Skip to main content
Log in

Integrated Discussion on Stereogenicity and Chirality for Restructuring Stereochemistry

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

Abstract

To discuss the difference between stereogenicity and chirality, we propose the concept of RS-stereoisomeric groups. Beginning with this concept, we have further proposed the concepts of holantimers, stereoisograms, and RS-stereogenicity. Thereby, we have clarified that the concept of RS-stereogenicity, but not conventional stereogenicity, is closely related to chirality. Thus, five RS-stereogenicity types are defined and examined to discuss the difference between stereogenicity and chirality. Combinatorial enumerations have also been studied by considering the RS-stereogenicity.

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. V. Prelog, Science 193 (1976) 17.

    Google Scholar 

  2. V. Prelog and G. Helmchen, Angew. Chem. Int. Ed. Eng. 21 (1982) 567.

    Google Scholar 

  3. K. Mislow and J. Siegel, J. Am. Chem. Soc. 106 (1984) 3319.

    Google Scholar 

  4. E. Eliel and S.H. Wilen, Stereochemistry of Organic Compounds (John Wiley & Sons, New York, 1994).

    Google Scholar 

  5. S.R. Buxton and S.M. Roberts, Guide to Organic Stereochemistry (Addison Wesley Longman, New York, 1996).

    Google Scholar 

  6. S. Fujita, J. Am. Chem. Soc. 112 (1990) 3390.

    Google Scholar 

  7. S. Fujita, J. Org. Chem. 67 (2002) 6055.

    Google Scholar 

  8. S. Fujita, Symmetry and Combinatorial Enumeration in Chemistry (Springer-Verlag, Berlin-Heidelberg, 1991).

    Google Scholar 

  9. S. Fujita, Bull. Chem. Soc. Jpn. 74 (2001) 1585.

    Google Scholar 

  10. S. Fujita, J. Math. Chem. 33 (2003) 113.

    Google Scholar 

  11. S. Fujita, Bull. Chem. Soc. Jpn. 63 (1990) 203.

    Google Scholar 

  12. S. Fujita, Tetrahedron 47 (1991) 31.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Fujita, S. Integrated Discussion on Stereogenicity and Chirality for Restructuring Stereochemistry. Journal of Mathematical Chemistry 35, 265–287 (2004). https://doi.org/10.1023/B:JOMC.0000033259.61553.25

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/B:JOMC.0000033259.61553.25

Navigation