Skip to main content
Log in

Crystallization of chiral compounds. 1. Spectroscopic, thermochemical, and crystallographic investigation of homochiral and racemic glycidyl p-toluenesulfonate

  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Crystalline specimens of homochiral and racemic glycidyl p-toluenesulfonate were studied by IR spectroscopy, differential scanning calorimetry, and X-ray diffraction analysis. The melting phase diagram of glycidyl p-toluenesulfonate was constructed. The stacking effect in the crystals of the racemic sulfonate is responsible for a more dense molecular packing, with the result that a heterochiral type of crystallization becomes more favorable.

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. J. Jaques, A. Collet, and S. H. Wilen, Enantiomers, Racemates, and Resolutions, Krieger Publishing Co., Malabar, FL, 1994, 447 pp.

    Google Scholar 

  2. Z. Bocskei, C. Kassai, K. Simon, E. Fogassy, and D. Kozma, J. Chem. Soc., Perkin Trans. 2, 1996, 1511.

  3. K. Kinbara, Y. Hashimoto, M. Sukegawa, H. Nohira, and K. Saigo, J. Am. Chem. Soc., 1996, 118, 3441.

    Google Scholar 

  4. S. M. Reutzel-Edens, V. A. Russell, and L. Yu, J. Chem. Soc., Perkin. Trans. 2, 2000, 913.

    Google Scholar 

  5. G. Muller and M. Lutz, Z. Naturforsch., 2001, 56B, 871.

    Google Scholar 

  6. R. G. Kostyanovsky, V. R. Kostyanovsky, G. K. Kadorkina, and K. A. Lyssenko, Mendeleev Commun., 2001, 1.

  7. C. P. Brock, W. B. Schweizer, and J. D. Dunitz, J. Am. Chem. Soc., 1991, 113, 9811.

    Google Scholar 

  8. A. Gavezzotti, Acc. Chem. Res., 1994, 27, 309.

    Google Scholar 

  9. J. Hulliger, Angew. Chem., Int. Ed. Engl., 1994, 33, 143.

    Google Scholar 

  10. S. H. Wilen, A. Collet, and J. Jacques, Tetrahedron, 1977, 33, 2725.

    Google Scholar 

  11. A. Collet, J. Jacques, and M. J. Brienne, Chem. Rev., 1980, 80, 215.

    Google Scholar 

  12. R. M. Hanson, Chem. Rev., 1991, 91, 437.

    Google Scholar 

  13. Beilst., EV, 17(1), 9.

  14. J. M. Klunder, T. Onami, and K.B. Sharpless, J. Org. Chem., 1989, 54, 1295.

    Google Scholar 

  15. Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune, and K. B. Sharpless, J. Am. Chem. Soc., 1987, 109, 5765.

    Google Scholar 

  16. N. Nakabayashi, E. Masuhara, and Y. Iwakura, Bull. Chem. Soc. Jpn., 1966, 39, 413.

    Google Scholar 

  17. A. Altomare, G. Cascarano, C. Giacovazzo, and D. Viterbo, Acta Crystallogr., Sect. A, 1991, 47, 744.

    Google Scholar 

  18. W. C. Hamilton, Acta Crystallogr., 1965, 18, 502.

    Google Scholar 

  19. L. H. Straver and A. J. Schierbeek, MolEN, Structure Determination System, Program Description, Nonius B.V., Delft, 1994, 1, 180.

    Google Scholar 

  20. A. L. Spek, Acta Crystallogr., Sect A, 1990, A46, 34.

    Google Scholar 

  21. E. L. Eliel, S. H. Wilen, and L. N. Mander, Stereochemistry of Organic Compounds, John Wiley and Sons, New York, 1994, p. 297; E. L. Eliel, S. H. Wilen, and M. P. Doyle, Basic Organic Stereochemistry, Wiley-Interscience, New York, 2001, p. 197.

    Google Scholar 

  22. C. P. Brock and J. D. Dunitz, Chem. Mater., 1994, 6, 1118.

    Google Scholar 

  23. A. I. Kitaigorodsky, Molecular Crystals and Molecules, Academic Press, New York-London, 1973.

    Google Scholar 

  24. M. C. Etter, Acc. Chem. Res., 1990, 23, 120.

    Google Scholar 

  25. J. Bernstein, R. E. Davis, L. Simoni, and N. L. Chang, Angew. Chem., Int. Ed. Engl., 1995, 34, 1555.

    Google Scholar 

  26. T. Dahl, Acta Chem. Scand., 1994, 48, 95.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bredikhin, A.A., Lazarev, S.N., Bredikhina, Z.A. et al. Crystallization of chiral compounds. 1. Spectroscopic, thermochemical, and crystallographic investigation of homochiral and racemic glycidyl p-toluenesulfonate. Russian Chemical Bulletin 52, 846–852 (2003). https://doi.org/10.1023/A:1024483822350

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1024483822350

Navigation