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Direct enantioselective separation of some propranolol analogs by HPLC on normal and reversed cellulose chiral stationary phases
Author(s) -
AboulEnein Hassan Y.,
AbouBasha Laila I.,
Bakr Soliman A.
Publication year - 1996
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/(sici)1520-636x(1996)8:1<153::aid-chir23>3.0.co;2-l
Subject(s) - chemistry , enantiomer , chiral derivatizing agent , aryl , enantioselective synthesis , chiral column chromatography , moiety , elution , cellulose , stacking , side chain , stereochemistry , chromatography , organic chemistry , alkyl , polymer , catalysis
The enantiomeric separation of several racemic aryloxyaminopropan‐2‐ol derivatives related to propranolol on normal and reversed phase of cellulose tris (3,5‐dimethylphenylcarbamate) chiral stationary phases known as Chiralcel OD and Chiralcel OD‐R were studied. It was observed that the chiral separation depends on the substitution pattern of the aryl group, i.e., 1‐naphthyl, 2‐naphthyl, and phenyl group and polarity on the basic nitrogen in the side chain. In both normal and reversed phase modes the (+)‐R‐enantiomer eluted first in all of the analogs resolved. It can be concluded that: (1) substituents on the side chain did affect the interaction of the enantiomers with the polar carbamate moiety in the CSP; and (2) the dipole‐dipole stacking between the π‐donor 3,5‐dimethylphenyl carbamate group pending from the glucose rings of the CSP and π‐acceptor aryl group of the analyte is crucial for the efficient chiral discrimination. The chiral recognition mechanism(s) between these analogs and the chiral stationary phases are proposed. © 1996 Wiley‐Liss, Inc.