The electrochemical reduction of fluorenone hydrazone, fluorenone fluorenylhydrazone, fluorenone azine and their benzophenone analogs in DMF

Coulometry Cyclic Voltammetry 1 Electrochemistry 1 In-situ EPR 1 Mechanism A detailed investigation on the reduction of 2-(l-naphthylhydrazono)dimedone (1-NHD) and 2-(2-naphthy1hydrazone)dimedone (2-NHD) in 0.1 M TEAI-DMSO was made using various electroanalytical techniques. Each of the two compounds gave two well-defined polarographic waves/cyclic voltammetric (CV) peaks. The first one-electron diffusion-limited wave/peak arises out of the formation of the corresponding anion radical and has been characterised to be of oxy type from in-situ EPR studies. However, the second wave/peak is attributed to an EC reaction involving a fast reverse disproportionation reaction by which the anion radical is regenerated, as confirmed from CV studies and also from the non-integral n value obtained for the second wave from microcoulometry. Macroscale CPE experiments carried out at the limiting regions of the first and second polarographic waves of 1-NHD and 2-NHD afforded the corresponding naphthylamines as the major product. Based on these results, a plausible mechanism for the electroreduction of 1-NHD and 2-NHD in DMSO has been proposed.

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Electroreduction of Substituted Naphthylhydrazones in DMSO

Vasudevan

Venkatachalam

Kalidas

1992

Ber Bunsenges Phys Chem

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Studies on the electroreduction of 4‐chloro‐1‐naphthylhydrazonodimedone (4‐Cl‐1‐NHD), 4‐sulpho‐1‐naphthylhydrazonodimedone (1‐NHD‐4‐SO3H) and 2‐hydroxy‐4‐sulpho‐1‐naphthylhydrazonodimedone (2‐OH‐1‐NHD‐4‐SO3H) have been carried out in 0.1 M TEAI‐DMSO using various electrochemical techniques. Each depolariser exhibits three polarographic dc waves, ac peaks or CV peaks, respectively, the nature of which have been discussed. Further, from the results of microcoulometry and macroscale cpe. a complex mechanism has been suggested for the electroreduction of these hydrazones. The mechanism has been supported by in‐situ EPR measurements, evaluations of the charge‐transfer rate constants and chromatographic analysis (by TLC and HPLC) on the products of macroscale cpe.

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The electrochemical reduction of fluorenone hydrazone, fluorenone fluorenylhydrazone, fluorenone azine and their benzophenone analogs in DMF

Cited by 9 publications

References 15 publications

Cathodic and Anodic Behaviour of Organic Compounds Possessing  N  N  or > N  N < Linkages

Cathodic and Anodic Behaviour of Organic Compounds Possessing  N  N  or > N  N < Linkages

Electroreduction of 1‐and 2‐naphthylhydrazonodimedones in DMSO

Electroreduction of Substituted Naphthylhydrazones in DMSO

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