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Enantiomeric Separation of Original Heterocyclic Organophosphorus Compounds in Supercritical Fluid Chromatography
Author(s) -
West Caroline,
CieslikiewiczBouet Monika,
Lewinski Krzysztof,
Gillaizeau Isabelle
Publication year - 2013
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.22133
Subject(s) - chemistry , enantiomer , supercritical fluid chromatography , chirality (physics) , elution , dichlorobenzene , chiral column chromatography , structural isomer , cellulose , organic chemistry , methanol , chromatography , asymmetric carbon , supercritical fluid , column chromatography , optically active , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
New and original heterocyclic α‐enamido phosphine chiral solutes were prepared: four structurally similar racemates with the chirality center placed on the phosphorus atom, and four other related pairs of enantiomers with chirality borne by the carbon atoms of the phospholane ring. The structural variations were placed on an aliphatic heterocycle (six‐ or seven‐member rings) and on the carbamate function (methyl or t ‐butyl). Their separation was achieved on a commercial cellulose tris ‐(3,5‐dimethylphenylcarbamate) stationary phase (Lux Cellulose‐1, Phenomenex) in supercritical fluid chromatography (SFC). The effects of molecular structure on SFC retention and enantioresolution were studied. Among these eight pairs of enantiomers, some reversal of elution order between similar compounds was observed. The effect of changing the organic solvent (methanol and ethanol) and its proportion (between 5 and 40%) in the mobile phase was investigated. Retention data were collected over the temperature range 0–50 °C, and the results interpreted from thermodynamic aspects. Chirality, 2013. © 2013 Wiley Periodicals, Inc.