Four-Carbon Criegee Intermediate from Isoprene Ozonolysis: Methyl Vinyl Ketone Oxide Synthesis, Infrared Spectrum, and OH Production

Barber, Victoria P.; Pandit, Shubhrangshu; Green, Amy M.; Trongsiriwat, Nisalak; Walsh, Patrick J.; Klippenstein, Stephen J.; Lester, Marsha I.

doi:10.1021/jacs.8b06010

Title: Four-Carbon Criegee Intermediate from Isoprene Ozonolysis: Methyl Vinyl Ketone Oxide Synthesis, Infrared Spectrum, and OH Production

Journal Article · 03 August 2018 · Journal of the American Chemical Society

DOI: https://doi.org/10.1021/jacs.8b06010 · OSTI ID:1598267

Barber, Victoria P. ^[1]; Pandit, Shubhrangshu ^[1]; Green, Amy M. ^[1]; Trongsiriwat, Nisalak ^[1];

^[1];

^[2];

^[1]

Univ. of Pennsylvania, Philadelphia, PA (United States)
Argonne National Lab. (ANL), Argonne, IL (United States)

The reaction of ozone with isoprene, one of the most abundant volatile organic compounds in the atmosphere, produces three distinct carbonyl oxide species (RR'COO) known as Criegee intermediates: formaldehyde oxide (CH₂OO), methyl vinyl ketone oxide (MVK-OO), and methacrolein oxide (MACR-OO). The nature of the substituents (R,R' = H, CH₃, CH＝CH₂) and conformations of the Criegee intermediates control their subsequent chemistry in the atmosphere. In particular, unimolecular decay of MVK-OO is predicted to be the major source of hydroxyl radicals (OH) in isoprene ozonolysis. Our study reports the initial laboratory synthesis and direct detection of MVK-OO through reaction of a photolytically generated, resonance-stabilized monoiodoalkene radical with O₂. MVK-OO is characterized utilizing infrared (IR) action spectroscopy, in which IR activation of MVK-OO with two quanta of CH stretch at ca. 6000 cm^–1 is coupled with ultraviolet detection of the resultant OH products. MVK-OO is identified by comparison of the experimentally observed IR spectral features with theoretically predicted IR absorption spectra. For syn-MVK-OO, the rate of appearance of OH products agrees with the unimolecular decay rate predicted using statistical theory with tunneling. This validates the hydrogen atom transfer mechanism and computed transition-state barrier (18.0 kcal mol^–1) leading to OH products. Theoretical calculations display a further roaming pathway between the separating radical fragments, which results in other products. Master equation modeling yields a thermal unimolecular decay rate for syn-MVK-OO of 33 s^–1 (298 K, 1 atm). For anti-MVK-OO, theoretical exploration of several unimolecular decay pathways predicts that isomerization to dioxole is the most likely initial step to products.

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Research Organization:: Univ. of Pennsylvania, Philadelphia, PA (United States); Argonne National Laboratory (ANL), Argonne, IL (United States)

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

Grant/Contract Number:: FG02-87ER13792; AC02-06CH11357; CHE-1664572; CHE-1464744; DMR-1628407

OSTI ID:: 1598267

Journal Information:: Journal of the American Chemical Society, Vol. 140, Issue 34; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 98 works

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