Issue 24, 2012
From the journal:

Physical Chemistry Chemical Physics

Vibrational Circular Dichroismversus Optical Rotation Dispersion and Electronic Circular Dichroism for diastereomers: the stereochemistry of 3-(1′-hydroxyethyl)-1-(3′-phenylpropanoyl)-azetidin-2-one†

Ewoud De Gussem,abc   Patrick Bultinck,*bc   Marion Feledziak,d   Jacqueline Marchand-Brynaert,d   Christian V. Stevense  and  Wouter Herreboutab  

* Corresponding authors

a Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, B-2020 Antwerp, Belgium

b European Centre for Chirality, EC2, Groenenborgerlaan 171, B-2020 Antwerp, Belgium
E-mail: www.chiralitycentre.eu

c Department of Inorganic and Physical Chemistry, Ghent University, Krijgslaan 281-S3, B-9000 Ghent, Belgium
E-mail: Patrick.Bultinck@ugent.be

d Institute of Condensed Matter and Nanosciences, Université Catholique de Louvain, Bt. Lavoisier L4.01.02, 1 Place L. Pasteur, B-1348 Louvain-la-Neuve, Belgium

e SynBioC, Department of Sustainable Organic Chemistry and Technology, Ghent University, Faculty of Bioscience Engineering, Coupure Links 653, B-9000 Ghent, Belgium

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.

Graphical abstract: 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

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Article information

DOI
https://doi.org/10.1039/C2CP40617A
Article type
Paper
Submitted
27 Feb 2012
Accepted
19 Apr 2012
First published
23 Apr 2012

Phys. Chem. Chem. Phys., 2012,14, 8562-8571

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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

E. D. Gussem, P. Bultinck, M. Feledziak, J. Marchand-Brynaert, C. V. Stevens and W. Herrebout, Phys. Chem. Chem. Phys., 2012, 14, 8562 DOI: 10.1039/C2CP40617A

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