N‐Phenyl‐substituted carbene precursors and their silver complexes: synthesis, characterization and antimicrobial activities

Abstract

A series of unsymmetrically substituted N‐heterocyclic carbene (NHC) precursors (1a, 1b, 1c, 1d, 1e) were synthesized from the reaction of N‐phenylbenzimidazole with various alkyl halides. These compounds were used to synthesize NHC–silver(I) complexes (2a, 2b, 2c, 2d, 2e). The five new 1‐phenyl‐3‐alkylbenzimidazolium salts (1a, 1b, 1c, 1d, 1e) and their NHC–silver complexes (2a, 2b, 2c, 2d, 2e) were characterized by the 1H NMR, 13C NMR and FT‐IR spectroscopic methods and elemental analysis techniques. Also, the two NHC–silver complexes 2b and 2c were characterized by single‐crystal X‐ray crystallography, which confirmed the linear C―Ag―Cl arrangements. The antibacterial activities of the NHC precursor and NHC–silver complexes were tested against three Gram‐positive bacterial strains (Bacillus subtilis, Listeria monocytogenes and Staphylococcus aureus) and three Gram‐negative bacterial strains (Escherichia coli, Klebsiella pneumoniae and Pseudomonas aeruginosa) using the microdilution broth method. The NHC–silver complexes showed higher antibacterial activity than the NHC precursors. In addition, silver complexes 2a, 2b, 2c, 2d showed high antibacterial activity against the Gram‐positive bacteria L. monocytogenes and S. aureus compared to the standard, tetracycline. Copyright © 2014 John Wiley & Sons, Ltd.