Yetkin GÖK, Senem AKKOÇ, Özlem Özeroğlu ÇELİKAL, İlknur ÖZDEMİR, Selami GÜNAL, Elif SAYIN

N-functionalized benzimidazol-2-ylidene silver complexes: synthesis, characterization, and antimicrobial studies

2-Methoxyethyl, 2-diethylaminoethyl, and 2-phenylethyl-substituted N-heterocyclic carbene (NHC) precursors were treated with Ag2CO3 to yield silver(I)-NHC complexes (1a--g) in dichloromethane as a solvent at room temperature. The 7 new silver-NHC complexes were fully characterized by means of 1H NMR, 13C NMR, and elemental analysis techniques. Using the agar dilution procedure recommended by the Laboratory and Clinical Standards Institute, the antimicrobial activities of all the silver-NHC complexes were studied against 2 gram-negative bacterial strains (Pseudomonas aeruginosa and Escherichia coli), 2 gram-positive bacterial strains (Enterococcus faecalis and Staphylococcus aureus), and 2 fungi (Candida tropicalis and Candida albicans).

Anahtar Kelimeler:

N-Heterocyclic carbene, benzimidazol-2-ylidene, silver complex, antimicrobial activity, medical inorganic chemistry

N -functionalized benzimidazol-2-ylidene silver complexes: synthesis, characterization, and antimicrobial studies

Keywords:

N-Heterocyclic carbene, benzimidazol-2-ylidene, silver complex, antimicrobial activity, medical inorganic chemistry,

PDF

___

¨ Ofele, K. J. Organomet. Chem. 1968, 12, 42–43.
Wanzlick, H. W.; Sch¨ onherr H. W. Angew. Chem. Int. Ed. 1968, 7, 141–142.
Arduengo, A. J.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361–363.
Karthikeyan, P.; Muskawar, P. N.; Aswar, S. A.; Bhagat, P. R.; Sythana, S. K. Arabian J. Chem. 2012, 26, 562–569.
Wiedemann, S. H.; Lewis, J. C.; Elman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2006, 128, 2452–2462.
¨ Ozdemir, ˙I.; G¨ ok, Y.; ¨ Ozero˘ glu, ¨ O.; Kalo˘ glu, M.; Doucet, H. Eur. J. Inorg. Chem. 2010, 12, 1798–1805.
¨ Ozdemir, ˙I.; G¨ urb¨ uz, N.; G¨ ok, Y.; C ¸ etinkaya, B.; C ¸ etinkaya, E. Trans. Metal Chem. 2005, 30, 367–371.
Tyrrell, E.; Whiteman, L.; Williams, N. J. Organomet. Chem. 2011, 696, 3465–3472.
Danopoulos, A. A.; Tsoureas, N.; Macgregor, S. A.; Smith, C. Organometallics 2007, 26, 253–263.
Wang, H. M. J.; Lin, I. J. B. Organometallics 1998, 17, 972–975.
Arnold, P. L. Heteroatom. Chem. 2002, 13, 534–539.
Yi˘ git, B.; G¨ ok, Y.; ¨ Ozdemir, ˙I.; G¨ unal, S. J. Coord. Chem. 2012, 3(65), 371–379.
Cheng, C-H.; Chen, D-F.; Song, H-B.; Tang, L-F. J. Organomet. Chem. 2013, 726, 1–88.
Akkurt, M.; Akko¸ c, S.; G¨ ok, Y.; Da˘ gdemir, Y.; Tahir, M. N. Acta Cryst. 2012, E68, 590–591.
Patil, S.; Deally, A.; Gleeson, B.; Hackenberg, F.; M¨ uller-Bunz, H.; Paradisi, F.; Tacke, M. M. Z. Anorg. Allg. Chem. 2011, 637, 386–396.
Patil, S.; Deally, A.; Gleeson, B.; Hackenberg, F.; M¨ uller-Bunz, H.; Paradisi, F.; Tacke, M. Metallomics 2011, 3, 74–
Hackenberg, F.; Lally, G.; M¨ uller-Bunz, H.; Paradisi, F.; Quaglia, D.; Streciwilk, W.; Tacke, M. Inorg. Chim. Acta 2013, 395, 135–144.
Haque, R. A.; Ghdhayeb, M. Z.; Salman, A. W.; Budagumpi, S.; Ahamed, M. B. K.; Majid, A. M. S. Inorg. Chem. Commun. 2012, 22, 113–119.
Youngs, W. J.; Knapp, A. R.; Wagers, P. O.; Tessier, C. A. Dalton Trans. 2012, 41, 327–336.
Lee, C. K.; Lee, K. M.; Lin, I. J. B. Organometallics 2002, 21, 10–12.
Lin, I. J. B.; Vasam, C. S. Coord. Chem. Rev. 2007, 251, 642–670.
National Clinical and Laboratory Standards Institute. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically: Approved Standard, 7th ed. CLSI Document M7-A7; National Clinical and Laboratory Standard Institute: Wayne, PA, USA (2003).
Clinical and Laboratory Standards Institute. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts: Approved Standard, 2nd ed. NCCLS document M27-A2; National Clinical and Laboratory Standards Institute: Wayne, PA, USA (2002).
G¨ ok, Y.; G¨ urb¨ uz, N.; ¨ Ozdemir, ˙I.; C ¸ etinkaya, B.; C ¸ etinkaya, E. Appl. Organometal. Chem. 2005, 19, 870–874. ¨ Ozdemir, ˙I.; G¨ urb¨ uz, N.; G¨ ok, Y.; C ¸ etinkaya, E.; C ¸ etinkaya, B. Synlett 2005, 15, 2394–2396.
Nielsen, D. J.; Cavell, K. J.; Skelton, B. W.; White, A. H. Inorg. Chim. Acta 2003, 352, 143–150.
Pytkowicz, J.; Roland, S.; Mangeney, P. J. Organomet. Chem. 2001, 631, 157–163.
Lee, H. M.; Chiu, P. L.; Hu, C. H.; Lai, C. L.; Chou, Y. C. J. Organomet. Chem. 2005, 690, 403–414.
G¨ unal, S.; Kalo˘ glu, N.; ¨ Ozdemir, ˙I.; Demir, S.; ¨ Ozdemir, ˙I. Inorg. Chem. Commun. 2012, 21, 142–146.