Criegee intermediates: production, detection and reactivity

Chhantyal-Pun, Rabi; Khan, M. Anwar H.; Taatjes, Craig A.; Percival, Carl J.; Orr-Ewing, Andrew J.; Shallcross, Dudley E.

doi:10.1080/0144235x.2020.1792104

Title: Criegee intermediates: production, detection and reactivity

Journal Article · Fri Jul 31 00:00:00 EDT 2020 · International Reviews in Physical Chemistry

DOI:https://doi.org/10.1080/0144235x.2020.1792104· OSTI ID:1670736

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Univ. of Bristol (United Kingdom)
Sandia National Lab. (SNL-CA), Livermore, CA (United States)
California Inst. of Technology (CalTech), Pasadena, CA (United States)

In the context of tropospheric chemistry, Criegee intermediates denote carbonyl oxides with biradical/zwitterionic character (R₁R₂COO) that form during the ozonolysis of alkenes. First discovered almost 70 years ago, stabilised versions of Criegee intermediates formed via collisional removal of excess energy have interesting kinetic and mechanistic properties. The direct production and detection of these intermediates were not reported in the literature until 2008. However, recent advances in their generation through the ultraviolet irradiation of the corresponding diiodoalkanes in excess O₂ and detection by various spectroscopic techniques (photoionisation, ultraviolet, infrared, microwave and mass spectrometry) have shown that these species can react rapidly with closed-shell molecules, in many cases at or exceeding the classical gas-kinetic limit, via multiple reaction pathways. These reactions can be complex, and laboratory measurements of products and the temperature and pressure dependence of the reaction kinetics have also revealed unusual behaviour. The possible role of these intermediates in atmospheric chemistry is significant, altering models of the oxidising capacity of the Earth's atmosphere and the rate of generation of secondary organic aerosol.

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Research Organization:: Sandia National Lab. (SNL-CA), Livermore, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Advanced Light Source (ALS)

Sponsoring Organization:: North American Electric Reliability Corporation (NERC); Primary Science Teaching Trust; Bristol ChemLabS; USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division; USDOE National Nuclear Security Administration (NNSA)

Grant/Contract Number:: AC04-94AL85000; NE/K004905/1; NE/K005316/1; NE/P013104/1; NA0003525; AC02-05CH11231

OSTI ID:: 1670736

Report Number(s):: SAND-2020-7129J; 687306

Journal Information:: International Reviews in Physical Chemistry, Vol. 39, Issue 3; ISSN 0144-235X

Publisher:: Taylor & FrancisCopyright Statement

Country of Publication:: United States

Language:: English

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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
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Unimolecular Decomposition Rate of the Criegee Intermediate (CH ₃ ) ₂ COO Measured Directly with UV Absorption Spectroscopy Smith, Mica C.; Chao, Wen; Takahashi, Kaito The Journal of Physical Chemistry A, Vol. 120, Issue 27 https://doi.org/10.1021/acs.jpca.5b12124	journal	February 2016
Direct Measurements of Unimolecular and Bimolecular Reaction Kinetics of the Criegee Intermediate (CH ₃ ) ₂ COO Chhantyal-Pun, Rabi; Welz, Oliver; Savee, John D. The Journal of Physical Chemistry A, Vol. 121, Issue 1 https://doi.org/10.1021/acs.jpca.6b07810	journal	December 2016
Measuring Rate Constants for Reactions of the Simplest Criegee Intermediate (CH ₂ OO) by Monitoring the OH Radical Liu, Yingdi; Bayes, Kyle D.; Sander, Stanley P. The Journal of Physical Chemistry A, Vol. 118, Issue 4 https://doi.org/10.1021/jp407058b	journal	January 2014
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Direct Observation of the Gas-Phase Criegee Intermediate (CH ₂ OO) Taatjes, Craig A.; Meloni, Giovanni; Selby, Talitha M. Journal of the American Chemical Society, Vol. 130, Issue 36 https://doi.org/10.1021/ja804165q	journal	September 2008
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The gas-phase ozonolysis of unsaturated volatile organic compounds in the troposphere Johnson, David; Marston, George Chemical Society Reviews, Vol. 37, Issue 4 https://doi.org/10.1039/b704260b	journal	January 2008
Kinetics of stabilised Criegee intermediates derived from alkene ozonolysis: reactions with SO ₂ , H ₂ O and decomposition under boundary layer conditions Newland, Mike J.; Rickard, Andrew R.; Alam, Mohammed S. Physical Chemistry Chemical Physics, Vol. 17, Issue 6 https://doi.org/10.1039/C4CP04186K	journal	January 2015
Direct measurement of Criegee intermediate (CH2OO) reactions with acetone, acetaldehyde, and hexafluoroacetone Taatjes, Craig A.; Welz, Oliver; Eskola, Arkke J. Physical Chemistry Chemical Physics, Vol. 14, Issue 30 https://doi.org/10.1039/c2cp40294g	journal	January 2012
Reactions between Criegee Intermediates and the Inorganic Acids HCl and HNO ₃ : Kinetics and Atmospheric Implications Foreman, Elizabeth S.; Kapnas, Kara M.; Murray, Craig Angewandte Chemie International Edition, Vol. 55, Issue 35 https://doi.org/10.1002/anie.201604662	journal	July 2016
Formation of a Criegee intermediate in the low-temperature oxidation of dimethyl sulfoxide Asatryan, Rubik; Bozzelli, Joseph W. Physical Chemistry Chemical Physics, Vol. 10, Issue 13 https://doi.org/10.1039/b716179d	journal	January 2008
Research frontiers in the chemistry of Criegee intermediates and tropospheric ozonolysis Taatjes, Craig A.; Shallcross, Dudley E.; Percival, Carl J. Physical Chemistry Chemical Physics, Vol. 16, Issue 5 https://doi.org/10.1039/c3cp52842a	journal	January 2014
Detection of transient infrared absorption of SO ₃ and 1,3,2-dioxathietane-2,2-dioxide [ cyc -(CH ₂ )O(SO ₂ )O] in the reaction CH ₂ OO+SO ₂ Wang, Yi-Ying; Dash, Manas Ranjan; Chung, Chao-Yu The Journal of Chemical Physics, Vol. 148, Issue 6 https://doi.org/10.1063/1.5019205	journal	February 2018
Kinetics and energetics of the criegee intermediate in the gas phase. I. The criegee intermediate in ozone-alkene reactions Herron, John T.; Martinez, Richard I.; Huie, Robert E. International Journal of Chemical Kinetics, Vol. 14, Issue 3 https://doi.org/10.1002/kin.550140302	journal	March 1982
The reaction of Criegee intermediates with acids and enols Vereecken, L. Physical Chemistry Chemical Physics, Vol. 19, Issue 42 https://doi.org/10.1039/C7CP05132H	journal	January 2017
Direct Kinetic and Atmospheric Modeling Studies of Criegee Intermediate Reactions with Acetone Chhantyal-Pun, Rabi; Khan, M. Anwar H.; Martin, Rebecca ACS Earth and Space Chemistry, Vol. 3, Issue 10 https://doi.org/10.1021/acsearthspacechem.9b00213	journal	August 2019
Identification of the Criegee intermediate reaction network in ethylene ozonolysis: impact on energy conversion strategies and atmospheric chemistry Rousso, Aric C.; Hansen, Nils; Jasper, Ahren W. Physical Chemistry Chemical Physics, Vol. 21, Issue 14 https://doi.org/10.1039/C9CP00473D	journal	January 2019
Detailed mechanism and kinetics of the reaction of Criegee intermediate CH ₂ OO with HCOOH investigated via infrared identification of conformers of hydroperoxymethyl formate and formic acid anhydride Chung, Chen-An; Su, Jou Wei; Lee, Yuan-Pern Physical Chemistry Chemical Physics, Vol. 21, Issue 38 https://doi.org/10.1039/C9CP04168K	journal	January 2019
Theoretical study of the reactions of Criegee intermediates with ozone, alkylhydroperoxides, and carbon monoxide Vereecken, L.; Rickard, A. R.; Newland, M. J. Physical Chemistry Chemical Physics, Vol. 17, Issue 37 https://doi.org/10.1039/C5CP03862F	journal	January 2015
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The Ethene−Ozone Reaction in the Gas Phase Neeb, Peter; Horie, Osamu; Moortgat, Geert K. The Journal of Physical Chemistry A, Vol. 102, Issue 34 https://doi.org/10.1021/jp981264z	journal	August 1998
Temperature-Dependence of the Rates of Reaction of Trifluoroacetic Acid with Criegee Intermediates Chhantyal-Pun, Rabi; McGillen, Max R.; Beames, Joseph M. Angewandte Chemie International Edition, Vol. 56, Issue 31 https://doi.org/10.1002/anie.201703700	journal	June 2017
Characterization of the simplest hydroperoxide ester, hydroperoxymethyl formate, a precursor of atmospheric aerosols Porterfield, Jessica P.; Lee, Kin Long Kelvin; Dell'Isola, Valentina Physical Chemistry Chemical Physics, Vol. 21, Issue 33 https://doi.org/10.1039/C9CP03466H	journal	January 2019
Kinetics of the simplest Criegee intermediate reaction with ozone studied using a mid-infrared quantum cascade laser spectrometer Chang, Yuan-Pin; Chang, Hsun-Hui; Lin, Jim Jr-Min Physical Chemistry Chemical Physics, Vol. 20, Issue 1 https://doi.org/10.1039/C7CP06653H	journal	January 2018
UV Absorption Spectrum and Photodissociation Channels of the Simplest Criegee Intermediate (CH ₂ OO) Dawes, Richard; Jiang, Bin; Guo, Hua Journal of the American Chemical Society, Vol. 137, Issue 1 https://doi.org/10.1021/ja510736d	journal	December 2014
Unimolecular decomposition kinetics of the stabilised Criegee intermediates CH ₂ OO and CD ₂ OO Stone, Daniel; Au, Kendrew; Sime, Samantha Physical Chemistry Chemical Physics, Vol. 20, Issue 38 https://doi.org/10.1039/C8CP05332D	journal	January 2018
Probing the conformational behavior of the doubly substituted methyl-ethyl Criegee intermediate by FTMW spectroscopy Cabezas, Carlos; Guillemin, Jean-Claude; Endo, Yasuki The Journal of Chemical Physics, Vol. 146, Issue 17 https://doi.org/10.1063/1.4982682	journal	May 2017
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
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The reaction of formaldehyde carbonyl oxide with the methyl peroxy radical and its relevance in the chemistry of the atmosphere Anglada, Josep M.; Olivella, Santiago; Solé, Albert Physical Chemistry Chemical Physics, Vol. 15, Issue 43 https://doi.org/10.1039/c3cp53100g	journal	January 2013
Rate coefficient of the reaction CH ₂ OO + NO ₂ probed with a quantum-cascade laser near 11 μm Luo, Pei-Ling; Chung, Chen-An; Lee, Yuan-Pern Physical Chemistry Chemical Physics, Vol. 21, Issue 32 https://doi.org/10.1039/C9CP03333E	journal	January 2019
Reaction of Perfluorooctanoic Acid with Criegee Intermediates and Implications for the Atmospheric Fate of Perfluorocarboxylic Acids Taatjes, Craig A.; Khan, M. Anwar H.; Eskola, Arkke J. Environmental Science & Technology, Vol. 53, Issue 3 https://doi.org/10.1021/acs.est.8b05073	journal	December 2018
Reactivity of stabilized Criegee intermediates (sCIs) from isoprene and monoterpene ozonolysis toward SO ₂ and organic acids Sipilä, M.; Jokinen, T.; Berndt, T. Atmospheric Chemistry and Physics, Vol. 14, Issue 22 https://doi.org/10.5194/acp-14-12143-2014	journal	January 2014
Communication: Spectroscopic characterization of an alkyl substituted Criegee intermediate syn -CH ₃ CHOO through pure rotational transitions Nakajima, Masakazu; Endo, Yasuki The Journal of Chemical Physics, Vol. 140, Issue 1 https://doi.org/10.1063/1.4861494	journal	January 2014
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
Criegee Intermediates: What Direct Production and Detection Can Teach Us About Reactions of Carbonyl Oxides Taatjes, Craig A. Annual Review of Physical Chemistry, Vol. 68, Issue 1 https://doi.org/10.1146/annurev-physchem-052516-050739	journal	May 2017
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
Role of the reaction of stabilized Criegee intermediates with peroxy radicals in particle formation and growth in air Zhao, Yue; Wingen, Lisa M.; Perraud, Véronique Physical Chemistry Chemical Physics, Vol. 17, Issue 19 https://doi.org/10.1039/C5CP01171J	journal	January 2015
The critical assessment of vapour pressure estimation methods for use in modelling the formation of atmospheric organic aerosol Barley, M. H.; McFiggans, G. Atmospheric Chemistry and Physics, Vol. 10, Issue 2 https://doi.org/10.5194/acp-10-749-2010	journal	January 2010
Unimolecular decay strongly limits the atmospheric impact of Criegee intermediates Vereecken, L.; Novelli, A.; Taraborrelli, D. Physical Chemistry Chemical Physics, Vol. 19, Issue 47 https://doi.org/10.1039/C7CP05541B	journal	January 2017
UV absorption probing of the conformer-dependent reactivity of a Criegee intermediate CH ₃ CHOO Sheps, Leonid; Scully, Ashley M.; Au, Kendrew Phys. Chem. Chem. Phys., Vol. 16, Issue 48 https://doi.org/10.1039/C4CP04408H	journal	January 2014
FTIR spectroscopic study of the mechanism for the gas-phase reaction between ozone and tetramethylethylene Niki, H.; Maker, P. D.; Savage, C. M. The Journal of Physical Chemistry, Vol. 91, Issue 4 https://doi.org/10.1021/j100288a035	journal	February 1987
Pressure-Dependent Criegee Intermediate Stabilization from Alkene Ozonolysis Hakala, Jani P.; Donahue, Neil M. The Journal of Physical Chemistry A, Vol. 120, Issue 14 https://doi.org/10.1021/acs.jpca.6b01538	journal	April 2016
Infrared Absorption Spectrum of the Simplest Criegee Intermediate CH2OO Su, Y. -T.; Huang, Y. -H.; Witek, H. A. Science, Vol. 340, Issue 6129 https://doi.org/10.1126/science.1234369	journal	April 2013
Decomposition pathways of the excited Criegee intermediates in the ozonolysis of simple alkenes Horie, O.; Moortgat, G. K. Atmospheric Environment. Part A. General Topics, Vol. 25, Issue 9 https://doi.org/10.1016/0960-1686(91)90271-8	journal	January 1991
Communication: Determination of the molecular structure of the simplest Criegee intermediate CH ₂ OO Nakajima, Masakazu; Endo, Yasuki The Journal of Chemical Physics, Vol. 139, Issue 10 https://doi.org/10.1063/1.4821165	journal	September 2013
Communication: Real time observation of unimolecular decay of Criegee intermediates to OH radical products Fang, Yi; Liu, Fang; Barber, Victoria P. The Journal of Chemical Physics, Vol. 144, Issue 6 https://doi.org/10.1063/1.4941768	journal	February 2016
Kinetics of CH ₂ OO reactions with SO ₂ , NO ₂ , NO, H ₂ O and CH ₃ CHO as a function of pressure Stone, Daniel; Blitz, Mark; Daubney, Laura Phys. Chem. Chem. Phys., Vol. 16, Issue 3 https://doi.org/10.1039/C3CP54391A	journal	January 2014
Theoretical Study of the Reaction of Carbonyl Oxide with Nitrogen Dioxide: CH ₂ OO + NO ₂ : THEORETICAL STUDY OF THE REACTION OF CARBONYL OXIDE WITH NITROGEN DIOXIDE Vereecken, L.; Nguyen, H. M. T. International Journal of Chemical Kinetics, Vol. 49, Issue 10 https://doi.org/10.1002/kin.21112	journal	August 2017
Gas-Phase Ozonolysis of Alkenes: Formation of OH from Anti Carbonyl Oxides Kroll, Jesse H.; Donahue, Neil M.; Cee, Victor J. Journal of the American Chemical Society, Vol. 124, Issue 29 https://doi.org/10.1021/ja0266060	journal	July 2002
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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