Articles | Volume 18, issue 11
https://doi.org/10.5194/acp-18-8453-2018
© Author(s) 2018. 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-18-8453-2018
© Author(s) 2018. This work is distributed under
the Creative Commons Attribution 4.0 License.
the Creative Commons Attribution 4.0 License.
High-molecular-weight esters in α-pinene ozonolysis secondary organic aerosol: structural characterization and mechanistic proposal for their formation from highly oxygenated molecules
Ariane Kahnt
Department of Pharmaceutical Sciences, University of Antwerp (Campus Drie Eiken), 2610 Antwerp, Belgium
now at: Development Bioanalysis, Janssen R & D, Turnhoutseweg 30, 2340 Beerse, Belgium
Reinhilde Vermeylen
Department of Pharmaceutical Sciences, University of Antwerp (Campus Drie Eiken), 2610 Antwerp, Belgium
now at: Soil Service of Belgium, W. de Croylaan 48, Heverlee, Belgium
Yoshiteru Iinuma
Leibniz-Institut für Troposphärenforschung (TROPOS), Permoserstr. 15, 04318 Leipzig, Germany
now at: Okinawa Institute of Science and Technology Graduate University, 1919-1 Tancha, Onna-son, Kunigami, Okinawa, 904-0495, Japan
Mohammad Safi Shalamzari
Department of Pharmaceutical Sciences, University of Antwerp (Campus Drie Eiken), 2610 Antwerp, Belgium
now at: Dr. Reddy's Laboratories Ltd., Zernikedreef 12, 2333 CL Leiden, the Netherlands
Willy Maenhaut
Department of Chemistry, Ghent University, Krijgslaan 281, S12, 9000 Ghent, Belgium
Department of Pharmaceutical Sciences, University of Antwerp (Campus Drie Eiken), 2610 Antwerp, Belgium
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Cited
38 citations as recorded by crossref.
- The Aarhus Chamber Campaign on Highly Oxygenated Organic Molecules and Aerosols (ACCHA): particle formation, organic acids, and dimer esters from <i>α</i>-pinene ozonolysis at different temperatures K. Kristensen et al. 10.5194/acp-20-12549-2020
- Aging of α-Pinene Secondary Organic Aerosol by Hydroxyl Radicals in the Aqueous Phase: Kinetics and Products B. Witkowski et al. 10.1021/acs.est.2c07630
- Synthesis of Carboxylic Acid and Dimer Ester Surrogates to Constrain the Abundance and Distribution of Molecular Products in α-Pinene and β-Pinene Secondary Organic Aerosol C. Kenseth et al. 10.1021/acs.est.0c01566
- A combined gas- and particle-phase analysis of highly oxygenated organic molecules (HOMs) from α-pinene ozonolysis J. Zhao et al. 10.5194/acp-23-3707-2023
- Phase Behavior of Hydrocarbon-like Primary Organic Aerosol and Secondary Organic Aerosol Proxies Based on Their Elemental Oxygen-to-Carbon Ratio F. Mahrt et al. 10.1021/acs.est.1c02697
- Highly Oxygenated Organic Molecules (HOM) from Gas-Phase Autoxidation Involving Peroxy Radicals: A Key Contributor to Atmospheric Aerosol F. Bianchi et al. 10.1021/acs.chemrev.8b00395
- Particle-phase accretion forms dimer esters in pinene secondary organic aerosol C. Kenseth et al. 10.1126/science.adi0857
- Can Online Aerosol Mass Spectrometry Analysis Classify Secondary Organic Aerosol (SOA) and Oxidized Primary Organic Aerosol (OPOA)? A Case Study of Laboratory and Field Studies of Indonesian Biomass Burning S. Budisulistiorini et al. 10.1021/acsearthspacechem.1c00319
- Prolonged Dark Chemical Processes in Secondary Organic Aerosols on Filters and in Aqueous Solution J. Resch et al. 10.1021/acs.est.4c01647
- On the fate of oxygenated organic molecules in atmospheric aerosol particles V. Pospisilova et al. 10.1126/sciadv.aax8922
- Acylperoxy Radicals as Key Intermediates in the Formation of Dimeric Compounds in α-Pinene Secondary Organic Aerosol Y. Zhao et al. 10.1021/acs.est.2c02090
- Quantitative constraints on autoxidation and dimer formation from direct probing of monoterpene-derived peroxy radical chemistry Y. Zhao et al. 10.1073/pnas.1812147115
- Gas-to-Particle Partitioning of Cyclohexene- and α-Pinene-Derived Highly Oxygenated Dimers Evaluated Using COSMOtherm N. Hyttinen et al. 10.1021/acs.jpca.0c11328
- Reaction between Peroxy and Alkoxy Radicals Can Form Stable Adducts S. Iyer et al. 10.1021/acs.jpclett.9b00405
- Application of time-of-flight aerosol mass spectrometry for the real-time measurement of particle-phase organic peroxides: an online redox derivatization–aerosol mass spectrometer (ORD-AMS) M. Weloe & T. Hoffmann 10.5194/amt-13-5725-2020
- The role of functional groups in the understanding of secondary organic aerosol formation mechanism from α-pinene L. Jia & Y. Xu 10.1016/j.scitotenv.2020.139831
- Particle-Bound Highly Oxidized Organic Molecules Derived from Aromatic Hydrocarbons in an Urban Atmosphere M. Zhu et al. 10.1021/acs.estlett.2c00841
- Aqueous Photochemistry of Secondary Organic Aerosol of α-Pinene and α-Humulene in the Presence of Hydrogen Peroxide or Inorganic Salts A. Klodt et al. 10.1021/acsearthspacechem.9b00222
- Ozonolysis of α-Pinene and Δ3-Carene Mixtures: Formation of Dimers with Two Precursors D. Thomsen et al. 10.1021/acs.est.2c04786
- Effects of NOx and NH3 on the secondary organic aerosol formation from α-pinene photooxidation Y. Zhao et al. 10.1016/j.atmosenv.2024.120778
- Structures and reactivity of peroxy radicals and dimeric products revealed by online tandem mass spectrometry S. Tomaz et al. 10.1038/s41467-020-20532-2
- Organic Peroxides in Aerosol: Key Reactive Intermediates for Multiphase Processes in the Atmosphere S. Wang et al. 10.1021/acs.chemrev.2c00430
- Large differences of highly oxygenated organic molecules (HOMs) and low-volatile species in secondary organic aerosols (SOAs) formed from ozonolysis of β-pinene and limonene D. Liu et al. 10.5194/acp-23-8383-2023
- Quantifying organic matter and functional groups in particulate matter filter samples from the southeastern United States – Part 1: Methods A. Boris et al. 10.5194/amt-12-5391-2019
- Interfacial Dimerization by Organic Radical Reactions during Heterogeneous Oxidative Aging of Oxygenated Organic Aerosols Z. Zhao et al. 10.1021/acs.jpca.9b10779
- Morphology and Viscosity Changes after Reactive Uptake of Isoprene Epoxydiols in Submicrometer Phase Separated Particles with Secondary Organic Aerosol Formed from Different Volatile Organic Compounds Z. Lei et al. 10.1021/acsearthspacechem.1c00156
- Accounting for Cloud Nucleation Activation Mechanism of Secondary Organic Matter from α-Pinene Oxidation Using Experimentally Retrieved Water Solubility Distributions W. Lee et al. 10.1021/acs.est.3c03039
- A new iodometric microwave-assisted method for peroxide determination in Secondary Organic Aerosols D. Alba-Elena et al. 10.1016/j.atmosenv.2023.119960
- Molecular Characterization of Atmospheric Organic Aerosol by Mass Spectrometry M. Johnston & D. Kerecman 10.1146/annurev-anchem-061516-045135
- Molecular and Structural Characterization of Isomeric Compounds in Atmospheric Organic Aerosol Using Ion Mobility-Mass Spectrometry C. West et al. 10.1021/acs.jpca.2c06459
- Analytical optical methods for measuring organic peroxides and hydroperoxides: An evaluation D. Alba-Elena et al. 10.1016/j.atmosenv.2024.120858
- Structural Characterisation of Dimeric Esters in α-Pinene Secondary Organic Aerosol Using N2 and CO2 Ion Mobility Mass Spectrometry Y. Iinuma et al. 10.3390/atmos12010017
- Mass spectrometry-based Aerosolomics: a new approach to resolve sources, composition, and partitioning of secondary organic aerosol M. Thoma et al. 10.5194/amt-15-7137-2022
- The effect of temperature and relative humidity on secondary organic aerosol formation from ozonolysis of Δ3-carene D. Thomsen et al. 10.1039/D3EA00128H
- Large Gas-Phase Source of Esters and Other Accretion Products in the Atmosphere O. Peräkylä et al. 10.1021/jacs.2c10398
- Importance of Hydroxyl Radical Chemistry in Isoprene Suppression of Particle Formation from α-Pinene Ozonolysis Y. Wang et al. 10.1021/acsearthspacechem.0c00294
- Gas-Phase Oxidation of Atmospherically Relevant Unsaturated Hydrocarbons by Acyl Peroxy Radicals D. Pasik et al. 10.1021/jacs.4c02523
- Radical Formation by Fine Particulate Matter Associated with Highly Oxygenated Molecules H. Tong et al. 10.1021/acs.est.9b05149
38 citations as recorded by crossref.
- The Aarhus Chamber Campaign on Highly Oxygenated Organic Molecules and Aerosols (ACCHA): particle formation, organic acids, and dimer esters from <i>α</i>-pinene ozonolysis at different temperatures K. Kristensen et al. 10.5194/acp-20-12549-2020
- Aging of α-Pinene Secondary Organic Aerosol by Hydroxyl Radicals in the Aqueous Phase: Kinetics and Products B. Witkowski et al. 10.1021/acs.est.2c07630
- Synthesis of Carboxylic Acid and Dimer Ester Surrogates to Constrain the Abundance and Distribution of Molecular Products in α-Pinene and β-Pinene Secondary Organic Aerosol C. Kenseth et al. 10.1021/acs.est.0c01566
- A combined gas- and particle-phase analysis of highly oxygenated organic molecules (HOMs) from α-pinene ozonolysis J. Zhao et al. 10.5194/acp-23-3707-2023
- Phase Behavior of Hydrocarbon-like Primary Organic Aerosol and Secondary Organic Aerosol Proxies Based on Their Elemental Oxygen-to-Carbon Ratio F. Mahrt et al. 10.1021/acs.est.1c02697
- Highly Oxygenated Organic Molecules (HOM) from Gas-Phase Autoxidation Involving Peroxy Radicals: A Key Contributor to Atmospheric Aerosol F. Bianchi et al. 10.1021/acs.chemrev.8b00395
- Particle-phase accretion forms dimer esters in pinene secondary organic aerosol C. Kenseth et al. 10.1126/science.adi0857
- Can Online Aerosol Mass Spectrometry Analysis Classify Secondary Organic Aerosol (SOA) and Oxidized Primary Organic Aerosol (OPOA)? A Case Study of Laboratory and Field Studies of Indonesian Biomass Burning S. Budisulistiorini et al. 10.1021/acsearthspacechem.1c00319
- Prolonged Dark Chemical Processes in Secondary Organic Aerosols on Filters and in Aqueous Solution J. Resch et al. 10.1021/acs.est.4c01647
- On the fate of oxygenated organic molecules in atmospheric aerosol particles V. Pospisilova et al. 10.1126/sciadv.aax8922
- Acylperoxy Radicals as Key Intermediates in the Formation of Dimeric Compounds in α-Pinene Secondary Organic Aerosol Y. Zhao et al. 10.1021/acs.est.2c02090
- Quantitative constraints on autoxidation and dimer formation from direct probing of monoterpene-derived peroxy radical chemistry Y. Zhao et al. 10.1073/pnas.1812147115
- Gas-to-Particle Partitioning of Cyclohexene- and α-Pinene-Derived Highly Oxygenated Dimers Evaluated Using COSMOtherm N. Hyttinen et al. 10.1021/acs.jpca.0c11328
- Reaction between Peroxy and Alkoxy Radicals Can Form Stable Adducts S. Iyer et al. 10.1021/acs.jpclett.9b00405
- Application of time-of-flight aerosol mass spectrometry for the real-time measurement of particle-phase organic peroxides: an online redox derivatization–aerosol mass spectrometer (ORD-AMS) M. Weloe & T. Hoffmann 10.5194/amt-13-5725-2020
- The role of functional groups in the understanding of secondary organic aerosol formation mechanism from α-pinene L. Jia & Y. Xu 10.1016/j.scitotenv.2020.139831
- Particle-Bound Highly Oxidized Organic Molecules Derived from Aromatic Hydrocarbons in an Urban Atmosphere M. Zhu et al. 10.1021/acs.estlett.2c00841
- Aqueous Photochemistry of Secondary Organic Aerosol of α-Pinene and α-Humulene in the Presence of Hydrogen Peroxide or Inorganic Salts A. Klodt et al. 10.1021/acsearthspacechem.9b00222
- Ozonolysis of α-Pinene and Δ3-Carene Mixtures: Formation of Dimers with Two Precursors D. Thomsen et al. 10.1021/acs.est.2c04786
- Effects of NOx and NH3 on the secondary organic aerosol formation from α-pinene photooxidation Y. Zhao et al. 10.1016/j.atmosenv.2024.120778
- Structures and reactivity of peroxy radicals and dimeric products revealed by online tandem mass spectrometry S. Tomaz et al. 10.1038/s41467-020-20532-2
- Organic Peroxides in Aerosol: Key Reactive Intermediates for Multiphase Processes in the Atmosphere S. Wang et al. 10.1021/acs.chemrev.2c00430
- Large differences of highly oxygenated organic molecules (HOMs) and low-volatile species in secondary organic aerosols (SOAs) formed from ozonolysis of β-pinene and limonene D. Liu et al. 10.5194/acp-23-8383-2023
- Quantifying organic matter and functional groups in particulate matter filter samples from the southeastern United States – Part 1: Methods A. Boris et al. 10.5194/amt-12-5391-2019
- Interfacial Dimerization by Organic Radical Reactions during Heterogeneous Oxidative Aging of Oxygenated Organic Aerosols Z. Zhao et al. 10.1021/acs.jpca.9b10779
- Morphology and Viscosity Changes after Reactive Uptake of Isoprene Epoxydiols in Submicrometer Phase Separated Particles with Secondary Organic Aerosol Formed from Different Volatile Organic Compounds Z. Lei et al. 10.1021/acsearthspacechem.1c00156
- Accounting for Cloud Nucleation Activation Mechanism of Secondary Organic Matter from α-Pinene Oxidation Using Experimentally Retrieved Water Solubility Distributions W. Lee et al. 10.1021/acs.est.3c03039
- A new iodometric microwave-assisted method for peroxide determination in Secondary Organic Aerosols D. Alba-Elena et al. 10.1016/j.atmosenv.2023.119960
- Molecular Characterization of Atmospheric Organic Aerosol by Mass Spectrometry M. Johnston & D. Kerecman 10.1146/annurev-anchem-061516-045135
- Molecular and Structural Characterization of Isomeric Compounds in Atmospheric Organic Aerosol Using Ion Mobility-Mass Spectrometry C. West et al. 10.1021/acs.jpca.2c06459
- Analytical optical methods for measuring organic peroxides and hydroperoxides: An evaluation D. Alba-Elena et al. 10.1016/j.atmosenv.2024.120858
- Structural Characterisation of Dimeric Esters in α-Pinene Secondary Organic Aerosol Using N2 and CO2 Ion Mobility Mass Spectrometry Y. Iinuma et al. 10.3390/atmos12010017
- Mass spectrometry-based Aerosolomics: a new approach to resolve sources, composition, and partitioning of secondary organic aerosol M. Thoma et al. 10.5194/amt-15-7137-2022
- The effect of temperature and relative humidity on secondary organic aerosol formation from ozonolysis of Δ3-carene D. Thomsen et al. 10.1039/D3EA00128H
- Large Gas-Phase Source of Esters and Other Accretion Products in the Atmosphere O. Peräkylä et al. 10.1021/jacs.2c10398
- Importance of Hydroxyl Radical Chemistry in Isoprene Suppression of Particle Formation from α-Pinene Ozonolysis Y. Wang et al. 10.1021/acsearthspacechem.0c00294
- Gas-Phase Oxidation of Atmospherically Relevant Unsaturated Hydrocarbons by Acyl Peroxy Radicals D. Pasik et al. 10.1021/jacs.4c02523
- Radical Formation by Fine Particulate Matter Associated with Highly Oxygenated Molecules H. Tong et al. 10.1021/acs.est.9b05149
Latest update: 05 Nov 2024
Short summary
High-molecular-weight esters present in α-pinene ozonolysis secondary organic aerosol have been structurally characterized with electrospray ionization mass spectrometry. Unambiguous evidence could be obtained for the linkage in the MW 368 hydroxypinonyl ester of pinic acid, while the same linkage could be supported for the MW 358 diaterpenylic ester of pinic acid. A mechanistic proposal is presented to explain their possible formation from highly oxygenated molecules reported in previous work.
High-molecular-weight esters present in α-pinene ozonolysis secondary organic aerosol have been...
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