Atmospheric oxidation of indene initiated by OH radical in the presence of O2 and NO: A mechanistic and kinetic study

Ding, Zhezheng; Yi, Yayi; Wang, Wenxing; Zhang, Qingzhu

doi:10.1016/j.chemosphere.2020.127331

Cited by 15 publications

(3 citation statements)

References 49 publications

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“…In this work, the Gaussian 09 program was applied to carry out theoretical calculations . The M06-2X level with the 6-31+G(d,p) basis set was used to optimize all of the geometric configurations. , Furthermore, the M06-2X method performed well for reactions of aromatic contaminants initiated by both HO • and SO 4 • – . − In the potential energy surface, all stationary points were determined to be the global minima (except for transition states, all species have zero imaginary frequency). The intrinsic reaction coordinates (IRCs) were calculated to refine reaction channels and ensure the correctness of transition states to corresponding reactants and products .…”

Section: Methodsmentioning

confidence: 99%

Degradation of Diethyl Phthalate by HO^• and SO₄^• ^– in the Aqueous Phase: Mechanisms, Kinetics, and Toxicity

Han

Yin

Zhao

2023

ACS Earth Space Chem.

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The chemical degradation processes of diethyl phthalate (DEP) induced by HO • and SO 4• − in aqueous solution were studied in a theoretical way. Not only radical addition and H-abstraction reactions but also singleelectron transfer processes of DEP were considered. The thermodynamic and kinetic results indicate that the more favorable pathways are the H abstraction occurring in aliphatic side chains for all HO • /SO 4• − -initiated degradation reactions of DEP. Subsequent reaction mechanisms of crucial primary intermediates were taken into account. At 298 K, the total rate constants for DEP degradation reactions induced by HO • and SO 4• − are 2.34 × 10 9 and 1.24 × 10 8 M −1 s −1 , respectively. They are in accordance with the experimental data. In comparison to SO 4• − , HO • has higher reactivity toward DEP in the research temperature range of 273−303 K. Considering the impact on the water ecoenvironment and human health, DEP and its 10 products have no bioaccumulation potential, but most products are developmentally toxic, except for (Z)-ethyl-2,5-dioxopent-3-enoate. Moreover, (Z)-ethyl-2,5-dioxopent-3-enoate is acutely toxic to fish; phthalic acid is mutagenicity positive; and we should pay more attention to them in the future.

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Section: Methodsmentioning

confidence: 99%

Degradation of Diethyl Phthalate by HO^• and SO₄^• ^– in the Aqueous Phase: Mechanisms, Kinetics, and Toxicity

Han

Yin

Zhao

2023

ACS Earth Space Chem.

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“…Similar to other C-centered radicals (Zhang et al, 2012;Guo et al, 2020;F. F. Ma et al, 2021a;Yu et al, 2016Yu et al, , 2017Ji et al, 2017;Ding et al, 2020a), the intermediates IM 1−7 , IM 2−5 and IM 2−6 will subsequently react with O 2 . Two different pathways (Fig.…”

Section: Subsequent Reactions Of Addition Intermediatesmentioning

confidence: 99%

Atmospheric oxidation mechanism and kinetics of indole initiated by ●OH and ●Cl: a computational study

Xue

Elm

et al. 2022

Atmos. Chem. Phys.

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Abstract. The atmospheric chemistry of organic nitrogen compounds (ONCs) is of great importance for understanding the formation of carcinogenic nitrosamines, and ONC oxidation products might influence atmospheric aerosol particle formation and growth. Indole is a polyfunctional heterocyclic secondary amine with a global emission quantity almost equivalent to that of trimethylamine, the amine with the highest atmospheric emission. However, the atmospheric chemistry of indole remains unclear. Herein, the reactions of indole with ⚫OH and ⚫Cl, and subsequent reactions of resulting indole radicals with O2 under 200 ppt NO and 50 ppt HO2⚫ conditions, were investigated by a combination of quantum chemical calculations and kinetics modeling. The results indicate that ⚫OH addition is the dominant pathway for the reaction of ⚫OH with indole. However, both ⚫Cl addition and H abstraction are feasible for the corresponding reaction with ⚫Cl. All favorably formed indole radicals further react with O2 to produce peroxy radicals, which mainly react with NO and HO2⚫ to form organonitrates, alkoxy radicals and hydroperoxide products. Therefore, the oxidation mechanism of indole is distinct from that of previously reported amines, which primarily form highly oxidized multifunctional compounds, imines or carcinogenic nitrosamines. In addition, the peroxy radicals from the ⚫OH reaction can form N-(2-formylphenyl)formamide (C8H7NO2), for the first time providing evidence for the chemical identity of the C8H7NO2 mass peak observed in the ⚫OH + indole experiments. More importantly, this study is the first to demonstrate that despite forming radicals by abstracting an H atom at the N site, carcinogenic nitrosamines were not produced in the indole oxidation reaction.

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“…22 The M06-2X functional has been widely used to calculate organic compounds with satisfying accuracy in calculating the large-scale conjugated system. [23][24][25][26][27][28] To further verify the reliability of the M06-2X functional, we used CBS-QB3, MPWB1K and WB97XD methods to calculate the energy barriers (DG*) of several initial reactions, which can be used to suggest favorable pathways in the initial reaction of IBU and OH. [29][30][31] The results are listed in Table S1 of the ESI.…”

Section: Quantum Chemical Calculationmentioning

confidence: 99%

New insights into the degradation mechanism of ibuprofen in the UV/H₂O₂ process: role of natural dissolved matter in hydrogen transfer reactions

Ding,

Zhang,

Fang

et al. 2023

Phys. Chem. Chem. Phys.

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Atmospheric oxidation of indene initiated by OH radical in the presence of O2 and NO: A mechanistic and kinetic study

Cited by 15 publications

References 49 publications

Degradation of Diethyl Phthalate by HO^• and SO₄^• ^– in the Aqueous Phase: Mechanisms, Kinetics, and Toxicity

Degradation of Diethyl Phthalate by HO^• and SO₄^• ^– in the Aqueous Phase: Mechanisms, Kinetics, and Toxicity

Atmospheric oxidation mechanism and kinetics of indole initiated by ●OH and ●Cl: a computational study

New insights into the degradation mechanism of ibuprofen in the UV/H₂O₂ process: role of natural dissolved matter in hydrogen transfer reactions

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Atmospheric oxidation of indene initiated by OH radical in the presence of O2 and NO: A mechanistic and kinetic study

Cited by 15 publications

References 49 publications

Degradation of Diethyl Phthalate by HO• and SO4• – in the Aqueous Phase: Mechanisms, Kinetics, and Toxicity

Degradation of Diethyl Phthalate by HO• and SO4• – in the Aqueous Phase: Mechanisms, Kinetics, and Toxicity

Atmospheric oxidation mechanism and kinetics of indole initiated by ●OH and ●Cl: a computational study

New insights into the degradation mechanism of ibuprofen in the UV/H2O2 process: role of natural dissolved matter in hydrogen transfer reactions

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Degradation of Diethyl Phthalate by HO^• and SO₄^• ^– in the Aqueous Phase: Mechanisms, Kinetics, and Toxicity

Degradation of Diethyl Phthalate by HO^• and SO₄^• ^– in the Aqueous Phase: Mechanisms, Kinetics, and Toxicity

New insights into the degradation mechanism of ibuprofen in the UV/H₂O₂ process: role of natural dissolved matter in hydrogen transfer reactions