Articles | Volume 19, issue 6
https://doi.org/10.5194/acp-19-4075-2019
© Author(s) 2019. This work is distributed under
the Creative Commons Attribution 4.0 License.
the Creative Commons Attribution 4.0 License.
https://doi.org/10.5194/acp-19-4075-2019
© Author(s) 2019. This work is distributed under
the Creative Commons Attribution 4.0 License.
the Creative Commons Attribution 4.0 License.
Research article
| 
02 Apr 2019
Research article |
| 02 Apr 2019
| 02 Apr 2019
Mechanistic and kinetics investigations of oligomer formation from Criegee intermediate reactions with hydroxyalkyl hydroperoxides
Long Chen
Key Lab of Aerosol Chemistry & Physics, Institute of Earth Environment, Chinese Academy of Sciences, Xi'an, Shaanxi, 710061, China
State Key Laboratory of Loess and Quaternary Geology, Institute of Earth Environment, Chinese Academy of Sciences, Xi'an 710061, China
CAS Center for Excellence in Quaternary Science and Global Change, Xi'an 710061, China
Yu Huang
CORRESPONDING AUTHOR
Key Lab of Aerosol Chemistry & Physics, Institute of Earth Environment, Chinese Academy of Sciences, Xi'an, Shaanxi, 710061, China
State Key Laboratory of Loess and Quaternary Geology, Institute of Earth Environment, Chinese Academy of Sciences, Xi'an 710061, China
CAS Center for Excellence in Quaternary Science and Global Change, Xi'an 710061, China
Yonggang Xue
Key Lab of Aerosol Chemistry & Physics, Institute of Earth Environment, Chinese Academy of Sciences, Xi'an, Shaanxi, 710061, China
State Key Laboratory of Loess and Quaternary Geology, Institute of Earth Environment, Chinese Academy of Sciences, Xi'an 710061, China
CAS Center for Excellence in Quaternary Science and Global Change, Xi'an 710061, China
Zhenxing Shen
Department of Environmental Sciences and Engineering, Xi'an Jiaotong University, Xi'an, 710049, China
Junji Cao
CORRESPONDING AUTHOR
Key Lab of Aerosol Chemistry & Physics, Institute of Earth Environment, Chinese Academy of Sciences, Xi'an, Shaanxi, 710061, China
State Key Laboratory of Loess and Quaternary Geology, Institute of Earth Environment, Chinese Academy of Sciences, Xi'an 710061, China
CAS Center for Excellence in Quaternary Science and Global Change, Xi'an 710061, China
Wenliang Wang
School of Chemistry and Chemical Engineering, Key Laboratory for Macromolecular Science of
Shaanxi Province, Shaanxi Normal University, Xi'an, Shaanxi, 710119, China
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Cited
26 citations as recorded by crossref.
- Quantification of the role of stabilized Criegee intermediates in the formation of aerosols in limonene ozonolysis Y. Gong & Z. Chen 10.5194/acp-21-813-2021
- Oligomer formation from the gas-phase reactions of Criegee intermediates with hydroperoxide esters: mechanism and kinetics L. Chen et al. 10.5194/acp-22-14529-2022
- OH-initiated atmospheric degradation of hydroxyalkyl hydroperoxides: mechanism, kinetics, and structure–activity relationship L. Chen et al. 10.5194/acp-22-3693-2022
- Barrierless reactions of C2 Criegee intermediates with H2SO4 and their implication to oligomers and new particle formation Y. Cheng et al. 10.1016/j.jes.2023.12.020
- Important Oxidants and Their Impact on the Environmental Effects of Aerosols M. Ge et al. 10.1021/acs.jpca.0c10236
- Contrasting impacts of humidity on the ozonolysis of monoterpenes: insights into the multi-generation chemical mechanism S. Zhang et al. 10.5194/acp-23-10809-2023
- Impact of temperature on the role of Criegee intermediates and peroxy radicals in dimer formation from β-pinene ozonolysis Y. Gong et al. 10.5194/acp-24-167-2024
- Effect of NO2 on nocturnal chemistry of isoprene: Gaseous oxygenated products and secondary organic aerosol formation Y. Chen et al. 10.1016/j.scitotenv.2022.156908
- Proton-Catalyzed Decomposition of α-Hydroxyalkyl-Hydroperoxides in Water J. Qiu et al. 10.1021/acs.est.0c03438
- Reaction mechanism and kinetics of Criegee intermediate and hydroperoxymethyl formate M. Chen et al. 10.1016/j.jes.2020.12.029
- Bimolecular sinks of Criegee intermediates derived from hydrofluoroolefins – a computational analysis N. Watson & J. Beames 10.1039/D3EA00102D
- Unusual Diradical Intermediates in Ozonolysis of Alkenes: A Combined Theoretical and Synchrotron Radiation Photoionization Mass Spectrometric Study on Ozonolysis of Alkyl Vinyl Ethers H. Fan et al. 10.1021/acs.jpca.2c04382
- Theoretical reinvestigation of the ozonolysis mechanism of allyl alcohol X. Lei et al. 10.1002/qua.26387
- A theoretical study of the addition of CH2OO to hydroxymethyl hydroperoxide and its implications on SO3 formation in the atmosphere R. Chow & D. Mok 10.1039/D0CP00961J
- Observational evidence for Criegee intermediate oligomerization reactions relevant to aerosol formation in the troposphere R. Caravan et al. 10.1038/s41561-023-01361-6
- Pressure and temperature dependent kinetics and the reaction mechanism of Criegee intermediates with vinyl alcohol: a theoretical study C. Sun et al. 10.1039/D3CP06115A
- Multiple evaluations of atmospheric behavior between Criegee intermediates and HCHO: Gas-phase and air-water interface reaction T. Zhang et al. 10.1016/j.jes.2022.06.004
- Nontrivial Impact of Relative Humidity on Organic New Particle Formation from Ozonolysis of cis-3-Hexenyl Acetate A. Flueckiger et al. 10.3390/air1040017
- Atmospheric oxidation of 1-butene initiated by OH radical: Implications for ozone and nitrous acid formations L. Chen et al. 10.1016/j.atmosenv.2020.118010
- Kinetics for the reaction of Criegee intermediate CH2OO with n-butyraldehyde and its atmospheric implications S. Liu et al. 10.1016/j.atmosenv.2023.120012
- Rapid Atmospheric Reactions between Criegee Intermediates and Hypochlorous Acid Y. Zhang et al. 10.1021/acs.jpca.3c06144
- Theoretical Investigations of the OH-Initialized Oxidation of 4-Methyl-3-Penten-2-One in the Atmosphere B. Du & W. Zhang 10.1021/acsearthspacechem.2c00231
- New insights into the mechanism and kinetics of the addition reaction of unsaturated Criegee intermediates to CF3COOH and tropospheric implications M. Lily et al. 10.1039/D3EM00554B
- Highly time-resolved chemical characterization and implications of regional transport for submicron aerosols in the North China Plain J. Li et al. 10.1016/j.scitotenv.2019.135803
- The spatiotemporal variation of PM2.5-O3 association and its influencing factors across China: Dynamic Simil-Hu lines C. Chen et al. 10.1016/j.scitotenv.2023.163346
- Quantification of primary and secondary sources to PM2.5 using an improved source regional apportionment method in an industrial city, China Y. Hao et al. 10.1016/j.scitotenv.2019.135715
23 citations as recorded by crossref.
- Quantification of the role of stabilized Criegee intermediates in the formation of aerosols in limonene ozonolysis Y. Gong & Z. Chen 10.5194/acp-21-813-2021
- Oligomer formation from the gas-phase reactions of Criegee intermediates with hydroperoxide esters: mechanism and kinetics L. Chen et al. 10.5194/acp-22-14529-2022
- OH-initiated atmospheric degradation of hydroxyalkyl hydroperoxides: mechanism, kinetics, and structure–activity relationship L. Chen et al. 10.5194/acp-22-3693-2022
- Barrierless reactions of C2 Criegee intermediates with H2SO4 and their implication to oligomers and new particle formation Y. Cheng et al. 10.1016/j.jes.2023.12.020
- Important Oxidants and Their Impact on the Environmental Effects of Aerosols M. Ge et al. 10.1021/acs.jpca.0c10236
- Contrasting impacts of humidity on the ozonolysis of monoterpenes: insights into the multi-generation chemical mechanism S. Zhang et al. 10.5194/acp-23-10809-2023
- Impact of temperature on the role of Criegee intermediates and peroxy radicals in dimer formation from β-pinene ozonolysis Y. Gong et al. 10.5194/acp-24-167-2024
- Effect of NO2 on nocturnal chemistry of isoprene: Gaseous oxygenated products and secondary organic aerosol formation Y. Chen et al. 10.1016/j.scitotenv.2022.156908
- Proton-Catalyzed Decomposition of α-Hydroxyalkyl-Hydroperoxides in Water J. Qiu et al. 10.1021/acs.est.0c03438
- Reaction mechanism and kinetics of Criegee intermediate and hydroperoxymethyl formate M. Chen et al. 10.1016/j.jes.2020.12.029
- Bimolecular sinks of Criegee intermediates derived from hydrofluoroolefins – a computational analysis N. Watson & J. Beames 10.1039/D3EA00102D
- Unusual Diradical Intermediates in Ozonolysis of Alkenes: A Combined Theoretical and Synchrotron Radiation Photoionization Mass Spectrometric Study on Ozonolysis of Alkyl Vinyl Ethers H. Fan et al. 10.1021/acs.jpca.2c04382
- Theoretical reinvestigation of the ozonolysis mechanism of allyl alcohol X. Lei et al. 10.1002/qua.26387
- A theoretical study of the addition of CH2OO to hydroxymethyl hydroperoxide and its implications on SO3 formation in the atmosphere R. Chow & D. Mok 10.1039/D0CP00961J
- Observational evidence for Criegee intermediate oligomerization reactions relevant to aerosol formation in the troposphere R. Caravan et al. 10.1038/s41561-023-01361-6
- Pressure and temperature dependent kinetics and the reaction mechanism of Criegee intermediates with vinyl alcohol: a theoretical study C. Sun et al. 10.1039/D3CP06115A
- Multiple evaluations of atmospheric behavior between Criegee intermediates and HCHO: Gas-phase and air-water interface reaction T. Zhang et al. 10.1016/j.jes.2022.06.004
- Nontrivial Impact of Relative Humidity on Organic New Particle Formation from Ozonolysis of cis-3-Hexenyl Acetate A. Flueckiger et al. 10.3390/air1040017
- Atmospheric oxidation of 1-butene initiated by OH radical: Implications for ozone and nitrous acid formations L. Chen et al. 10.1016/j.atmosenv.2020.118010
- Kinetics for the reaction of Criegee intermediate CH2OO with n-butyraldehyde and its atmospheric implications S. Liu et al. 10.1016/j.atmosenv.2023.120012
- Rapid Atmospheric Reactions between Criegee Intermediates and Hypochlorous Acid Y. Zhang et al. 10.1021/acs.jpca.3c06144
- Theoretical Investigations of the OH-Initialized Oxidation of 4-Methyl-3-Penten-2-One in the Atmosphere B. Du & W. Zhang 10.1021/acsearthspacechem.2c00231
- New insights into the mechanism and kinetics of the addition reaction of unsaturated Criegee intermediates to CF3COOH and tropospheric implications M. Lily et al. 10.1039/D3EM00554B
3 citations as recorded by crossref.
- Highly time-resolved chemical characterization and implications of regional transport for submicron aerosols in the North China Plain J. Li et al. 10.1016/j.scitotenv.2019.135803
- The spatiotemporal variation of PM2.5-O3 association and its influencing factors across China: Dynamic Simil-Hu lines C. Chen et al. 10.1016/j.scitotenv.2023.163346
- Quantification of primary and secondary sources to PM2.5 using an improved source regional apportionment method in an industrial city, China Y. Hao et al. 10.1016/j.scitotenv.2019.135715
Latest update: 18 Apr 2024
Short summary
The present calculations show that the sequential addition of CIs to HHPs affords oligomers containing CIs as chain units. The addition of an –OOH group in HHPs to the central carbon atom of CIs is identified as the most energetically favorable channel, with a barrier height strongly dependent on both CI substituent number (one or two) and position (syn- or anti-). In particular, the introduction of a methyl group into the anti-position significantly increases the rate coefficient.
The present calculations show that the sequential addition of CIs to HHPs affords oligomers...
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