Stereoselective transport of 2-aryl propionic acid enantiomers in porous media subjected to chiral organic acids.

ABSTRACT

The study examined the transport behavior of the 2-aryl propionic acid (2-APA) chiral pharmaceutical enantiomers by means of a laboratory-scale saturated quartz sand column experiment. Four typical of 2-APA and their enantiomers were selected for the study under different types of chiral organic acids (COAs)-mediated effects. Differences in the transport of the 2-APA enantiomeric pairs have been identified in response to various pH, types of COAs, and enantiomeric structures of COAs. Redundancy analysis identified the factors responsible for the largest differences in transport of 2-APA enantiomeric pairs, while spectroscopic characterization and density function theory (DFT) studies elucidated the underlying mechanisms contributing to the differences in transport of enantiomeric pairs. Obvious correlations among homochirality or heterochirality between COAs and 2-APA enantiomeric pairs were observed for changes in the mobility of 2-APA. The results indicate widespread COAs significantly affect the transport behavior of chiral man-made chemicals, suggesting more attention is needed to fill the gap in the perception of the transport behavior of chiral compounds.