http://www.cnr.it/ontology/cnr/individuo/prodotto/ID280326
Insights into the impact of shape and electronic properties on the enantioseparation of polyhalogenated 4,4'-bipyridines on polysaccharide-type selectors. Evidence of stereoselective halogen bonding interactions (Articolo in rivista)
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- Insights into the impact of shape and electronic properties on the enantioseparation of polyhalogenated 4,4'-bipyridines on polysaccharide-type selectors. Evidence of stereoselective halogen bonding interactions (Articolo in rivista) (literal)
- Anno
- 2014-01-01T00:00:00+01:00 (literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
- 10.1016/j.chroma.2014.04.040 (literal)
- Alternative label
Peluso P., Mamane V., Aubert E., Cossu S. (2014)
Insights into the impact of shape and electronic properties on the enantioseparation of polyhalogenated 4,4'-bipyridines on polysaccharide-type selectors. Evidence of stereoselective halogen bonding interactions
in Journal of chromatography (Print)
(literal)
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- Peluso P., Mamane V., Aubert E., Cossu S. (literal)
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- http://www.sciencedirect.com/science/article/pii/S0021967314005925 (literal)
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- ISI Web of Science (WOS) (literal)
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- Istituto di Chimica Biomolecolare ICB CNR, CNRS Université de Lorraine, Università Ca' Foscari di Venezia (literal)
- Titolo
- Insights into the impact of shape and electronic properties on the enantioseparation of polyhalogenated 4,4'-bipyridines on polysaccharide-type selectors. Evidence of stereoselective halogen bonding interactions (literal)
- Abstract
- Starting from the high-performance liquid chromatography (HPLC) enantioseparation data collected by
using twelve polyhalogenated 2,2?-dichloro-3-substituted-5,5?-dihalo-4,4?-bipyridines as test probes on
seven polysaccharide-based chiral stationary phases (CSPs) under multimodal elution, the impact of
substitution pattern, shape and electronic properties of the molecules on the separation behaviour was
investigated through the evaluation of the chromatographic parameters (k, ?, Rs) and molecular properties
determined by means of quantum chemistry calculations. The computational/chromatographic
screening furnished relevant structure-chromatographic behaviour relationships and some molecular
interactions involved in the chiral discrimination process could be identified. In particular, a halogen
bonding interaction (I.O) could reasonably explain the high enantioseparation (? = 1.80, Rs = 8.2) observed
for the 2,2?-dichloro-3,5?-diiodo-5-bromo-4,4?-bipyridine on Lux Cellulose-1. To the best of our knowledge,
this is the first report supporting the involvement of a stereoselective halogen bonding interaction
in polysaccharide-based CSPs. Moreover, having at disposal a sufficient set of data, the unknown absolute
configurations of the eluted enantiomers of 3-methyl-, 3-thiomethyl- and 3-diphenylphosphinoyl-
2,2?-dichloro-5,5?-dibromo-4,4?-bipyridines could be deduced by chromatographic correlation with the
enantiomer elution order (EEO) of the related compounds of known absolute configuration. (literal)
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