Dramatic Conformer-Dependent Reactivity of the Acetaldehyde Oxide Criegee Intermediate with Dimethylamine Via a 1,2-Insertion Mechanism

Vansco, Michael F.; Zou, Meijun; Antonov, Ivan O.; Ramasesha, Krupa; Rotavera, Brandon; Osborn, David L.; Georgievskii, Yuri; Percival, Carl J.; Klippenstein, Stephen J.; Taatjes, Craig A.; Lester, Marsha I.; Caravan, Rebecca L.

doi:10.1021/acs.jpca.1c08941

Title: Dramatic Conformer-Dependent Reactivity of the Acetaldehyde Oxide Criegee Intermediate with Dimethylamine Via a 1,2-Insertion Mechanism

Journal Article · Thu Dec 23 00:00:00 EST 2021 · Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory

DOI:https://doi.org/10.1021/acs.jpca.1c08941· OSTI ID:1865338

Vansco, Michael F. ^[1]; Zou, Meijun ^[2]; Antonov, Ivan O. ^[3];

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Argonne National Lab. (ANL), Lemont, IL (United States)
Univ. of Pennsylvania, Philadelphia, PA (United States)
Northwestern Univ., Evanston, IL (United States); Sandia National Lab. (SNL-CA), Livermore, CA (United States)
Sandia National Lab. (SNL-CA), Livermore, CA (United States)
Sandia National Lab. (SNL-CA), Livermore, CA (United States); Univ. of Georgia, Athens, GA (United States)
Sandia National Lab. (SNL-CA), Livermore, CA (United States); Univ. of California, Davis, CA (United States)
California Institute of Technology (CalTech), Pasadena, CA (United States)
Argonne National Lab. (ANL), Lemont, IL (United States); Sandia National Lab. (SNL-CA), Livermore, CA (United States)

The reactivity of carbonyl oxides has previously been shown to exhibit strong conformer and substituent dependencies. Through a combination of synchrotron multiplexed photoionization mass spectrometry experiments (298 K, 4 Torr) and high-level theory (CCSD(T)-F12/cc-pVTZ-F12//B2PLYP-D3/cc-pVTZ with an added CCSDT(Q) correction), we explore the conformer dependence of the reaction of acetaldehyde oxide (CH₃CHOO) with dimethyl amine (DMA). The experimental data supports the theoretically predicted 1,2-insertion mechanism and the formation of an amine-functionalized hydroperoxide reaction product. Tunable-VUV photoionization probing of anti- or anti- + syn-CH₃CHOO reveals a strong conformer dependence of the title reaction. Here, the rate coefficient of DMA with anti-CH₃CHOO is predicted to exceed that for the reaction with syn-CH₃CHOO by a factor of ~34,000, which is attributed to submerged barrier (syn) vs. barrierless (anti) mechanisms for energetically downhill reactions.

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Research Organization:: Univ. of Pennsylvania, Philadelphia, PA (United States); Sandia National Lab. (SNL-NM), Albuquerque, NM (United States); Sandia National Lab. (SNL-CA), Livermore, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division

Grant/Contract Number:: FG02-87ER13792; AC02-06CH11357; AC02-05CH11231; NA0003525

OSTI ID:: 1865338

Alternate ID(s):: OSTI ID: 1887413

Report Number(s):: SAND2022-11977J; TRN: US2305855

Journal Information:: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory, Vol. 126, Issue 5; ISSN 1089-5639

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

References (46)

Observation of hydroperoxyethyl formate from the reaction between the methyl Criegee intermediate and formic acid Cabezas, Carlos; Endo, Yasuki Physical Chemistry Chemical Physics, Vol. 22, Issue 2 https://doi.org/10.1039/c9cp05030b	journal	January 2020
Formation of secondary organic aerosol from the reaction of styrene with ozone in the presence and absence of ammonia and water Na, K.; Song, C.; Cockeriii, D. Atmospheric Environment, Vol. 40, Issue 10 https://doi.org/10.1016/j.atmosenv.2005.10.063	journal	March 2006
Effect of Ammonia on Secondary Organic Aerosol Formation from α-Pinene Ozonolysis in Dry and Humid Conditions Na, Kwangsam; Song, Chen; Switzer, Cameron Environmental Science & Technology, Vol. 41, Issue 17 https://doi.org/10.1021/es061956y	journal	September 2007
Aerosol formation from sulphur dioxide in the presence of ozone and olefinic hydrocarbons Cox, R. A.; Penkett, S. A. Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases, Vol. 68, Issue 0 https://doi.org/10.1039/f19726801735	journal	January 1972
Observations and Contributions of Real-Time Indoor Ammonia Concentrations during HOMEChem Ampollini, Laura; Katz, Erin F.; Bourne, Stephen Environmental Science & Technology, Vol. 53, Issue 15 https://doi.org/10.1021/acs.est.9b02157	journal	June 2019
Temperature and isotope effects in the reaction of CH 3 CHOO with methanol Chao, Wen; Lin, Yen-Hsiu; Yin, Cangtao Physical Chemistry Chemical Physics, Vol. 21, Issue 25 https://doi.org/10.1039/c9cp02534k	journal	January 2019
Elucidating the molecular mechanisms of Criegee-amine chemistry in the gas phase and aqueous surface environments Kumar, Manoj; Francisco, Joseph S. Chemical Science, Vol. 10, Issue 3 https://doi.org/10.1039/c8sc03514h	journal	January 2019
The Criegee intermediate-formic acid reaction explored by rotational spectroscopy Cabezas, Carlos; Endo, Yasuki Physical Chemistry Chemical Physics, Vol. 21, Issue 33 https://doi.org/10.1039/c9cp03001h	journal	January 2019
Detection and Identification of the Keto-Hydroperoxide (HOOCH ₂ OCHO) and Other Intermediates during Low-Temperature Oxidation of Dimethyl Ether Moshammer, Kai; Jasper, Ahren W.; Popolan-Vaida, Denisia M. The Journal of Physical Chemistry A, Vol. 119, Issue 28 https://doi.org/10.1021/acs.jpca.5b00101	journal	February 2015
Synergy of Water and Ammonia Hydrogen Bonding in a Gas-Phase Reaction Chao, Wen; Yin, Cangtao; Li, Yu-Lin The Journal of Physical Chemistry A, Vol. 123, Issue 7 https://doi.org/10.1021/acs.jpca.9b00672	journal	January 2019
Oxidation of Atmospheric SO2 by Products of the Ozone–Olefin Reaction Cox, R. A.; Penkett, S. A. Nature, Vol. 230, Issue 5292 https://doi.org/10.1038/230321a0	journal	April 1971
Kinetics of the Reactions between the Criegee Intermediate CH ₂ OO and Alcohols Tadayon, Sara V.; Foreman, Elizabeth S.; Murray, Craig The Journal of Physical Chemistry A, Vol. 122, Issue 1 https://doi.org/10.1021/acs.jpca.7b09773	journal	December 2017
Direct kinetic measurements and theoretical predictions of an isoprene-derived Criegee intermediate Caravan, Rebecca L.; Vansco, Michael F.; Au, Kendrew Proceedings of the National Academy of Sciences, Vol. 117, Issue 18 https://doi.org/10.1073/pnas.1916711117	journal	April 2020
A new atmospherically relevant oxidant of sulphur dioxide Mauldin III, R. L.; Berndt, T.; Sipilä, M. Nature, Vol. 488, Issue 7410 https://doi.org/10.1038/nature11278	journal	August 2012
Determination of aniline and related mono-aromatic amines in indoor air in selected Canadian residences by a modified thermal desorption GC/MS method Zhu, Jiping; Aikawa, Bio Environment International, Vol. 30, Issue 2 https://doi.org/10.1016/s0160-4120(03)00168-5	journal	April 2004
The atmospheric importance of methylamine additions to Criegee intermediates Mull, Henry F.; Aroeira, Gustavo J. R.; Turney, Justin M. Physical Chemistry Chemical Physics, Vol. 22, Issue 39 https://doi.org/10.1039/d0cp03781h	journal	January 2020
Oxidation of SO ₂ by stabilized Criegee intermediate (sCI) radicals as a crucial source for atmospheric sulfuric acid concentrations Boy, M.; Mogensen, D.; Smolander, S. Atmospheric Chemistry and Physics, Vol. 13, Issue 7 https://doi.org/10.5194/acp-13-3865-2013	journal	January 2013
Particulate air pollution and acute health effects Seaton, A.; Godden, D.; MacNee, W. The Lancet, Vol. 345, Issue 8943 https://doi.org/10.1016/s0140-6736(95)90173-6	journal	January 1995
The multiplexed chemical kinetic photoionization mass spectrometer: A new approach to isomer-resolved chemical kinetics Osborn, David L.; Zou, Peng; Johnsen, Howard Review of Scientific Instruments, Vol. 79, Issue 10 https://doi.org/10.1063/1.3000004	journal	October 2008
Temperature dependence of the reaction of anti-CH ₃ CHOO with water vapor Lin, Liang-Chun; Chao, Wen; Chang, Chun-Hung Physical Chemistry Chemical Physics, Vol. 18, Issue 40 https://doi.org/10.1039/c6cp05171e	journal	January 2016
Formic acid catalyzed isomerization and adduct formation of an isoprene-derived Criegee intermediate: experiment and theory Vansco, Michael F.; Caravan, Rebecca L.; Pandit, Shubhrangshu Physical Chemistry Chemical Physics, Vol. 22, Issue 46 https://doi.org/10.1039/d0cp05018k	journal	January 2020
Kinetics of the reaction of the simplest Criegee intermediate with ammonia: a combination of experiment and theory Liu, Yiqiang; Yin, Cangtao; Smith, Mica C. Physical Chemistry Chemical Physics, Vol. 20, Issue 47 https://doi.org/10.1039/c8cp05920a	journal	January 2018
Reaction mechanisms of a cyclic ether intermediate: Ethyloxirane Christianson, Matthew G.; Doner, Anna C.; Davis, Matthew M. International Journal of Chemical Kinetics https://doi.org/10.1002/kin.21423	journal	September 2020
Human Ammonia Emission Rates under Various Indoor Environmental Conditions Li, Mengze; Weschler, Charles J.; Bekö, Gabriel Environmental Science & Technology, Vol. 54, Issue 9 https://doi.org/10.1021/acs.est.0c00094	journal	April 2020
Gas-Phase Reactions of OH with Methyl Amines in the Presence or Absence of Molecular Oxygen. An Experimental and Theoretical Study Onel, L.; Thonger, L.; Blitz, M. A. The Journal of Physical Chemistry A, Vol. 117, Issue 41 https://doi.org/10.1021/jp406522z	journal	October 2013
Evaluated kinetic and photochemical data for atmospheric chemistry: Volume I - gas phase reactions of O<sub>x</sub>, HO<sub>x</sub>, NO<sub>x</sub> and SO<sub>x</sub> species Atkinson, R.; Baulch, D. L.; Cox, R. A. Atmospheric Chemistry and Physics, Vol. 4, Issue 6 https://doi.org/10.5194/acp-4-1461-2004	journal	January 2004
Experimental and computational studies of Criegee intermediate reactions with NH ₃ and CH ₃ NH ₂ Chhantyal-Pun, Rabi; Shannon, Robin J.; Tew, David P. Physical Chemistry Chemical Physics, Vol. 21, Issue 26 https://doi.org/10.1039/c8cp06810k	journal	January 2019
Criegee Intermediate–Alcohol Reactions, A Potential Source of Functionalized Hydroperoxides in the Atmosphere McGillen, Max R.; Curchod, Basile F. E.; Chhantyal-Pun, Rabi ACS Earth and Space Chemistry, Vol. 1, Issue 10 https://doi.org/10.1021/acsearthspacechem.7b00108	journal	December 2017
Re-examining ammonia addition to the Criegee intermediate: converging to chemical accuracy Misiewicz, Jonathon P.; Elliott, Sarah N.; Moore, Kevin B. Physical Chemistry Chemical Physics, Vol. 20, Issue 11 https://doi.org/10.1039/c7cp08582f	journal	January 2018
Atmospheric amines – Part I. A review Ge, Xinlei; Wexler, Anthony S.; Clegg, Simon L. Atmospheric Environment, Vol. 45, Issue 3 https://doi.org/10.1016/j.atmosenv.2010.10.012	journal	January 2011
Visibility as related to atmospheric aerosol constituents Appel, B. R.; Tokiwa, Y.; Hsu, J. Atmospheric Environment (1967), Vol. 19, Issue 9 https://doi.org/10.1016/0004-6981(85)90290-2	journal	January 1985
The global tropospheric ammonia distribution as seen in the 13-year AIRS measurement record Warner, Juying X.; Wei, Zigang; Strow, L. Larrabee Atmospheric Chemistry and Physics, Vol. 16, Issue 8 https://doi.org/10.5194/acp-16-5467-2016	journal	January 2016
Indoor acids and bases Nazaroff, William W.; Weschler, Charles J. Indoor Air, Vol. 30, Issue 4 https://doi.org/10.1111/ina.12670	journal	April 2020
Atmospheric Chemistry of Criegee Intermediates: Unimolecular Reactions and Reactions with Water Long, Bo; Bao, Junwei Lucas; Truhlar, Donald G. Journal of the American Chemical Society, Vol. 138, Issue 43 https://doi.org/10.1021/jacs.6b08655	journal	October 2016
An Extended Computational Study of Criegee Intermediate–Alcohol Reactions Watson, Nathan A. I.; Black, Joshua A.; Stonelake, Thomas M. The Journal of Physical Chemistry A, Vol. 123, Issue 1 https://doi.org/10.1021/acs.jpca.8b09349	journal	December 2018
Reformulation and Solution of the Master Equation for Multiple-Well Chemical Reactions Georgievskii, Yuri; Miller, James A.; Burke, Michael P. The Journal of Physical Chemistry A, Vol. 117, Issue 46 https://doi.org/10.1021/jp4060704	journal	May 2013
Direct Measurements of Conformer-Dependent Reactivity of the Criegee Intermediate CH3CHOO Taatjes, C. A.; Welz, O.; Eskola, A. J. Science, Vol. 340, Issue 6129 https://doi.org/10.1126/science.1234689	journal	April 2013
Variable reaction coordinate transition state theory: Analytic results and application to the C2H3+H→C2H4 reaction Georgievskii, Yuri; Klippenstein, Stephen J. The Journal of Chemical Physics, Vol. 118, Issue 12 https://doi.org/10.1063/1.1539035	journal	March 2003
Determination of the levels of aromatic amines in indoor and outdoor air in Italy Palmiotto, G.; Pieraccini, G.; Moneti, G. Chemosphere, Vol. 43, Issue 3 https://doi.org/10.1016/s0045-6535(00)00109-0	journal	April 2001
CCN Activity and Hygroscopic Growth of Organic Aerosols Following Reactive Uptake of Ammonia Dinar, E.; Anttila, T.; Rudich, Y. Environmental Science & Technology, Vol. 42, Issue 3 https://doi.org/10.1021/es071874p	journal	February 2008
Functionalized Hydroperoxide Formation from the Reaction of Methacrolein-Oxide, an Isoprene-Derived Criegee Intermediate, with Formic Acid: Experiment and Theory Vansco, Michael F.; Zuraski, Kristen; Winiberg, Frank A. F. Molecules, Vol. 26, Issue 10 https://doi.org/10.3390/molecules26103058	journal	May 2021
Reactive Oxygen Species Generation Linked to Sources of Atmospheric Particulate Matter and Cardiorespiratory Effects Bates, Josephine T.; Weber, Rodney J.; Abrams, Joseph Environmental Science & Technology, Vol. 49, Issue 22 https://doi.org/10.1021/acs.est.5b02967	journal	October 2015
Atmospheric Kinetics: Bimolecular Reactions of Carbonyl Oxide by a Triple-Level Strategy Long, Bo; Wang, Ying; Xia, Yu Journal of the American Chemical Society, Vol. 143, Issue 22 https://doi.org/10.1021/jacs.1c02029	journal	May 2021
Long-range transition state theory Georgievskii, Yuri; Klippenstein, Stephen J. The Journal of Chemical Physics, Vol. 122, Issue 19 https://doi.org/10.1063/1.1899603	journal	May 2005
Indoor Chemistry Weschler, Charles J.; Carslaw, Nicola Environmental Science & Technology, Vol. 52, Issue 5 https://doi.org/10.1021/acs.est.7b06387	journal	February 2018
Criegee Intermediate Reactions with Carboxylic Acids: A Potential Source of Secondary Organic Aerosol in the Atmosphere Chhantyal-Pun, Rabi; Rotavera, Brandon; McGillen, Max R. ACS Earth and Space Chemistry, Vol. 2, Issue 8 https://doi.org/10.1021/acsearthspacechem.8b00069	journal	June 2018

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Title: Dramatic Conformer-Dependent Reactivity of the Acetaldehyde Oxide Criegee Intermediate with Dimethylamine Via a 1,2-Insertion Mechanism

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