The Kinetics and Mechanism of Nucleophilic Addition of Hydrogen Cyanide to $ {\alpha}$-Cyano-$ {\beta}$-piperonylacrylic Acid

$ {\alpha}$-Cyano-$ {\beta}$-Piperonylacrylic Acid에 대한 Hydrogen Cyanide의 친핵성 첨가반응에 관한 연구

  • Ki Sung Kwon (Department of Chemistry, College of Liberal Arts and Science, Chungnam National University) ;
  • Tae Rin Kim (Department of Chemistry, College of Liberal Arts and Science, Chungnam National University)
  • 권기성 (충남대학교 문리과대학 화학과) ;
  • 김태린 (충남대학교 문리과대학 화학과)
  • Published : 1974.12.30

Abstract

The rate constant of the addition of hydrogen cyanide to $ ${\alpha}$-cyano-\beta-piperonylacrylic$ acid (CPA) were determined by UV spectrophotometry at various pH and a rate equation which can be applied over wide pH range was obtained. From this equation, one may conclude that below pH 3 the reaction is started by the addition of hydrogen cyanide molecule to CPA, however, at pH 6~8, hydrogen cyanide is added to $ {\alpha}$-cyano-$ {\beta}$-piperonyl acrylate anion. From pH 3 to 6, these two reaction are competitive. Above pH 9, the reaction is proceeded by the addition of cyanide ion to $ {\alpha}$-cyano-$ {\beta}$-piperonyl acrylate ion. From pH 3 to 9, the complex reaction mechanism can also be fully explained by the rate equation obtained.

Keywords

References

  1. The Chemistry of Alkene S. Patai;Z. Rapport
  2. J. Amer. Chem. Soc. v.83 T.I. Crowell;A.W. Francis Jr.
  3. J. Chem. Soc. no.B W.G. Devies;E.W. Hegarty;T.P. Nevell;R.H. Peter
  4. J. Chem. Soc. L. Nann;Hell
  5. J. Chem. Soc. Y. Ogata;A. Kawasaki;I. Kishi
  6. J. Amer. Chem. Soc. v.77 M.J. Kamlet
  7. J. Korean, Chem. Soc. v.17 T.R. Kim;K.I. Lee
  8. J. Amer. Chem. Soc. T. I. Crowall;T. R. Kim
  9. J. Korean Chem. Soc. v.13 T.R. Kim;Y.S. Choi
  10. J. Korean Chem. Soc. v.13 K. S. Kwon;T. R. Kim
  11. J. Chem. Soc. v.105 W.J. Jones
  12. J. Amer. Chem. Soc. v.17 T.R. Kim;T.S. Hub