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Issue 3, 2011
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Theoretical investigations into the enantiomeric and racemic forms of α-(trifluoromethyl)lactic acid

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Abstract

There are many different hypotheses on the origin of biomolecular homochirality. One possible scenario concerns the enantiomeric enrichment of a nearly racemic solid via self-disproportionation of enantiomers. In particular, in a recent paper Soloshonok and co-workers showed a first example of optical self-purification of α-(trifluoromethyl)lactic acid by sublimation [V. A. Soloshonok et al., J. Am. Chem. Soc. 2007, 129, 12112]. Here we present detailed theoretical studies of α-(trifluoromethyl)lactic acid in the solid state as well as in the gas-phase dimeric form. The calculations of energy differences between dimers show that in the solid state the enantiomeric pure compound is energetically preferred, while in the gas phase the equilibrium shifts towards the racemic mixture although thermodynamic corrections cannot be neglected, thus providing a detailed microscopic explanation for the enantio-purification process for the first time.

Graphical abstract: Theoretical investigations into the enantiomeric and racemic forms of α-(trifluoromethyl)lactic acid

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Publication details

The article was received on 13 Jul 2010, accepted on 24 Aug 2010 and first published on 14 Oct 2010


Article type: Paper
DOI: 10.1039/C0CP01155J
Phys. Chem. Chem. Phys., 2011,13, 811-817

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    Theoretical investigations into the enantiomeric and racemic forms of α-(trifluoromethyl)lactic acid

    R. Tonner, V. A. Soloshonok and P. Schwerdtfeger, Phys. Chem. Chem. Phys., 2011, 13, 811
    DOI: 10.1039/C0CP01155J

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