COMPUTATIONAL STUDIES OF THE CHIRAL SEPARATIONS OF 3 N-ACYL-1-ARYL-1-AMINOETHANES ON AN (R)-N-DINITROBENZOYLPHENYLGLYCINE STATIONARY PHASE

The chiral chromatographic separations of three N-acyl-1-aryl-1-aminoethanes on silica modified with (R)-N-dinitrobenzoylphenylglycine-N′-propylamide have been modeled by use of molecular mechanics. Formyl groups were substituted for the nitro groups, and a methyl group was tested as a replacement for the propyl group. With the propyl group, the correct elution order was obtained for the two pairs that had the largest α-values, and the third pair had a calculated α-value very close to unity. The relative sizes of the α-values were correctly predicted for all three. Substitution of methyl for propyl gave data that did not agree as well with the experimental values, thereby confirming the important role of the spacer in these separations. © 1990.