Publication:
Criegee intermediate decomposition pathways for the formation of o-toluic acid and 2-methylphenylformate

Issued Date

2020-06-01

Resource Type

Article

ISSN

00092614

DOI

10.1016/j.cplett.2020.137399

Other identifier(s)

2-s2.0-85082866810

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Chemical Physics Letters. Vol.748, (2020)

Suggested Citation

Chaiyaporn Lakmuang, Asja A. Kroeger, Amir Karton Criegee intermediate decomposition pathways for the formation of o-toluic acid and 2-methylphenylformate. Chemical Physics Letters. Vol.748, (2020). doi:10.1016/j.cplett.2020.137399 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/54514

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Title

Criegee intermediate decomposition pathways for the formation of o-toluic acid and 2-methylphenylformate

Author(s)

Chaiyaporn Lakmuang
 Asja A. Kroeger
 Amir Karton

Other Contributor(s)

University of Western Australia
 Mahidol University

Abstract

© 2020 Elsevier B.V. We use Gaussian-4 theory to investigate the reaction mechanism for the conversion of a 2-methylstyrene-based Criegee intermediate into o-toluic acid and 2-methylphenylformate. o-Toluic acid can be formed via an α-hydroxyalkyl-hydroperoxide intermediate with an activation energy of ΔG‡298 = 82.9 kJ mol−1 for the rate-determining-step (RDS). The RDS for the formation of 2-methylphenylformate has an activation energy of ΔG‡298 = 61.9 kJ mol−1. Formation of the o-toluic acid product is more exergonic by 67.4 kJ mol−1. Consistent with recent experimental results, our high-level calculations show that o-toluic acid is the thermodynamic product and 2-methylphenylformate is the kinetic product.

Keyword(s)

Chemistry
 Physics and Astronomy

Availability

URI

https://repository.li.mahidol.ac.th/handle/20.500.14594/54514

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Scopus 2020