Density-functional theory and ab initio Hartree–Fork studies on the structural parameters and chemical activity of the free radicals generated by benzoquinone and hydroquinone

Song, Y. Z.; Xie, Jimin; Shu, Huoming; Zhao, Gan-Qing; Lv, Xiaomeng; Cai, Hao

doi:10.1016/j.bmc.2005.05.029

Cited by 20 publications

(12 citation statements)

References 29 publications

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“…The mineralization of paracetamol occurs through ortho, meta and para substituted oxidation pathways, leading to the formation of dihydroxy aromatic rings: catechol, resorcinol and hydroquinone; and trihydroxylated rings: pyrogallol, phloroglucinol and hydroxyhydroquinone [18][19]. These species are in equilibrium with their corresponding para and ortho benzoquinones [20][21].…”

Section: Chemical Pathway Of Paracetamol Degradationmentioning

confidence: 98%

Study of the paracetamol degradation pathway that generates color and turbidity in oxidized wastewaters by photo-Fenton technology

Villota

Lomas

Camarero

2016

Journal of Photochemistry and Photobiology A: Chemistry

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Section: Chemical Pathway Of Paracetamol Degradationmentioning

confidence: 98%

Study of the paracetamol degradation pathway that generates color and turbidity in oxidized wastewaters by photo-Fenton technology

Villota

Lomas

Camarero

2016

Journal of Photochemistry and Photobiology A: Chemistry

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“…Several studies showed that density functional theory is a powerful method for predicting the geometry and other features related to the structure. [224][225][226] Song et al 227 carried out an exhaustive DFT and ab initio hartree-fock studies on the structural parameters and chemical reactivity of all the free radicals generated by benzoquinones and hydroquinone. The highlight of this study is that the free radicals can be easily generated in aqueous solution and are more reactive.…”

Section: Computational Investigations On 14-benzoquinonesmentioning

confidence: 99%

Recent advances in 1,4-benzoquinone chemistry

Abraham¹,

Joshi²,

Pardasani³

et al. 2011

J. Braz. Chem. Soc.

165

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As 1,4-benzoquinonas são encontradas em toda a natureza, podendo ser sintetizadas por diversas estratégias. Esta revisão apresenta os desenvolvimentos recentes das metodologias de síntese, das reações de ciclo adição, da química computacional e dos estudos de pulso radiolítico. Destaca ainda a sua significância química e biológica e de seus compostos derivados.1,4-Benzoquinones are ubiquitous in nature and can be synthesized by diverse strategies. Recent developments on their synthetic methodologies, cycloaddition reactions, computational chemistry and pulse radiolytic studies are reported in this review. Their chemical and biological significance as well as their derivates' are also covered.

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“…48,49,51 The C1-C2-C3 and C4-C5-C6 bond angles decreased by 2.21 ° to 2.63 °, whereas the remaining four bond angles in the benzoquinone moiety increased by 0.84 ° to 1.75 °. The only exception was 3,4′,6-Cl-2,5-Q, where the C1-C2-C3 and C4-C5-C6 bond angles decreased by 3.15 ° and 3.06 °, respectively, due to the presence of the chlorine and phenyl substituents.…”

Section: Resultsmentioning

confidence: 95%

Density Functional Theory Study of Semiquinone Radical Anions of Polychlorinated Biphenyls in the Syn- and Anti-like Conformation

et al. 2012

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Polychlorinated biphenyls can be metabolized to reactive metabolites, such as PCB semiquinone radical anions (SQ•−), whose structure and role in PCB-induced toxicity are difficult to investigate due to their relative instability. The unrestricted UB3LYP/6-311G** method was used to investigate several molecular descriptors of the syn- and anti-like conformation of SQs•−. The bond lengths and angles of the quinone moiety of the SQs•− were in between the values reported for PCB quinones and hydroquinones, which is consistent with the distribution of the α-HOMO. The dihedral angles between the two ring systems increased in the presence of ortho chlorine substituents and were smaller compared to the corresponding PCB quinones. The ground state energies indicate that the anti-like conformation of the SQs•− is more favorable than the syn-like conformation. Molecular descriptor used for modeling of quantitative structure-activity relationships displayed some dependence on the conformation. These findings suggest that SQs•− in both the syn- and anti-like conformation may interact differently with target molecules, which may have implications for the toxicity of PCBs.

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Density-functional theory and ab initio Hartree–Fork studies on the structural parameters and chemical activity of the free radicals generated by benzoquinone and hydroquinone

Cited by 20 publications

References 29 publications

Study of the paracetamol degradation pathway that generates color and turbidity in oxidized wastewaters by photo-Fenton technology

Study of the paracetamol degradation pathway that generates color and turbidity in oxidized wastewaters by photo-Fenton technology

Recent advances in 1,4-benzoquinone chemistry

Density Functional Theory Study of Semiquinone Radical Anions of Polychlorinated Biphenyls in the Syn- and Anti-like Conformation

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