Synthesis of putative herbicides and effect of the substituents in its electrochemical reduction

ANYL 71

Karina Martínez-Mayorga, sasu@email.arizona.edu, Martha Aguilar-Martinez, Norma Macias, and Lino, J. Reyes Trejo. Facultad de Quimica, UNAM, Av. Universidad 3000, Mexico City, 04510, Mexico
Some amides of the cinnamic acid or their derivatives show a great variety of pharmacologic activities going from central nervous system depressors to muscular relaxants and anti-convulsive. Besides, some others have anti-fungi properties. In this work, we analyzed the influence of the structural modification in the redox properties of a series of N-(R-phenyl)-3-phenyl-2(E)-propenamides (PPA) considering different substituents at para and meta positions with electrodonor and electro-windrowing groups (see figure below). The electrochemical behavior of PPA in acetonitrile was followed using cyclic voltammetry. Elucidation of the mechanism for the electrochemical reduction of these compounds was obtained through preparative-scale electrolysis. Aimed to establish a quantitative relationship between the substituent effects with the electrochemical reduction, the correlation of the ΔEred with the Hammett constants (σx) of the different substituents, was performed. Where ΔEred is the difference of the potential reduction of the PPA with the reference compound (R=H). KMM and NM: Actual address, University of Arizona, Tucson, AZ,85721 USA.

Figure N-(R-phenyl)-3-phenyl-2(E)-propenamides (PPA)

 

General Papers
7:00 PM-9:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Division of Analytical Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006