Synthesis, Structure, Surface and Antimicrobial Properties of New Oligomeric Quaternary Ammonium Salts with Aromatic Spacers
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 o...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2017-10-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/22/11/1810 |
| _version_ | 1818574727957970944 |
|---|---|
| author | Bogumił Brycki Anna Koziróg Iwona Kowalczyk Tomasz Pospieszny Paulina Materna Jędrzej Marciniak |
| author_facet | Bogumił Brycki Anna Koziróg Iwona Kowalczyk Tomasz Pospieszny Paulina Materna Jędrzej Marciniak |
| author_sort | Bogumił Brycki |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-15T00:30:23Z |
| format | Article |
| id | doaj.art-644b739d53724134a1ec2d64cab4cc1d |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-15T00:30:23Z |
| publishDate | 2017-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-644b739d53724134a1ec2d64cab4cc1d2022-12-21T22:42:01ZengMDPI AGMolecules1420-30492017-10-012211181010.3390/molecules22111810molecules22111810Synthesis, Structure, Surface and Antimicrobial Properties of New Oligomeric Quaternary Ammonium Salts with Aromatic SpacersBogumił Brycki0Anna Koziróg1Iwona Kowalczyk2Tomasz Pospieszny3Paulina Materna4Jędrzej Marciniak5Laboratory of Microbiocides Chemistry, Faculty of Chemistry, Adam Mickiewicz University in Poznań, Umultowska 89b, 61-614 Poznań, PolandInstitute of Fermentation Technology and Microbiology, Faculty of Biotechnology and Food Sciences, Lodz University of Technology, Wólczańska 171/173, 90-924 Łódź, PolandLaboratory of Microbiocides Chemistry, Faculty of Chemistry, Adam Mickiewicz University in Poznań, Umultowska 89b, 61-614 Poznań, PolandLaboratory of Microbiocides Chemistry, Faculty of Chemistry, Adam Mickiewicz University in Poznań, Umultowska 89b, 61-614 Poznań, PolandLaboratory of Microbiocides Chemistry, Faculty of Chemistry, Adam Mickiewicz University in Poznań, Umultowska 89b, 61-614 Poznań, PolandDepartment of Materials Chemistry, Faculty of Chemistry, Adam Mickiewicz University in Poznań, Umultowska 89b, 61-614 Poznań, PolandNew 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.https://www.mdpi.com/1420-3049/22/11/1810quaternary ammonium saltsoligomeric surfactantsrigid spacerspectroscopysynthesisCMCantimicrobial properties |
| spellingShingle | Bogumił Brycki Anna Koziróg Iwona Kowalczyk Tomasz Pospieszny Paulina Materna Jędrzej Marciniak Synthesis, Structure, Surface and Antimicrobial Properties of New Oligomeric Quaternary Ammonium Salts with Aromatic Spacers Molecules quaternary ammonium salts oligomeric surfactants rigid spacer spectroscopy synthesis CMC antimicrobial properties |
| title | Synthesis, Structure, Surface and Antimicrobial Properties of New Oligomeric Quaternary Ammonium Salts with Aromatic Spacers |
| title_full | Synthesis, Structure, Surface and Antimicrobial Properties of New Oligomeric Quaternary Ammonium Salts with Aromatic Spacers |
| title_fullStr | Synthesis, Structure, Surface and Antimicrobial Properties of New Oligomeric Quaternary Ammonium Salts with Aromatic Spacers |
| title_full_unstemmed | Synthesis, Structure, Surface and Antimicrobial Properties of New Oligomeric Quaternary Ammonium Salts with Aromatic Spacers |
| title_short | Synthesis, Structure, Surface and Antimicrobial Properties of New Oligomeric Quaternary Ammonium Salts with Aromatic Spacers |
| title_sort | synthesis structure surface and antimicrobial properties of new oligomeric quaternary ammonium salts with aromatic spacers |
| topic | quaternary ammonium salts oligomeric surfactants rigid spacer spectroscopy synthesis CMC antimicrobial properties |
| url | https://www.mdpi.com/1420-3049/22/11/1810 |
| work_keys_str_mv | AT bogumiłbrycki synthesisstructuresurfaceandantimicrobialpropertiesofnewoligomericquaternaryammoniumsaltswitharomaticspacers AT annakozirog synthesisstructuresurfaceandantimicrobialpropertiesofnewoligomericquaternaryammoniumsaltswitharomaticspacers AT iwonakowalczyk synthesisstructuresurfaceandantimicrobialpropertiesofnewoligomericquaternaryammoniumsaltswitharomaticspacers AT tomaszpospieszny synthesisstructuresurfaceandantimicrobialpropertiesofnewoligomericquaternaryammoniumsaltswitharomaticspacers AT paulinamaterna synthesisstructuresurfaceandantimicrobialpropertiesofnewoligomericquaternaryammoniumsaltswitharomaticspacers AT jedrzejmarciniak synthesisstructuresurfaceandantimicrobialpropertiesofnewoligomericquaternaryammoniumsaltswitharomaticspacers |