Synthesis and properties of chiral ammonium-based ionic liquids.
New chiral ammonium-based ionic liquids containing the (1R,2S,5R)-(-)-menthyl group can be easily and efficiently prepared under ambient conditions. The preparation and characterization of trialkyl[(1R,2S,5R)-(-)-menthoxymethyl]ammonium salts is reported. The salts have been demonstrated to be air- and moisture-stable under ambient conditions and can be readily used in a variety of standard experimental procedures. The single-crystal X-ray structure of butyldimethyl[(1R,2S,5R)-(-)-menthoxymethyl]ammonium chloride has been determined. The chiral, room-temperature ionic liquids have been characterized by physical properties such as specific rotation, density, viscosity, thermal degradation, and glass transition temperature. Trialkyl[(1R,2S,5R)-(-)-menthoxymethyl]ammonium chloride prototype ionic liquids have also been found to exhibit strong antimicrobial and high antielectrostatic activities.
Pernak
Juliusz
J
Poznań University of Technology, Department of Chemical Technology pl. Skłodowskiej-Curie 2, 60-965 Poznań, Poland. juliusz.pernak@put.poznan.pl
Feder-Kubis
Joanna
J
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018360:Crystallography, X-Ray; D007477:Ions; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D007477:Ions; D000644:Quaternary Ammonium Compounds