Title
Vibrational circular dichroism versus optical rotation dispersion and electronic circular dichroism for diastereomers : the stereochemistry of 3-(1 '-hydroxyethyl)-1-(3 '-phenylpropanoyl)-azetidin-2-one Vibrational circular dichroism versus optical rotation dispersion and electronic circular dichroism for diastereomers : the stereochemistry of 3-(1 '-hydroxyethyl)-1-(3 '-phenylpropanoyl)-azetidin-2-one
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
Cambridge ,
Subject
Physics
Chemistry
Source (journal)
Physical chemistry, chemical physics / Chemical Society [London] - Cambridge, 1999, currens
Volume/pages
14(2012) :24 , p. 8562-8571
ISSN
1463-9076
1463-9084
ISI
000304605600014
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
The absolute configuration of a relatively large and conformationally flexible chiral compound, 3-(1 '-hydroxyethyl)-1-(3 '-phenylpropanoyl)-azetidin-2-one, is determined using Vibrational Circular Dichroism (VCD) spectroscopy, Optical Rotation Dispersion (ORD) and Electronic Circular Dichroism (ECD). To that end a state of the art experimental VCD spectrum is compared to a theoretical spectrum and the absolute configuration is assigned. ORD and ECD are also used in the assignment to investigate the complementarity of the three techniques. VCD spectroscopy is found to have important advantages over ORD and ECD for diastereomers. The concept of robust modes is applied to this conformationally flexible molecule, showing that its use is limited for such large and flexible molecules.
E-info
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