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

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

Journal Article · Tue Jul 31 04:00:00 EDT 2018 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.8b06010· OSTI ID:1477500

Barber, Victoria P. ^[1]; Pandit, Shubhrangshu ^[1]; Green, Amy M. ^[1]; Trongsiriwat, Nisalak ^[1]; ^[1]; ^[2]; ^[1]

Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, United States
Chemical Sciences and Engineering Division, Argonne National Laboratory, Argonne, Illinois 60439, 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. This study reports the initial laboratory synthesis and direct detection of MVK-OO through reaction of a photolytically generated, resonance-stabilized monoiodoalkene radical with O-2. 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 reveal an additional 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.

Research Organization:: Argonne National Laboratory (ANL)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

DOE Contract Number:: AC02-06CH11357

OSTI ID:: 1477500

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

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

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