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Title: Experimental and computational studies of Criegee intermediate reactions with NH 3 and CH 3NH 2

Abstract

Ammonia and amines are emitted into the troposphere by various natural and anthropogenic sources, where they have a significant role in aerosol formation. Here, we explore the significance of their removal by reaction with Criegee intermediates, which are produced in the troposphere by ozonolysis of alkenes. Rate coefficients for the reactions of two representative Criegee intermediates, formaldehyde oxide (CH 2OO) and acetone oxide ((CH 3) 2COO) with NH 3 and CH 3NH 2 were measured using cavity ring-down spectroscopy. Temperature-dependent rate coefficients, k(CH 2OO + NH 3) = (3.1 ± 0.5) × 10 -20T 2exp(1011 ± 48/T) cm 3 s -1 and k(CH 2OO + CH 3NH 2) = (5 ± 2) × 10 -19T 2 exp(1384 ± 96/T) cm 3 s -1 were obtained in the 240 to 320 K range. Both the reactions of CH 2OO were found to be independent of pressure in the 10 to 100 Torr (N 2) range, and average rate coefficients k(CH 2OO + NH 3) = (8.4 ± 1.2) × 10 -14 cm 3 s -1 and k(CH 2OO + CH 3NH 2) = (5.6 ± 0.4) × 10 -12 cm 3 s -1 were deduced at 293 K. An upper limitmore » of ≤2.7 × 10 -15 cm 3 s -1 was estimated for the rate coefficient of the (CH 3) 2COO + NH3 reaction. Complementary measurements were performed with mass spectrometry using synchrotron radiation photoionization giving k(CH 2OO + CH 3NH 2) = (4.3 ± 0.5) × 10-12 cm3 s-1 at 298 K and 4 Torr (He). Photoionization mass spectra indicated production of NH 2CH 2OOH and CH 3N(H)CH 2OOH functionalized organic hydroperoxide adducts from CH 2OO + NH 3 and CH 2OO + CH 3NH 2 reactions, respectively. Ab initio calculations performed at the CCSD(T)(F12*)/cc-pVQZ-F12//CCSD(T)(F12*)/cc-pVDZ-F12 level of theory predicted pre-reactive complex formation, consistent with previous studies. Master equation simulations of the experimental data using the ab initio computed structures identified submerged barrier heights of -2.1 ± 0.1 kJ mol -1 and -22.4 ± 0.2 kJ mol -1 for the CH 2OO + NH 3 and CH 2OO + CH 3NH 2 reactions, respectively. The reactions of NH3 and CH3NH2 with CH 2OO are not expected to compete with its removal by reaction with (H 2O) 2 in the troposphere. Similarly, losses of NH 3 and CH 3NH 2 by reaction with Criegee intermediates will be insignificant compared with reactions with OH radicals.« less

Authors:
ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [3]; ORCiD logo [4];  [1];  [1];  [1];  [1]; ORCiD logo [1]; ORCiD logo [1];  [4]; ORCiD logo [5];  [4]; ORCiD logo [4]; ORCiD logo [4]; ORCiD logo [6]; ORCiD logo [1]; ORCiD logo [1]
  1. Univ. of Bristol, Bristol (United Kingdom). School of Chemistry
  2. Univ. of Bristol, Bristol (United Kingdom). School of Chemistry; Stanford Univ., CA (United States). Mechanical Engineering
  3. Max Planck Inst. for Medical Research, Stuttgart (Germany)
  4. Sandia National Lab. (SNL-CA), Livermore, CA (United States). Combustion Research Facility
  5. Univ. of Georgia, Athens, GA (United States). College of Engineering, and Dept. of Chemistry
  6. California Inst. of Technology (CalTech), Pasadena, CA (United States). Jet Propulsion Lab.
Publication Date:
Research Org.:
Sandia National Lab. (SNL-CA), Livermore, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1492350
Report Number(s):
SAND-2019-0214J
Journal ID: ISSN 1463-9076; PPCPFQ; 671413
Grant/Contract Number:  
AC04-94AL85000
Resource Type:
Journal Article: Accepted Manuscript
Journal Name:
Physical Chemistry Chemical Physics. PCCP (Print)
Additional Journal Information:
Journal Volume: 21; Journal Issue: 26; Journal ID: ISSN 1463-9076
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Chhantyal-Pun, Rabi, Shannon, Robin J., Tew, David P., Caravan, Rebecca L., Duchi, Marta, Wong, Callum, Ingham, Aidan, Feldman, Charlotte, McGillen, Max R., Khan, M. Anwar H., Antonov, Ivan O., Rotavera, Brandon, Ramasesha, Krupa, Osborn, David L., Taatjes, Craig A., Percival, Carl J., Shallcross, Dudley E., and Orr-Ewing, Andrew J. Experimental and computational studies of Criegee intermediate reactions with NH3 and CH3NH2. United States: N. p., 2019. Web. doi:10.1039/C8CP06810K.
Chhantyal-Pun, Rabi, Shannon, Robin J., Tew, David P., Caravan, Rebecca L., Duchi, Marta, Wong, Callum, Ingham, Aidan, Feldman, Charlotte, McGillen, Max R., Khan, M. Anwar H., Antonov, Ivan O., Rotavera, Brandon, Ramasesha, Krupa, Osborn, David L., Taatjes, Craig A., Percival, Carl J., Shallcross, Dudley E., & Orr-Ewing, Andrew J. Experimental and computational studies of Criegee intermediate reactions with NH3 and CH3NH2. United States. doi:10.1039/C8CP06810K.
Chhantyal-Pun, Rabi, Shannon, Robin J., Tew, David P., Caravan, Rebecca L., Duchi, Marta, Wong, Callum, Ingham, Aidan, Feldman, Charlotte, McGillen, Max R., Khan, M. Anwar H., Antonov, Ivan O., Rotavera, Brandon, Ramasesha, Krupa, Osborn, David L., Taatjes, Craig A., Percival, Carl J., Shallcross, Dudley E., and Orr-Ewing, Andrew J. Tue . "Experimental and computational studies of Criegee intermediate reactions with NH3 and CH3NH2". United States. doi:10.1039/C8CP06810K. https://www.osti.gov/servlets/purl/1492350.
@article{osti_1492350,
title = {Experimental and computational studies of Criegee intermediate reactions with NH3 and CH3NH2},
author = {Chhantyal-Pun, Rabi and Shannon, Robin J. and Tew, David P. and Caravan, Rebecca L. and Duchi, Marta and Wong, Callum and Ingham, Aidan and Feldman, Charlotte and McGillen, Max R. and Khan, M. Anwar H. and Antonov, Ivan O. and Rotavera, Brandon and Ramasesha, Krupa and Osborn, David L. and Taatjes, Craig A. and Percival, Carl J. and Shallcross, Dudley E. and Orr-Ewing, Andrew J.},
abstractNote = {Ammonia and amines are emitted into the troposphere by various natural and anthropogenic sources, where they have a significant role in aerosol formation. Here, we explore the significance of their removal by reaction with Criegee intermediates, which are produced in the troposphere by ozonolysis of alkenes. Rate coefficients for the reactions of two representative Criegee intermediates, formaldehyde oxide (CH2OO) and acetone oxide ((CH3)2COO) with NH3 and CH3NH2 were measured using cavity ring-down spectroscopy. Temperature-dependent rate coefficients, k(CH2OO + NH3) = (3.1 ± 0.5) × 10-20T2exp(1011 ± 48/T) cm3 s-1 and k(CH2OO + CH3NH2) = (5 ± 2) × 10-19T2 exp(1384 ± 96/T) cm3 s-1 were obtained in the 240 to 320 K range. Both the reactions of CH2OO were found to be independent of pressure in the 10 to 100 Torr (N2) range, and average rate coefficients k(CH2OO + NH3) = (8.4 ± 1.2) × 10-14 cm3 s-1 and k(CH2OO + CH3NH2) = (5.6 ± 0.4) × 10-12 cm3 s-1 were deduced at 293 K. An upper limit of ≤2.7 × 10-15 cm3 s-1 was estimated for the rate coefficient of the (CH3)2COO + NH3 reaction. Complementary measurements were performed with mass spectrometry using synchrotron radiation photoionization giving k(CH2OO + CH3NH2) = (4.3 ± 0.5) × 10-12 cm3 s-1 at 298 K and 4 Torr (He). Photoionization mass spectra indicated production of NH2CH2OOH and CH3N(H)CH2OOH functionalized organic hydroperoxide adducts from CH2OO + NH3 and CH2OO + CH3NH2 reactions, respectively. Ab initio calculations performed at the CCSD(T)(F12*)/cc-pVQZ-F12//CCSD(T)(F12*)/cc-pVDZ-F12 level of theory predicted pre-reactive complex formation, consistent with previous studies. Master equation simulations of the experimental data using the ab initio computed structures identified submerged barrier heights of -2.1 ± 0.1 kJ mol-1 and -22.4 ± 0.2 kJ mol-1 for the CH2OO + NH3 and CH2OO + CH3NH2 reactions, respectively. The reactions of NH3 and CH3NH2 with CH2OO are not expected to compete with its removal by reaction with (H2O)2 in the troposphere. Similarly, losses of NH3 and CH3NH2 by reaction with Criegee intermediates will be insignificant compared with reactions with OH radicals.},
doi = {10.1039/C8CP06810K},
journal = {Physical Chemistry Chemical Physics. PCCP (Print)},
issn = {1463-9076},
number = 26,
volume = 21,
place = {United States},
year = {2019},
month = {1}
}

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    Works referencing / citing this record:

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    journal, October 2011

    • Hanson, D. R.; McMurry, P. H.; Jiang, J.
    • Environmental Science & Technology, Vol. 45, Issue 20
    • DOI: 10.1021/es201819a

    Mechanism of Ozonolysis
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    • Criegee, Rudolf
    • Angewandte Chemie International Edition in English, Vol. 14, Issue 11
    • DOI: 10.1002/anie.197507451

    Reaction of Hydroxyl Radical with Nitric Acid:  Insights into Its Mechanism
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    • Foreman, Elizabeth S.; Kapnas, Kara M.; Murray, Craig
    • Angewandte Chemie International Edition, Vol. 55, Issue 35
    • DOI: 10.1002/anie.201604662

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    • Lewis, Tom R.; Blitz, Mark A.; Heard, Dwayne E.
    • Physical Chemistry Chemical Physics, Vol. 17, Issue 7
    • DOI: 10.1039/c4cp04750h

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    Unimolecular decay strongly limits the atmospheric impact of Criegee intermediates
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    • Physical Chemistry Chemical Physics, Vol. 19, Issue 47
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    Criegee Intermediates: What Direct Production and Detection Can Teach Us About Reactions of Carbonyl Oxides
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    • The Journal of Physical Chemistry A, Vol. 120, Issue 27
    • DOI: 10.1021/acs.jpca.5b12124

    Atmospheric Chemistry of Criegee Intermediates: Unimolecular Reactions and Reactions with Water
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    • Long, Bo; Bao, Junwei Lucas; Truhlar, Donald G.
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    Direct kinetic measurement of the reaction of the simplest Criegee intermediate with water vapor
    journal, January 2015


    Re-examining ammonia addition to the Criegee intermediate: converging to chemical accuracy
    journal, January 2018

    • Misiewicz, Jonathon P.; Elliott, Sarah N.; Moore, Kevin B.
    • Physical Chemistry Chemical Physics, Vol. 20, Issue 11
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    A kinetic study of the CH 2 OO Criegee intermediate self-reaction, reaction with SO 2 and unimolecular reaction using cavity ring-down spectroscopy
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    Criegee Intermediate–Alcohol Reactions, A Potential Source of Functionalized Hydroperoxides in the Atmosphere
    journal, December 2017


    The reaction of Criegee intermediate CH 2 OO with water dimer: primary products and atmospheric impact
    journal, January 2017

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    • Physical Chemistry Chemical Physics, Vol. 19, Issue 33
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    Structure-dependent reactivity of Criegee intermediates studied with spectroscopic methods
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    • Jr-Min Lin, Jim; Chao, Wen
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    Accelerated chemistry in the reaction between the hydroxyl radical and methanol at interstellar temperatures facilitated by tunnelling
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    • Shannon, Robin J.; Blitz, Mark A.; Goddard, Andrew
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    Kinetics of a Criegee intermediate that would survive high humidity and may oxidize atmospheric SO 2
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    Atmospheric amines – Part I. A review
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    Atmospheric amines – Part II. Thermodynamic properties and gas/particle partitioning
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    Gas-Phase Reactions of OH with Methyl Amines in the Presence or Absence of Molecular Oxygen. An Experimental and Theoretical Study
    journal, October 2013

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    Research frontiers in the chemistry of Criegee intermediates and tropospheric ozonolysis
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    • Physical Chemistry Chemical Physics, Vol. 16, Issue 5
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    New correlation factors for explicitly correlated electronic wave functions
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    Four-Carbon Criegee Intermediate from Isoprene Ozonolysis: Methyl Vinyl Ketone Oxide Synthesis, Infrared Spectrum, and OH Production
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    Tropospheric OH and HO2 radicals: field measurements and model comparisons
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    Heteroatom Tuning of Bimolecular Criegee Reactions and Its Implications
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    Temperature-Dependence of the Rates of Reaction of Trifluoroacetic Acid with Criegee Intermediates
    journal, June 2017

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    Temperature-Dependent Rate Coefficients for the Reaction of CH 2 OO with Hydrogen Sulfide
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    • The Journal of Physical Chemistry A, Vol. 121, Issue 5
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    Estimating the atmospheric concentration of Criegee intermediates and their possible interference in a FAGE-LIF instrument
    journal, January 2017

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    • Atmospheric Chemistry and Physics, Vol. 17, Issue 12
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    From the Time-Dependent, Multiple-Well Master Equation to Phenomenological Rate Coefficients
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    Communication: Real time observation of unimolecular decay of Criegee intermediates to OH radical products
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    M ASTER E QUATION M ODELS FOR C HEMICAL R EACTIONS OF I MPORTANCE IN C OMBUSTION
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    Kinetics of CH 2 OO reactions with SO 2 , NO 2 , NO, H 2 O and CH 3 CHO as a function of pressure
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    Atmospheric Fate of Criegee Intermediate Formed During Ozonolysis of Styrene in the Presence of H 2 O and NH 3 : The Crucial Role of Stereochemistry
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    Kinetics of the Reactions between the Criegee Intermediate CH 2 OO and Alcohols
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    The gas-phase ozonolysis of unsaturated volatile organic compounds in the troposphere
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    Kinetics of the reaction of the simplest Criegee intermediate with ammonia: a combination of experiment and theory
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    Theoretical Investigation of the Reaction between Carbonyl Oxides and Ammonia
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    Direct Kinetic Measurements of Criegee Intermediate (CH2OO) Formed by Reaction of CH2I with O2
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    Direct Measurements of Unimolecular and Bimolecular Reaction Kinetics of the Criegee Intermediate (CH 3 ) 2 COO
    journal, December 2016

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    The multiplexed chemical kinetic photoionization mass spectrometer: A new approach to isomer-resolved chemical kinetics
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    MESMER: An Open-Source Master Equation Solver for Multi-Energy Well Reactions
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    Sulfuric acid nucleation: power dependencies, variation with relative humidity, and effect of bases
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    Competition between H 2 O and (H 2 O) 2 reactions with CH 2 OO/CH 3 CHOO
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    • Physical Chemistry Chemical Physics, Vol. 18, Issue 6
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    Rate Coefficients of C1 and C2 Criegee Intermediate Reactions with Formic and Acetic Acid Near the Collision Limit: Direct Kinetics Measurements and Atmospheric Implications
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