TY - JOUR
T1 - The gas-phase ozonolysis reaction of methylbutenol
T2 - A mechanistic study
AU - Almatarneh, Mansour H.
AU - Elayan, Ismael A.
AU - Abu-Saleh, Abd Al Aziz A.
AU - Altarawneh, Mohammednoor
AU - Ariya, Parisa A.
N1 - Funding Information:
information Deanship of Academic Research at the University of JordanMansour H. Almatarneh is grateful to the Deanship of Academic Research at the University of Jordan for the grant. We also gratefully acknowledge the Atlantic Computational Excellence Network (ACENET) and Compute Canada for the computer time.
Funding Information:
Mansour H. Almatarneh is grateful to the Deanship of Academic Research at the University of Jordan for the grant. We also gratefully acknowl-
Publisher Copyright:
© 2018 Wiley Periodicals, Inc.
PY - 2019/5/15
Y1 - 2019/5/15
N2 - 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.
AB - 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.
KW - Criegee intermediate
KW - epoxide
KW - methylbutenol
KW - ozonolysis
KW - volatile organic compounds
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U2 - 10.1002/qua.25888
DO - 10.1002/qua.25888
M3 - Article
AN - SCOPUS:85058971880
VL - 119
JO - International Journal of Quantum Chemistry
JF - International Journal of Quantum Chemistry
SN - 0020-7608
IS - 10
M1 - e25888
ER -