A molecular dynamics study of analyte resolution on the Whelk-O 1 chiral stationary phase

PHYS 555

Chunfeng Zhao, zhaoc@chem.queensu.ca and Natalie M. Cann, ncann@chem.queensu.ca. Department of Chemistry, Queen's University, Chernoff Hall, Kingston, ON K7L 3N6, Canada
The docking of analytes on the Whelk-O1 chiral stationary phase is explored for enantiomers with different structural moieties. Density functional theory calculations are employed to develop a semi-flexible model for the (3R,4S)-Whelk-O 1 selector and models for analytes, including phenyl epoxides, 1,2-diphenyl cyclopropane, and aromatic and aliphatic alcohols. Molecular dynamics simulations of the racemates in the presence of the Whelk-O1 chiral stationary phase reveal the distribution of the enantiomers at the interface. The importance of p-p stacking, CH-p interactions, and hydrogen bonding on the chiral recognition mechanism is explored along with the major docking arrangements. The interactions between the Whelk-O1 molecules and the enantiomers can be quite distinct. Predictions of elution orders are made. The effect of solvent on chiral selectivity is discussed by comparing simulation results for a hexane solvent with those for an 80/20 hexane/2-propanol solvent.

General Posters
7:30 PM-10:00 PM, Wednesday, March 28, 2007 Hyatt Regency Chicago -- Riverside Center, Poster

Division of Physical Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007