Skip to main content
SpringerLink
Log in

Crystal structure of 2-{(R)-1-hydroxy-1-[(2S)-1-tritylaziridin-2-yl] methyl}acrylate and spectroscopic properties of the (R,S) and (S,S) stereoisomers

  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

The crystal and molecular structure of 2-{(R)-1-Hydroxy-1-[(2S)-1-tritylaziridin-2-y1] methy1}acrylate is described. Crystal data: C26H25NO3, orthorhombic, space group P212121, a = 9.6954(5), b = 13.1458(5), c = 16.7885(7) Å, V = 2139.8(2) Å3, Z = 4. The (R,S) diastereomer shows an intramolecular hydrogen bonding N···H—O under formation of a five-membered ring with N···O distance of 2.664 Å. IR, 1H NMR and 13C NMR data are discussed. The 1H NMR of the (R,S) diastereomer shows a singlet- whereas the (S,S) diastereomer exhibits a doublet-pattern for the hydroxyl proton.

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. Hwang, G.-II; Chung, J.-H; Lee, W.K. J. Org. Chem. 1996, 61, 6183.

    Google Scholar 

  2. Ohno, H.; Mimura; N; Otaka, A.; Tamamura, H; Fujii, N.; Ibuka, T. Tetrahedron 1997, 53, 12933.

    Google Scholar 

  3. Tamamura, H.; Yamashita, M.; Muramatsu, H.; Ohno, H.; Ibuka, T.; Otaka, A.; Fujii, N. Chem. Comm. 1997, 2327.

  4. Nayak, S.K., Thijs, L.; Zwanenburg, B. Tetrahedron Lett. 1999, 40. 981.

    Google Scholar 

  5. Nayak, S.K.; Thijs, L.; Zwanenburg, B., Synlett 1998, 11, 1187.

    Google Scholar 

  6. Gelder, R. de; Graaff, R.A.G. de; Schenk, H. CRUNCH, Acta Crystallogr. 1993, A49, 287.

    Google Scholar 

  7. Spek, A.L. PLUTON. A program for plotting molecular and crystal structures; University of Utrecht: The Netherlands; 1995.

    Google Scholar 

  8. Spek, A.L. Acta Crystallography 1990, A46, C-34.

  9. Spek, A.L. PLATON-93. Program for display and analysis of crystal and molecular structures: University of Utrecht: The Netherlands, 1995.

    Google Scholar 

  10. Becker, E.D. Encyclopedia of nuclear magnetic resonance; Editors Grant, D.M.; Harris, R.K, Eds.; —–, 1996; Vol. 4, p 2409. 1996.

  11. Emsley, J. Chem. Soc. Rev. 1980, 9, 91.

    Google Scholar 

  12. North, A.C. T.; Philips, D. C.; Mathews, F. S. Acta Crystallogr. 1968, A24, 351.

    Google Scholar 

  13. Sheldrick, G.M. SHELXL-97. Program for the refinement of crystal structures; University of Gottingen: Germany, 1997.

    Google Scholar 

  14. Johnson, C.K. ORTEP. Report ORNL-3794; Oak Ridge National Laboratory: TN, 1965.

    Google Scholar 

  15. Rader, C.P., J. Am. Chem. Soc. 1969, 91, 3248.

    Google Scholar 

  16. Jardetzky, O. Encyclopedia of Nuclear magnetic resonance; Grant, D.M.; Harris, R.K, Eds.; Publishers?; 1996; Vol. 2, p 927.

Download references

Author information

Authors and Affiliations

  1. Department of Organic Chemistry, NSR Center for Molecular Structure, Design and Synthesis, University of Nijmegen, Toernooiveld 1, 6525 ED, Nijmegen, The Netherlands

    Frans G. Moers, Sandip K. Nayak, Lambertus Thijs & Binne Zwanenburg

  2. Department of Inorganic Chemistry, NSR Center for Molecular Structure, Design and Synthesis, University of Nijmegen, Toernooiveld 1, 6525 ED, Nijmegen, The Netherlands

    René de Gelder & Jan M.M. Smits

Authors
  1. Frans G. Moers
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sandip K. Nayak
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. René de Gelder
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jan M.M. Smits
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Lambertus Thijs
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Binne Zwanenburg
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Moers, F.G., Nayak, S.K., de Gelder, R. et al. Crystal structure of 2-{(R)-1-hydroxy-1-[(2S)-1-tritylaziridin-2-yl] methyl}acrylate and spectroscopic properties of the (R,S) and (S,S) stereoisomers. Journal of Chemical Crystallography 29, 1053–1056 (1999). https://doi.org/10.1023/A:1009585119769

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1009585119769

Search

Navigation