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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

Ewoud De Gussem UGent, Patrick Bultinck UGent, Marion Feledziak, Jacqueline Marchand-Brynaert, Chris Stevens UGent and Wouter Herrebout (2012) PHYSICAL CHEMISTRY CHEMICAL PHYSICS. 14(24). p.8562-8571
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.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
FORCE-FIELDS, DFT, SPECTRA, ABSOLUTE-CONFIGURATION, DENSITY-FUNCTIONAL THEORY, VCD, SPECTROSCOPY, ELUCIDATION, INTENSITIES, DEPENDENCE
journal title
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
Phys. Chem. Chem. Phys.
volume
14
issue
24
pages
8562 - 8571
Web of Science type
Article
Web of Science id
000304605600014
JCR category
PHYSICS, ATOMIC, MOLECULAR & CHEMICAL
JCR impact factor
3.829 (2012)
JCR rank
6/34 (2012)
JCR quartile
1 (2012)
ISSN
1463-9076
DOI
10.1039/c2cp40617a
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
2914246
handle
http://hdl.handle.net/1854/LU-2914246
date created
2012-06-21 10:57:07
date last changed
2012-06-22 17:02:11
@article{2914246,
  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.},
  author       = {De Gussem, Ewoud and Bultinck, Patrick and Feledziak, Marion and Marchand-Brynaert, Jacqueline and Stevens, Chris and Herrebout, Wouter},
  issn         = {1463-9076},
  journal      = {PHYSICAL CHEMISTRY CHEMICAL PHYSICS},
  keyword      = {FORCE-FIELDS,DFT,SPECTRA,ABSOLUTE-CONFIGURATION,DENSITY-FUNCTIONAL THEORY,VCD,SPECTROSCOPY,ELUCIDATION,INTENSITIES,DEPENDENCE},
  language     = {eng},
  number       = {24},
  pages        = {8562--8571},
  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},
  url          = {http://dx.doi.org/10.1039/c2cp40617a},
  volume       = {14},
  year         = {2012},
}

Chicago
De Gussem, Ewoud, Patrick Bultinck, Marion Feledziak, Jacqueline Marchand-Brynaert, Chris Stevens, and Wouter Herrebout. 2012. “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.” Physical Chemistry Chemical Physics 14 (24): 8562–8571.
APA
De Gussem, E., Bultinck, P., Feledziak, M., Marchand-Brynaert, J., Stevens, C., & Herrebout, W. (2012). 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. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 14(24), 8562–8571.
Vancouver
1.
De Gussem E, Bultinck P, Feledziak M, Marchand-Brynaert J, Stevens C, Herrebout W. 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. PHYSICAL CHEMISTRY CHEMICAL PHYSICS. 2012;14(24):8562–71.
MLA
De Gussem, Ewoud, Patrick Bultinck, Marion Feledziak, et al. “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.” PHYSICAL CHEMISTRY CHEMICAL PHYSICS 14.24 (2012): 8562–8571. Print.