Calculation of two-electron reduction potentials for some quinone derivatives in aqueous solution using Møller–Plesset perturbation theory

Namazian, Mansoor; Siahrostami, Samira; Noorbala, Mohammad R.; Coote, Michelle L.

doi:10.1016/j.theochem.2005.11.011

Cited by 20 publications

(20 citation statements)

References 14 publications

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“…18,[42][43][44][45][46][47][48][49][50] For example, gas phase and solution phase acidities of some organic compounds investigated by Namazian et al and Kheirjou et al reported good correlation between ab initio calculations of pKa values with the experimental data. 19,21,[51][52] However, to the best of our knowledge, there is no data on pKa calculations of arsonic acids by quantum chemical methods, and experimentally determined pKa values are limited to a small group of arsonic acid derivatives. Accordingly, we have calculated the relative pKa values of some of aryl arsonic acids using using the DFT/B3LYP approach in conjunction with some selected basis sets such as (6-31G(d), 6-31+G(d), 6-311++G(d,p) and 6-311++G(2d,2p)).…”

Section: Introductionmentioning

confidence: 99%

Theoretical calculations of the relative pKa values of some selected aromatic arsonic acids in water using density functional theory

Khalili¹,

Rimaz²

2016

10.5267/j.ccl

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With the focus on calculating the equilibrium constant (Ka) of arsonic acids (RAsO(OH)2) in aqueous media, the behavior of both neutral and negatively charged species of some arsonic acids have been considered through the isodesmic reaction scheme with polarized continuum model of solvation. The relative pKa values of a number of arsonic acids were calculated using density functional theory (DFT), with methylarsonic acid (CH3AsO(OH)2) used as a reference molecule. Various basis sets such as (6-31G(d), 6-31+G(d), 6-311++G(d,p) and 6-311++G(2d,2p)) in conjunction with B3LYP computational method were examined. Finally the latter one was found to give better results. The results of applied B3LYP 6-311++G(2d,2p) method for pKa values of 25 arsonic acids in aqueous media showed good agreement with corresponding experimental pKa values. In this level of theory the average error was less than 0.3 pKa units. The type of substituent affected the acid strength, with electron withdrawing substituents lowering the pKa and electron releasing groups increasing it.

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Section: Introductionmentioning

confidence: 99%

Theoretical calculations of the relative pKa values of some selected aromatic arsonic acids in water using density functional theory

Khalili¹,

Rimaz²

2016

10.5267/j.ccl

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“…[1][2][3][4][5] Recently many theoretical approaches for prediction redox potentials for wide range of compounds have been developed. [3][4][5][6][7][8] Most of them evaluate Gibbs free energy of reduction in solution in two steps.…”

Section: Introductionmentioning

confidence: 99%

Toward robust computational electrochemical predicting the environmental fate of organic pollutants

Sviatenko

Isayev

Gorb³

et al. 2011

J Comput Chem

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A number of density functionals was utilized for the calculation of electron attachment free energy for nitrocompounds, quinones and azacyclic compounds. Different solvation models have been tested on the calculation of difference in free energies of solvation of oxidized and reduced forms of nitrocompounds in aqueous solution, quinones in acetonitrile, and azacyclic compounds in dimethylformamide. Gas-phase free energies evaluated at the mPWB1K/tzvp level and solvation energies obtained using SMD model to compute solvation energies of neutral oxidized forms and PCM(Pauling) to compute solvation energies of anion-radical reduced forms provide reasonable accuracy of the prediction of electron attachment free energy, difference in free solvation energies of oxidized and reduced forms, and as consequence yield reduction potentials in good agreement with experimental data (mean absolute deviation is 0.15 V). It was also found that SMD/M05-2X/tzvp method provides reduction potentials with deviation of 0.12 V from the experimental values but in cases of nitrocompounds and quinones this accuracy is achieved due to the cancelation of errors. To predict reduction ability of naturally occurred iron containing species with respect to organic pollutants we exploited experimental data within the framework of Pourbaix (Eh - pH) diagrams. We conclude that surface-bound Fe(II) as well as certain forms of aqueous Fe(II)aq are capable of reducing a variety of nitroaromatic compounds, quinones and novel high energy materials under basic conditions (pH > 8). At the same time, zero-valent iron is expected to be active under neutral and acidic conditions.

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“…Several articles have been published on redox potential prediction of quinone derivatives [6][7][8][9][10][11][12]. Since many electrochemical reactions occur in liquid solutions, the redox potential predictions have been carried out by considering quinones in either aqueous or non-aqueous solutions using different models of solvation such as Direct Polarized Continuum Model (DPCM) [5].…”

Section: Introductionmentioning

confidence: 99%

“…Since many electrochemical reactions occur in liquid solutions, the redox potential predictions have been carried out by considering quinones in either aqueous or non-aqueous solutions using different models of solvation such as Direct Polarized Continuum Model (DPCM) [5]. On the other hand several levels of computational methods were tested in order to obtain more and more reasonable theoretical redox potentials in comparison to experimental values [10]. In the case of aqueous solution, Namazian et al employed B3LYP [7], and recently Moller-Plesset (MP3) level of theory [10] for a set of eight quinone derivatives.…”

Section: Introductionmentioning

confidence: 99%

“…On the other hand several levels of computational methods were tested in order to obtain more and more reasonable theoretical redox potentials in comparison to experimental values [10]. In the case of aqueous solution, Namazian et al employed B3LYP [7], and recently Moller-Plesset (MP3) level of theory [10] for a set of eight quinone derivatives. Though the results of B3LYP were far from experimental values, theoretical results of MP3 showed the best agreement.…”

Section: Introductionmentioning

confidence: 99%

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Application of Density Functional Theory for evaluation of standard two-electron reduction potentials in some quinone derivatives

Pakiari

Siahrostami

Mohajeri

2008

Journal of Molecular Structure: THEOCHEM

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Calculation of two-electron reduction potentials for some quinone derivatives in aqueous solution using Møller–Plesset perturbation theory

Cited by 20 publications

References 14 publications

Theoretical calculations of the relative pKa values of some selected aromatic arsonic acids in water using density functional theory

Theoretical calculations of the relative pKa values of some selected aromatic arsonic acids in water using density functional theory

Toward robust computational electrochemical predicting the environmental fate of organic pollutants

Application of Density Functional Theory for evaluation of standard two-electron reduction potentials in some quinone derivatives

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