Solvation and selectivity at the interface of the N-(3,5-dinitrobenzoyl)-phenylglycine chiral stationary phase

PHYS 564

Sorin Nita,, J. Hugh Horton,, and Natalie M. Cann, Department of Chemistry, Queen's University, Chernoff Hall, Kingston, ON K7L 3N6
A theoretical and experimental study of different solvent mixtures near a surface of N-(3,5-dinitrobenzoyl)-phenylglycine, a commonly used Pirkle-type chiral stationary phase, is presented. The experimental interface is prepared by attaching the molecules to AFM tips and oxidized Si(111) substrates and these are analysed using AFM, XPS and FTIR. Chemical force spectrometric measurements between the functionalized tips and samples are employed to probe the selectivity of the chiral interfaces. A semi-flexible representation of the chiral stationary phase molecules is prepared from B3LYP/6-311G** calculations and it is used to prepare a model chiral surface for molecular dynamics simulations. An analysis of the solvent composition and solvent hydrogen bonding at the interface will be presented. Other Pirkle-type chiral stationary phases are discussed and compared to the N-(3,5-dinitrobenzoyl)-phenylglycine interface.

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