Skip to main content
SpringerLink
Log in

Enantioselectivity of 6-O-alkyldimethylsilyl-2,3-di-O-methyl-β-cyclodextrins as chiral stationary phases in capillary GC

  • Originals
  • Published:
Chromatographia Aims and scope Submit manuscript

Summary

Three new 2,3-di-O-methyl-β-cyclodextrins having different 6-O-alkyldimethylsilyl groups, 6-O-isopropyldimethylsilyl-2,3-di-O-methyl-β-cyclodextrin (IPDM-β-CD), 6-O-thexyldimethylsilyl-2,3-di-O-methyl-β-cyclodextrin (TXDM-β-CD) and 6-O-cyclohexyldimethylsilyl-2,3-di-O-methyl-β-cyclodextrin (CHDM-β-CD), have been prepared and their enantioselectivities for the separation of a range of test racemic compounds in capillary gas chromatography investigated. IPDM-β-CD gave good separations of all of the test componds studied while TXDM-β-CD showed the highest enantioselectivity for the test compounds except for three nonpolar compounds. CHDM-β-CD showed very low enantioselectivity. Differences in enantioselectivities among the CD derivatives were rationalized in terms of the steric hindrance and hydrophobicity effects influencing the inclusion of the guest in the host CD derivatives.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. V. Schurig, H.-P. Nowotny, Angew. Chem. Int. Ed. Engl.29, 939 (1990).

    Article  Google Scholar 

  2. A. Dietrich, B. Maas, A. Mosandl, HRC18, 152 (1995).

    CAS  Google Scholar 

  3. V. Schurig, H.-P. Nowotny, J. Chromatogr.441, 155 (1988).

    Article  CAS  Google Scholar 

  4. D. Schmalzing, M. Jung, S. Mayer, J. Rickert, V. Schurig, HRC5, 723 (1992).

    Google Scholar 

  5. T. Takeichi, H. Toriyama, S. Shimura, Y. Takayama, HRC18, 179 (1995).

    CAS  Google Scholar 

  6. F. Kober, K. Angermund, G. Schomburg, HRC16, 299 (1993).

    Google Scholar 

  7. A. Venema, H. Henderiks, R. Geest, HRC14, 676 (1991).

    CAS  Google Scholar 

  8. S. P. van Helden, M. J. van Drooge, A. J. Claessen, A. C. A. Jansen, L. H. M. Janssen. Carbodydrate Res.215, 251 (1991).

    Article  Google Scholar 

  9. D. R. Black, C. G. Parker, S. Scott Zimmerman, M. L. Lee, J. Comput. Chem.17, 931 (1996).

    Article  CAS  Google Scholar 

  10. A. Dietrich, B. Maas, V. Karl, P. Kreis, D. Lehmann, B. Weber, A. Mosandl, HRC15, 176 (1992).

    CAS  Google Scholar 

  11. A. Dietrich, B. Maas, W. Messer, G. Bruche, V. Karl, A. Kaunzinger, A. Mosandl, HRC15, 590 (1992).

    CAS  Google Scholar 

  12. F. Kober, G. Schomburg, HRC16 693 (1993).

    Google Scholar 

  13. B. Maas, A. Dietric A. Mosandl, J. Microcol. Sep.8, 47 (1996).

    Article  CAS  Google Scholar 

  14. B. E. Kim, S. H. Lee, K. S. Park, K. P. Lee, J. H. Park, HRC,20, 208 (1997).

    CAS  Google Scholar 

  15. B. E. Kim, K. P. Lee, K. S. Park, S. H. Lee, J. H. Park, HRC, in press (1997).

  16. A. W. Coleman, Z. Ping, C. C. Ling, H. Parrotlopez, H. Galons, Carbohydrate Res.224, 307 (1992).

    Article  CAS  Google Scholar 

  17. K. Takeo, H. Mitoh, K. Uemura, Carbohydrate Res.187, 203 (1989).

    Article  CAS  Google Scholar 

  18. P. Fugeti, Carbohydrate Res.192, 366 (1989).

    Article  Google Scholar 

  19. J. Bouche, M. Verzele, J. Gas Chromatogr.6, 501 (1968).

    CAS  Google Scholar 

  20. J. S. Bradshaw, Z. Chen, G. Yi, B. E. Rossiter, A. Malik, D. Pyo, H. Yun, D. R. Black, S. Scott Zimmerman, M. L. Lee, W. Tong, V. T. D'Souza, Anal. Chem.67 (1995) 437.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Research Institute of Industrial Science and Technology, 790-330, Pohang, Korea

    B. E. Kim

  2. Department of Chemistry, Kyungpook National University, 702-701, Taegu, Korea

    K. -P. Lee, K. -S. Park & S. H. Lee

  3. Department of Chemistry, Yeungnam University, 712-749, Kyongsan, Korea

    J. H. Park

Authors
  1. B. E. Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. K. -P. Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. K. -S. Park
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. H. Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. J. H. Park
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Deceased

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kim, B.E., Lee, K.P., Park, K.S. et al. Enantioselectivity of 6-O-alkyldimethylsilyl-2,3-di-O-methyl-β-cyclodextrins as chiral stationary phases in capillary GC. Chromatographia 46, 145–150 (1997). https://doi.org/10.1007/BF02495325

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02495325

Key Words

Search

Navigation