The physical chemistry of Criegee intermediates in the gas phase

Osborn, David L.; Taatjes, Craig A.

doi:10.1080/0144235X.2015.1055676

Title: The physical chemistry of Criegee intermediates in the gas phase

Journal Article · Fri Jul 24 00:00:00 EDT 2015 · International Reviews in Physical Chemistry

DOI:https://doi.org/10.1080/0144235X.2015.1055676· OSTI ID:1329620

Osborn, David L. ^[1]; Taatjes, Craig A. ^[1]

Sandia National Lab. (SNL-CA), Livermore, CA (United States)

Here, carbonyl oxides, also known as Criegee intermediates, are key intermediates in both gas phase ozonolysis of unsaturated hydrocarbons in the troposphere and solution phase organic synthesis via ozonolysis. Although the study of Criegee intermediates in both arenas has a long history, direct studies in the gas phase have only recently become possible through new methods of generating stabilised Criegee intermediates in sufficient quantities. This advance has catalysed a large number of new experimental and theoretical investigations of Criegee intermediate chemistry. In this article we review the physical chemistry of Criegee intermediates, focusing on their molecular structure, spectroscopy, unimolecular and bimolecular reactions. These recent results have overturned conclusions from some previous studies, while confirming others, and have clarified areas of investigation that will be critical targets for future studies. In addition to expanding our fundamental understanding of Criegee intermediates, the rapidly expanding knowledge base will support increasingly predictive models of their impacts on society.

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Research Organization:: Sandia National Lab. (SNL-CA), Livermore, CA (United States)

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

Grant/Contract Number:: AC04-94AL85000

OSTI ID:: 1329620

Report Number(s):: SAND-2016-10077J; 648113

Journal Information:: International Reviews in Physical Chemistry, Vol. 34, Issue 3; ISSN 0144-235X

Publisher:: Taylor & FrancisCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 184 works

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Mechanisms of gas-phase and liquid-phase ozonolysis Harding, Lawrence B.; Goddard, William A. Journal of the American Chemical Society, Vol. 100, Issue 23 https://doi.org/10.1021/ja00491a010	journal	November 1978
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Matrix Isolation Study of the Early Intermediates in the Ozonolysis of Cyclopentene and Cyclopentadiene: Observation of Two Criegee Intermediates Hoops, Michael D.; Ault, Bruce S. Journal of the American Chemical Society, Vol. 131, Issue 8 https://doi.org/10.1021/ja8065286	journal	March 2009
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
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
Study of low‐lying electronic states of ozone by anion photoelectron spectroscopy of O ⁻ ₃ Arnold, Don W.; Xu, Cangshan; Kim, Eun H. The Journal of Chemical Physics, Vol. 101, Issue 2 https://doi.org/10.1063/1.467745	journal	July 1994
Theoretical study of photochemical processes involving singlet excited states of formaldehyde carbonyl oxide in the atmosphere Aplincourt, P.; Henon, E.; Bohr, F. Chemical Physics, Vol. 285, Issue 2-3 https://doi.org/10.1016/S0301-0104(02)00804-2	journal	December 2002
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
On the Cover Vashi, Preeti European Journal of Inorganic Chemistry https://doi.org/10.1002/(ISSN)1099-0682	journal	May 2022
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
Barrierless tautomerization of Criegee intermediates via acid catalysis Kumar, Manoj; Busch, Daryle H.; Subramaniam, Bala Phys. Chem. Chem. Phys., Vol. 16, Issue 42 https://doi.org/10.1039/C4CP03065F	journal	January 2014
Probing the dynamics of polyatomic multichannel elementary reactions by crossed molecular beam experiments with soft electron-ionization mass spectrometric detection Casavecchia, Piergiorgio; Leonori, Francesca; Balucani, Nadia Phys. Chem. Chem. Phys., Vol. 11, Issue 1 https://doi.org/10.1039/B814709D	journal	January 2009
Free tropospheric measurements of formic acid (HCOOH) from infrared ground-based solar absorption spectra: Retrieval approach, evidence for a seasonal cycle, and comparison with model calculations Rinsland, Curtis P. Journal of Geophysical Research, Vol. 109, Issue D18 https://doi.org/10.1029/2004JD004917	journal	January 2004
Measuring rate Constants for Reactions of the Simplest Criegee Intermediate Ch2oo by Monitoring the oh Radical Liu, Yingdi; Sander, Stanley; Bayes, Kyle Proceedings of the 69th International Symposium on Molecular Spectroscopy https://doi.org/10.15278/isms.2014.wh08	conference	June 2014
Rate Coefficients of C1 and C2 Criegee Intermediate Reactions with Formic and Acetic Acid Near the Collision Limit: Direct Kinetics Measurements and Atmospheric Implications Welz, Oliver; Eskola, Arkke J.; Sheps, Leonid Angewandte Chemie, Vol. 126, Issue 18 https://doi.org/10.1002/ange.201400964	journal	March 2014
Handbook of Combustion Walker, James S. Wiley-VCH https://doi.org/10.1002/9783527628148.hoc002	book	July 2010
Submillimeter Measurements of the Criegee Intermediate, Ch2oo, in the gas Phase Daly, Adam; Yu, Shanshan; Drouin, Brian Proceedings of the 69th International Symposium on Molecular Spectroscopy https://doi.org/10.15278/isms.2014.wh07	conference	June 2014
Sneaking Up On The Criegee Intermediate From Below: Predicted Photoelectron Spectrum Of The CH_2OO^- Anion And W3-F12 Electron Affinity Of CH_2OO Karton, Amir; Kettner, Marcus; Wild, Duncan Andrew arXiv https://doi.org/10.48550/arxiv.1309.2554	text	January 2013

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Kinetic studies of C ₁ and C ₂ Criegee intermediates with SO ₂ using laser flash photolysis coupled with photoionization mass spectrometry and time resolved UV absorption spectroscopy Howes, N. U. M.; Mir, Z. S.; Blitz, M. A. Physical Chemistry Chemical Physics, Vol. 20, Issue 34 https://doi.org/10.1039/c8cp03115k	journal	January 2018
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Nascent energy distribution of the Criegee intermediate CH ₂ OO from direct dynamics calculations of primary ozonide dissociation Pfeifle, Mark; Ma, Yong-Tao; Jasper, Ahren W. The Journal of Chemical Physics, Vol. 148, Issue 17 https://doi.org/10.1063/1.5028117	journal	May 2018
Communication: Thermal unimolecular decomposition of syn-CH ₃ CHOO: A kinetic study Nguyen, Thanh Lam; McCaslin, Laura; McCarthy, Michael C. The Journal of Chemical Physics, Vol. 145, Issue 13 https://doi.org/10.1063/1.4964393	journal	October 2016
Theoretical investigation on the reaction mechanism and kinetics of a Criegee intermediate with ethylene and acetylene Sun, Cuihong; Xu, Baoen; Lv, Liqiang Physical Chemistry Chemical Physics, Vol. 21, Issue 30 https://doi.org/10.1039/c9cp02644d	journal	January 2019
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
Impact of the water dimer on the atmospheric reactivity of carbonyl oxides Anglada, Josep M.; Solé, Albert Physical Chemistry Chemical Physics, Vol. 18, Issue 26 https://doi.org/10.1039/c6cp02531e	journal	January 2016
Direct observation of unimolecular decay of CH ₃ CH ₂ CHOO Criegee intermediates to OH radical products Fang, Yi; Liu, Fang; Klippenstein, Stephen J. The Journal of Chemical Physics, Vol. 145, Issue 4 https://doi.org/10.1063/1.4958992	journal	July 2016
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
The ozonolysis of cyclic monoterpenes: a computational review Almatarneh, Mansour H.; Elayan, Ismael A.; Poirier, Raymond A. Canadian Journal of Chemistry, Vol. 96, Issue 3 https://doi.org/10.1139/cjc-2017-0587	journal	March 2018
Infrared absorption spectrum of the simplest deuterated Criegee intermediate CD ₂ OO Huang, Yu-Hsuan; Nishimura, Yoshifumi; Witek, Henryk A. The Journal of Chemical Physics, Vol. 145, Issue 4 https://doi.org/10.1063/1.4958932	journal	July 2016
The reactivity of the Criegee intermediate CH ₃ CHOO with water probed by FTMW spectroscopy Cabezas, Carlos; Endo, Yasuki The Journal of Chemical Physics, Vol. 148, Issue 1 https://doi.org/10.1063/1.5009033	journal	January 2018
Unimolecular dissociation dynamics of vibrationally activated CH3CHOO Criegee intermediates to OH radical products Kidwell, Nathanael M.; Li, Hongwei; Wang, Xiaohong Nature Chemistry, Vol. 8, Issue 5 https://doi.org/10.1038/nchem.2488	journal	April 2016
Vibrational energy levels of the simplest Criegee intermediate (CH ₂ OO) from full-dimensional Lanczos, MCTDH, and MULTIMODE calculations Yu, Hua-Gen; Ndengue, Steve; Li, Jun The Journal of Chemical Physics, Vol. 143, Issue 8 https://doi.org/10.1063/1.4929707	journal	August 2015
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
Products of Criegee intermediate reactions with NO ₂ : experimental measurements and tropospheric implications Caravan, Rebecca L.; Khan, M. Anwar H.; Rotavera, Brandon Faraday Discussions, Vol. 200 https://doi.org/10.1039/c7fd00007c	journal	January 2017
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
Mechanism and kinetics of the atmospheric reaction of 1,3,5-trimethylbenzene bicyclic peroxy radical with OH Lin, Xiaoxiao; Yang, Zhenli; Yu, Hui RSC Advances, Vol. 9, Issue 56 https://doi.org/10.1039/c9ra06562h	journal	January 2019
Infrared spectral identification of the Criegee intermediate (CH ₃ ) ₂ COO Wang, Yi-Ying; Chung, Chao-Yu; Lee, Yuan-Pern The Journal of Chemical Physics, Vol. 145, Issue 15 https://doi.org/10.1063/1.4964658	journal	October 2016
Deep tunneling in the unimolecular decay of CH ₃ CHOO Criegee intermediates to OH radical products Fang, Yi; Liu, Fang; Barber, Victoria P. The Journal of Chemical Physics, Vol. 145, Issue 23 https://doi.org/10.1063/1.4972015	journal	December 2016
Tunneling effects in the unimolecular decay of (CH ₃ ) ₂ COO Criegee intermediates to OH radical products Fang, Yi; Barber, Victoria P.; Klippenstein, Stephen J. The Journal of Chemical Physics, Vol. 146, Issue 13 https://doi.org/10.1063/1.4979297	journal	April 2017
High resolution quantum cascade laser spectroscopy of the simplest Criegee intermediate, CH ₂ OO, between 1273 cm ⁻¹ and 1290 cm ⁻¹ Chang, Yuan-Pin; Merer, Anthony J.; Chang, Hsun-Hui The Journal of Chemical Physics, Vol. 146, Issue 24 https://doi.org/10.1063/1.4986536	journal	June 2017
Fourier transform microwave spectroscopy of Criegee intermediates: The conformational behaviour of butyraldehyde oxide Cabezas, Carlos; Guillemin, Jean-Claude; Endo, Yasuki The Journal of Chemical Physics, Vol. 150, Issue 10 https://doi.org/10.1063/1.5088566	journal	March 2019
Fourier-transform microwave spectroscopy on weakly bound complexes of CH ₂ OO with Ar, CO, and N ₂ Nakajima, Masakazu; Endo, Yasuki The Journal of Chemical Physics, Vol. 151, Issue 6 https://doi.org/10.1063/1.5116165	journal	August 2019
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
Calculation of the absolute photoionization cross-sections for C1–C4 Criegee intermediates and vinyl hydroperoxides Huang, Can; Yang, Bin; Zhang, Feng The Journal of Chemical Physics, Vol. 150, Issue 16 https://doi.org/10.1063/1.5088408	journal	April 2019
Rapid unimolecular reaction of stabilized Criegee intermediates and implications for atmospheric chemistry Long, Bo; Bao, Junwei Lucas; Truhlar, Donald G. Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-09948-7	journal	May 2019

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