Synthesis and characterization of chiral ionic liquids based on quinine, L-proline and L-valine for enantiomeric recognition


The separation of enantiomers remains a major challenge for the pharmaceutical industry. In this work, eight chiral ionic liquids (CILs) directly derived from the 'chiral pool' were synthesized and characterized in order to develop enantioselective systems, for the chiral resolution. According to their chiral cations, three different groups of CILs were prepared, namely based on quinine, L-proline and L-valine, and their enantiomeric recognition ability evaluated. For that purpose the diastereomeric interactions between a racemic mixture of Mosher's acid sodium salt and each CIL were studied using F-19 NMR spectroscopy. The remarkable chemical shift dispersion induced by some CILs demonstrates their potential application in chiral resolution. Additionally the optical rotation, thermophysical properties and ecotoxicity against the marine bacteria Aliivibrio fischeri of these chiral ionic liquids were addressed. (C) 2019 Elsevier B.V. All rights reserved.



subject category

Chemistry; Physics


Sintra, TE; Gantman, MG; Ventura, SPM; Coutinho, JAP; Wasserscheid, P; Schulz, PS

our authors


This work was developed within the scope of the project CICECO-Aveiro Institute of Materials, FCT Ref. UID/CTM/50011/2019, financed by national funds through the FCT/MCTES. This work was also financially supported by the projects Multi-purpose strategies for broadband agro-forest and fisheries by-products valorization: a step forward for a truly integrated biorefinery (POCI-01-0145-FEDER 016403) and ChiResus-Chiral resolution of drugs in centrifugal partition chromatography using enantioselective aqueous biphasic systems (POCI-01-0145-FEDER-030750),funded by FEDER, through COMPETE2020 - Programa Operacional Competitividade e Internacionalizacao (POCI), and by national funds (OE), through FCT/MCTES. T.E. Sintra acknowledges COST Action CM1206 (EXIL - Exchange on Ionic Liquids) for the STSM grant (COST-STSM-CM1206-34926). S.P.M. Ventura acknowledges FCT/MEC for a contract under Investigador FCT 2015 contract number IF/00402/2015.

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