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Ab Initio Study of the Decomposition of 2,5-Dimethylfuran

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    Ab Initio Study of the Decomposition of 2,5-Dimethylfuran
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    Combustion Chemistry Centre, National University of Ireland, Galway, Ireland
    E-mail: [email protected]
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    The Journal of Physical Chemistry A

    Cite this: J. Phys. Chem. A 2011, 115, 32, 8877–8888
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    https://doi.org/10.1021/jp2039477
    Published June 16, 2011
    Copyright © 2011 American Chemical Society
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    Abstract

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    The initial steps in the thermal decomposition of 2,5-dimethylfuran are identified as scission of the C–H bond in the methyl side chain and formation of β- and α-carbenes via 3,2-H and 2,3-methyl shifts, respectively. A variety of channels are explored which prise the aromatic ring open and lead to a number of intermediates whose basic properties are essentially unknown. Once the furan ring is opened demethylation to yield highly unsaturated species such as allenylketenes appears to be a feature of this chemistry. The energetics of H abstraction by the hydroxyl radical (and other abstracting species) from a number of mono- and disubstituted methyl furans has been studied. H-atom addition to 2,5-dimethylfuran followed by methyl elimination is shown to be the most important route to formation of the less reactive 2-methylfuran. Identification of 2-ethenylfuran as an C6H6O intermediate in 2,5-dimethylfuran flames is probably not correct and is more likely the isomeric 2,5-dimethylene-2,5-dihydrofuran for which credible formation channels exist.

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    Table of calculated rate constants and geometries, frequencies, hindered rotor barriers, and energetics of most species, including transition states. This material is available free of charge via the Internet at http://pubs.acs.org.

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    The Journal of Physical Chemistry A

    Cite this: J. Phys. Chem. A 2011, 115, 32, 8877–8888
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    https://doi.org/10.1021/jp2039477
    Published June 16, 2011
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