The ozonolysis of cyclic monoterpenes: A computational review

Mansour H. Almatarneh, Ismael A. Elayan, Raymond A. Poirier, Mohammednoor Altarawneh

Research output: Contribution to journalReview articlepeer-review

13 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)281-292
Number of pages12
JournalCanadian Journal of Chemistry
Volume96
Issue number3
DOIs
Publication statusPublished - 2018
Externally publishedYes

Keywords

  • Atmospheric oxidation
  • Criegee intermediates
  • Criegee mechanism
  • Monoterpenes
  • Ozonolysis

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Organic Chemistry

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