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Absolute Configuration of C 2 ‐Symmetric Spiroselenurane: 3,3,3′,3′‐Tetramethyl‐1,1′‐spirobi[3 H ,2,1]Benzoxaselenole
Author(s) -
Petrovic Ana G.,
Polavarapu Prasad L.,
Drabowicz Jozef,
Zhang Yingru,
McConnell Oliver J.,
Duddeck Helmut
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200401331
Subject(s) - vibrational circular dichroism , enantiomer , absolute configuration , optical rotation , circular dichroism , spectral line , chemistry , optical rotatory dispersion , density functional theory , dispersion (optics) , molecular physics , analytical chemistry (journal) , computational chemistry , crystallography , stereochemistry , physics , optics , chromatography , organic chemistry , astronomy
The enantiomers of 3,3,3′,3′‐tetramethyl‐1,1′‐spirobi[3 H ,2,1]benzoxaselenole have been separated on a chiral preparative chromatographic column. The experimental vibrational circular dichroism (VCD) spectra have been obtained for both enantiomers in CH 2 Cl 2 . The theoretical VCD spectra have been obtained by means of density functional theoretical calculations with the B3 LYP density functional. From a comparison of experimental and theoretical VCD spectra, the absolute configuration of an enantiomer with positive specific rotation in CH 2 Cl 2 at 589 nm is determined to be R . This conclusion has been verified by comparing results of experimental optical rotatory dispersion (ORD) and electronic circular dichroism (ECD) to predictions of the same properties using the B3 LYP functional for the title compound.