The role of acids and bases on the electrochemical oxidation of hydroquinone: Hydrogen bonding interactions in acetonitrile

Astudillo, Pablo D.; Tiburcio, Jorge; González, Felipe J.

doi:10.1016/j.jelechem.2007.02.031

Cited by 86 publications

(83 citation statements)

References 29 publications

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“…The electrochemical responses of CA, DHCA, and CAPE under these experimental conditions are similar to that found for catechol, and are in good agreement with the anodic oxidation of hydroquinone (an isomer of catechol) reported before, [28][29][30][31][32] which follows an ECE mechanism that involves the lost of one electron in the system, followed by a fast deprotonation reaction and, finally, the lost of a second electron. Scheme 1 shows the complete mechanism, which is the starting point for the following discussion.…”

Section: Resultssupporting

confidence: 88%

“…On the other hand, Astudillo et al 32 reported that hydrogen bonding acceptor solvents play an important role on the anodic oxidation of hydroquinone. They proposed that DMSO interacts with hydroquinone through hydrogen bonding associations, causing the shift of the oxidation peaks toward less positive potentials.…”

Section: Electrochemical Oxidation Of Caffeic and Ferulic Acid Derivamentioning

confidence: 99%

“…This observation can be explained considering the fact that the proton affinity is higher in DMSO than in AN, and that the proton transfer in pure DMSO is carried out into a hydrogen bonding complex formed between the hydroxyl groups of catechol and the DMSO molecules. 32,34 (1)…”

Section: Electrochemical Oxidation Of Caffeic and Ferulic Acid Derivamentioning

confidence: 99%

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Electrochemical Oxidation of Caffeic and Ferulic Acid Derivatives in Aprotic Medium

Salas-Reyes¹,

Hernández²,

Domínguez³

et al. 2011

J. Braz. Chem. Soc.

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O comportamento eletroquímico em função da estrutura de uma série de derivados dos ácidos cafeico e ferúlico, assim como de seus precursores catecol e guaiacol, eletroquimicamente ativos, foi avaliado por voltametria cíclica. Os resultados revelaram que as condições experimentais são a chave para as mudanças no mecanismo de oxidação do guaiacol e ácido ferúlico. A oxidação eletroquímica dos derivados amida do ácido ferúlico revelou que o átomo de nitrogênio desempenha um papel importante na derivatização da superfície do eletrodo. Além disso, a atividade sequestradora de radicais dos compostos, avaliada através da porcentagem de inibição do radical 2,2'-difenil-1-picril-hidrazila, mostrou uma boa correlação com os potenciais de oxidação.We studied the electrochemical behaviour as a function of the structure of a series of caffeic and ferulic acids derivatives as well as their corresponding redox moieties catechol and guaiacol by cyclic voltammetry. Results revealed that the medium is key for changes in the oxidation mechanism of guaiacol and ferulic acid. Electrochemical oxidation of the ferulic acid amide derivatives revealed that the nitrogen atom plays an important role in the derivatization of the electrode surface. In addition, radical scavenging activity of the compounds evaluated through the percentage of inhibition of the 2,2'-diphenyl-1-picrylhidrazyl radical showed a good relationship with the oxidation potentials.

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Section: Resultssupporting

confidence: 88%

Section: Electrochemical Oxidation Of Caffeic and Ferulic Acid Derivamentioning

confidence: 99%

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Electrochemical Oxidation of Caffeic and Ferulic Acid Derivatives in Aprotic Medium

Salas-Reyes¹,

Hernández²,

Domínguez³

et al. 2011

J. Braz. Chem. Soc.

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“…This peak corresponds certainly to the tow-electron oxidation of calix [4]arenedihydroquinone to the monoprotonated calix [4]arenequinone. This result is in agreement with the oxidation of the dihydroquinone to quinhydrone form [24,29]. In the potential range between 1.9 V versus SCE and 2 V versus SCE, two overlapped waves were noticed.…”

Section: Electrochemical Behaviour Of the Recovered Platinum Electrodesupporting

confidence: 89%

Self-assembled calix[4]arenequinhydrone on the platinum electrode by cathodic reduction of calix[4]arenediquinone

Youchret-Zallez¹,

Besbes-Hentati²,

Bouvet

et al. 2011

J Incl Phenom Macrocycl Chem

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The electrochemical reduction of di(methoxyp-tert-butyl)calix [4]arenediquinone led to its calix[4]arenedihydroquinone. The presence of both in the solution refers to the generation of calix[4]arenequinhydrone charge-transfer complex at the electrode surface through a donor/acceptor process type. Self-assembled adlayers of calix[4]arenequinhydrone was obtained by partial electrochemical reduction. Electrochemical deposition of the last form was achieved on the platinum disk electrode at -1.16 V versus SCE (saturated calomel electrode) in aprotic solution by cathodic reduction of the starting substrate. The deposit was first characterized by cyclic voltammetry (CV) in electrolytic solution and then in electrolyte support solution and finally in a ferricyannure solution. The self-assembled product was characterized by MALDI-TOF Mass and IR spectroscopy techniques. It was observed too by SEM technique. Calix[4]arenequinhydrone is observed on the electrode surface as hexangular prisms with a length of few micrometers.

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“…[13][14][15] It is generally accepted that the redox chemistry of these compounds involves elementary steps comprising 2 H + and 2 e À for the quinone/hydroquinone reaction. [12] However, these reactions are an oversimplification of a very complex mechanism that depends on the protic nature of the solvent, the presence of Brønsted acids or bases, [12] and the interrelations of the reactants, intermediates, and products by electron-and proton-transfer reactions.…”

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confidence: 99%

Towards a Further Generation of High‐Energy Carbon‐Based Capacitors by Using Redox‐Active Electrolytes

et al. 2011

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An active contribution: The specific capacitance of carbon‐based supercapacitors can be significantly improved by the addition of an electrochemically active compound (hydroquinone) to the supporting electrolyte. The strong contribution of the redox‐active electrolyte to the pseudocapacitance of the system results in the largest capacitance values obtained for an activated carbon‐based supercapacitor.

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The role of acids and bases on the electrochemical oxidation of hydroquinone: Hydrogen bonding interactions in acetonitrile

Cited by 86 publications

References 29 publications

Electrochemical Oxidation of Caffeic and Ferulic Acid Derivatives in Aprotic Medium

Electrochemical Oxidation of Caffeic and Ferulic Acid Derivatives in Aprotic Medium

Self-assembled calix[4]arenequinhydrone on the platinum electrode by cathodic reduction of calix[4]arenediquinone

Towards a Further Generation of High‐Energy Carbon‐Based Capacitors by Using Redox‐Active Electrolytes

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