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. 2017 Oct 25;22(11):1810.
doi: 10.3390/molecules22111810.

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

Bogumił Brycki  1 , Anna Koziróg  2 , Iwona Kowalczyk  3 , Tomasz Pospieszny  4 , Paulina Materna  5 , Jędrzej Marciniak  6
Affiliations

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

Bogumił Brycki et al. Molecules. .

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 (3-9) 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.

Keywords: CMC; antimicrobial properties; oligomeric surfactants; quaternary ammonium salts; rigid spacer; spectroscopy; synthesis.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Structures of di- (2–9) tri- (10–17) and tetrameric (18–23) alkylammonium surfactants with aromatic spacer.
Figure 1
Figure 1
Melting points of dimeric (2–9), trimeric (10–17) and tetrameric surfactants (18–23).
Figure 2
Figure 2
13C DEPT spectrum of 1,3,5-tris[(N-(1-dodecyl)-N,N-dimethylammoniummethyl)benzene tribromide (14).
Figure 3
Figure 3
HSQC spectrum (CD3OD) of 1,2,4,5-tetrakis[(N-(1-dodecyl)-N,N-dimethylammoniummethyl) benzene tetrabromide (21).
Figure 4
Figure 4
HMBC spectrum (CD3OD) of 1,3,5-tris[(N-(1-dodecyl)-N,N-dimethylammoniummethyl)benzene tribromide (14).
Figure 5
Figure 5
FT-IR spectra (KBr pellets) of 1,2-di(bromomethyl)benzene (―) and 9 (―) (a) and 23 (―) (b).
Figure 6
Figure 6
Molecular models of representative compounds 6 (a), 14 (b) and 21 (c) calculated by the PM5 method.
Figure 7
Figure 7
Comparison of the X-ray (a) and PM5 (b) structures of compound 21.
Figure 7
Figure 7
Comparison of the X-ray (a) and PM5 (b) structures of compound 21.
Figure 8
Figure 8
Crystal packing of compound 21.
Figure 9
Figure 9
Specific conductivity (κ) versus concentration of 7 in water at 50 °C.
Figure 10
Figure 10
Antibacterial activity of compounds 2–9.
Figure 11
Figure 11
Antifungal activity of compounds 2–9.
See this image and copyright information in PMC

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