Chiral isothiocyanates – An approach to determination of the absolute configuration using circular dichroism measurement

Oskar Michalski , Dariusz Cież


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.
Author Oskar Michalski (FoAaE / DoChaP)
Oskar Michalski,,
- Department of Chemistry and Physics
, Dariusz Cież
Dariusz Cież,,
Journal seriesJournal of Molecular Structure, ISSN 0022-2860, (A 20 pkt)
Issue year2013
Publication size in sheets0.5
Keywords in EnglishIsothiocyanates, Absolute configuration, Cotton effect, CD spectroscopy, TD DFT calculations
ASJC Classification1604 Inorganic Chemistry; 1605 Organic Chemistry; 1607 Spectroscopy; 1602 Analytical Chemistry
Internal identifierWRE/2013/5
Languageen angielski
Score (nominal)20
Score sourcejournalList
Publication indicators WoS Citations = 3; Scopus SNIP (Source Normalised Impact per Paper): 2013 = 0.843; WoS Impact Factor: 2013 = 1.599 (2) - 2013=1.585 (5)
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FinansowanieMNiSW - grant nr N N204 310037
FinansowanieProgram Operacyjny Innowacyjna Gospodarka (POIG) - kontrakt nr POIG.02.01.00-12-023/08
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