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Paper
Faraday Discuss., 2005, 129, 169 - 177, DOI: 10.1039/b404539d
Gibbs energies of transfer of chiral anions across the interface water|chiral organic solvent determined with the help of three-phase electrodes
Fritz Scholz and Rubin Gulaboski
For the first time the differences in free energies have been experimentally determined for the solvation of two enantiomeric ions in two enantiomeric solvents. Three-phase electrodes consisting of a droplet of a solution of decamethylferrocene in a chiral solvent (D- and L-2-octanol) attached to a graphite electrode and immersed in an aqueous solution containing chiral anions, allow the measurement of these data for the transfer of the enantiomeric ions across the water|chiral solvent interface. In all studied combinations the Gibbs energy to transfer an L-ion from water to the L-solvent was equal to the Gibbs energy of transfer of the D-ion from water to the D-solvent, and the same was found for the transfer of a L-ion from water to the D-solvent and for the D-ion from water to the L-solvent. In all cases, the combinations D-anion/D-solvent and L-anion/L-solvent have smaller standard Gibbs energies than the combinations D-anion/L-solvent and L-anion/D-solvent. This can be explained by less favourable interactions between an anion and a solvent molecule in the latter cases.
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