Reversed-phase chromatography as an effective tool for the chiral separation of anionic and zwitterionic carboranes using polysaccharide-based chiral selectors

0557516 - ÚACH 2023 RIV NL eng J - Journal Article
Horáček, O. - Marvalová, J. - Štilcová, K. - Holub, Josef - Grüner, Bohumír - Kučera, R.
Reversed-phase chromatography as an effective tool for the chiral separation of anionic and zwitterionic carboranes using polysaccharide-based chiral selectors.
Journal of Chromatography A. Roč. 1672, JUN (2022), č. článku 463051. ISSN 0021-9673. E-ISSN 1873-3778
R&D Projects: GA ČR(CZ) GA21-14409S
Institutional support: RVO:61388980
Keywords : Boron clusters * Carboranes * Chiral separation * HPLC * Polysaccharides * Reversed-phase
OECD category: Inorganic and nuclear chemistry
Impact factor: 4.1, year: 2022
Method of publishing: Limited access
https://doi.org/10.1016/j.chroma.2022.463051

The aspect of the different spatial arrangement of anionic cobalt bis(dicarbollides) and dicarba-nido-undecaboranes remains grossly overlooked despite increased scientific interest. Regarding their growing potential, which does not limit only to medicinal chemistry, suitable enantioseparation methods are needed. The presented paper explores the possibilities of chiral separations of anionic cobalt bis(dicarbollide) and dicarba-7,8-nido-undecaborane derivatives on four polysaccharide-based columns under reversed-phase conditions. The chromatographic behavior of anionic derivatives was evaluated and compared with that of zwitterionic clusters. The isocratic procedure for HPLC method development was suggested. The main parameters for the optimization of separations were described. Successful chiral separations were critically compared to previously reported results in normal phase and polar-organic mode. Reversed-phase separations are superior in resolution, lower consumption of organic solvents, and flexibility during the method development. Moreover, the first chiral discrimination of some hydroxyalkyl derivatives of anionic cobalt bis(dicarbollides) is reported. The outcomes of this work may be used for method development in any area, where the chirality of these interesting molecules is of concern.
Permanent Link: http://hdl.handle.net/11104/0331487