Electrochemical reduction of 1,2,4,6-substituted pyridinium cations

Volke, J.; Urban, Jiřı́; Volkeová, V.

doi:10.1016/0013-4686(94)85087-9

Cited by 11 publications

(15 citation statements)

References 15 publications

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“…The same effect was observed for the reduction of 1-methylpyridinium ion in acetonitrile 26 . Volke et al 28 studied the substituted pyridinium cations by the phenyl groups in the positions 2, 4 and 6 in dimethylformamide, acetonitrile and dimethylsulfoxide solvents. An overall two electron reduction of substituted pyridinium cation was observed instead of the dimerization process.…”

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confidence: 99%

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Electrochemical reduction of dodecylpyridinium bromide in aprotic solvents: Mechanistic studies

Hromadová

Pospı́šil

Sokolová

et al. 2011

Collect. Czech. Chem. Commun.

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Reduction mechanism of 1-dodecylpyridin-1-ium bromide (DPBr) in dimethylsulfoxide has been studied on mercury electrode. Based on the classical polarographic methods as well as on the use of AC techniques it was shown that DPBr is reduced in a reversible one electron transfer step followed by dimerization of the corresponding radical species. Reduction process is accompanied by the adsorption phenomena even in the non-aqueous solvents. Possible modes of DPBr adsorption have been studied by the ex situ scanning tunnelling microscopy (STM) imaging of these molecules on highly oriented pyrolytic graphite.

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“…Only few works reported on the reduction of pyridinium cations in organic solvents [25][26][27][28] . Santhanam and Elving 25 studied the reduction properties of 1-substituted 3-nicotinamides in acetonitrile and DMSO.…”

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confidence: 99%

Electrochemical reduction of dodecylpyridinium bromide in aprotic solvents: Mechanistic studies

Hromadová

Pospı́šil

Sokolová

et al. 2011

Collect. Czech. Chem. Commun.

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“…The pyridinium structure is also reflected in the cyclic voltammogram of the gold/organicus liquor regius solution in acetonitrile, where the reduction peak potential at À1.28 V (see Figure S21 in the Supporting Information) in the cathodic scan falls in the range of the reduction potentials of pyridinium compounds. [28] Dimers and trimers of 4-chloropyridine and their derivatives are present in the mass spectra of GTP-RT (see Figures S10 and S11 in the Supporting Information) and the precipitate from the longstanding Au/SOCl 2 /py solution (see Figures S22 and S23 in the Supporting Information). We postulate that 4-chloropyridine might form as an intermediate and Au III catalyzes the oligomerization of 4-chloropyridine.…”

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confidence: 99%

“Organic Aqua Regia”—Powerful Liquids for Dissolving Noble Metals

Lin¹,

Zhang²,

Jang³

et al. 2010

Angewandte Chemie

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We are grateful to Zhong-Lin Wang for his valuable advice, Bo Xu for collecting NMR data and helpful discussions, Meilin Liu and Min-Kyu Song for their help with CV experiments, and Anselm Griffin for his helpful discussions on the chemistry of thionyl chloride and pyridine. We acknowledge Josh Agar for his help in preparing the manuscript, and Ziyin Lin for his discussions.Supporting information for this article is available on the WWW under http://dx.

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“…Others (3-5) have proposed a series of possible reaction routes for the reduction of nicotinamide under varying pH conditions. Also, a similar reduction mechanism to that in Scheme 1 for analogous substituted pyridinium compounds, but in aprotic solvents, has been suggested (18,21). In addition, it has been reported that dialkylcarbamoylpyridinium could be reduced to form 1,4-dihydropyridine in an aqueous solution (22).…”

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confidence: 59%

“…For example, when two of these species react together, a dimer (Scheme 2a) could be formed if steric hindrance is not a factor (21). Each dimer would then undergo a two-electron reduction process, not involving protons.…”

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The reductive deposition of quaternary pyridinium corrosion inhibitor multilayers on glassy carbon electrodes

Wong¹,

Birss²

2004

Can. J. Chem.

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Abstract:The redox behaviour of several quaternary pyridinium corrosion inhibitors ("Quats") at glassy carbon (GC) electrodes has been investigated in neutral aqueous solutions. The primary emphasis is on n-butyl-3-(N-octylcarbamyl)pyridinium bromide, one of the Quats determined to have very good corrosion inhibition properties based on parallel weight loss experiments. It is demonstrated that the reduction of the Quats, which occurs in a two-electron reaction at potentials negative of -1.0 V vs. SSCE, results in the formation of a neutral product. This forms a porous film on the electrode surface, with clusters that expand and thicken as more Quat deposits, as confirmed by atomic force microscopy. The film charge density reaches a maximum of~4 mC/cm 2 , equivalent to more than 100 monolayers of Quat, after which no further Quat can be deposited, suggesting full surface coverage by a nonconducting product. The Quat multilayer can then be redissolved at potentials positive of~-0.2 V, during its oxidation back to its original solution-soluble form.Key words: quaternarized pyridinium compounds, reductive film deposition, glassy carbon, multilayer, corrosion inhibitors, cyclic voltammetry, AFM.Résumé : Opérant dans des solutions aqueuses neutres, on a étudié le comportement redox, au niveau d'électrodes de carbone vitreux (CV), de plusieurs sels de pyridinium quaternaires, des inhibiteurs de la corrosion (« Quats »). L'accent a principalement été mis sur le bromure de n-butyl-3-(N-octylcarbamyl)pyridinium, un des quatre Quats qui, sur la base d'expériences parallèles de pertes de poids, devrait présenter de très bonnes propriétés d'inhibition de la corrosion. Il a été démontré que la réduction du Quats, une réaction à deux électrons à des potentiels négatifs de -1,0 V vs. SSCE, conduit à la formation d'un produit neutre. Tel que confirmé par une microscopie de forces atomiques, celui-ci forme un film poreux sur la surface de l'électrode, avec des agrégats qui conduisent à une expansion et un épaississement avec les dépôts additionnels de Quats. La densité de charge du film atteint un maximum dẽ 4 mC/cm 2 , équivalent à plus de 100 monocouches de Quat, après quoi il ne peut plus se déposer de Quat, ce qui suggère que la surface totale est couverte par un produit qui ne conduit pas l'électricité. La multicouche de Quat peut alors être redissoute à des potentiels positifs de~-0.2 V, durant sa réoxydation à sa forme originale soluble dans la solution.Mots clés : dérivés pyridinium quaternaires, dépôt d'un film de réduction, carbone vitreux, multicouche, inhibiteurs de corrosion, voltampérométrie cyclique, AFM.[Traduit par la Rédaction] Wong et al. 1544

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Electrochemical reduction of 1,2,4,6-substituted pyridinium cations

Cited by 11 publications

References 15 publications

Electrochemical reduction of dodecylpyridinium bromide in aprotic solvents: Mechanistic studies

Electrochemical reduction of dodecylpyridinium bromide in aprotic solvents: Mechanistic studies

“Organic Aqua Regia”—Powerful Liquids for Dissolving Noble Metals

The reductive deposition of quaternary pyridinium corrosion inhibitor multilayers on glassy carbon electrodes

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