The gas-phase ozonolysis reaction of methylbutenol: A mechanistic study

Mansour H. Almatarneh, Ismael A. Elayan, Abd Al Aziz A. Abu-Saleh, Mohammednoor Altarawneh, Parisa A. Ariya

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)


The gas-phase ozonolysis reaction of methylbutenol through the Criegee mechanism is investigated. The initial reaction leads to a primary ozonide (POZ) formation with barriers in the range of 10–28 kJ mol −1 . The formation of 2-hydroxy-2-methyl-propanal (HMP) and formaldehyde-oxide is more favorable, by 10 kJ mol −1 , than the syn-CI and formaldehyde. The unimolecular dissociation of the more stable syn-CI via 1,5-H transfer into an epoxide is more favored than the epoxide and 3 O 2 formation. The ester channel led to the formation of the acetone and formic acid favorably from the anti-CI. The hydration of the anti-CI with H 2 O and (H 2 O) 2 is significantly barrierless with a higher plausibility to the latter, and thus they may lead to the formation of peroxides and ultimately OH radicals, as well as airborne particulate matter. Reaction of anti-CI with water dimers enhances its atmospheric reactivity by a factor of 28 in reference to water monomers.

Original languageEnglish
Article numbere25888
JournalInternational Journal of Quantum Chemistry
Issue number10
Publication statusPublished - May 15 2019
Externally publishedYes


  • Criegee intermediate
  • epoxide
  • methylbutenol
  • ozonolysis
  • volatile organic compounds

ASJC Scopus subject areas

  • Atomic and Molecular Physics, and Optics
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry


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