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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

(2012) PHYSICAL CHEMISTRY CHEMICAL PHYSICS. 14(24). p.8562-8571
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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.
Keywords
FORCE-FIELDS, DFT, SPECTRA, ABSOLUTE-CONFIGURATION, DENSITY-FUNCTIONAL THEORY, VCD, SPECTROSCOPY, ELUCIDATION, INTENSITIES, DEPENDENCE

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Citation

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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.
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.
Chicago author-date
De Gussem, Ewoud, Patrick Bultinck, Marion Feledziak, Jacqueline Marchand-Brynaert, Christian 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.
Chicago author-date (all authors)
De Gussem, Ewoud, Patrick Bultinck, Marion Feledziak, Jacqueline Marchand-Brynaert, Christian 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.
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.
IEEE
[1]
E. De Gussem, P. Bultinck, M. Feledziak, J. Marchand-Brynaert, C. Stevens, and W. Herrebout, “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, vol. 14, no. 24, pp. 8562–8571, 2012.
@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, Christian and Herrebout, Wouter},
  issn         = {1463-9076},
  journal      = {PHYSICAL CHEMISTRY CHEMICAL PHYSICS},
  keywords     = {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},
}

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