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N ‐Phenyl‐substituted carbene precursors and their silver complexes: synthesis, characterization and antimicrobial activities
Author(s) -
Gök Yetkin,
Akkoç Senem,
Albayrak Sevil,
Akkurt Mehmet,
Tahir Muhammad Nawaz
Publication year - 2014
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.3116
Subject(s) - chemistry , carbene , escherichia coli , bacillus subtilis , antibacterial activity , antimicrobial , alkyl , broth microdilution , staphylococcus aureus , stereochemistry , bacteria , organic chemistry , minimum inhibitory concentration , catalysis , biochemistry , genetics , biology , gene
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 1 H NMR, 13 C 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.