Issue 51, 2017

Renewable sources from plants as the starting material for designing new terpene chiral ionic liquids used for the chromatographic separation of acidic enantiomers

Abstract

Synthesis of cheap and natural resources is an important topic in green chemistry. For that reason, new chiral ionic liquids (CILs) containing a bicyclic terpene moiety were designed and prepared from renewable plant resources. The synthesis route was comprehensively described, especially a specific type of Menschutkin reaction, which gives high energy efficiency during the process. The physicochemical characteristics of the obtained chiral salts, including the spectral properties, melting point, crystal shape, specific rotation and solubility in various solvents were examined. The study presents the effect of new chiral ionic liquids as mobile phase additives on the chiral recognition of acidic enantiomers on a teicoplanin-based chiral stationary phase (CSP). Based on the van't Hoff relationships, the thermodynamic functions were determined. The plots revealed that the chiral recognition was enthalpy driven. The chiral salts obtained exhibited a synergistic effect with the teicoplanin-based stationary phase in the chromatographic system, enhancing the resolution of acidic enantiomers. Structural task-specific properties of the new terpene-based chiral ionic liquids were confirmed by molecular modeling and docking simulations.

Graphical abstract: Renewable sources from plants as the starting material for designing new terpene chiral ionic liquids used for the chromatographic separation of acidic enantiomers

Supplementary files

Article information

Article type
Paper
Submitted
21 Mar 2017
Accepted
16 Jun 2017
First published
23 Jun 2017
This article is Open Access
Creative Commons BY license

RSC Adv., 2017,7, 32344-32356

Renewable sources from plants as the starting material for designing new terpene chiral ionic liquids used for the chromatographic separation of acidic enantiomers

J. Feder-Kubis, J. Flieger, M. Tatarczak-Michalewska, A. Płazińska, A. Madejska and M. Swatko-Ossor, RSC Adv., 2017, 7, 32344 DOI: 10.1039/C7RA03310A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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