Synthesis, Properties, and Antimicrobial Activity of 1-Alkyl-4-hydroxy-1-methylpiperidinium Ionic Liquids with Mandelate Anion
Tomasz Rzemieniecki , Daniela Gwiazdowska , Karolina Rybak , Katarzyna Materna , Krzysztof Juś , Juliusz Pernak
AbstractIn the framework of our study, three homologous series of ionic liquids containing the 1-alkyl-4-hydroxy-1-methylpiperidinium cation with the alkyl chain length ranging from ethyl to hexadecyl and anions of natural origin derived from three forms (S, R, and RS) of mandelic acid were obtained in high yields that exceeded 90%. The obtained compounds were subjected to a thorough analysis of their physicochemical properties, including the specific rotation, density, refractive index, surface activity, and solubility in solvents with diverse ranges of polarity. The minimum concentration at which the ionic liquids exhibited antimicrobial activity was also examined. Among the tested ionic liquids, compounds comprising an alkyl chain longer than octyl possessed noticeable biological activity toward model pathogenic microorganisms, including Gram-positive bacteria, Gram-negative bacteria, and fungi. In addition, a correlation between the surface properties and biological activity was observed for all homologous series of synthesized mandelates; this observation can significantly facilitate the design of chemical structures of new and more potent antiseptics.
|Journal series||ACS Sustainable Chemistry & Engineering, ISSN 2168-0485, (N/A 140 pkt)|
|Publication size in sheets||0.5|
|Keywords in Polish||ciecze jonowe, migdalany, środki przeciwdrobnoustrojowie, właściwości powierzchniowe, aktywność biologiczna|
|Keywords in English||Chiral ionic liquids, Mandelates, Antimicrobial agents, Homologous series, Surface properties, Biological activity|
|ASJC Classification||; ; ;|
|Score||= 140.0, 03-04-2020, ArticleFromJournal|
|Publication indicators||= 0; : 2018 = 1.371; : 2018 = 6.97 (2) - 2018=7.185 (5)|
|Citation count*||6 (2020-07-01)|
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.