SYNTHESIS OF SILVER- AND GOLD-N-HETEROCYCLIC CARBENE COMPLEXES INCLUDING STRONG METAL-CARBON BINDING

Abstract

In this study, the new benzimidazolium salt (1) containing ether functionalized alkyl group as the NHC ligand precursor was synthesized. Ag-NHC complex (2) was synthesized by interaction with Ag2O of this ligand precursor. The Au-NHC complex was synthesized by interaction the [AuCl(PPh3)] complex with the synthesized Ag-NHC complex. The structures of prepared all new compounds were characterized by different spectroscopic methods. Bu çalışmada, NHC ligand öncüsü olarak eter fonksiyonlu alkil grubu içeren yeni benzimidazol tuzu (1) sentezlendi. Ag-NHC kompleksi (2) bu ligand öncüsünün Ag2O ile etkileştirilmesiyle sentezlendi. Au-NHC kompleksi (3) sentezlenmiş Ag-NHC kompleksi ile [AuCl(PPh3)] kompleksinin etkileştirilmesiyle sentezlendi. Hazırlanan tüm yeni bileşiklerin yapısı farklı spektroskopik metotlar ile karakterize edildi.

Keywords

• Benzimidazolium salt
• gold
• N-Heterocyclic carbene

References

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18. 2. D. Nemcsok, K. Wichmann, G. Frenking, The significance of π interactions in group 11 complexes with N-heterocyclic carbenes, Organometallics, 23(15) (2004) 3640-3646.
19. 3. S. Patil, A. Deall, B. Gleeson, F. Hackenberg, H. Müller-Bunz, F. Paradisi, M. Tacke, Synthesis, cytotoxicity and antibacterial studies of novel symmetrically and non-symmetrically p-nitrobenzyl-substituted N-heterocyclic carbene silver(I) acetate complexes, Zeitschrift für Anorganische und Allgemeine Chemie, 637(3-4) (2011) 386-396.
20. 4. S.Y. Hussaini, R.A. Haque, M.R. Razali, Recent progress in silver(I)-, gold(I)/(III)- and palladium(II)-N-heterocyclic carbene complexes: A review towards biological perspectives, Journal of Organometallic Chemistry, 882 (2019) 882:96-111.
21. 5. N.A. Johnson, M.R. Southerland, W.J. Youngs. Recent Developments in the Medicinal Applications of Silver-NHC Complexes and Imidazolium Salts, Molecules, 22 (2017) 1263-1282.
22. 6. S. Medici, M. Peana, G. Crisponi, V.M. Nurch, JI. Lachowicz, M. Remelli, M.A. Zoroddu, Silver coordination compounds: A new horizon in medicine, Coordination Chemistry Reviews, 327-328 (2016) 349–359.
23. 7. L. Kaps, B. Biersack, H. Müller-Bunz, K. Mahal, J. Münzner, M. Tacke, T. Mueller, R. Schobert, Gold(I)–NHC complexes of antitumoral diarylimidazoles: Structures, cellular uptake routes and anticancer activities, Journal of Inorganic Biochemistry, 1(106) (2012) 52-58.
24. 8. A. Gautier, F. Cisnetti, Advances in metal–carbene complexes as potent anti-cancer agents, Metallomics, 4 (2012) 23-32.
25. 9. L. Oehninger, R. Rubbiani, I. Ott, N-Heterocyclic carbene metal complexes in medicinal chemistry, Dalton Transaction, 42 (2013) 3269-3284.
26. 10. M. Juntti, D. Russel, J. Turnpenny, Evidence, politics and power in public policy for the environment, 12 (2009) 207-215.
27. 11. A.B.G. Lansdown, A review of the use of silver in wound care: facts and fallacies, British Journal of Nursing, 13 (2004) S6.
28. 12. A. Melaiye, W. Youngs, Silver and its application as an antimicrobial agent, Expert Opinion on Therapeutic Patents, 15 (2005) 125-130.
29. 13. E.R. Jamieson, SJ. Lippard, Structure, recognition, and processing of cisplatin DNA adducts, Chemical Reviews. 99 (1999) 2467-2498.
30. 14. G. Chu, Cellular responses to cisplatin. The roles of DNA-binding proteins and DNA repair, The Journal of Biological Chemistry, 269 (1994) 787-790.
31. 15. C.G. Hartinger, P.J. Dyson, Bioorganometallic chemistry from teaching paradigms to medicinal applications, Chemical Society Reviews, 38 (2009) 391-396.
32. 16. S.P. Fricker, Medical uses of gold compounds: Past, present and future, Gold Bulletin, 29 (1996) 53-60.
33. 17. R.S. Melaiye, A. Simons, F. Milsted, C. Pingitore, C.A. Wesdwmiotis, Tessier, W.J. Youngs, Formation of Water-Soluble Pincer Silver(I)-Carbene Complexes: A Novel Antimicrobial Agent, Journal of Medicinal Chemistry, 47 (2004) 973-977.