Acta Phys. -Chim. Sin. ›› 2010, Vol. 26 ›› Issue (02): 277-282.doi: 10.3866/PKU.WHXB20100223

• ELECTROCHEMISTRY • Previous Articles     Next Articles

Electrochemical Reduction Reaction Mechanism of Cinnamonitrile

WANG Huan, ZHAO Shu-Feng, LAN Yang-Chun, LIU Xiao, LU Jia-Xing   

  1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, Shanghai 200062, P. R. China
  • Received:2009-08-20 Revised:2009-10-29 Published:2010-01-26
  • Contact: LU Jia-Xing E-mail:jxlu@chem.ecnu.edu.cn

Abstract:

The electroreduction of cinnamonitrile in MeCN solution was studied using cyclic voltammetry, with two reduction peaks at -1.46 and -2.0 V. Linear, cyclic hydrodimers, and 3-phenyl pentanedinitrile were synthesized at the first peak, while additional saturated hydro product was synthesized at the second peak. The reduction mechanism was proposed based on the experimental and cyclic voltammogram simulation results. Linear and cyclic hydrodimers were synthesized by a radical-radical (RR) route while a saturated hydro product was obtained via an electrochemical-electrochemical-chemical-chemical (EECC) process. 3-Phenyl pentanedinitrile was synthesized by the reaction of cinnamonitrile with the conjugate base of MeCN. Finally, the dynamic constants were calculated using cyclic voltammogramsimulation. Result indicated that the rate constant of the RRreaction was found to be 104 L·mol-1·s-1, and the rate constant of the second electron transfer reaction was 0.3 cm·s -1, while the rate constant of the subsequent proton reaction was 105 s-1.

Key words: Cinnamonitrile, Electroreduction, Cyclic voltammogramsimulation, Reaction mechanism

MSC2000: 

  • O646