Chiral resolution of a series of antiphlogistic methyl and ethyl 2-ary
loxypropionates on R-DNBPG and S-DNBL analytical columns was attempted
. Most of the resolved enantiomers were eluted in a very short time on
both CSPs and the alpha and K' values of the chromatographic separati
ons performed by R-DNBPG phase were generally better than those using
S-DNBL. The elution order of the compounds was determined: the S isome
r of all esters was eluted last from the R-DNBPG and viceversa from th
e S-DNBL column. The role of the substituents on the chiral resolution
was also elucidated. It was hypothesized that the chiral interactions
between the solutes and the CSPs were more influenced by the electron
ic features than by their steric hindrance. Finally, the chiral recogn
ition mechanism which permitted resolution of the enantiomers was indi
viduated.