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International Journal of Spectroscopy
Volume 2011, Article ID 905045, 11 pages
http://dx.doi.org/10.1155/2011/905045
Research Article

Conformational Analysis in Solution of a Chiral Bisoxazoline Molecule: Vibrational Circular Dichroism Spectroscopy and Density Functional Theory Study

1Faculté Polydisciplinaire de Safi, Université Cadi Ayyad, 46000 Safi, Morocco
2Department of Chemistry, University of Southern California, Los Angeles, CA 90089-0482, USA

Received 26 July 2011; Accepted 30 August 2011

Academic Editor: Jean-Valère Naubron

Copyright © 2011 A. Aamouche and P. J. Stephens. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

The conformations of the chiral bisoxazoline: 2,2′-methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole] (also named IndaBOX), have been studied. Density functional theory (DFT) calculations identify four inequivalent stable conformations. Two, I and II have, C2 symmetry; two, III and IV, have C1 symmetry. The electronic energies of I–IV are ordered: . The span in energy is <1.0 kcal/mole. Vibrational unpolarised absorption and circular dichroism spectra have been predicted for the four conformations using DFT. Comparison of population-weighted spectra to experimental spectra of CHCl3 and CDCl3 solutions in mid-IR region strongly supports the DFT predictions of the number, structures, and relative energies of the conformations of IndaBOX. This shows that DFT predicts spectra with a high degree of reliability. We will undoubtedly illustrate the advantage added by vibrational circular dichroism spectroscopy in conformational analysis and in the absolute configuration determination.