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The ozonolysis of cyclic monoterpenes: A computational review

Almatarneh, M.H., Elayan, I.A., Poirier, R.A. and Altarawneh, M. (2018) The ozonolysis of cyclic monoterpenes: A computational review. Canadian Journal of Chemistry, 96 (3). pp. 281-292.

Link to Published Version: https://doi.org/10.1139/cjc-2017-0587
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Abstract

Monoterpenes are prevalent organic compounds emitted to the atmosphere, via biogenic activities in various types of plants. Monoterpenes undergo atmospheric decomposition reactions derived by the potent atmospheric oxidizing agents, OH, O3, and NOx. This review critically surveys literature pertinent to the atmospheric removal of monoterpenes by ozone. In general, the ozonolysis reactions of monoterpenes occur through the so-called Criegee mechanism. These classes of reactions generate a wide array of chemical organic and inorganic low vapor pressure (LVP) species. Carbonyl oxides, commonly known as Criegee intermediates (CIs), are the main intermediates from the gas-phase ozonolysis reaction. Herein, we present mechanistic pathways, reactions rate constants, product profiles, thermodynamic, and kinetic results dictating the ozonolysis reactions of selected monoterpenes (namely carene, camphene, limonene, α-pinene, β-pinene, and sabinene). Furthermore, the unimolecular (vinyl hydroperoxide and ester channels) and bimolecular reactions (cycloaddition, insertion, and radical recombination) of the resulting CIs are fully discussed. The orientations and conformations of the resulting primary ozonides (POZs) and CIs of monoterpenes are classified to reveal their plausible effects on reported thermokinetic parameters.

Publication Type: Journal Article
Murdoch Affiliation: School of Engineering and Information Technology
Publisher: NRC Research Press
Copyright: © 2018 Canadian Science Publishing
URI: http://researchrepository.murdoch.edu.au/id/eprint/40502
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