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Enantiomeric Separations of Ruthenium (II) Polypyridyl Complexes Using HPLC With Cyclofructan Chiral Stationary Phases
Author(s) -
Shu Yang,
Breitbach Zachary S.,
Dissanayake Milan K.,
Perera Sirantha,
Aslan Joseph M.,
Alatrash Nagham,
MacDonnell Frederick M.,
Armstrong Daniel W.
Publication year - 2015
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.22389
Subject(s) - chemistry , ruthenium , enantiomer , chiral stationary phase , high performance liquid chromatography , chiral column chromatography , chromatography , chirality (physics) , stationary phase , combinatorial chemistry , enantiomeric excess , enantioselective synthesis , organic chemistry , catalysis , chiral symmetry , physics , quantum mechanics , nambu–jona lasinio model , quark
The enantiomeric separation of 21 ruthenium (II) polypyridyl complexes was achieved with a novel class of cyclofructan‐based chiral stationary phases (CSPs) in the polar organic mode. Aromatic derivatives on the chiral selectors proved to be essential for enantioselectivity . The R‐napthylethyl carbamate functionalized cyclofructan 6 (LARIHC CF6‐RN) column proved to be the most effective overall, while the dimethylphenyl carbamate cyclofructan 7 (LARIHC CF7‐DMP) showed complementary selectivity. A combination of acid and base additives was necessary for optimal separations. The retention factor vs . acetonitrile/methanol ratio plot showed a U‐shaped retention curve, indicating that different interactions take place at different polar organic solvent compositions. The separation results indicated that π–π interactions, steric effects, and hydrogen bonding contribute to the enantiomeric separation of ruthenium (II) polypyridyl complexes with cyclofructan chiral stationary phases in the polar organic mode. Chirality 27:64–70, 2015 . © 2014 Wiley Periodicals, Inc.