DFT and QTAIM based investigation on the structure and antioxidant behavior of lichen substances Atranorin, Evernic acid and Diffractaic acid

Ahamed, Tangir; Rajan, Vijisha K.; Sabira, K.; Muraleedharan, K.

doi:10.1016/j.compbiolchem.2019.03.009

Cited by 36 publications

(15 citation statements)

References 52 publications

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“…The significant decrease in both parameters (predominantly the PDE values) in aqueous phase implies the ease in the proton transfer and electron abstraction processes respectively. This observation is sim-DOI: 10.4236/cc.2021.93010 172 Computational Chemistry ilar to that obtained in [31].…”

Section: Evaluation Of the Set-pt Mechanismsupporting

confidence: 76%

“…As stated before now the antioxidant capacity of phenolic compounds has been elucidated through several mechanisms. The commonly used ones are hydrogen atom transfer (HAT), single electron transfer followed by proton transfer (SET-PT), and sequential proton loss electron transfer (SPLET) [31]. These mechanisms individually offer an approach on how these molecules respond in the presence of a radical [15] [32].…”

Section: Antioxidant Potentialmentioning

confidence: 99%

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Investigation of the Antioxidant and UV Absorption Properties of 2-(2’-hydroxy-5’-methylphenyl)-benzotriazole and Its Ortho-Substituted Derivatives via DFT/TD-DFT

Tasheh

Fouégué

Ghogomu

2021

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The demand and pursuit of chemical entities with UV filtration and antioxidant properties for enhanced photoprotection have been driven in recent times by acute exposure of humans to solar ultraviolet radiations. The structural, electronic, antioxidant and UV absorption properties of drometrizole (PBT) and designed ortho-substituted derivatives are reported via DFT and TD-DFT in the gas and aqueous phases. DFT and TD-DFT computations were performed at the M062x-D3Zero/6-311++G(d,p)//B97-3c and PBE0-D3(BJ)/def2-TZVP levels of theory respectively. Reaction enthalpies related to hydrogen atom transfer (HAT), single-electron transfer followed by proton transfer (SET-PT), and sequential proton loss electron transfer (SPLET) mechanisms were computed and compared with those of phenol. Results show that the presence of -NH2 substituent reduces the O-H bond dissociation enthalpy and ionization potential, while that of -CN increases the proton affinity. The HAT and SPLET mechanisms are the most plausible in the gas and aqueous phases respectively. The molecule with the -NH2 substituent (PBT1) was identified to be the compound with the highest antioxidant activity. The UV spectra of the studied compounds are characterized by two bands in the 280 -400 nm regions. Results from this study provide a better comprehension antioxidant mechanism of drometrizole and present a new perspective for the design of electron-donor antioxidant molecules with enhanced antioxidant-photoprotective efficiencies for applications in commercial sunscreens.

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Section: Evaluation Of the Set-pt Mechanismsupporting

confidence: 76%

Section: Antioxidant Potentialmentioning

confidence: 99%

Investigation of the Antioxidant and UV Absorption Properties of 2-(2’-hydroxy-5’-methylphenyl)-benzotriazole and Its Ortho-Substituted Derivatives via DFT/TD-DFT

Tasheh

Fouégué

Ghogomu

2021

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“…The greater SD value of 0.153 indicates that the electron density concentrate on that region itself. DI values of a radical quantitatively explain the extent of the delocalization of that radical [40,41]. The lower the SD, the higher the DI implies that the one-electron formed at a site are more delocalized and hence stable.…”

Section: Analysis Of Hat Mechanismmentioning

confidence: 99%

Quantum chemical investigation of the antiradical property of avenanthramides, oat phenolics

Sumayya

Babu

Muraleedharan

2021

Heliyon

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Avenanthramides (AVs) are polyphenolic components found in oats. The present work is devoted to the exploration of structure-based radical scavenging activity of nine AVs; 2p, 2f, 2c, 1p, 1c, 1f, 1s, 2s, and 3f, using M06-2X functional level of density functional theory with basis set 6-31þG(d, p) both in gas and ethanol medium. The act of compounds towards the electron transfer mechanism was analyzed with the help of a Donor-acceptor map (DAM) and classified as antioxidants and anti-reductants. The main mechanism of radical action, HAT, SET-PT, and SPLET were examined and found to be the preference of HAT and SPLET respectively in the gas phase and ethanol medium. The computed quantum mechanical atom in molecule (QTAIM) parameters; the intramolecular H-bonding, Noncovalent interactions, aromaticity also acted as pillars to supports the activity of compounds. The activity was found to be increasing with the stabilizing group ortho to the reactive phenolic OH group.

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“…The more stable the radical formed from an -OH bond, the more the corresponding C-O bond will be the delocalization index. The DI of C-O bonds in each radical site are calculated using Fuzzy atomic space analysis [44][45][46]. The SD contours of 1c are represented in Figure 4.…”

Section: Analysis Of Hat Mechanismmentioning

confidence: 99%

DFT Study of Structure and Radical Scavenging Activity of Natural Pigment Delphinidin and Derivatives

Pottachola¹,

Kaniyantavida²,

Karuvanthodiyil³

2022

Density Functional Theory - Recent Advances, New Perspectives and Applications

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A theoretical evaluation of the antioxidant activity of natural pigment delphinidin (1a) and derivatives 1b, 1c, 1d & 1e was performed using the DFT-B3LYP/6–311 + G (d, p) level of theory. Three potential working mechanisms, hydrogen atom transfer (HAT), stepwise electron transfer proton transfer (SET-PT), and sequential proton loss electron transfer (SPLET), have been investigated. The physiochemical parameters, including O–H bond dissociation enthalpy (BDE), ionization potential (IP), proton dissociation enthalpy (PDE), proton affinity (PA), and electron transfer enthalpy (ETE), have been calculated in the gas phase and aqueous phase. The study found that the most suitable mechanism for explaining antioxidant activity is HAT in the gas phase and SPLET in the aqueous medium in this level of theory. Spin density calculation and delocalization index of studied molecules also support the radical scavenging activity. When incorporated into natural pigment delphinidin, the gallate moiety can enhance the activity and stability of the compounds.

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DFT and QTAIM based investigation on the structure and antioxidant behavior of lichen substances Atranorin, Evernic acid and Diffractaic acid

Cited by 36 publications

References 52 publications

Investigation of the Antioxidant and UV Absorption Properties of 2-(2’-hydroxy-5’-methylphenyl)-benzotriazole and Its Ortho-Substituted Derivatives via DFT/TD-DFT

Investigation of the Antioxidant and UV Absorption Properties of 2-(2’-hydroxy-5’-methylphenyl)-benzotriazole and Its Ortho-Substituted Derivatives via DFT/TD-DFT

Quantum chemical investigation of the antiradical property of avenanthramides, oat phenolics

DFT Study of Structure and Radical Scavenging Activity of Natural Pigment Delphinidin and Derivatives

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