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Synthesis, characterization, crystal structure, and antimicrobial studies of 2-morpholinoethyl-substituted benzimidazolium salts and their silver(I)-N-heterocyclic carbene complexes

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Abstract

This article describes synthesis of N-morpholinoethylbenzimidazole (1), 2-morpholinoethyl-substituted benzimidazolium salts (NHC precursors, 2a–c), and their Ag(I) N-heterocyclic carbene (NHC) complexes (3a–c). All compounds were characterized by 1H and 13C Nuclear Magnetic Resonance (NMR), Fourier Transform Infrared Spectroscopy (FTIR), and elemental analysis, and their antimicrobial effects examined. The molecular structure of the NHC precursor 2a 1 was established by single-crystal X-ray diffraction analysis. Minimum Inhibition Concentration (MIC) values were determined to evaluate their antimicrobial activity against Gram-negative Escherichia coli and Gram-positive Staphylococcus aureus bacterial strains and Candida albicans fungal species. All tested samples were compared with silver nitrate. All the compounds exhibited strong antimicrobial activity.

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Acknowledgements

The authors are grateful for financial support provided by Inonu University, Research Project Unit (project no. I.U.A.F:2011/25), and support for NMR and elemental analyses provided by Inonu University Central Research Laboratory. The authors acknowledge Dokuz Eylül University for use of the Agilent Xcalibur Eos diffractometer (purchased under university research grant no. 2010.KB.FEN.13). CCDC 1499376 contains the supplementary crystallographic data for 2a 1. Copies of the data can be obtained free of charge at http://www.ccdc.cam.ac.uk/conts/retrieving.html or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge, CB2 1EZ, UK. fax: (+44) 1223-336-033, email: deposit@ccdc.cam.ac.uk.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Inonu University, 44280, Malatya, Turkey

    Işıl Yıldırım, Aydın Aktaş, Türkan Kutlu & Yetkin Gök

  2. Department of Physics, Faculty of Science, Dokuz Eylül University, 35160, İzmir, Turkey

    Duygu Barut Celepci & Muhittin Aygün

  3. Department of Biology, Faculty of Science, Fırat University, 23200, Elazığ, Turkey

    Sevda Kırbağ

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  1. Işıl Yıldırım
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Correspondence to Işıl Yıldırım.

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Yıldırım, I., Aktaş, A., Celepci, D.B. et al. Synthesis, characterization, crystal structure, and antimicrobial studies of 2-morpholinoethyl-substituted benzimidazolium salts and their silver(I)-N-heterocyclic carbene complexes. Res Chem Intermed 43, 6379–6393 (2017). https://doi.org/10.1007/s11164-017-2995-3

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