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PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
23
pubmed:dateCreated
2009-12-2
pubmed:abstractText
The atropenantiomers of stable 1,2,3,4-tetrahalo-1,3-butadiene derivatives (where halogeno stands for bromine or iodine) were separated with use of chiral HPLC. The barriers for the enantiomerization process were determined on-line by dynamic HPLC (DHPLC) or off-line by classical kinetic measurements. In the case of the tetrachloro compound, the barrier was too low for DHPLC and its value was obtained by dynamic NMR experiments. The obtained barriers for chloro, bromo, and iodo derivatives correlate with the van der Waals radii of the halogens. The absolute configuration of the isolated enantiomers of the tetraiodo and tetrabromo compounds was assigned by comparison of the experimental and conformations averaged calculated VCD spectra. The identification of a signature band of the absolute configuration of the butadiene core, the sign and location of which are independent from the different conformations and substituents, allowing the safe assignment of the absolute configuration of the enantiomers of chiral 1,3-butadienes, is also reported.
pubmed:language
eng
pubmed:journal
pubmed:status
PubMed-not-MEDLINE
pubmed:month
Dec
pubmed:issn
1520-6904
pubmed:author
pubmed:issnType
Electronic
pubmed:day
4
pubmed:volume
74
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
9062-70
pubmed:year
2009
pubmed:articleTitle
Synthesis, structural analysis, and chiral investigations of some atropisomers with EE-tetrahalogeno-1,3-butadiene core.
pubmed:affiliation
Faculty of Chemistry and Chemical Engineering, Babes-Bolyai University, Cluj-Napoca, 11 Arany Janos str., 400028, Cluj-Napoca, Romania.
pubmed:publicationType
Journal Article