The Electrochemical Oxidation of 6-Aminoquinoline: Computational and Voltammetric Study
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Stevic, Milica C.Ćirić-Marjanović, Gordana
Marjanovic, Budimir
Ignjatovic, Ljubisa M.
Manojlović, Dragan D.
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The theoretical study of the 6-aminoquinoline (6-QNH(2)) electrochemical oxidation mechanism, based on the semi-empirical quantum chemical computations of the heat of formation, ionization energy, and spin density of reaction intermediates, taking into account the influence of pH and solvation effects, has been conducted. Two possible 6-QNH(2) electro-oxidation pathways are investigated, namely, the initial single-electron oxidation of 6-QNH(2) at lower electrode potentials, leading to the formation of cation radicals [6-QNH(2)](center dot+) in acidic solutions and neutral radicals [6-QNH](center dot) in alkaline solutions, as well as the two-electron oxidation of 6-QNH(2) leading to the initial formation of nitrenium cations [6-QNH](+) at higher electrode potentials. The regioselectivity of 6-QNH(2) dimerization reactions, which follow both the single- and two-electron transfer reactions, is computationally studied. Cyclic voltammetry experiments, conducted at a glassy carbon paste el...ectrode in Britton-Robinson buffer/methanol media, are correlated with the computationally predicted 6-QNH(2) electro-oxidation mechanism. Differential pulse voltammetric and adsorptive stripping differential pulse voltammetric analyses of 6-QNH(2) oxidation have also been performed. (C) 2012 The Electrochemical Society. [DOI: 10.1149/2.004212jes] All rights reserved.
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Journal of the Electrochemical Society, 2012, 159, 11Publisher:
- Electrochemical Soc Inc, Pennington
Funding / projects:
- Application of advanced oxidation processes and nanostructured oxide materials for the removal of pollutants from the environment, development and optimisation of instrumental techniques for efficiency monitoring (RS-MESTD-Basic Research (BR or ON)-172030)
- Electroconducting and redox-active polymers and oligomers: synthesis, structure, properties and applications (RS-MESTD-Basic Research (BR or ON)-172043)
DOI: 10.1149/2.004212jes
ISSN: 0013-4651
WoS: 000309107200078
Scopus: 2-s2.0-84875618449
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Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Stevic, Milica C. AU - Ćirić-Marjanović, Gordana AU - Marjanovic, Budimir AU - Ignjatovic, Ljubisa M. AU - Manojlović, Dragan D. PY - 2012 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1534 AB - The theoretical study of the 6-aminoquinoline (6-QNH(2)) electrochemical oxidation mechanism, based on the semi-empirical quantum chemical computations of the heat of formation, ionization energy, and spin density of reaction intermediates, taking into account the influence of pH and solvation effects, has been conducted. Two possible 6-QNH(2) electro-oxidation pathways are investigated, namely, the initial single-electron oxidation of 6-QNH(2) at lower electrode potentials, leading to the formation of cation radicals [6-QNH(2)](center dot+) in acidic solutions and neutral radicals [6-QNH](center dot) in alkaline solutions, as well as the two-electron oxidation of 6-QNH(2) leading to the initial formation of nitrenium cations [6-QNH](+) at higher electrode potentials. The regioselectivity of 6-QNH(2) dimerization reactions, which follow both the single- and two-electron transfer reactions, is computationally studied. Cyclic voltammetry experiments, conducted at a glassy carbon paste electrode in Britton-Robinson buffer/methanol media, are correlated with the computationally predicted 6-QNH(2) electro-oxidation mechanism. Differential pulse voltammetric and adsorptive stripping differential pulse voltammetric analyses of 6-QNH(2) oxidation have also been performed. (C) 2012 The Electrochemical Society. [DOI: 10.1149/2.004212jes] All rights reserved. PB - Electrochemical Soc Inc, Pennington T2 - Journal of the Electrochemical Society T1 - The Electrochemical Oxidation of 6-Aminoquinoline: Computational and Voltammetric Study VL - 159 IS - 11 DO - 10.1149/2.004212jes ER -
@article{ author = "Stevic, Milica C. and Ćirić-Marjanović, Gordana and Marjanovic, Budimir and Ignjatovic, Ljubisa M. and Manojlović, Dragan D.", year = "2012", abstract = "The theoretical study of the 6-aminoquinoline (6-QNH(2)) electrochemical oxidation mechanism, based on the semi-empirical quantum chemical computations of the heat of formation, ionization energy, and spin density of reaction intermediates, taking into account the influence of pH and solvation effects, has been conducted. Two possible 6-QNH(2) electro-oxidation pathways are investigated, namely, the initial single-electron oxidation of 6-QNH(2) at lower electrode potentials, leading to the formation of cation radicals [6-QNH(2)](center dot+) in acidic solutions and neutral radicals [6-QNH](center dot) in alkaline solutions, as well as the two-electron oxidation of 6-QNH(2) leading to the initial formation of nitrenium cations [6-QNH](+) at higher electrode potentials. The regioselectivity of 6-QNH(2) dimerization reactions, which follow both the single- and two-electron transfer reactions, is computationally studied. Cyclic voltammetry experiments, conducted at a glassy carbon paste electrode in Britton-Robinson buffer/methanol media, are correlated with the computationally predicted 6-QNH(2) electro-oxidation mechanism. Differential pulse voltammetric and adsorptive stripping differential pulse voltammetric analyses of 6-QNH(2) oxidation have also been performed. (C) 2012 The Electrochemical Society. [DOI: 10.1149/2.004212jes] All rights reserved.", publisher = "Electrochemical Soc Inc, Pennington", journal = "Journal of the Electrochemical Society", title = "The Electrochemical Oxidation of 6-Aminoquinoline: Computational and Voltammetric Study", volume = "159", number = "11", doi = "10.1149/2.004212jes" }
Stevic, M. C., Ćirić-Marjanović, G., Marjanovic, B., Ignjatovic, L. M.,& Manojlović, D. D.. (2012). The Electrochemical Oxidation of 6-Aminoquinoline: Computational and Voltammetric Study. in Journal of the Electrochemical Society Electrochemical Soc Inc, Pennington., 159(11). https://doi.org/10.1149/2.004212jes
Stevic MC, Ćirić-Marjanović G, Marjanovic B, Ignjatovic LM, Manojlović DD. The Electrochemical Oxidation of 6-Aminoquinoline: Computational and Voltammetric Study. in Journal of the Electrochemical Society. 2012;159(11). doi:10.1149/2.004212jes .
Stevic, Milica C., Ćirić-Marjanović, Gordana, Marjanovic, Budimir, Ignjatovic, Ljubisa M., Manojlović, Dragan D., "The Electrochemical Oxidation of 6-Aminoquinoline: Computational and Voltammetric Study" in Journal of the Electrochemical Society, 159, no. 11 (2012), https://doi.org/10.1149/2.004212jes . .