Electrochemical Oxidation of Iminobibenzyl and Related Compounds

Abstract

Electrochemical oxidation of iminobibenzyl and several related compounds has been investigated in acetonitrile. The mechanism of the oxidation is best described by an ECE process with coupling of the product of an initial oneelectron oxidation in a subsequent but very fast reaction to form a dimeric compound that is further oxidized by an overall two-electron process at potentials more negative than those required for oxidation of the parent compounds. The electrochemistry of these compounds is complicated by the release of protons during the oxidation which protonate the starting materials and the neutral dimerized products rendering them electrochemically inactive. Differences in the electrochemistries of the various coupled products are discussed in terms of structural variations. * Electrochemical Society Active Member.

Use of Graphite Polyurethane Composite Electrode for Imipramine Oxidation—Mechanism Proposal and Electroanalytical Determination

“…Only a few studies in the literature have mentioned the oxidation reaction mechanism of the imipramine molecule (Frank et al 1975;Ivandini et al 2002), which encouraged us to do a more complete work by knowing the substantial importance of this kind of molecule in medicine and in pharmaceutical areas. Many analytical methods for quantitative determination of imipramine in commercial formulations have been reported using potentiometry, spectrophotometry, and atomic absorption spectrometry (Elnemma et al 1993), voltammetry with a polymer-modified carbon paste electrode (Biryol et al 1996) and electrogenerated chemiluminescence (Greenway and Dolman 1999).…”

Determination of Trimipramine and Metabolites in Plasma by Liquid Chromatography with Electrochemical Detection

“…This profile, not surprisingly, resembles that of imipramine and its major analogous metabolites (4). Proposed mechanisms for the electrochemical oxidation of these compounds have been presented (5)(6)(7). The electrochemical oxidation profile for mianserin has been reported with the optimum being -+1.1 V uersus the silver-silver chloride reference electrode (8).…”

“…-A chromaiogram of a spiked I -mL plasma extract coniaining 25 ng each of 111 and IV ( 2 and I ) and 50 ng each ofI, 11, and V ( 5 , 4 , and 6). Actual patient samples showed liitle or no V(6).Mianserin 13) is the internal standard.…”

Determination of Mianserin and Metabolites in Plasma by Liquid Chromatography with Electrochemical Detection

“…Similar current-potential curves were observed with imipramine, desmethylimipramine, and their 2-hydroxy metabolites under similar experimental conditions (2). A mechanism of electrochemical oxidation of imipramine and chemically related dibenzazepines was recently described by a two-step three-electron ECE processz1 (9). Mianserin and its metabolites, which contain the dibenzazepine nucleus, may undergo similar mechanisms.…”