Kinetic reaction mechanism of sinapic acid scavenging NO2 and OH Radicals: A theoretical study

Yang Lu; Ai Hua Wang; Peng Shi; Hui Zhang; Ze Sheng Li

doi:10.1371/journal.pone.0162729

Kinetic reaction mechanism of sinapic acid scavenging NO2 and OH Radicals: A theoretical study

Yang Lu, Ai Hua Wang, Peng Shi, Hui Zhang^*, Ze Sheng Li

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Harbin University of Science and Technology

Research output: Contribution to journal › Article › peer-review

17 Citations (Scopus)

Abstract

The mechanism and kinetics underlying reactions between the naturally-occurring antioxidant sinapic acid (SA) and the very damaging NO2 and OH were investigated through the density functional theory (DFT). Two most possible reaction mechanisms were studied: hydrogen atom transfer (HAT) and radical adduct formation (RAF). Different reaction channels of neutral and anionic sinapic acid (SA- ) scavenging radicals in both atmosphere and water medium were traced independently, and the thermodynamic and kinetic parameters were calculated. We find the most active site of SA/SA- scavenging NO2 and OH is the -OH group in benzene ring by HAT mechanism, while the RAF mechanism for SA/SA-scavenging NO2 seems thermodynamically unfavorable. In water phase, at 298 K, the total rate constants of SA eliminating NO2 and OH are 1.30×108 and 9.20×109 M-1 S-1 respectively, indicating that sinapic acid is an efficient scavenger for both NO2 and OH.

Original language	English
Article number	e0162729
Journal	PLoS ONE
Volume	11
Issue number	9
DOIs	https://doi.org/10.1371/journal.pone.0162729
Publication status	Published - Sept 2016

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Lu, Y., Wang, A. H., Shi, P., Zhang, H., & Li, Z. S. (2016). Kinetic reaction mechanism of sinapic acid scavenging NO2 and OH Radicals: A theoretical study. PLoS ONE, 11(9), Article e0162729. https://doi.org/10.1371/journal.pone.0162729

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title = "Kinetic reaction mechanism of sinapic acid scavenging NO2 and OH Radicals: A theoretical study",

abstract = "The mechanism and kinetics underlying reactions between the naturally-occurring antioxidant sinapic acid (SA) and the very damaging NO2 and OH were investigated through the density functional theory (DFT). Two most possible reaction mechanisms were studied: hydrogen atom transfer (HAT) and radical adduct formation (RAF). Different reaction channels of neutral and anionic sinapic acid (SA- ) scavenging radicals in both atmosphere and water medium were traced independently, and the thermodynamic and kinetic parameters were calculated. We find the most active site of SA/SA- scavenging NO2 and OH is the -OH group in benzene ring by HAT mechanism, while the RAF mechanism for SA/SA-scavenging NO2 seems thermodynamically unfavorable. In water phase, at 298 K, the total rate constants of SA eliminating NO2 and OH are 1.30×108 and 9.20×109 M-1 S-1 respectively, indicating that sinapic acid is an efficient scavenger for both NO2 and OH.",

author = "Yang Lu and Wang, {Ai Hua} and Peng Shi and Hui Zhang and Li, {Ze Sheng}",

note = "Publisher Copyright: {\textcopyright} 2016 Lu et al. This is an open access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.",

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T2 - A theoretical study

AU - Lu, Yang

AU - Wang, Ai Hua

AU - Shi, Peng

AU - Zhang, Hui

AU - Li, Ze Sheng

N1 - Publisher Copyright: © 2016 Lu et al. This is an open access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

PY - 2016/9

Y1 - 2016/9

N2 - The mechanism and kinetics underlying reactions between the naturally-occurring antioxidant sinapic acid (SA) and the very damaging NO2 and OH were investigated through the density functional theory (DFT). Two most possible reaction mechanisms were studied: hydrogen atom transfer (HAT) and radical adduct formation (RAF). Different reaction channels of neutral and anionic sinapic acid (SA- ) scavenging radicals in both atmosphere and water medium were traced independently, and the thermodynamic and kinetic parameters were calculated. We find the most active site of SA/SA- scavenging NO2 and OH is the -OH group in benzene ring by HAT mechanism, while the RAF mechanism for SA/SA-scavenging NO2 seems thermodynamically unfavorable. In water phase, at 298 K, the total rate constants of SA eliminating NO2 and OH are 1.30×108 and 9.20×109 M-1 S-1 respectively, indicating that sinapic acid is an efficient scavenger for both NO2 and OH.

AB - The mechanism and kinetics underlying reactions between the naturally-occurring antioxidant sinapic acid (SA) and the very damaging NO2 and OH were investigated through the density functional theory (DFT). Two most possible reaction mechanisms were studied: hydrogen atom transfer (HAT) and radical adduct formation (RAF). Different reaction channels of neutral and anionic sinapic acid (SA- ) scavenging radicals in both atmosphere and water medium were traced independently, and the thermodynamic and kinetic parameters were calculated. We find the most active site of SA/SA- scavenging NO2 and OH is the -OH group in benzene ring by HAT mechanism, while the RAF mechanism for SA/SA-scavenging NO2 seems thermodynamically unfavorable. In water phase, at 298 K, the total rate constants of SA eliminating NO2 and OH are 1.30×108 and 9.20×109 M-1 S-1 respectively, indicating that sinapic acid is an efficient scavenger for both NO2 and OH.

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VL - 11

JO - PLoS ONE

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Kinetic reaction mechanism of sinapic acid scavenging NO2 and OH Radicals: A theoretical study

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