Formic acid catalyzed isomerization and adduct formation of an isoprene-derived Criegee intermediate: experiment and theory

Vansco, Michael F.; Caravan, Rebecca L.; Pandit, Shubhrangshu; Zuraski, Kristen; Winiberg, Frank A. F.; Au, Kendrew; Bhagde, Trisha; Trongsiriwat, Nisalak; Walsh, Patrick J.; Osborn, David L.; Percival, Carl J.; Klippenstein, Stephen J.; Taatjes, Craig A.; Lester, Marsha I.

doi:10.1039/d0cp05018k

Title: Formic acid catalyzed isomerization and adduct formation of an isoprene-derived Criegee intermediate: experiment and theory

Journal Article · Wed Nov 11 00:00:00 EST 2020 · Physical Chemistry Chemical Physics. PCCP

DOI:https://doi.org/10.1039/d0cp05018k· OSTI ID:1738934

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Univ. of Pennsylvania, Philadelphia, PA (United States)
California Institute of Technology (CalTech), Pasadena, CA (United States). Jet Propulsion Lab. (JPL); Sandia National Lab. (SNL-CA), Livermore, CA (United States); Argonne National Lab. (ANL), Argonne, IL (United States)
Univ. of Pennsylvania, Philadelphia, PA (United States); Univ. of California, San Diego, CA (United States)
California Institute of Technology (CalTech), Pasadena, CA (United States). Jet Propulsion Lab. (JPL)
Sandia National Lab. (SNL-CA), Livermore, CA (United States)
Argonne National Lab. (ANL), Argonne, IL (United States)

Isoprene is the most abundant non-methane hydrocarbon emitted into the Earth’s atmosphere. Ozonolysis is an important atmospheric sink for isoprene, which generates reactive carbonyl oxide species (R1R2C=O+O-) known as Criegee intermediates. This study focuses on characterizing the catalyzed isomerization and adduct formation pathways for the reaction between formic acid and methyl vinyl ketone oxide (MVK-oxide), a four-carbon unsaturated Criegee intermediate generated from isoprene ozonolysis. Specific conformational forms of MVK-oxide (syn) undergo intramolecular 1,4 Hatom transfer to form an isomeric vinyl hydroperoxide intermediate, 2-hydroperoxybuta-1,3-diene (HPBD), which subsequently decomposes to hydroxyl and vinoxy radical products. Here, we report direct observation of HPBD generated by formic acid catalyzed isomerization of MVK-oxide under thermal conditions (298 K, 10 Torr) using multiplexed photoionization mass spectrometry. The acid catalyzed isomerization of MVK-oxide proceeds by a double hydrogen-bonded interaction followed by a concerted H-atom transfer via submerged barriers to produce HPBD and regenerate formic acid. The analogous isomerization pathway catalyzed with deuterated formic acid (D2-formic acid) enables migration of a D atom to yield partially deuterated HPBD (DPBD), which is identified by its distinct mass (m/z 87) and photoionization threshold. In addition, bimolecular reaction of MVK-oxide with D2-formic acid forms a functionalized hydroperoxide adduct, which is the dominant product channel, and is compared to a previous bimolecular reaction study with normal formic acid. Complementary high-level theoretical calculations are performed to further investigate the reaction pathways and kinetics.

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Research Organization:: Sandia National Lab. (SNL-CA), Livermore, CA (United States); Argonne National Laboratory (ANL), Argonne, IL (United States); Univ. of Pennsylvania, Philadelphia, PA (United States)

Sponsoring Organization:: USDOE National Nuclear Security Administration (NNSA); USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF); USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division

Grant/Contract Number:: AC04-94AL85000; FG02-87ER13792; NA0003525; AC02-06CH11357; AC02-05CH11231; CHE-1902509

OSTI ID:: 1738934

Alternate ID(s):: OSTI ID: 1720197; OSTI ID: 1775135; OSTI ID: 1782238

Report Number(s):: SAND-2020-13940J; 692938

Journal Information:: Physical Chemistry Chemical Physics. PCCP, Vol. 22, Issue 46; ISSN 1463-9076

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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