ON/OFF receptor-like enantioseparation of planar chiral 1,2-ferrocenes on an amylose-based chiral stationary phase: The role played by 2-propanol.
2-Propanol
Chiralpak AD-3
Enantioselective HPLC
Planar chiral 1,2-ferrocenes
Receptor-like enantioseparation
Journal
Analytica chimica acta
ISSN: 1873-4324
Titre abrégé: Anal Chim Acta
Pays: Netherlands
ID NLM: 0370534
Informations de publication
Date de publication:
08 Jun 2022
08 Jun 2022
Historique:
received:
16
03
2022
revised:
20
04
2022
accepted:
25
04
2022
entrez:
19
5
2022
pubmed:
20
5
2022
medline:
24
5
2022
Statut:
ppublish
Résumé
A set of nine planar chiral 1,2-ferrocenes was analyzed by high-performance liquid chromatography (HPLC) on the amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phase. The enantioseparations were carried out using neat methanol, ethanol, 1-propanol, and 2- propanol as well as mixtures of n-hexane-2-propanol as mobile phases. The differences in retention times between the second eluted (Rp)-enantiomers and the first eluted (Sp)-enantiomers were significantly influenced by elution modes and the steric hindrance of substituents at the aromatic rings of the ferrocene backbone. It has been demonstrated an ON/OFF switching of receptor-like chiral discrimination through the employment of different alcohols as mobile phases. In particular, the presence of pure 2-propanol triggers exceptional conditions of enantioselectivity that for some ferrocenes result in values of the enantioseparation factor higher than 80.
Identifiants
pubmed: 35589221
pii: S0003-2670(22)00451-2
doi: 10.1016/j.aca.2022.339880
pii:
doi:
Substances chimiques
Metallocenes
0
Ethanol
3K9958V90M
Amylose
9005-82-7
2-Propanol
ND2M416302
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
339880Informations de copyright
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