Voltammetric studies of the reduction of cis- and trans-α-nitrostilbene

Studies of the electrochemical reduction of some dinitroaromatics

“…We earlier encountered similar behavior with cis-and trans-a-nitrostilbene [12]. The following mechanism was found to explain the results (C indicates cis and T indicates trans forms of the neutral, anion radical or dianion):…”

“…Reactions (4) and (5) are the chain-propagating reactions that result in C being converted to T. Thus, in the partial electrolysis described above, Reactions (3)-(5) cause complete isomerization with passage of only 0.5% of the charge that would have been required to reduce the compound. This very efficient isomerization speaks to the rapidity of the chain-propagating reactions and the lack of obvious termination reactions, in contrast to the reduction of the isomers of a-nitrostilbene where termination by dimerization of the anion radicals reduced the efficiency of the isomerization, 5% of the theoretical charge being required to reach equilibrium [12].…”

“…In this work we examined the electrochemical behavior of additional dinitro compounds and have discovered unusual behavior, two cases of dimerization of the anion radicals and one case of redox-catalyzed isomerization of the dinitro compound [12]. …”

Pure and mixed films of a nitrostilbene derivative at the air–water interface, Langmuir–Blodgett multilayer fabrication, and optical characterization

“…Thus, a typical push-pull stilbene, 4-amino-4 -nitrostilbene, has been recently calculated to have [23] a molecular quadratic hyperpolarizability, β, as high as 200 × 10 −30 esu. Push-pull chromophores also serve as solvation probes [24,25] and as model systems for electron transfer [26][27][28].…”

Investigation on redox mechanism of 1,4-naphthoquinone by in situ FT-IR spectroelectrochemistry

“…The electrochemical redox process, including the possible electrode reactions and proton-transfer reactions, can be depicted by the well-known nine-membered square scheme [6,16,17]. Dimerization is one of the significant organic radical reactions [18][19][20][21][22][23].…”