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Evaluation of non‐polar interactions in chiral recognition by alkylated β‐ and γ‐cyclodextrin chiral stationary phases
Author(s) -
Spanik Ivan,
Oswald Peter,
Krupcik Jan,
Benicka Eva,
Sandra Pat,
Armstrong Daniel W.
Publication year - 2002
Publication title -
journal of separation science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.72
H-Index - 102
eISSN - 1615-9314
pISSN - 1615-9306
DOI - 10.1002/1615-9314(20020101)25:1/2<45::aid-jssc45>3.0.co;2-l
Subject(s) - cyclodextrin , polar , alkylation , chiral stationary phase , chemistry , computational chemistry , organic chemistry , chromatography , combinatorial chemistry , enantiomer , catalysis , physics , astronomy
The gas chromatographic separation of enantiomers of seven N ‐TFA‐ O ‐alkyl amino acid derivatives was studied on four different permethyl‐ and 2,6‐di‐ O ‐methyl‐3‐ O ‐pentyl‐β‐ and ‐γ‐CD stationary phases.It was shown that the separation of enantiomers N ‐TFA‐ O ‐alkyl amino acid derivatives depends both on the length of the linear alkyl chain attached to the stereogenic carbon (R 1 ) and to the ester part of the amino acid derivative (R 2 ). The cyclodextrin cavity size also affected selectivity. The separation of the amino acid derivatives decreases with increasing length of both the R 1 and R 2 alkyl chains on β‐CD stationary phases, but improves on γ‐CD stationary phases. The separation of enantiomers of all N ‐TFA‐ O ‐methyl amino acid esters, is better on the larger γ‐cyclodextrin CSPs except for enantiomers of N ‐TFA‐ O ‐alkyl esters of alanine which are better separated on β‐CD stationary phases.