Document Type

Post-Print

Publication Date

2008

Subjects

Fluoroform--Thermal properties, Ionic solutions, Asymmetric synthesis, Chirality

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.

Description

This is an Author's Accepted Manuscript of an article published in Chirality; Feb 2008; 20(2): 151–158. This articles is available online at: http://onlinelibrary.wiley.com/doi/10.1002/chir.20517/abstract

DOI

10.1039/B917900C

Persistent Identifier

http://archives.pdx.edu/ds/psu/11147

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