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

Abstract

In 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.
Author Tomasz Rzemieniecki
Tomasz Rzemieniecki,,
-
, Daniela Gwiazdowska (WT / KPPJ)
Daniela Gwiazdowska,,
- Department of Natural Science and Quality Assurance
, Karolina Rybak
Karolina Rybak,,
-
, Katarzyna Materna
Katarzyna Materna,,
-
, Krzysztof Juś (WT / KPPJ)
Krzysztof Juś,,
- Department of Natural Science and Quality Assurance
, Juliusz Pernak
Juliusz Pernak,,
-
Journal seriesACS Sustainable Chemistry & Engineering, ISSN 2168-0485, (N/A 140 pkt)
Issue year2019
Vol7
No17
Pages15053-15063
Publication size in sheets0.5
Keywords in Polishciecze jonowe, migdalany, środki przeciwdrobnoustrojowie, właściwości powierzchniowe, aktywność biologiczna
Keywords in EnglishChiral ionic liquids, Mandelates, Antimicrobial agents, Homologous series, Surface properties, Biological activity
ASJC Classification1500 General Chemical Engineering; 1600 General Chemistry; 2105 Renewable Energy, Sustainability and the Environment; 2304 Environmental Chemistry
DOIDOI:10.1021/acssuschemeng.9b03690
URL https://pubs.acs.org/doi/10.1021/acssuschemeng.9b03690
Languageen angielski
Score (nominal)140
Score sourcejournalList
ScoreMinisterial score = 140.0, 03-04-2020, ArticleFromJournal
Publication indicators WoS Citations = 0; Scopus SNIP (Source Normalised Impact per Paper): 2018 = 1.371; WoS Impact Factor: 2018 = 6.97 (2) - 2018=7.185 (5)
Citation count*6 (2020-07-01)
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* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.
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