Recognition in Chiral Ionic Liquids: The Achiral Cation Makes the Difference!

J Blasius and P Zaby and O Holloczki and B Kirchner, JOURNAL OF ORGANIC CHEMISTRY, 87, 1867-1873 (2022).

DOI: 10.1021/acs.joc.1c00939

By simulating butan-2-ol dissolved in the chiral ionic liquid 1-ethyl-3methylimidazolium (S)-alaninate, we investigate the chiral recognition of butan-2-ol in the ionic liquid. The hydrogen bonding between the chiral anion and both enantiomers of butan-2-ol is similar; however, both chiral molecules (anion and alcohol) induce an asymmetry in the achiral cation which leads to a more favorable environment for the alcohol in the heterochiral system as compared to the homochiral system and hence provides an energetic stabilization of the former.

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