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

Sintra TE, Gantman M, Ventura SP, Coutinho JA, Wasserscheid P, Schulz P (2019)

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Publication Type: Journal article

Publication year: 2019

Journal

Book Volume: 283

Pages Range: 410-416

DOI: 10.1016/j.molliq.2019.03.084

Abstract

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 ¹⁹ F 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.

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How to cite

APA:

Sintra, T.E., Gantman, M., Ventura, S.P., Coutinho, J.A., Wasserscheid, P., & Schulz, P. (2019). Synthesis and characterization of chiral ionic liquids based on quinine, L-proline and L-valine for enantiomeric recognition. Journal of Molecular Liquids, 283, 410-416. https://dx.doi.org/10.1016/j.molliq.2019.03.084

MLA:

Sintra, Tânia E., et al. "Synthesis and characterization of chiral ionic liquids based on quinine, L-proline and L-valine for enantiomeric recognition." Journal of Molecular Liquids 283 (2019): 410-416.

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