Solvent effects on the intramolecular hydrogen-bond and anti-oxidative properties of apigenin: A DFT approach

Zheng, Yujun; Zhou, Yu; Qin, Liang; Chen, Dafu; Guo, Rui; Xiong, Cui-Ling; Xu, Xi-Jian; Zhang, Zhaonan; Huang, Zhijian

doi:10.1016/j.dyepig.2017.02.021

Cited by 46 publications

(25 citation statements)

References 54 publications

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“…However, positive of ΔBDE for the compounds indicate that adsorption of APG on B 12 N 12 nanocluster in the HAT mechanism with higher BDEs may exhibit weaker antioxidant activity in comparison to APG in the studied systems. The above conclusions are similar with the references, which confirms the accuracy of this work.…”

Section: Resultssupporting

confidence: 93%

“…Table and show that IP and PDE values calculated in polar (ethanol and water) solvents are lower than nonpolar (gas and benzene) solvents and have especial sensitive to the polarity change of the solvents. The above conclusions are similar with the references, which confirms the accuracy of this work. In other words, the electron‐donating ability and the proton donation ability of APG and APG/B 12 N 12 complex in polar solvents are more.…”

Section: Resultssupporting

confidence: 93%

“…In the HAT analysis, a hydrogen atom of flavonoids is transferred to the free radical via O−H bond dissociation that is characterized by the BDE . The lower BDE shows an easier reaction and the greater antioxidant activity of the compounds.…”

Section: Resultsmentioning

confidence: 99%

“…In recent years, a lot of research showed that APG have different pharmacological activities, such as anti‐oxidant, anti‐inflammatory, anti‐depressant, anti‐mutagenic, anti‐cancer, anti‐viral, anti‐bacterial, anti‐thrombotic, cardioprotective, hepatoprotective, and immunostimulant effects . The antioxidant activity of APG was previously reported using DFT method . But these studies were carried out only on the pristine APG structure.…”

Section: Introductionmentioning

confidence: 99%

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Improvement of Antioxidative Activity of Apigenin by B₁₂N₁₂ Nanocluster: Antioxidative Mechanism Analysis

2020

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Adsorption and antiradical activity of apigenin on the surface of B12N12 nanocluster has been investigated by using density functional theory (DFT) within B3PW91‐D and M06‐2X−D methods. Adsorption values and analysis of topologies showed that the molecule has chemisorbed to the nanocluster surface and induces significant changes in electronic properties of the fullerene. Antioxidative activities of the APG and APG/B12N12 complex have been investigated using the M06‐2X−D level of theory based on the hydrogen atom transfer (HAT), single electron transfer followed by proton transfer (SET‐PT) and sequential proton loss electron transfer (SPLET). For this purpose, the bond dissociation enthalpy (BDE), ionization potential (IP), proton dissociation enthalpy (PDE), proton affinity (PA) and electron transfer enthalpy (ETE) values were calculated in gas, benzene, ethanol, and water phases to better understand the antioxidative properties of the investigated compounds. The results showed that in the gas and the solvent phases, the BDE and IP values of APG are slightly smaller than those of APG/B12N12 complex. Also, in gas and the phases, the PA values of APG/B12N12 complex are much smaller than those of APG especially in the gas and benzene phases. This work confirms the adsorption of APG on B12N12 nanocluster would enhance the antiradical activity of the APG.

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Section: Resultssupporting

confidence: 93%

Section: Resultssupporting

confidence: 93%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Improvement of Antioxidative Activity of Apigenin by B₁₂N₁₂ Nanocluster: Antioxidative Mechanism Analysis

2020

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“…where E LUMO denotes electron energies of the lowest unoccupied molecular orbital (i.e., LUMO) and E HOMO indicates electron energies of the highest occupied molecular orbital for a neutral component (i.e., HOMO). Higher HOMO energy corresponds to stronger electron-donating ability of the molecule [41][42][43][44][45][46]. The FT-IR spectra were recorded for UP seed ( Figure 5).…”

Section: Theoreticalmentioning

confidence: 99%

A Theoretical and Experimental Study for Screening Inhibitors for Styrene Polymerization

2019

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Styrene is one of the most important monomers utilized in the synthesis of various polymers. Nevertheless, during distillation, storage, and transportation of ST, undesired polymer (i.e., UP) formation can take place. Thus, the control of undesired polymerization of styrene is a challenging issue facing industry. To tackle the mentioned issue, the antipolymer and antioxidant activity of stable nitroxide radicals (i.e., SNRs) and phenolics in styrene polymerization were studied by density functional theory (DFT) calculation and experimental approach. The electrophilicity index and growth percentage have been determined by DFT calculation and experimental approach, respectively. It is depicted that 2,6-di-tert-butyl-4-methoxyphenol (DTBMP) and 2,6-di-tert-butyl-4-methylphenol (BHT) from phenolics, and 4-hydroxy-2,2,6,6-tetramethyl piperidine 1-Oxyl (4-hydroxy-TEMPO) and 4-oxo-2,2,6,6-tetramethylpiperidine 1-Oxyl (4-oxo-TEMPO) from stable nitroxide radicals were the most effective inhibitors. Also, the growth percentage of DTMBP, BHT, 4-hydroxy-TEMPO, and 4-oxo-TEMPO after 4 h were 16.40, 42.50, 24.85, and 46.8, respectively. In addition, the conversion percentage of DTMBP, BHT, 4-hydroxy-TEMPO, and 4-oxo-TEMPO after 4 h were obtained to be 0.048, 0.111, 0.065, and 0.134, respectively. Furthermore, the synergistic effect of these inhibitors was investigated experimentally, indicating that DTMBP/4-hydroxy-TEMPO exerted the best synergistic effects on the inhibition of polymerization. The optimum inhibition effect was observed at the blend of 4-hydroxy-TEMPO (25 wt.%) and DTMBP (75 wt.%,) corresponding to 6.8% polymer growth after 4 h.

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Theoretical and experimental assessment of UV resistance of high‐density polyethylene: Screening and optimization of hindered amine light stabilizers

Davand

Rahimpour

Hassanajili

et al. 2021

J of Applied Polymer Sci

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Hindered amine light stabilizers (HALS) are widely used chemical stabilizers for preventing polymer degradation. In this study, the effects of type of HALS and its content in high‐density polyethylene (HDPE) over the stabilization process are investigated employing density functional theory (DFT) and experimental approach. The electrophilicity index of four types of commercial HALS are compared by DFT to select the most effective one. Besides, the HDPE sample containing a phenolic antioxidant and different contents of the selected HALS are experimentally exposed to UV irradiation. The effect of HALS content on the changes in chain microstructure and molecular weight of HDPE are evaluated using gel permeation chromatography and frequency sweep rheometry. In the absence of HALS, HDPE suffers degradation and the phenolic antioxidant causes chain scission. However, by adding HALS, the chain branching and crosslinking mechanisms are predominant. The results of FTIR, DSC, and tensile analyses follow similar trends, revealing that the best stabilization performance corresponds to adding 600 ppm HALS to HDPE.

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Solvent effects on the intramolecular hydrogen-bond and anti-oxidative properties of apigenin: A DFT approach

Cited by 46 publications

References 54 publications

Improvement of Antioxidative Activity of Apigenin by B₁₂N₁₂ Nanocluster: Antioxidative Mechanism Analysis

Improvement of Antioxidative Activity of Apigenin by B₁₂N₁₂ Nanocluster: Antioxidative Mechanism Analysis

A Theoretical and Experimental Study for Screening Inhibitors for Styrene Polymerization

Theoretical and experimental assessment of UV resistance of high‐density polyethylene: Screening and optimization of hindered amine light stabilizers

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Solvent effects on the intramolecular hydrogen-bond and anti-oxidative properties of apigenin: A DFT approach

Cited by 46 publications

References 54 publications

Improvement of Antioxidative Activity of Apigenin by B12N12 Nanocluster: Antioxidative Mechanism Analysis

Improvement of Antioxidative Activity of Apigenin by B12N12 Nanocluster: Antioxidative Mechanism Analysis

A Theoretical and Experimental Study for Screening Inhibitors for Styrene Polymerization

Theoretical and experimental assessment of UV resistance of high‐density polyethylene: Screening and optimization of hindered amine light stabilizers

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Product

Resources

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Improvement of Antioxidative Activity of Apigenin by B₁₂N₁₂ Nanocluster: Antioxidative Mechanism Analysis

Improvement of Antioxidative Activity of Apigenin by B₁₂N₁₂ Nanocluster: Antioxidative Mechanism Analysis