Structural investigations of C-nitrosobenzenes. Part 1. Solution state 1H NMR studies

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

Daniel A. Fletcher, Brian G. Gowenlock and Keith G. Orrell


Abstract

Ambient and low temperature 1H NMR spectra of a wide range of 3- and 4-monosubstituted, and some di- and tri-substituted C-nitrosobenzenes have enabled –N[double bond, length half m-dash]O substituent constants for the static and rotating ring molecules to be calculated. This has provided information on the shielding anisotropy of the N[double bond, length half m-dash]O group which in turn leads to the firm identification of the monomeric and dimeric solution species. In all cases lowering the solution temperature enhances the relative populations of dimers to monomers, with the (Z)-azodioxy dimer being preferred over the (E)-form, irrespective of the nature of the solid state dimeric structure.


References

  1. W. Lüttke, Z. Elektrochem., 1957, 61, 302 Search PubMed.
  2. W. Lüttke, Z. Elektrochem., 1957, 61, 976 Search PubMed.
  3. K. G. Orrell, V. Šik and D. Stephenson, Magn. Reson. Chem., 1987, 25, 1007 CAS.
  4. K. G. Orrell, D. Stephenson and T. Rault, Magn. Reson. Chem., 1989, 27, 368 CAS.
  5. K. G. Orrell, D. Stephenson and J. H. Verlaque, J. Chem. Soc., Perkin Trans. 2, 1990, 1297 RSC.
  6. D. A. Fletcher, B. G. Gowenlock, K. G. Orrell, V. Šik, D. E. Hibbs and M. B. Hursthouse, J. Chem. Soc., Perkin Trans. 2, 1996, 191 RSC.
  7. W. J. Mijs, Ph.D. Thesis, University of Leiden, 1959.
  8. K. Nakamoto and R. E. Rundle, J. Am. Chem. Soc., 1958, 78, 1113.
  9. D. A. Dieterich, Ph.D. Thesis, University of Illinois, 1973.
  10. C. Darwin and D. C. Hodgkin, Nature, 1950, 166, 827 CAS.
  11. F. M. Miao and C. K. Prout, unpublished work cited in F. M. Miao, D. Chantry, T. Harper and D. C. Hodgkin, Acta Crystallogr., Sect. B 1982323152 Search PubMed.
  12. F. Bosch and J. K. Kochi, J. Org. Chem., 1994, 59, 5573 CrossRef CAS.
  13. H. J. Talberg, Acta Chem. Scand., Ser. A, 1979, 33, 289.
  14. D. A. Fletcher, Ph.D. Thesis, University of Exeter, 1996.
  15. H. J. Talberg, Acta Chem. Scand., Ser. A, 1978, 32, 401.
  16. H. J. Talberg, Acta Chem. Scand., Ser. A, 1977, 31, 485.
  17. G. Binsch and D. A. Kleier, DNMR3, Program 165, Quantum Chemistry Program Exchange, Indiana University, USA, 1970.
  18. V. Šik, Ph.D. Thesis, University of Exeter, 1979.
  19. R. W. Taft, E. Price, I. R. Fox, I. C. Lewis, K. K. Anderson and G. T. Davies, J. Am. Chem. Soc., 1963, 85, 709 CrossRef CAS.
  20. R. D. Haworth and A. Lapworth, J. Chem. Soc., 1921, 119, 768 Search PubMed.
  21. R. E. Lutz and M. R. Lytton, J. Org. Chem., 1937, 2, 68 CrossRef CAS.
  22. E. Bamberger, Ber., 1895, 28, 245 Search PubMed.
  23. G. Olah, A. Parláth and I. Kuhn, Acta Chim. Sci. Hung., 1955, 7, 65 Search PubMed; see Chem. Abstr. 1956, 11 261 Search PubMed.
  24. A. Schors, A. Kraaijeveld and E. Havinga, Rec. Trav. Chim. Pay-Bas, 1955, 74, 1243 Search PubMed.
  25. E. C. Taylor, R. H. Danforth and A. McKillop, J. Org. Chem., 1973, 38, 2088 CrossRef CAS.
  26. D. A. Fletcher, B. G. Gowenlock, K. G. Orrell and V. Šik, Magn. Reson. Chem., 1995, 33, 561 CAS.
  27. I. C. Calder and P. J. Garratt, Tetrahedron, 1969, 25, 4023 CrossRef CAS.
  28. A. A. Bothner-by and S. M. Castellano, in Computer Programs for Chemistry, ed. D. F. Tar, W. A. Benjamin Inc., New York, 1968, vol. 1 Search PubMed.
  29. S. M. Castellano, Tetrahedron Lett., 1967, 5205 CrossRef CAS.
  30. D. H. Williams and I. Fleming, Spectroscopic Methods in Organic Chemistry, McGraw-Hill, London, 4th edn., 1989 Search PubMed.
  31. J. E. Anderson, V. Bru-Capdeville, P. A. Kirsch and J. S. Lomas, J. Chem. Soc., Chem. Commun., 1994, 1077 RSC.
  32. M. Azoulay and E. Fischer, J. Chem. Soc., Perkin Trans. 2, 1982, 637 RSC.
Click here to see how this site uses Cookies. View our privacy policy here.