Summary
The silanization/hydrosilation bonding method is used to attach four different chiral olefins to a silica hydride surface. Three of these olefins ((R)-(+)-limonene, (R)-(+)-acroyloxy-β,β-dimethyl-λ-butyrolactone and 2-hydroxy-3-methacryloyloxypropyl-β-cyclodextrin) are successfully bonded to the hydride intermediate as confirmed by DRIFT and solid state NMR spectroscopy. Chromatographic evaluation of these three chiral stationary phases using a number of test solutes resulted in no separations of enantiomers for the limonene phase, two marginal resolutions for the lactone phase and six successful separations for the β-cyclodextrin material. Among the types of compounds that were resolved on the β-cyclodextrin column were benzodiazepines, danysl amino acids and a novel selenium compound.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Dalgleish, C.E.J. Chem. Soc. 1952,47, 3940.
Davankov, V.A.; Navratil, J.D.; Walton, H.F.Ligand Exchange Chromatography, CRC Press, Inc. Boca Raton, Florida,1988.
Hermansson, J.Trends in Analytical Chemistry 1989,8, 251.
Yang, J.; Hage, D.J. Chromatogr. A 1996,725, 273.
Risley, D.S.; Sharp, V.S.; Palmer, J.R.J. Liq. Chromatogr. & Rel. Technol. 1996,19, 449.
Shoaf, S.; Schmall, B.J. Pharmacol. & Exper. Therap. 1996,277, 219.
Han, S.M.Biomed. Chromatogr. 1997,11, 259.
Montes, M.C.; Chu, C.-H.; Jonsson, E.; Auvinen, M.; Pesek, J.J.; Sandoval, J.E.Anal. Chem. 1993,65, 808.
Pesek, J.J.; Matyska, M.T.; Sandoval, J.E.; Williamsen, E.J.J. Liq. Chromatogr. & Rel. Technol. 1996,19, 2843.
Pesek, J.J.; Swedberg, S.A.J. Chromatogr. 1986,361, 83.
Cobb, K.A.; Dolnik, V.; Novotny, M.Anal. Chem. 1990,62, 1550.
Marciniec, B.Comprehensive Handbook of Hydrosilylation, Pergamon Press, Oxford,1992.
Pesek, J.J.; Matyska, M.T.; Kamath, S.Analusis 1997,25, 253.
Pesek, J.J.; Matyska, M.T.; Williamsen, E.J.; Tam, R.Chromatographia 1995,41, 301.
Pesek, J.J.; Matyska, M.T.; Williamsen, E.J.; Evanchic, M.; Hazari, V.; Konjuh, K.; Takhar, S.; Tranchina, R.J. Chromatogr. A 786, 219.
Sandoval, J.E.; Pesek, J.J.Anal. Chem.,1991,63, 2634.
Berendsen, G.E.; DeGalan, L.,J. Liq. Chromaotgr. 1978,1, 561.
Pesek, J.J.; Matyska, M.T.Adsorption and Its Application in Industry and Environmental Protection Dabrowski, A., Ed., Elsevier, Amsterdam,1999, 117.
Schurig, V.; Negura, S.; Mayer, S.; Reich, S.J. Chromatogr. A 1996,755, 299.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Pesek, J.J., Matyska, M.T. & Fu, P.F. Evaluation of the silanization/Hydrosilation process for the synthesis of chiral stationary phases. Chromatographia 53, 635–640 (2001). https://doi.org/10.1007/BF02493011
Received:
Revised:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02493011