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Information Theoretical Study of the Chirality of Enantiomers

Sara Janssens, Alex Borgoo, Christian Van Alsenoy, Patrick Bultinck UGent and Paul Geerlings (2009)
abstract
In this work [1] we probed the Kullback-Leibler information entropy as a chirality measure, as an extension of previous studies on molecular quantum similarity evaluated for different enantiomers (enantiomers possessing two asymmetric centra in [2], with a single asymmetric carbon atom in [3] and with a chiral axis in [4]). The entropy was calculated using the shape functions of the R and S enantiomers considering one as reference for the other, resulting in an information theory based expression useful for quantifying chirality. It was evaluated for 5 chiral halomethanes possessing one asymmetric carbon atom with H, F, Cl, Br and I as substituents. To demonstrate the general applicability, a study of two halogensubstituted ethanes possessing two asymmetric carbon atoms has been included as well. Avnir’s Continuous Chirality Measure (CCM) [5] has been computed and confronted with the information deficiency. By these means we quantified the dissimilarity of enantiomers and illustrated Mezey’s Holographic Electron Density Theorem in chiral systems [6]. A comparison is made with the optical rotation and with the Carbó similarity index. As an alternative chirality index, we recently also calculated the information deficiency in a way which is consistent with experiments as VCD spectroscopy and optical rotation measurements. The entropy calculates the difference in information between the shape function of one enantiomer and a normalized shape function of the racemate. Comparing the latter index with the optical rotation reveals a similar trend. [1] S. Janssens, A. Borgoo, C. Van Alsenoy, P. Geerlings, J. Phys. Chem. A 2008, 112, 10560. [2] S. Janssens, C. Van Alsenoy, P. Geerlings, J. Phys. Chem. A 2007, 111, 3143. [3] G. Boon, C. Van Alsenoy, F. De Proft, P. Bultinck, P. Geerlings, J. Phys. Chem. A 2006, 110, 5114. [4] S. Janssens, G. Boon, P. Geerlings, J. Phys. Chem. A 2006, 110, 9267. [5] H. Zabrodsky, D. Avnir, J. Am. Chem. Soc. 1995, 117, 462. [6] P.G. Mezey, Mol. Phys. 1999, 96, 169.
Please use this url to cite or link to this publication:
author
organization
year
type
conference
publication status
published
subject
keyword
Information theory
editor
Trygve Helgaker
pages
1 pages
place of publication
Oslo, Norway
conference name
Molecular Properties '09
conference location
Oslo, Norway
conference start
2009-06-18
conference end
2009-06-21
project
HPC-UGent: the central High Performance Computing infrastructure of Ghent University
language
English
UGent publication?
yes
classification
C3
copyright statement
I don't know the status of the copyright for this publication
id
764599
handle
http://hdl.handle.net/1854/LU-764599
date created
2009-10-16 18:51:47
date last changed
2013-09-17 10:49:28
@inproceedings{764599,
  abstract     = {In this work [1] we probed the Kullback-Leibler information entropy as a chirality
measure, as an extension of previous studies on molecular quantum similarity evaluated for
different enantiomers (enantiomers possessing two asymmetric centra in [2], with a single
asymmetric carbon atom in [3] and with a chiral axis in [4]). The entropy was calculated using
the shape functions of the R and S enantiomers considering one as reference for the other,
resulting in an information theory based expression useful for quantifying chirality. It was
evaluated for 5 chiral halomethanes possessing one asymmetric carbon atom with H, F, Cl, Br
and I as substituents. To demonstrate the general applicability, a study of two halogensubstituted
ethanes possessing two asymmetric carbon atoms has been included as well.
Avnir{\textquoteright}s Continuous Chirality Measure (CCM) [5] has been computed and confronted with the
information deficiency. By these means we quantified the dissimilarity of enantiomers and
illustrated Mezey{\textquoteright}s Holographic Electron Density Theorem in chiral systems [6]. A
comparison is made with the optical rotation and with the Carb{\'o} similarity index.
As an alternative chirality index, we recently also calculated the information
deficiency in a way which is consistent with experiments as VCD spectroscopy and optical
rotation measurements. The entropy calculates the difference in information between the
shape function of one enantiomer and a normalized shape function of the racemate.
Comparing the latter index with the optical rotation reveals a similar trend.
[1] S. Janssens, A. Borgoo, C. Van Alsenoy, P. Geerlings, J. Phys. Chem. A 2008, 112,
10560.
[2] S. Janssens, C. Van Alsenoy, P. Geerlings, J. Phys. Chem. A 2007, 111, 3143.
[3] G. Boon, C. Van Alsenoy, F. De Proft, P. Bultinck, P. Geerlings, J. Phys. Chem. A
2006, 110, 5114.
[4] S. Janssens, G. Boon, P. Geerlings, J. Phys. Chem. A 2006, 110, 9267.
[5] H. Zabrodsky, D. Avnir, J. Am. Chem. Soc. 1995, 117, 462.
[6] P.G. Mezey, Mol. Phys. 1999, 96, 169.},
  author       = {Janssens, Sara and Borgoo, Alex and Van Alsenoy, Christian and Bultinck, Patrick and Geerlings, Paul},
  editor       = {Helgaker, Trygve},
  keyword      = {Information theory},
  language     = {eng},
  location     = {Oslo, Norway},
  pages        = {1},
  title        = {Information Theoretical Study of the Chirality of Enantiomers},
  year         = {2009},
}

Chicago
Janssens, Sara, Alex Borgoo, Christian Van Alsenoy, Patrick Bultinck, and Paul Geerlings. 2009. “Information Theoretical Study of the Chirality of Enantiomers.” In , ed. Trygve Helgaker. Oslo, Norway.
APA
Janssens, Sara, Borgoo, A., Van Alsenoy, C., Bultinck, P., & Geerlings, P. (2009). Information Theoretical Study of the Chirality of Enantiomers. In T. Helgaker (Ed.), . Presented at the Molecular Properties  ’09, Oslo, Norway.
Vancouver
1.
Janssens S, Borgoo A, Van Alsenoy C, Bultinck P, Geerlings P. Information Theoretical Study of the Chirality of Enantiomers. In: Helgaker T, editor. Oslo, Norway; 2009.
MLA
Janssens, Sara, Alex Borgoo, Christian Van Alsenoy, et al. “Information Theoretical Study of the Chirality of Enantiomers.” Ed. Trygve Helgaker. Oslo, Norway, 2009. Print.