Isomerization of Second-Generation Isoprene Peroxy Radicals: Epoxide Formation and Implications for Secondary Organic Aerosol Yields

D’Ambro, Emma L.; Møller, Kristian H.; Lopez-Hilfiker, Felipe D.; Schobesberger, Siegfried; Liu, Jiumeng; Shilling, John E.; Lee, Ben Hwan; Kjaergaard, Henrik G.; Thornton, Joel A.

doi:10.1021/acs.est.7b00460

Title: Isomerization of Second-Generation Isoprene Peroxy Radicals: Epoxide Formation and Implications for Secondary Organic Aerosol Yields

Journal Article · Fri Apr 07 00:00:00 EDT 2017 · Environmental Science and Technology

DOI:https://doi.org/10.1021/acs.est.7b00460· OSTI ID:1390604

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^[2]; Lopez-Hilfiker, Felipe D. ^[3]; Schobesberger, Siegfried ^[3]; Liu, Jiumeng ^[4]; Shilling, John E. ^[5]; Lee, Ben Hwan ^[3];

^[2];

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Univ. of Washington, Seattle, WA (United States). Dept. of Atmospheric Sciences, Dept. of Chemistry
Univ. of Copenhagen (Denmark). Dept. of Chemistry
Univ. of Washington, Seattle, WA (United States). Dept. of Atmospheric Sciences
Pacific Northwest National Lab. (PNNL), Richland, WA (United States). Atmospheric Sciences and Global Change Division
Pacific Northwest National Lab. (PNNL), Richland, WA (United States). Atmospheric Sciences and Global Change Division, Environmental Molecular Sciences Lab.

Here, we report chamber measurements of secondary organic aerosol (SOA) formation from isoprene photochemical oxidation, in which radical concentrations were systematically varied and the molecular composition of semi- to low-volatility gases and SOA were measured online. Using a detailed chemical kinetics box model, we find that to explain the behavior of low-volatility products and SOA mass yields relative to input H₂O₂ concentrations, the secondgeneration dihydroxy hydroperoxy peroxy radical (C₅H₁₁O₆·) must undergo an intramolecular H-shift with a net forward rate constant of order 0.1 s^-1 or higher. Our finding is consistent with quantum chemical calculations that suggest a net forward rate constant of 0.3-0.9 s^-1 . Furthermore, these calculations suggest that the dominant product of this isomerization is a dihydroxy hydroperoxy epoxide (C₅H₁₀O₅), which is expected to have a saturation vapor pressure ~2 orders of magnitude higher, as determined by group-contribution calculations, than the dihydroxy dihydroperoxide, ISOP(OOH)₂(C₅H₁₂O₆), a major product of the peroxy radical reacting with HO₂. These results provide strong constraints on the likely volatility distribution of isoprene oxidation products under atmospheric conditions and, thus, on the importance of nonreactive gas-particle partitioning of isoprene oxidation products as an SOA source.

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Research Organization:: Univ. of Washington, Seattle, WA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Biological and Environmental Research (BER); National Science Foundation (NSF)

Grant/Contract Number:: SC0011791; DGE-1256082; AC05-76RL01830

OSTI ID:: 1390604

Journal Information:: Environmental Science and Technology, Vol. 51, Issue 9; ISSN 0013-936X

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 46 works

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