Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Studies on the Linear Free Energy Relationship in Methyl Cinnamates by $^1$H-NMR Spectrometry

  • Shim, Sang-Chul (Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Park, Joon-Won (Department of Chemistry, Korea Advanced Institute of Science and Technology)
  • Published : 1981.03.30
Download PDF
⟨ Previous Next ⟩

Abstract

Chemical shift values of ${\alpha}$-proton of trans- and cis-methyl cinnamates are well correlated with ${\sigma}({\sigma}_1,\; {{\sigma}_R}^{\alpha})$, and (F, R) (r=0.999-0.879). It is observed that (1) the degree of variation of ${\delta}H_{\alpha}$ value by varying the substituents in trans-cinnamates is similar to that of cis-cinnamates $({\rho}_{trans}=0.296,\;{\rho}_{cis}=0.2840, (2) resonance contribution is larger in the trans-cinnamates than that in the cis-cinnamates, but inductive contribution is reversed, (3) for m-substitued derivatives, resonance contribution is very small compared to that for p-substituted derivatives.

Keywords

References

  1. J. Amer. Chem. Soc. v.85 K. L. Williamson
  2. J. Org. Chem. v.31 S. H. Marcus;W. F. Reynolds;S. I. Miller
  3. J. Amer. Chem. Soc. v.83 S. Reddy;J. H. Goldstein;L. Mandell
  4. J. Amer. Chem. Soc. v.85 R. W. Taft;E. Price;J. R. Fox;I. C. Lewis;K. K. Anderson;G. T. Davis
  5. J. Chem. Phys. v.35 H. Spieseke;W. G. Schneider
  6. J. Chem. Phys. v.37 J. I. Musher
  7. The Chemist's Companion A. J. Gordon;R. A. Ford
  8. J. Amer. Chem. Soc. v.69 C. Walling;K. B. Wolfstirn
  9. A Textbook of Practical Organic Chemistry (3rd Ed.) A. I. Vogel
  10. J. Amer. Chem. Soc. v.98 S. G. Williams;F. E. Norrington
  11. Progr. Phys. Org. Chem. v.6 P. R. Wells;S. Ehrenson;R. W. Taft
  12. Physical Organic Chemistry (2nd Ed.) L. P. Hammett
  13. J. Chem. Soc. A. R. Katritzky;F. J. Swinbourne
  14. Helv. Chim. Acta. v.50 F. W. Wehrli;E. Pretsch;W. Simon
  15. J. Amer. Chem. Soc. v.89 T. A. Wittstruck;E. N. Trachtenberg