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Molecules 2017, 22(11), 1810; doi:10.3390/molecules22111810

Synthesis, Structure, Surface and Antimicrobial Properties of New Oligomeric Quaternary Ammonium Salts with Aromatic Spacers

1
Laboratory of Microbiocides Chemistry, Faculty of Chemistry, Adam Mickiewicz University in Poznań, Umultowska 89b, 61-614 Poznań, Poland
2
Institute of Fermentation Technology and Microbiology, Faculty of Biotechnology and Food Sciences, Lodz University of Technology, Wólczańska 171/173, 90-924 Łódź, Poland
3
Department of Materials Chemistry, Faculty of Chemistry, Adam Mickiewicz University in Poznań, Umultowska 89b, 61-614 Poznań, Poland
*
Author to whom correspondence should be addressed.
Received: 12 October 2017 / Revised: 22 October 2017 / Accepted: 24 October 2017 / Published: 25 October 2017
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [5893 KB, uploaded 25 October 2017]   |  

Abstract

New dimeric, trimeric and tetrameric quaternary ammonium salts were accomplished by reaction of tertiary alkyldimethyl amines with appropriate bromomethylbenzene derivatives. A series of new cationic surfactants contain different alkyl chain lengths (C4–C18), aromatic spacers and different numbers of quaternary nitrogen atoms. The structure of the products was confirmed by spectral analysis (FT-IR, 1H-NMR, 13C-NMR and 2D-NMR), mass spectroscopy (ESI-MS), elemental analysis, as well as PM5 semiempirical methods. Compound (21) was also analyzed using X-ray crystallography. Critical micelle concentration (CMC) of 1,4-bis-[N-(1-alkyl)-N,N-dimethylammoniummethyl]benzene dibromides (39) was determined to characterize the aggregation behavior. The antimicrobial properties of novel QACs (Quaternary Ammonium Salts) were examined to set their minimal inhibitory concentration (MIC) values against fungi Aspergillus niger, Candida albicans, Penicillium chrysogenum and bacteria Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa. View Full-Text
Keywords: quaternary ammonium salts; oligomeric surfactants; rigid spacer; spectroscopy; synthesis; CMC; antimicrobial properties quaternary ammonium salts; oligomeric surfactants; rigid spacer; spectroscopy; synthesis; CMC; antimicrobial properties
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Brycki, B.; Koziróg, A.; Kowalczyk, I.; Pospieszny, T.; Materna, P.; Marciniak, J. Synthesis, Structure, Surface and Antimicrobial Properties of New Oligomeric Quaternary Ammonium Salts with Aromatic Spacers. Molecules 2017, 22, 1810.

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