ISSN:
0899-0042
Keywords:
enantioselective chromatography
;
oxadiazolines
;
quantitative structure-enantioselective retention relationships
;
comparative molecular field analysis
;
Chemistry
;
Food Science, Agricultural, Medicinal and Pharmaceutical Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A series of racemic 3-phenyl-4-(1-adamantyl)-5-X-phenyl-Δ2-1,2,4-oxadiazolines (PAdOx) were directly resolved by HPLC using a Pirkle-type stationary phase containing N,N′-(3,5-dinitrobenzoyl)-1 (R),2(R)-diaminocyclohexane as chiral selector. The more retained enantiomers have S configuration, as demonstrated by X-ray crystallography and circular dichroism measurements. The influence of aromatic ring substituents on enantioselective retention was quantitatively assessed by traditional linear free energy-related (LFER) equations and comparative molecular field analysis (CoMFA). In good agreement with previous findings, the results from this study indicate that the increase in retention (k′) is favoured mainly by the π-basicity and the hydrophilicity of solute, whereas enantioselectivity (α) can be satisfactorily modeled by electronic and bulk parameters or CoMFA descriptors. The LFER equations and CoMFA models gave helpful insights into chiral recognition mechanisms. Chirality 8:556-566, 1996. © 1997 Wiley-Liss, Inc.
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
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