Comparative Study of Antioxidant Potential of Selected Dietary Vitamins; Computational Insights

Pandithavidana, Dinesh R.; Jayawardana, S.B.

doi:10.3390/molecules24091646

Cited by 36 publications

(47 citation statements)

References 21 publications

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“…The minimum value appears to be the SMD one. In general, vitamins with higher IP values are more susceptible to ionization and they have stronger antioxidant potential (Pandithavidana and Jayawardana, 2019). Thermodynamics of heterolytic dissociation of chemical bonds can be described using through proton affinity (PA), which is for the anion formation defined as:…”

Section: Resultsmentioning

confidence: 99%

Thermodynamic prediction of proton and hydrogen atom abstraction in dehydroascorbic acid and its bicyclic form

Štellerová

Lukeš

2021

Acta Chimica Slovaca

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Conformation analysis of dehydroascorbic acid and its bicyclic form was performed using the density functional theory. For the energetically preferred conformations, ionization potentials (IP) and bond dissociation enthalpies (BDE) were calculated using the B3LYP functional and 6-311++G** basis set. The effects of aqueous solution were estimated using the solvation model based on density (SMD) and the polarizable continuum model (IEF-PCM). The obtained results were compared with available experimental data for reference L-ascorbic acid (vitamin C). Our calculations indicate that the investigated bicyclic metabolic product of vitamin C can also exhibit limited radical scavenging ability due to the thermodynamically preferred dissociation of tertiary —CH bonds.

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Section: Resultsmentioning

confidence: 99%

Thermodynamic prediction of proton and hydrogen atom abstraction in dehydroascorbic acid and its bicyclic form

Štellerová

Lukeš

2021

Acta Chimica Slovaca

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“…However, little is known about the radical-scavenging mechanism of PTS. There are three mechanisms for the initial step of the radical-scavenging reaction of phenolic antioxidants: one-step hydrogen-atom transfer (HAT) from the phenolic OH group; electron transfer followed by proton transfer (ET–PT); and sequential proton-loss electron transfer (SPLET) [ 7 ]. Redox-inactive metal ions, such as magnesium ion (Mg 2+ ), are a powerful tool to examine the involvement of electron-transfer processes [ 8 , 9 , 10 , 11 , 12 , 13 ], because it has been reported that electron-transfer reactions are significantly accelerated by their presence [ 14 , 15 ].…”

Section: Introductionmentioning

confidence: 99%

Effect of Magnesium Ion on the Radical-Scavenging Rate of Pterostilbene in an Aprotic Medium: Mechanistic Insight into the Antioxidative Reaction of Pterostilbene

et al. 2022

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Pterostilbene (PTS), a methylated analog of resveratrol (RSV), has recently attracted much attention due to its enhanced bioavailability compared to RSV. However, little is known about the radical-scavenging mechanism of PTS. In this study, we investigated the effect of Mg(ClO4)2 on the scavenging reaction of galvinoxyl radical (GO•) by PTS in acetonitrile (MeCN). GO• was used as a model for reactive oxygen radicals. The second-order rate constant (kH) for the GO•-scavenging reaction by PTS was more than threefold larger than that by RSV, although thermodynamic parameters, such as the relative O–H bond dissociation energies of the phenolic OH groups, ionization potentials, and HOMO energies calculated by the density functional theory are about the same between PTS and RSV. The oxidation peak potential of PTS determined by the cyclic voltammetry in MeCN (0.10 M Bu4NClO4) was also virtually the same as that of RSV. On the other hand, no effect of Mg (ClO4)2 on the kH values was observed for PTS, in contrast to the case for RSV. A kinetic isotope effect of 3.4 was observed when PTS was replaced by a deuterated PTS. These results suggest that a one-step hydrogen-atom transfer from PTS to GO• may be the rate-determining step in MeCN.

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“…One of the principal goals of theoretical chemists is to develop new and useful rules and theories to explain the reactivity properties and to predict the directions and mechanisms of chemical reactions [1][2][3][4][5][6][7][8][9][10]. Density Functional Theory (DFT) that was revealed in accordance with this goal uses the electron density to identify the reactivity or stability [11][12][13][14][15][16][17].…”

Section: Introductionmentioning

confidence: 99%

Theoretical Analysis of OLED Performances of Some Aromatic Nitrogen-Containing Ligands

Elik

2021

Preprint

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It is well-known that tris(8‐hydroxyquinoline) aluminum (Alq3) complex and N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-diphenyl-4,4'-diamine compound (TPD) are widely used as electron transfer material (ETL) and hole transfer material (HTL) in organic light emitting diode (OLED) structure, respectively. Considering the reference materials, in the present work, the OLED performances of some cyclic aromatic structures such as 4,4ꞌ-azopyridine [AZPY], 4,4ꞌ-bipyridine [BIPY], 1,2-bis[4ꞌ-(4-methylphenyl)2,2ꞌ:6ꞌ2ꞌꞌ-terpyridin-6-yl]ethyne (BISTERPY), 5,5ꞌ-diamino-2,2ꞌ-bipyridine (DABP), dipyrido[3,2-a:2ꞌ,3ꞌ-c]phenazine (DPP), 4,7-phenanthroline (PHEN) including nitrogen atom have been theoretically analyzed. It is important to note that B3LYP/6-31G(d) and B3LYP/TZP levels of the theory were taken into account for the calculations about monomeric and dimeric structures, respectively. For a detailed theoretical analysis, the reorganization energies (λe and λh), adiabatic and vertical ionization potentials and electron affinities, the effective transfer integrals (Ve and Vh), and the charge transfer rates (We and Wh) of all compounds were computed by means of computational chemistry tools. In the light of calculated parameters, it is determined that these mentioned aromatic cyclic structures will be used in which layers of OLED structure. The results obtained in this study will be helpful in the design and applications of new molecules as OLED materials in the future.

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Comparative Study of Antioxidant Potential of Selected Dietary Vitamins; Computational Insights

Cited by 36 publications

References 21 publications

Thermodynamic prediction of proton and hydrogen atom abstraction in dehydroascorbic acid and its bicyclic form

Thermodynamic prediction of proton and hydrogen atom abstraction in dehydroascorbic acid and its bicyclic form

Effect of Magnesium Ion on the Radical-Scavenging Rate of Pterostilbene in an Aprotic Medium: Mechanistic Insight into the Antioxidative Reaction of Pterostilbene

Theoretical Analysis of OLED Performances of Some Aromatic Nitrogen-Containing Ligands

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