SEPARAÇÃO ENANTIOSSELETIVA DA OXIBUTININA: UMA INVESTIGAÇÃO TEÓRICA E EXPERIMENTAL

ENANTIOSELECTIVE SEPARATION OF OXYBUTYNIN: A THEORETICAL AND EXPERIMENTAL INVESTIGATION

In this work, we have studied both experimentally and theoretically the oxybutynin chiral discrimination. According to the main results, the enantioseparation of oxybutynin was efficiently achieved by high performance liquid chromatography in normal phase using the Chiralpak^® AD column, which has amylose tris (3,5‐dimethylphenylcarbamate) as a chiral selector. The energetic and structural parameters obtained via density functional theory calculations pointed out the chiral discrimination as well as the enantiomeric elution order of oxybutynin, thus explaining, at molecular level, the experimental data. Finally, the strength of the hydrogen bonds played a key role in the discrimination between the oxybutynin diastereomeric complexes formed.

Keywords:
theoretical calculations; Density Functional Theory; chiral separation; diasteroisomeric complexes; oxybutynin