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.
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.
authors.affiliation: Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, B-2020 Antwerp, Belgium.
authors.forename: Ewoud De
authors.initials: ED
authors.lastname: Gussem
authors.forename: Patrick
authors.initials: P
authors.lastname: Bultinck
authors.forename: Marion
authors.initials: M
authors.lastname: Feledziak
authors.forename: Jacqueline
authors.initials: J
authors.lastname: Marchand-Brynaert
authors.forename: Christian V
authors.initials: CV
authors.lastname: Stevens
authors.forename: Wouter
authors.initials: W
authors.lastname: Herrebout