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Bwambok DK, Marwani HM, Fernand VE, et al. Synthesis and characterization of novel chiral ionic liquids and investigation of their enantiomeric recognition properties. Chirality. 2008;20(2):151-8doi: 10.1002/chir.20517.
Bwambok, D. K., Marwani, H. M., Fernand, V. E., Fakayode, S. O., Lowry, M., Negulescu, I., Strongin, R. M., & Warner, I. M. (2008). Synthesis and characterization of novel chiral ionic liquids and investigation of their enantiomeric recognition properties. Chirality, 20(2), 151-8. https://doi.org/10.1002/chir.20517
Bwambok, David K, et al. "Synthesis and characterization of novel chiral ionic liquids and investigation of their enantiomeric recognition properties." Chirality vol. 20,2 (2008): 151-8. doi: https://doi.org/10.1002/chir.20517
Bwambok DK, Marwani HM, Fernand VE, Fakayode SO, Lowry M, Negulescu I, Strongin RM, Warner IM. Synthesis and characterization of novel chiral ionic liquids and investigation of their enantiomeric recognition properties. Chirality. 2008 Feb;20(2):151-8. doi: 10.1002/chir.20517. PMID: 18092298; PMCID: PMC2650422.
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Chirality. 2008 Feb;20(2):151-8. doi: 10.1002/chir.20517.

Synthesis and characterization of novel chiral ionic liquids and investigation of their enantiomeric recognition properties.

Chirality

David K Bwambok, Hadi M Marwani, Vivian E Fernand, Sayo O Fakayode, Mark Lowry, Ioan Negulescu, Robert M Strongin, Isiah M Warner

Affiliations

  1. Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana, USA.

PMID: 18092298 PMCID: PMC2650422 DOI: 10.1002/chir.20517

Abstract

We report the synthesis and characterization of amino acid ester based chiral ionic liquids, derived from L- and D-alanine tert butyl ester chloride. The synthesis was accomplished via an anion metathesis reaction between commercially available L- and D-alanine tert butyl ester chloride using a variety of counterions such as lithium bis (trifluoromethane) sulfonimide, silver nitrate, silver lactate, and silver tetrafluoroborate. Both enantiomeric forms were obtained as confirmed by bands of opposite sign in the circular dichroism spectra. The L- and D-alanine tert butyl ester bis (trifluoromethane) sulfonimide were obtained as liquids at room temperature and intriguingly exhibited the highest thermal stability (up to 263 degrees C). In addition, the ionic liquids demonstrated enantiomeric recognition ability as evidenced by splitting of racemic Mosher's sodium salt signal using a liquid state (19)F nuclear magnetic resonance (NMR) and fluorescence spectroscopy. The L- and D-alanine tert butyl ester chloride resulted in solid salts with nitrate, lactate, and tetrafluoroborate anions. This illustrates the previously observed tunability of ionic liquid synthesis, resulting in ionic liquids of varying properties as a function of varying the anion.

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