Skip to main content
Log in

Desymmetrization and degree of chirality

  • Published:
Journal of Mathematical Chemistry Aims and scope Submit manuscript

Abstract

Chiral objects, viewed as distorted derivatives of achiral ones, may be represented by points in a configuration space that is spanned by a set of symmetry coordinates derived for the symmetry group of the achiral object of highest symmetry. We propose a measure (d) that quantifies the displacement of the representative point for a chiral object away from thenearest point representing an achiral object in such a multi-dimensional configuration space. If the symmetry coordinates are chosen so as to yield a similarity invariant measure, then the valuesd; obtained for a series ofi chiral objects can serve as a basis for comparing the degrees of chirality of these objects. The chirality of triangles inE 2 is studied by this method, and it is shown that the most chiral triangle in terms of this measure corresponds to one that is infinitely flat, and that may be approached but is never attained. This result is compared to others obtained previously for the same system by the use of different measures of chirality.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. WT. Kelvin,Baltimore Lectures on Molecular Dynamics and the Wave Theory of Light (C.J. Clay, London, 1941 p. 619.

    Google Scholar 

  2. A.I. Kitaigorodskii,Organic Chemical Crystallography (Consultants Bureau, New York, 1961), p. 230.

    Google Scholar 

  3. G. Gilat and L.S. Schulman, Chem. Phys. Lett. 121 (1985)13;

    Google Scholar 

  4. G. Gilat, J. Phys. A22 (1989)L545;

    Google Scholar 

  5. G. Gilat, Foundat. Phys. Lett. 3 (1990)189.

    Google Scholar 

  6. V.E. Kuzmin and I.B. Stelmakh, Zh. Strukt. Khim. 28 (1987)45, 50;

    Google Scholar 

  7. V.E. Kuzmin and I.B. Stelmakh, Dokl. Akad. Nauk SSSR 307 (1989)150;

    Google Scholar 

  8. L.A. Kutulya, V.E. Kuzmin, I.B. Stelmakh, I.B. Nemchenok and T.V. Khandrimailova, Zh. Obshch. Khim. 60 (1990)737.

    Google Scholar 

  9. F.M. Jaeger,Lectures on the Principle of Symmetry and Its Applications in All Natural Sciences (Elsevier, Amsterdam, 1917), ch. 2.

    Google Scholar 

  10. K. Mislow and J. Siegel, J. Amer. Chem. Soc. 106 (1984)3319;

    Google Scholar 

  11. [6](b) See also: E.A. Halevi, J. Chem. Res. (S)(1985)206; S. Fujita, J. Amer. Chem. Soc. 112(1990)3390.

  12. P. Murray-Rust, H.B. Bürgi and J.D. Dunitz, Acta Cryst. B34 (1978)1787.

    Google Scholar 

  13. P. Murray-Rust, H.B. Bürgi and J.D. Dunitz, Acta Cryst. A35 (1979)703.

    Google Scholar 

  14. R.S. McDowell, J, Mol. Spectrosc. 17 (1965)365.

    Google Scholar 

  15. A.B. Buda and K. Mislow, J. Mol. Struct. (THEOCHEM), in press.

  16. J.P. Glusker and K.N. Trueblood,Crystal Structure Analysis: A Primer, 2nd ed. (Oxford University Prey, New York, 1985), 225.

    Google Scholar 

  17. A.B. Buda and K. Mislow, Elem. Math., in press.

  18. A.B. Buda, T.P.E. Auf der Heyde and K. Mislow, J. Math. Chem., preceding paper.

  19. F.A. Cotton,Chemical Applications of Group Theory, 2nd ed. (Whey -Interscience, New York, 1971).

    Google Scholar 

  20. S.F.A. Kettle,Symmetry and Structure Whey, New York, 1985).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

On leave from the Department of Chemistry, University of the Western Cape, Bellville 7530, South Africa.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Auf der heyde, T.P.E., Buda, A.B. & Mislow, K. Desymmetrization and degree of chirality. J Math Chem 6, 255–265 (1991). https://doi.org/10.1007/BF01192584

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01192584

Keywords

Navigation