Investigation of a broadly applicable chiral selector used in enantioselective chromatography (Whelk-O 1) as a chiral solvating agent for NMR determination of enantiomeric composition |
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| Institution: | 1. Department of Frontier Materials, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya, Aichi 466-8555, Japan;2. Department of Materials Science and Chemistry, University of Hyogo, 2167 Shosha, Himeji, Hyogo 671-2280, Japan;3. Department of Electrical and Electronic Information Engineering, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi, Aichi 441-8580, Japan;4. LARMAUR Équipe Verres ERL CNRS 6274, Université de Rennes 1, Campus de Beaulieu, Rennes Cedex 35042, France |
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| Abstract: | A chiral solvating agent (CSA) based on the chiral selector used in the Whelk-O 1 chiral stationary phase (CSP) was prepared and its scope evaluated. This chiral selector possesses a cleft flanked with aromatic groups and produces upfield chemical shifts for analytes, which are held in this cleft. The enantiomers of each of the Whelk-O 1 resolvable analytes surveyed show non-equivalent 1H NMR spectra at room temperature with the addition of only 0.5 equiv of the CSA. Similar non-equivalence is sometimes noted for enantiomers, which do not resolve on this CSP. In such cases, it is apparent that a hydrogen bond acceptor is required and higher CSA to substrate ratios and/or lower temperatures may be needed if adequate resolution of enantiomeric signals is to be obtained. |
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