Open AccessSEPARAÇÃO ENANTIOSSELETIVA DA OXIBUTININA: UMA INVESTIGAÇÃO TEÓRICA E EXPERIMENTAL
Author(s) -
Lilian Christina Zin,
Camilla Silva,
Lia Buarque de Macedo Guimarães,
Keyller Borges,
Clebio Nascimento
Publication year - 2021
Publication title -
química nova
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.214
H-Index - 73
eISSN - 1678-7064
pISSN - 0100-4042
DOI - 10.21577/0100-4042.20170815
Subject(s) - oxybutynin , diastereomer , enantiomer , chemistry , enantioselective synthesis , hydrogen bond , ionization , chromatography , elution , stereochemistry , organic chemistry , molecule , catalysis , ion , medicine , alternative medicine , pathology , overactive bladder
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.