17O NMR of benzamide derivatives: ground state torsion angle does not affect transmission of substituent effect by through-conjugation

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

Michael De Rosa


Abstract

Through-conjugation is possible in the localized excited state and transmission of the resonance effect, as measured by σ+, is not affected by ground state torsion angle.


References

  1. (a) A. L. Baumstark, P. Balakrishnan, M. Dotrong, C. J. McCloskey, M. G. Oakley and D. W. Boykin, J. Am. Chem. Soc., 1987, 109, 1059 CrossRef CAS; (b) H. Dahn, P. Péchy and V. V. Toan, Angew. Chem., Int. Ed. Engl., 1990, 29, 647 CrossRef; (c) J. Spychala and D. W. Boykin, J. Chem. Res. (S), 1993, 426 Search PubMed; (d) M. De Rosa, D. W. Boykin and A. L. Baumstark, J. Chem. Soc., Perkin Trans. 2, 1997, 1547 RSC; (e) M. De Rosa, J. Chem. Soc., Perkin Trans. 2, 1997, 1551 RSC.
  2. Y. Okamoto and H. C. Brown, J. Org. Chem., 1957, 22, 485 CrossRef CAS.
  3. (a) Y. Yukawa and Y. Tsuno, Bull. Chem. Soc. Jpn., 1959, 32, 971 CAS; (b) Y. Tsuno and M. Fujio, Chem. Soc. Rev., 1996, 25, 129 RSC.
  4. K. Nakata, M. Fujio, Y. Saeki, M. Mishima, Y. Tsuno and K. Nishimoto, J. Phys. Org. Chem., 1996, 9, 573 CrossRef CAS.
  5. M. De Rosa, K. Brown, M. McCoy, K. Ong and K. Sanford, J. Chem. Soc., Perkin Trans. 2, 1993, 1787 RSC.
  6. M. Fujio, M. Goto, M. Mishima and Y. Tsuno, Bull. Chem. Soc. Jpn., 1990, 63, 1121 CAS.
  7. S. Chimichi, C. Dell'Erba, M. Gruttadauria, R. Noto, M. Novi, G. Petrillo, F. Sancassan and D. Spinelli, J. Chem. Soc., Perkin Trans. 2, 1995, 1021 RSC.
  8. J. Shorter, in Correlation Analysis in Chemistry: Recent Advances, N. B. Chapman and J. Shorter, Eds., Plenum Press, New York, 1978, p. 138 Search PubMed.
  9. For a discussion and references on this point see ref. 1e.
  10. M. Karplus and J. A. Pople, J. Chem. Phys., 1963, 38, 2803 CrossRef CAS.
  11. H. Dahn and P.-A. Carrupt, Magn. Reson. Chem., 1997, 577 CrossRef CAS.
  12. C. J. Byrne and D. A. R. Happer, Aust. J. Chem., 1993, 46, 887 CAS.
Click here to see how this site uses Cookies. View our privacy policy here.