The influence of solute structure,temperature, and eluent composition on the chiral separation of 21 aminotetralins on a cellulose tris-3,5-dimethylcarbamate stationary phase in high-performance liquid chromatography |
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Authors: | Dirk T Witte Jan-Piet Franke Frank J Bruggeman Durk Dijkstra Rokus A De Zeeuw |
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Abstract: | In the present study 21 different chiral aminotetralins were used to investigate the mechanism behind their enantiomeric resolution (Rs) on a commercially available high-performance liquid chromatography (HPLC) cellulose tris-3,5-dimethylcarbamate stationary phase. The differences in the chemical structures of the aminotetralins used were never directly located on the chiral carbon. Their chromatographic behavior was studied for two eluent compositions at six different temperatures. Hydrogen bonding and π? π interactions are two possible solute–chiral stationary phase (CSP) interactions. Differences between the enantiomers in their spatial arrangement of positions involved in solute–CSP interactions were the major forces behind enantiomeric separation. Lowering the temperature increased the Rs for the aminotetralins having π-electrons not directly bonded to that part of the molecule where the hydrogen bonding with the CSP is located. Primary amines and secondary amines, with a sufficiently short N-alkyl substituent, showed a decrease of Rs with lower temperatures, all other aminotetralins yielding an increase of Rs with lower temperatures. © 1992 Wiley-Liss, Inc. |
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Keywords: | chiral stationary phase CHIRALCEL OD temperature effect enantiomeric separation aminotetralins dopamine agonists resolution chiral recognition mechanism |
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