Haloacetamides and halophenylacetamides are an important class of compounds often utilized for the synthesis of pharmaceuticals and agrochemicals. In this work, electrochemical analysis of 2-iodo- and 2-bromo-N-phenylacetamide was conducted for better understanding of this class of compounds. Mechanisms have been proposed for the reduction of the aforementioned molecules at carbon cathodes in dimethylformamide; the reactions of these model compounds can aid in our understanding more complex pollutants. One such pollutant is acetochlor, or 2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methylphenyl)acetamide, a chlorophenylacetamide-type herbicide that, since its registration in 1994, has become commonly used in the United States. Preliminary investigation of the electrochemical behavior of acetochlor at carbon and silver cathodes has been conducted; reduction of acetochlor at silver occurs at more positive potentials than at carbon and affords primarily the dechlorinated parent compound. Cyclic voltammetry was used to evaluate the electrochemical behavior of each analyte; controlled-potential (bulk) electrolysis coupled with traditional analytical methods such as gas chromatography–mass spectrometry (GC–MS) led to the identification and quantitation of reduction products.
Moreover, efforts have been made towards covalent modification of a carbon electrode via electrochemical methods. Given that surfaces have an important role in many chemical processes, we are working towards better understanding the electrochemical grafting process for the development of a covalently modified electrode. Initial attempts include electrochemical grafting experiments of perfluorobutyl iodide, a simple haloalkane, as well as several acetamide-type compounds (more complex molecules). X-ray photoelectron spectroscopy (XPS) was used as an ex situ technique for surface analysis of the electrodes.