A Short Review on Structural Concepts of Metal Complexes of Proton Transfer Salts of Pyridine-2-Carboxylic Acid

Year 2023, Volume: 10 Issue: 1, 11 - 20, 28.02.2023

Nurgün Büyükkıdan

https://doi.org/10.18596/jotcsa.1135570

Cited By: 3

Abstract

In this study, a brief review of the proton transfer salts synthesized from the reaction of piperazine with pyridine-2-carboxylic acid and their metal complexes since 2009 was made. The metals in the studied compounds are mostly d-block metals. In complexes, the anionic component of the salt is coordinated to the metal, while the cationic component is present only as a complementary ion in a complex.

Keywords

Pyridine , piperazine , acid , base , salt

References

• 1. Celestine MJ, Bullock JL, Boodram S, Rambaran VH, Holder AA. Interesting properties of p-, d-, and f-block elements when coordinated with dipicolinic acid and its derivatives as ligands: their use as inorganic pharmaceuticals. Reviews in Inorganic Chemistry. 2015 Jun 1;35(2):57–67.
• 2. Mihajlović-Lalić LE, Poljarević J, Grgurić-Šipka S. Metal complexes with α-picolinic acid frameworks and their antitumor activity. Inorganica Chimica Acta. 2021 Nov;527:120582.
• 3. Soares-Santos PCR, Paz FAA, Ferreira RAS, Klinowski J, Carlos LD, Trindade T, et al. Coordination modes of pyridine-carboxylic acid derivatives in samarium (III) complexes. Polyhedron. 2006 Aug;25(12):2471–82.
• 4. Moore JW, Glick MD, Baker WA. Crystal structures of hydrated lanthanide(III) nicotinates, La2(C5H4NCO2)6(H2O)4 and Sm2(C5H4NCO2)6(H2O)4. Journal of the American Chemical Society. 1972 Mar;94(6):1858–65.
• 5. Mahler HR, Cordes EH. In: Biological Chemistry. 2nd edition. New York: Harper and Row Publishers; 1971. p. 801–3.
• 6. Ogata S, Takeuchi M, Okumura K, Taguchi H. Apoptosis Induced by Niacin-related Compounds in HL-60 Cells. Bioscience, Biotechnology, and Biochemistry. 1998 Jan;62(12):2351–6.
• 7. Berner TO, Murphy MM, Slesinski R. Determining the safety of chromium tripicolinate for addition to foods as a nutrient supplement. Food and Chemical Toxicology. 2004 Jun;42(6):1029–42.
• 8. Maret W. Chromium supplementation in human health, metabolic syndrome, and diabetes. Metal Ions in Life Sciences. 2019;19:231–51.
• 9. Avcı D, Altürk S, Sönmez F, Tamer Ö, Başoğlu A, Atalay Y, et al. Three novel Cu(II), Cd(II) and Cr(III) complexes of 6−Methylpyridine−2−carboxylic acid with thiocyanate: Synthesis, crystal structures, DFT calculations, molecular docking and α-Glucosidase inhibition studies. Tetrahedron. 2018 Dec;74(50):7198–208.
• 10. Avcı D, Altürk S, Sönmez F, Tamer Ö, Başoğlu A, Atalay Y, et al. A novel series of mixed-ligand M(II) complexes containing 2,2′-bipyridyl as potent α-glucosidase inhibitor: synthesis, crystal structure, DFT calculations, and molecular docking. Journal of Biological Inorganic Chemistry. 2019 Aug 1;24(5):747–64.
• 11. Avcı D, Altürk S, Sönmez F, Tamer Ö, Başoğlu A, Atalay Y, et al. Novel Cu(II), Co(II) and Zn(II) metal complexes with mixed-ligand: Synthesis, crystal structure, α-glucosidase inhibition, DFT calculations, and molecular docking. Journal of Molecular Structure. 2019 Dec;1197:645–55.
• 12. Zhang M, Chen C, Wang Q, Fu W, Huang K, Zhou W. A metal–organic framework functionalized with piperazine exhibiting enhanced CH 4 storage. Journal of Materials Chemistry A. 2017;5(1):349–54.
• 13. Reddy JS, Ganesh SV, Nagalapalli R, Dandela R, Solomon KA, Kumar KA, et al. Fluoroquinolone salts with carboxylic acids. Journal of Pharmaceutical Sciences. 2011 Aug;100(8):3160–76.
• 14. Stepanovs D, Jure M, Mishnev A. Preparation and crystal structure of sildenafil salicylate. Mendeleev Communications. 2015 Jan;25(1):49–50.
• 15. Vepuri SB, Devarajegowda HC, Soliman ME. Synthesis, characterization and molecular modelling of a novel dipyridamole supramolecule – X-ray structure, quantum mechanics and molecular dynamics study to comprehend the hydrogen bond structure–activity relationship. Journal of Molecular Structure. 2016 Feb;1105:194–204.
• 16. Satyanarayana Reddy J, Ravikumar N, Gaddamanugu G, Naresh KN, Rajan SS, Anand Solomon K. Synthesis, crystal structure, spectral characterization and fluorescence studies of salts of α-mangostin with APIs. Journal of Molecular Structure. 2013 May;1039:137–43.
• 17. Aghabozorg H, Manteghi F, Sheshmani S. A brief review on structural concepts of novel supramolecular proton transfer compounds and their metal complexes. Journal of the Iranian Chemical Society. 2008 Jun;5(2):184–227.
• 18. Moghimi A, Moosavi SM, Kordestani D, Maddah B, Shamsipur M, Aghabozorg H, et al. Pyridine-2,6-bis(monothiocarboxylic) acid and 2-aminopyridine as building blocks of a novel proton transfer compound: Solution and X-ray crystal structural studies. Journal of Molecular Structure. 2007 Feb;828(1–3):38–45.
• 19. Pytka K, Rapacz A, Zygmunt M, Olczyk A, Waszkielewicz A, Sapa J, et al. Antidepressant-like activity of a new piperazine derivative of xanthone in the forced swim test in mice: The involvement of serotonergic system. Pharmacological Reports. 2015 Feb;67(1):160–5.
• 20. Thamban Chandrika N, Shrestha SK, Ngo HX, Tsodikov OV, Howard KC, Garneau-Tsodikova S. Alkylated Piperazines and Piperazine-Azole Hybrids as Antifungal Agents. Journal of Medicinal Chemistry. 2018 Jan 11;61(1):158–73.
• 21. McNair TJ, Wibin FA, Hoppe ET, Schmidt JL, dePeyster FA. Antitumor action of several new piperazine derivatives compared to certain standard anticancer agents. Journal of Surgical Research. 1963 May;3(3):130–6.
• 22. Ananda Kumar CS, Nanjunda Swamy S, Thimmegowda NR, Benaka Prasad SB, Yip GW, Rangappa KS. Synthesis and evaluation of 1-benzhydryl-sulfonyl-piperazine derivatives as inhibitors of MDA-MB-231 human breast cancer cell proliferation. Medicinal Chemistry Research. 2007 Sep;16(4):179–87.
• 23. Ahmadi A, Khalili M, Nafarie A, Yazdani A, Nahri-Niknafs B. Synthesis and anti-inflammatory effects of new piperazine and ethanolamine derivatives of H1-antihistaminic drugs. Mini-Reviews in Medicinal Chemistry. 2012 Sep 1;12(12):1282–92.
• 24. Brown AM, Patch TL, Kaumann AJ. The antimigraine drugs ergotamine and dihydroergotamine are potent 5-HT1C receptor agonists in piglet choroid plexus. British Journal of Pharmacology. 1991 Sep;104(1):45–8.
• 25. Kumar Parai M, Panda G, Srivastava K, Kumar Puri S. Design, synthesis and antimalarial activity of benzene and isoquinoline sulfonamide derivatives. Bioorganic & Medicinal Chemistry Letters. 2008 Jan;18(2):776–81.
• 26. Fazil S, Ravindran R, Sarau Devi A, Bijili BK. Structural studies of 1-phenyl-2,3-dimethyl-5-oxo-1,2-dihydro-1H-pyrazol-4-ammonium 2[(2-carboxyphenyl) disulfanyl]benzoate. Journal of Molecular Structure. 2012 Aug;1021:147–52.
• 27. Ghasemi K, Ghasemi F, Rezvani AR, Shokrollahi A, Refahi M, García-Granda S, et al. Mn(II) and Zn(II) ions catalytic oxidation of o-phenylenediamine and characterization, X-ray crystal structure and solution study of the final products DAPH+Cl−·3H2O and [DAPH][Zn(dipicH)(dipic)]·4H2O. Polyhedron. 2016 May;110:55–62.
• 28. Majerz I, Olovsson I. Influence of proton transfer on the geometry of the donor and acceptor in NHN+ hydrogen bonds. Journal of Molecular Structure. 2010 Jul;976(1–3):11–8.
• 29. Özdemir N. Structural and spectroscopic characterization of 2-mesityl-1H-benzo[d]imidazol-3-ium chloride: A combined experimental and theoretical analysis. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2012 Jun;91:51–60.
• 30. Ghasemi K, Rezvani AR, Shokrollahi A, Zarghampour F, Moghimi A, García-Granda S, et al. Synthesis, characterization, crystal structure and solution studies of a novel proton transfer (charge transfer) complex of 2,2′-dipyridylamine with 2,6-pyridine dicarboxylic acid. Journal of Molecular Structure. 2015 Jun;1089:184–90.
• 31. Takaiwa T, Koyama A, Nagaishi Y, Nakajima K, Sumimoto M, Hori K, et al. Structural characterization of 2,3,5,6-tetramethyl-p-phenylenediamine radical cation and its dimer in molecular crystals. Journal of Molecular Structure. 2015 Mar;1083:260–7.
• 32. Ghasemi K, Rezvani AR, Habibi-Khorassani SM, Shahraki M, Shokrollahi A, Moghimi A, et al. An experimental and theoretical study of a hydrogen-bonded complex: O-phenylenediamine with 2,6-pyridinedicarboxylic acid. Journal of Molecular Structure. 2015 Nov;1100:597–604.
• 33. Gopi R, Ramanathan N, Sundararajan K. Hydrogen-bonded complexes of acetylene and acetonitrile: A matrix isolation infrared and computational study. Journal of Molecular Structure. 2015 Mar;1083:364–73.
• 34. Shehab OR, Mansour AM. Sparfloxacin charge transfer complexes with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and tetracyanoquinodimethane: Molecular structures, spectral, and DFT studies. Journal of Molecular Structure. 2015 Aug;1093:186–94.
• 35. Rzokee AA, Ahmad A. Synthesis, spectroscopic studies and thermal analysis of charge-transfer complex of 2,2′-bipyridine with 4-hydroxybenzoic acid in different polar solvents. Journal of Molecular Structure. 2014 Nov;1076:453–60.
• 36. Refat MS, Adam AMA, Saad HA. Utility of charge-transfer complexation for the assessment of macrocyclic polyethers: Spectroscopic, thermal and surface morphology characteristics of two highly crown ethers complexed with acido acceptors. Journal of Molecular Structure. 2015 Apr;1085:178–90.
• 37. Singh N, Ahmad A. Synthesis and spectrophotometric studies of charge transfer complexes of p-nitroaniline with benzoic acid in different polar solvents. Journal of Molecular Structure. 2014 Sep;1074:408–15.
• 38. Ghadermazi M, Soleimannejad J, Sheshmani S, Shamsipur M, Ghanbari M, Eslami MR. Characterization, crystal structures and solution studies of Zn(II), Cd(II) and Mg(II) complexes obtained from a proton transfer compound including pyridine-2-carboxylic acid and piperazine. Journal of the Iranian Chemical Society. 2012 Aug;9(4):579–89.
• 39. Sheshmani S, Soleimannejad J, Ghadermazi M, Shamsipur M, Ghanbari M, Motieian E, et al. Comparative study on MnII, NiII and CuII supramolecular complexes obtained from a proton transfer methodology: solid- and solution-state studies. Journal of the Iranian Chemical Society. 2013 Aug;10(4):817–29.
• 40. Rekha P, Chakkaravarthi G, Mohan Kumar R, Vinitha G, Kanagadurai R. Growth, structural and optical limiting property of a new third order nonlinear optical material: piperazinium bis (2-carboxypyridine) monohydrate. Journal of Materials Science: Materials in Electronics. 2019 May;30(10):9471–88.