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Chiral isothiocyanates: an approach to determination of the absolute configuration using circular dichroism measurement

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Chiral isothiocyanates: an approach to determination of the absolute configuration using circular dichroism measurement

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dc.contributor.author Michalski, Oskar pl
dc.contributor.author Cież, Dariusz [SAP11016140] pl
dc.date.accessioned 2015-06-09T07:39:14Z
dc.date.available 2015-06-09T07:39:14Z
dc.date.issued 2013 pl
dc.identifier.issn 0022-2860 pl
dc.identifier.uri http://ruj.uj.edu.pl/xmlui/handle/item/9058
dc.language eng pl
dc.title Chiral isothiocyanates: an approach to determination of the absolute configuration using circular dichroism measurement pl
dc.type JournalArticle pl
dc.description.physical 225-235 pl
dc.abstract.en Chiral alkyl 2-isothiocyanates have been obtained from enantiopure, aliphatic amines. ECD measurements allowed us to correlate an absolute configuration at C-2 with a sign of the Cotton effect (CE) observed for n–π* transition at the longer-wavelength range of the spectrum. Chirooptical data calculated for all enantiomers were consistent with the measured CE values and indicated that the weak absorption band at 240 nm could give an important information concerning the stereochemistry of simple, chiral isothiocyanates. Optically active esters of 2-isothiocyanatocarboxylic acids, prepared from α-amino acids, showed two absorption bands located over 195 nm. The more intensive band near 200 nm and the weak absorption located at 250 nm were related to n–π* transitions in NCS group. TD DFT calculations carried out for methyl esters of 2-isothiocyanatocarboxylic acids showed the correlation between signs of CE determined for both absorption bands, and the absolute configuration on C-2. pl
dc.subject.en Isothiocyanates pl
dc.subject.en Absolute configuration pl
dc.subject.en Cotton effect pl
dc.subject.en CD spectroscopy pl
dc.subject.en TD DFT calculations pl
dc.description.volume 1037 pl
dc.identifier.doi 10.1016/j.molstruc.2012.12.048 pl
dc.identifier.eissn 1872-8014 pl
dc.title.journal Journal of Molecular Structure pl
dc.language.container eng pl
dc.affiliation Wydział Chemii : Zakład Chemii Organicznej pl
dc.subtype Article pl
dc.rights.original bez licencji pl
.pointsMNiSW [2013 A]: 20


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