Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Kinetic Studies on the Addition of Potassium Cyanide to α,N-Diphenylnitrone

  • Published : 1999.06.20
Download PDF
⟨ Previous Next ⟩

Abstract

The rate constants for the nucleophilic addition of potassium cyanide to α,N-diphenylnitrone and its derivatives (p-OCH3, p-CH3, p-Cl, and p-NO2) were determined by ultraviolet spectrophotometer at 25℃, and the rate equations which can be applied over a wide pH range were obtained. On the basis of pH-rate profile, adduct analysis, general base catalysis and substituent effect, a plausible mechanism of this addition reaction was proposed: At high pH, the cyanide ion to carbon-nitrogen double bond was rate controlling, however, in acidic media, the reaction proceeded by the addition of hydrogen cyanide molecule to carbon-nitrogen double bond after protonation at oxygen of a,N-diphenylnitrone. In the range of neutral pH, these two reactions occured competitively.

Keywords

References

  1. Catalysis in Chemistry and Enzymolgy Jencks, W. P.
  2. The Chemistry of Alkene Patai, S.;Rapport, Z.
  3. The Chemistry of Carbon-Nitrogen Double Bond Sandrfy, S.
  4. J. Am. Chem. Soc. v.110 Bernasconi, C. F.;Killion, R. B. Jr.
  5. J. Am. Chem. Soc. v.112 Bernasconi, C. F.;Fassberg, J.;Killion, R. B., Jr.;Rapport, Z.
  6. J. Org. Chem. v.57 Bernasconi, C. F.;Schuck, D. F.
  7. J. Org. Chem. v.59 Bernasconi, C. F.;Renfrow, R. A.
  8. Chem. Rev. v.77 Albert, P.
  9. Quat. Rev. v.19 no.4 Delpierre, G. R.;Lamchem, M.
  10. J. Chem. Soc. Perkin Trans. v.15 Masui, M.;Suda, K.;amauchi, M.
  11. J. Chem. Soc. Boyland, E.;Nery, R.
  12. J. Chem. Soc. Perkin Trans. Ohmori, H.;Ueda, C.
  13. Tetrahedron Lett. v.31 Clark, N. G.;Carokill, E.
  14. J. Chem. Soc. Perkin Trans. Ogata, Y.;Kswashi, A.
  15. Chem. Comm. Masui, M.;Yamauchi, M.;Yijima, C.;Suda, K.;Yoshida, K.
  16. Chem. Rev. v.23 Smith, L. I.
  17. Gazz. Chim. Ital. v.70 Bellavita, V.
  18. Comprehensive Organic Chemistry Barton, D.;Dovllis, W. D.
  19. Bull. Korean Chem. Soc. v.12 Kim, T. R.;Lee, K. I.
  20. J. Am. Chem. Soc. v.87 Wheeler, O. H.;Gore, P. H.