Kinetik und Mechanismus der Anodischen Anilin-Oxydation

Dunsch, Lothar

doi:10.1016/s0022-0728(75)80138-0

Cited by 49 publications

(14 citation statements)

References 34 publications

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“…(see for example refs. [8–14, 52–59]). These processes may pass through different intermediates among which the radical cation of aniline (PhNH 2 +• ) is possible [8–14, 52–57].…”

Section: Relative Stabilitiesmentioning

confidence: 99%

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Consequence of one-electron oxidation and one-electron reduction for aniline

2011

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Quantum-chemical calculations were performed for all possible isomers of neutral aniline and its redox forms, and intramolecular proton-transfer (prototropy) accompanied by π-electron delocalization was analyzed. One-electron oxidation (PhNH2 – e → [PhNH2]+•) has no important effect on tautomeric preferences. The enamine tautomer is preferred for oxidized aniline similarly as for the neutral molecule. Dramatical changes take place when proceeding from neutral to reduced aniline. One-electron reduction (PhNH2 + e → [PhNH2]-•) favors the imine tautomer. Independently on the state of oxidation, π- and n-electrons are more delocalized for the enamine than imine tautomers. The change of the tautomeric preferences for reduced aniline may partially explain the origin of the CH tautomers for reduced nucleobases (cytosine, adenine, and guanine).

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“…(see for example refs. [8–14, 52–59]). These processes may pass through different intermediates among which the radical cation of aniline (PhNH 2 +• ) is possible [8–14, 52–57].…”

Section: Relative Stabilitiesmentioning

confidence: 99%

“…[8–14, 52–59]). These processes may pass through different intermediates among which the radical cation of aniline (PhNH 2 +• ) is possible [8–14, 52–57]. Oxidation of aniline by oxygen from air, catalyzed by sunlight or UV light, is also a very complex process [13, 60–62].…”

Section: Relative Stabilitiesmentioning

confidence: 99%

Consequence of one-electron oxidation and one-electron reduction for aniline

2011

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“…[1][2][3][4][5] The conducting polymers formed are of great interest in the fields of electronic or electrochromic devices, electronic displays, [4,5] and in corrosion protection. [6] The polymerization of aniline passes through different intermediates.…”

Section: Introductionmentioning

confidence: 99%

“…An in situ ESR-UV/Vis/near-infrared (NIR) spectroelectrochemical study has permitted their detection and attribution. [1] Besides the extensively described anilines, the oxidation of aromatic diamines has also been widely studied. [7][8][9][10][11][12] While there are numerous voltammetric studies available, only a few UV/Vis spectroscopic studies of chemical p-phenylenediamine oxidation have been published.…”

Section: Introductionmentioning

confidence: 99%

The Reaction Mechanism of p‐Toluenediamine Anodic Oxidation: An In Situ ESR‐UV/Vis/NIR Spectroelectrochemical Study

2007

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In situ ESR-UV/Vis spectroelectrochemistry is applied to obtain new insights into the intermediates and reaction products of the anodic oxidation of p-toluenediamine in aqueous solution at different pH values. A strong pH dependence of the stability of the cation radical is found. While the absence of a stable radical was proved by ESR spectroscopy at pH 2 and 10, this radical is detected at medium pH values and assigned to the semiquinonediimine structure. The UV/Vis absorption of the radical is observed at these pH values as well. The p-toluenediimine intermediate and the trimeric reaction product were followed during the electrode reaction by UV/Vis spectroscopy at all pH values.

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“…The electrochemical oxidation of conducting polymers induces three different redox states. Starting from the reduced state A, most of the conducting polymers are oxidized in the first wave into different oxidation states B and C. The first state B is characterized by an unpaired delocalized spin, which was shown for a lot of different conducting polymers by in situ ESR spectroscopy. − It is nowadays described as the polaronic state B. The other redox state C gives no ESR signal.…”

Section: Introductionmentioning

confidence: 99%

Separation of the Ultraviolet−Visible Spectra of the Redox States of Conducting Polymers by Simultaneous Use of Electron-Spin Resonance and Ultraviolet−Visible Spectroscopy

Neudeck¹,

Petr²,

Dunsch³

1999

J. Phys. Chem. B

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The electrochemical oxidation of polyaniline (PAni) films on gold electrodes is studied by simultaneous electron spin resonance (ESR) and UV−vis spectroelectrochemistry. The technique permits the separation of the superimposed UV−vis spectra of three redox states: the protonated reduced polyaniline chains, the deprotonated polaronic state, and the bipolaronic state. The separated UV−vis spectra as well as the potential dependence of each redox state concentration enables a more precise determination of the energy levels and the stability of paramagnetic species.

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Kinetik und Mechanismus der Anodischen Anilin-Oxydation

Cited by 49 publications

References 34 publications

Consequence of one-electron oxidation and one-electron reduction for aniline

Consequence of one-electron oxidation and one-electron reduction for aniline

The Reaction Mechanism of p‐Toluenediamine Anodic Oxidation: An In Situ ESR‐UV/Vis/NIR Spectroelectrochemical Study

Separation of the Ultraviolet−Visible Spectra of the Redox States of Conducting Polymers by Simultaneous Use of Electron-Spin Resonance and Ultraviolet−Visible Spectroscopy

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