Publication: The docking of chiral epoxides on the Whelk-O1 stationary phase: A molecular dynamics study
All || By Area || By Year| Title | The docking of chiral epoxides on the Whelk-O1 stationary phase: A molecular dynamics study | Authors/Editors* | C. Zhao, N.M. Cann |
|---|---|
| Where published* | Journal of Chromatography A |
| How published* | Journal |
| Year* | 2007 |
| Volume | -1 |
| Number | -1 |
| Pages | |
| Publisher | |
| Keywords | Whelk-O1; Chiral epoxides; Molecular dynamics simulation; Chiral stationary phase; Selectivity mechanism; Chiral recognition |
| Link | http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TG8-4NB2WN5-1&_user=10&_coverDate=03%2F23%2F2007&_rdoc=68&_fmt=summary&_orig=browse&_srch=doc-info(%23toc%235248%239999%23999999999%2399999%23FLA%23display%23Articles)&_cdi=5248&_sort=d&_docanchor=&view=c&_ct=349&_acct=C000050221&_version=1&_urlVersion=0&_userid=10&md5=cb73869aff2ba54f6bd0d8e2026b126d |
| Abstract |
The docking of analytes on the Whelk-O1 chiral stationary phase is explored for two chiral epoxides in a hexane solvent. Density functional theory calculations are employed to develop flexible models for R/S-styrene oxide (phenyl oxirane) and (R,R/S,S)-stilbene oxide (2,3-diphenyl oxirane). 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 hydrogen bonding and ringâring interactions is explored along with an examination of the major docking arrangements. The interactions between the Whelk-O1 molecules and the chiral epoxide enantiomers are quite distinct and consistent with the experimental elution orders [S.E. Schaus, B.D. Brandes, J.F. Larrow, M. Tokunage, K.B. Hansen, A.E. Gould, M.E. Furrow, E.N. Jacobsen, J. Am. Chem. Soc. 124 (2001) 1307] and separation factors [W.H. Pirkle, C.J. Welch, Tetrahedron: Asymm. 5 (1994) 777]. The impact of a polar solvent modifier is examined for R/S-styrene oxide where selectivity in 80:20 n-hexane:2-propanol is assessed. |
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