http://www.cnr.it/ontology/cnr/individuo/prodotto/ID273232
Optimization of the HPLC enantioseparation of 3,3'?-dibromo-5,5?'-disubstituted-4,4'?-bipyridines using immobilized polysaccharide-based chiral stationary phases (Articolo in rivista)
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- Optimization of the HPLC enantioseparation of 3,3'?-dibromo-5,5?'-disubstituted-4,4'?-bipyridines using immobilized polysaccharide-based chiral stationary phases (Articolo in rivista) (literal)
- Anno
- 2013-01-01T00:00:00+01:00 (literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
- 10.1002/jssc.201300576 (literal)
- Alternative label
Peluso P., Mamane V., Aubert E., Cossu S. (2013)
Optimization of the HPLC enantioseparation of 3,3'?-dibromo-5,5?'-disubstituted-4,4'?-bipyridines using immobilized polysaccharide-based chiral stationary phases
in Journal of separation science (Print)
(literal)
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- Peluso P., Mamane V., Aubert E., Cossu S. (literal)
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- http://onlinelibrary.wiley.com/doi/10.1002/jssc.201300576/abstract (literal)
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- ISI Web of Science (WOS) (literal)
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- 1) Istituto di Chimica Biomolecolare, ICB-CNR, UOS di Sassari;
2) Laboratoire SRSMC, UMR CNRS-UHP 7565, Université de Lorraine, Vandoeuvre-les-Nancy, France;
3) Cristallographie, Résonance, Magnétique et Modélisations (CRM2), UMR CNRS-UHP 7036, Université de Lorraine, Vandoeuvre-les-Nancy, France;
4) Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca' Foscari di Venezia, Venezia, Italy (literal)
- Titolo
- Optimization of the HPLC enantioseparation of 3,3'?-dibromo-5,5?'-disubstituted-4,4'?-bipyridines using immobilized polysaccharide-based chiral stationary phases (literal)
- Abstract
- The HPLC enantioseparation of nine atropisomeric 3,3?',5,5'?-tetrasubstituted-4,4'?-
bipyridines was performed in normal and polar organic (PO) phase modes using two
immobilized polysaccharide-based chiral columns, namely, Chiralpak IA and Chiralpak
IC. The separation of all racemic analytes, the effect of the chiral selector, and mobile
phase (MP) composition on enantioseparation and the enantiomer elution order (EEO)
were studied. The beneficial effect of nonstandard solvents, such as tetrahydrofuran (THF),
dichloromethane (DCM), and methyl t-butyl ether on enantioseparation was investigated.
All selected 4,4?'-bipyridines were successfully enantioseparated on Chiralpak IA under normal
or PO MPs with separation factors from 1.14 to 1.70 and resolutions from 1.3 to 6.5. Two
bipyridines were enantioseparated at the multimilligram level on Chiralpak IA. Differently,
Chiralpak IC was less versatile toward the considered class of compounds and only five
bipyridines out of nine could be efficiently separated. In particular, on these columns, the
ternary mixture n-heptane/THF/DCM (90:5:5) as MP had a positive effect on enantioseparation.
An interesting phenomenon of reversal of the EEO depending on the composition of
the MP for the 3,3?'-dibromo-5,5'?-bis-(E)-phenylethenyl-4,4'?-bipyridine along with an exceptional
enantioseparation for the 3,3'?-dibromo-5,5?'-bis-ferrocenylethynyl-4,4'?-bipyridine (? =
8.33, Rs = 30.6) were observed on Chiralpak IC. (literal)
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