from these metal cation structures, the difference according to these structures can be interpreted as the coordination of furan oxygen with the secondary metal center due to the octet coordination of the Ca2+ cation. From the thermal analysis curves, it was determined that only the Mg2+ cation complex contained hydrate. As a result of thermal decomposition, it was determined that relevant metal oxide residues remained in all structures, and this situation was defined by powder XRD.

Supporting Institution

Hitit University

Project Number

Project No. FEF19004.18.001

References

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  • 3. Hiremath SM, Suvitha A, Patil NR, Hiremath CS, Khemalapure SS, Pattanayak SK, et al. Molecular structure, vibrational spectra, NMR, UV, NBO, NLO, HOMO-LUMO and molecular docking of 2-(4, 6-dimethyl-1-benzofuran-3-yl) acetic acid (2DBAA): Experimental and theoretical approach. Journal of Molecular Structure. 2018 Nov;1171:362–74. Doi: https://doi.org/10.1016/j.molstruc.2018.05.109.
  • 4. Radadiya A, Shah A. Bioactive benzofuran derivatives: An insight on lead developments, radioligands and advances of the last decade. European Journal of Medicinal Chemistry. 2015 Jun;97:356–76. Doi: https://doi.org/10.1016/j.ejmech.2015.01.021.
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  • 6. Naik R, Harmalkar DS, Xu X, Jang K, Lee K. Bioactive benzofuran derivatives: Moracins A–Z in medicinal chemistry. European Journal of Medicinal Chemistry. 2015 Jan;90:379–93. Doi: https://doi.org/10.1016/j.ejmech.2014.11.047.
  • 7. Oka T. Enantioselective synthesis and absolute configuration of (−)-1-(benzofuran-2-yl)-2-propylaminopentane, ((−)-BPAP), a highly potent and selective catecholaminergic activity enhancer. Bioorganic & Medicinal Chemistry. 2001 May;9(5):1213–9. Doi: https://doi.org/10.1016/S0968-0896(00)00341-2.
  • 8. Fukai T, Oku Y, Hano Y, Terada S. Antimicrobial Activities of Hydrophobic 2-Arylbenzofurans and an Isoflavone against Vancomycin-Resistant Enterococci and Methicillin-Resistant Staphylococcus aureus. Planta med. 2004 Jul;70(7):685–7. Doi: https://doi.org/10.1055/s-2004-827196.
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  • 12. Cui B, Chai H, Santisuk T, Reutrakul V, Farnsworth NR, Cordell GA, et al. Novel cytotoxic 1H-cyclopenta[b]benzofuran lignans from Aglaia elliptica. Tetrahedron. 1997 Dec;53(52):17625–32. Doi: https://doi.org/10.1016/S0040-4020(97)10231-9.
  • 13. Lee SK, Cui B, Mehta RR, Kinghorn AD, Pezzuto JM. Cytostatic mechanism and antitumor potential of novel 1H-cyclopenta[b]benzofuran lignans isolated from Aglaiaelliptica. Chemico-Biological Interactions. 1998 Oct;115(3):215–28. Doi: https://doi.org/10.1016/S0009-2797(98)00073-8.
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  • 17. Masche UP, Rentsch KM, von Felten A, Meier PJ, Fattinger KE. No clinically relevant effect of Iornoxicam intake on acenocoumarol pharmacokinetics and pharmacodynamics. European Journal of Clinical Pharmacology. 1999 Jan 20;54(11):865–8. Doi: https://doi.org/10.1007/s002280050568.
  • 18. Karaliota A, Kretsi O, Tzougraki C. Synthesis and characterization of a binuclear coumarin-3-carboxylate copper(II) complex. Journal of Inorganic Biochemistry. 2001 Mar;84(1–2):33–7. Doi: https://doi.org/10.1016/S0162-0134(00)00214-2.
  • 19. Kossakowski J, Krawiecka M, Kuran B, Stefańska J, Wolska I. Synthesis and Preliminary Evaluation of the Antimicrobial Activity of Selected 3-Benzofurancarboxylic Acid Derivatives. Molecules. 2010 Jul 6;15(7):4737–49. Doi: https://doi.org/10.3390/molecules15074737.
  • 20. Tsuji H, Mitsui C, Ilies L, Sato Y, Nakamura E. Synthesis and Properties of 2,3,6,7-Tetraarylbenzo[1,2- b :4,5- b ‘]difurans as Hole-Transporting Material. J Am Chem Soc. 2007 Oct 1;129(39):11902–3. Doi: https://doi.org/10.1021/ja074365w.
  • 21. Anderson S, Taylor PN, Verschoor GLB. Benzofuran Trimers for Organic Electroluminescence. Chem Eur J. 2004 Jan 23;10(2):518–27. Doi: https://doi.org/10.1002/chem.200305284.
  • 22. Creaven BS, Devereux M, Georgieva I, Karcz D, McCann M, Trendafilova N, et al. Molecular structure and spectroscopic studies on novel complexes of coumarin-3-carboxylic acid with Ni(II), Co(II), Zn(II) and Mn(II) ions based on density functional theory. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2011 Dec;84(1):275–85. Doi: https://doi.org/10.1016/j.saa.2011.09.041.
  • 23. Castellani CB, Carugo O. Studies on fluorescent lanthanide complexes. New complexes of lanthanides(III) with coumarinic-3-carboxylic acid. Inorganica Chimica Acta. 1989 May;159(2):157–61. Doi: https://doi.org/10.1016/S0020-1693(00)80560-5.
  • 24. Georgieva I, Trendafilova N, Aquino AJA, Lischka H. Theoretical Study of Metal−Ligand Interaction in Sm(III), Eu(III), and Tb(III) Complexes of Coumarin-3-Carboxylic Acid in the Gas Phase and Solution. Inorg Chem. 2007 Dec 1;46(25):10926–36. Doi: https://doi.org/10.1021/ic7016616.
  • 25. Georgieva I, Trendafilova N, Creaven BS, Walsh M, Noble A, McCann M. Is the CO frequency shift a reliable indicator of coumarin binding to metal ions through the carbonyl oxygen? Chemical Physics. 2009 Nov;365(1–2):69–79. Doi: https://doi.org/10.1016/j.chemphys.2009.10.004.
  • 26. Mihaylov Tz, Trendafilova N, Kostova I, Georgieva I, Bauer G. DFT modeling and spectroscopic study of metal–ligand bonding in La(III) complex of coumarin-3-carboxylic acid. Chemical Physics. 2006 Sep;327(2–3):209–19. Doi: https://doi.org/10.1016/j.chemphys.2006.04.009.
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There are 53 citations in total.

Details

Primary Language English
Subjects Inorganic Chemistry
Journal Section Articles
Authors

Emrah Karaer 0000-0003-3854-7768

Dursun Ali Köse 0000-0003-4767-6799

Project Number Project No. FEF19004.18.001
Publication Date May 31, 2021
Submission Date April 10, 2021
Acceptance Date May 10, 2021
Published in Issue Year 2021 Volume: 8 Issue: 2

Cite

Vancouver Karaer E, Köse DA. Novel Mixed Ligand Complexes of Alkaline Earth Metals with Coumarilic Acid and Nicotinamide. JOTCSA. 2021;8(2):659-76.