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Comparative enantioseparation of planar chiral ferrocenes on polysaccharide-based chiral stationary phases.

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Comparative enantioseparation of planar chiral ferrocenes on polysaccharide-based chiral stationary phases.

dc.contributor.author	Dessì, Alessandro
dc.contributor.author	Sechi, Barbara
dc.contributor.author	Dallocchio, Roberto
dc.contributor.author	Chankvetadze, Bezhan
dc.contributor.author	Pérez Baeza, Mireia
dc.contributor.author	Cossu, Sergio
dc.contributor.author	Mamane, Victor
dc.contributor.author	Pale, Patrick
dc.contributor.author	Peluso, Paola
dc.date.accessioned	2023-05-30T09:00:48Z
dc.date.available	2023-05-30T09:00:48Z
dc.date.issued	2022
dc.identifier.citation	Dessì, Alessandro Sechi, Barbara Dallocchio, Roberto Chankvetadze, Bezhan Pérez Baeza, Mireia Cossu, Sergio Mamane, Victor Pale, Patrick Peluso, Paola 2022 Comparative enantioseparation of planar chiral ferrocenes on polysaccharide-based chiral stationary phases. Chirality 34 4 609 619
dc.identifier.uri	https://hdl.handle.net/10550/87095
dc.description.abstract	Planar chiral ferrocenes are well-known compounds that have attracted interest for application in synthesis, catalysis, material science, and medicinal chemistry for several decades. In spite of the fact that asymmetric synthesis procedures for obtaining enantiomerically enriched ferrocenes are available, sometimes, the accessible enantiomeric excess of the chiral products is unsatisfactory. In such cases and for resolution of racemic planar chiral ferrocenes, enantioselective high-performance liquid chromatography (HPLC) on polysaccharide-based chiral stationary phases (CSPs) has been used in quite a few literature articles. However, although moderate/high enantioselectivities have been obtained for planar chiral ferrocenes bearing polar substituents, the enantioseparation of derivatives containing halogens, or exclusively alkyl groups, remains rather challenging. In this study, the enantioseparation of ten planar chiral 1,2- and 1,3-disubstituted ferrocenes was explored by using five polysaccharide-based CSPs under multimodal elution conditions. Baseline enantioseparations were achieved for nine analytes with separation factors (α) ranging from 1.20 to 2.92. The presence of π-extended systems in the analyte structure was shown to impact affinity of the most retained enantiomer toward amylose-based selectors, observing retention times higher than 80 min with methanol-containing mobile phases (MPs). Electrostatic potential (V) analysis and molecular dynamics (MD) simulations were used in order to study interaction modes at the molecular level.
dc.language.iso	eng
dc.relation.ispartof	Chirality, 2022, vol. 34, num. 4, p. 609-619
dc.subject	Química analítica
dc.title	Comparative enantioseparation of planar chiral ferrocenes on polysaccharide-based chiral stationary phases.
dc.type	journal article
dc.date.updated	2023-05-30T09:00:49Z
dc.identifier.doi	10.1002/chir.23417
dc.identifier.idgrec	159165
dc.rights.accessRights	open access