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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
Author(s) -
Witte Dirk T.,
Franke JanPiet,
Bruggeman Frank J.,
Dijkstra Durk,
De Zeeuw Rokus A.
Publication year - 1992
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530040610
Subject(s) - chemistry , enantiomer , cellulose , chiral column chromatography , column chromatography , hydrogen bond , high performance liquid chromatography , substituent , chiral stationary phase , phase (matter) , molecule , tris , alkyl , chromatography , organic chemistry , biochemistry
Abstract In the present study 21 different chiral aminotetralins were used to investigate the mechanism behind their enantiomeric resolution ( R s ) 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 ππ 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 R s 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 R s with lower temperatures, all other aminotetralins yielding an increase of R s with lower temperatures. © 1992 Wiley‐Liss, Inc.