Non-planar structures of Et3N and Pri3N: a contradiction between the X-ray, and NMR and electron diffraction data for Pri3N

(Note: The full text of this document is currently only available in the PDF Version )

Roland Boese, Dieter Bläser, Mikhail Y. Antipin, Roland Boese, Mikhail Y. Antipin, Vladimir Chaplinski and Armin de Meijere


Abstract

The crystal structures of Et3N and Pri3N were determined by X-ray analysis using the in situ crystallization technique for single crystal growth on the diffractometer; both have a pyramidal configuration of the nitrogen atom, even Pri3N, which was considered to be planar in accord with electron diffraction and NMR data.


References

  1. Review: C. H. Bushweller, in Acyclic Organonitrogen Stereodynamics, ed. J. B. Lambert and Y. Takeuchi, VCH, New York, 1992 Search PubMed .
  2. J. E. Anderson, D. Casarini and L. Lunazzi, J. Org. Chem., 1996, 61, 1290 CrossRef CAS .
  3. J. H. Brown and C. H. Bushweller, J. Am. Chem. Soc., 1992, 114, 8153 CrossRef CAS .
  4. J. H. Brown and C. H. Bushweller, J. Am. Chem. Soc., 1995, 117, 12 567 CrossRef CAS .
  5. J. H. Brown and C. H. Bushweller, J. Phys. Chem., 1994, 98, 11 411 CrossRef CAS .
  6. J. H. Brown and C. H. Bushweller, J. Phys. Chem., 1997, 101, 5700 Search PubMed .
  7. T. C. Wong, L. R. Colazzo and F. S. Guziec, Jr., Tetrahedron, 1995, 51, 649 CrossRef CAS .
  8. A. M. Belostotskii, P. Aped and A. Hassner, J. Mol. Struct. (THEOCHEM), 1997, 398, 427 CrossRef .
  9. (a) A. M. Halpern and R. R. Ramachandran, J. Phys. Chem., 1992, 96, 9832 CrossRef CAS ; (b) C. Kölmel, C. Ochsenfeld and R. Ahlrichs, Theor. Chim. Acta, 1991, 82, 271 .
  10. For details, see L. V. Vilkov and N. I. Sadova, in Stereochemical Applications of Gas-Phase Electron Diffraction, Part 2, ed. I. Hargittai and M. Hargittai, VCHWeinheim, 1988, pp. 35–92 Search PubMed .
  11. A. J. Blake, E. A. V. Ebsworth and A. J. Welch, Acta Crystallogr., Sect. C., 1984, 40, 413 CrossRef .
  12. H. Bürger, H. Niepel, G. Pawelke and H. Oberhammer, J. Mol. Struct., 1979, 54, 159 CrossRef .
  13. H. Takeuchi, T. Kojima, T. Egawa and S. Konaka, J. Phys. Chem., 1992, 96, 4389 CrossRef CAS .
  14. A. Dimitrov, H.-G. Mack, S. Rüdiger, K. Seppelt and H. Oberhammer, J. Phys. Chem., 1994, 98, 11 401 CrossRef CAS .
  15. M. Gaensslen, U. Gross, H. Oberhammer and S. Rüdiger, Angew. Chem., 1994, 104, 1525 ; Angew. Chem., Int. Ed. Engl., 1992, 31, 1467 Search PubMed .
  16. H. Bock, I. Göbel, Z. Havlas, S. Liedle and H. Oberhammer, Angew. Chem., 1991, 103, 193 CAS ; Angew. Chem., Int. Ed. Engl., 1991, 30, 187 Search PubMed .
  17. J. D. Dunitz and P. Seiler, Acta Crystallogr., Sect. B, 1973, 29, 589 CrossRef CAS .
  18. R. Boese, N. Niederprüm, D. Bläser, A. Maulitz, M. Antipin and P. Mallinson, J. Phys. Chem. B, 1997, 101, 5794 CrossRef CAS .
  19. The sample was prepared according to the procedure described by F. Kuffner and W. Koechlin, Monatsh. Chem., 1962, 93, 476 Search PubMed  , with an overall yield of 17%; using MeMgBr instead of MeMgCl increases the yield in the last step from 45 to 89%.
  20. A. de Meijere, V. Chaplinski, P. Rademacher, R. Boese, T. Haumann, P. v. R. Schleyer, T. Zywietz, H. Jiao, P. Merstetter and F. Gerson, Angew. Chem., 1998, submitted for publication Search PubMed .
  21. R. Boese and M. Nussbaumer, Organic Crystal Chemistry, ed. D. W. Jones, Oxford University Press, Oxford, England, 1994, p. 20 Search PubMed .
Click here to see how this site uses Cookies. View our privacy policy here.