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Circular dichroism of the benzene group vibrations and molecular stereochemistry

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Abstract

Circular dichroism (CD) in the vibrational transitions of three different series of molecules-namely, phenylcarbinols, carboxylic acids, and oxiranes-containing the benzene group is measured. It is found that a benzene-group vibration, where the hydrogen atoms in the meta and para positions vibrate in a concerted semicircular path, gives rise to CD that is consistent with the molecular stereochemistry. This observation provides a practical approach to the use of the benzene group as a probe of molecular chirality.

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References

  1. 1.

    Mason, S. F.Optical Activity and Chiral Discrimination, D. Reidel: Boston, 1979.

  2. 2.

    Holzwarth, G.; Hsu, E. C., Mosher, H. S.; Faulkner, T. R.; Moscowitz, A.J. Am. Chem. Soc. 1974,96, 251.

  3. 3.

    Barron, L. D.; Buckingham, A. D.Mol. Phys. 1971,20, 1111.

  4. 4.

    Whiffen, D. H.Philos. Trans. Roy. Soc. London Ser A. 1955,248, 131; Dwinker, J. C.; Mills, I. M.Spectrochim. Acta. 1971,27A, 2073.

  5. 5.

    Su, C. N.; Keiderling, T. A.Chem. Phys. Lett. 1981,77, 494; Barron, L. D.J. Chem. Soc. Perkin II 1977, 1790; Yasui, S. C.; Keiderling, T. A.J. Am. Chem. Soc. 1987,109, 2311.

  6. 6.

    Polavarapu, P. L. InFourier Transform Infrared Spectroscopy, Basile, L. J. and Ferraro, J. R., Eds.; Vol. 4, Academic Press: NY (1985), pp. 61–94.

  7. 7.

    Frisch, M. J.; Binkley, J. S.; Schlegel, H. B.; Raghavachari, K.; Melius, C.; Martin, R. L.; Stewart, J. J. P.; Bobrowicz, F. W.; Rohlfing, C. M.; Kahn, R. L.; Defrees, D. J.; Seeger, R.; Whiteside, R. A.; Fox, D. J.; Fleuder, E. M.; Pople, J. A.Gaussian 86, Carnegie-Mellon Quantum Chemistry Publishing Unit: Pittsburgh, PA (1986).

  8. 8.

    Amos, R. D.; Rice, J. E.CADPAC: The Cambridge Analytical Derivatives Package, Issue 4.0, Cambridge (1987).

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Correspondence to Prasad L. Polavarapu.

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Bose, P.K., Polavarapu, P.L. Circular dichroism of the benzene group vibrations and molecular stereochemistry. Struct Chem 1, 205–209 (1990). https://doi.org/10.1007/BF00674263

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Keywords

  • Hydrogen
  • Physical Chemistry
  • Benzene
  • Hydrogen Atom
  • Carboxylic Acid