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Thermochemical properties and decomposition pathways of three isomeric semiquinone radicals
Journal article   Peer reviewed

Thermochemical properties and decomposition pathways of three isomeric semiquinone radicals

M. Altarawneh, B.Z. Dlugogorski, E.M. Kennedy and J.C. Mackie
The Journal of Physical Chemistry A, Vol.114(2), pp.1098-1108
2010
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Abstract

Semiquinones are persistent free environmental radicals formed as important initial products from the decomposition of dihydroxylated benzene isomers. This study develops detailed decomposition pathways for the thermal decomposition of the three isomeric semiquinone radicals. Branching ratios based on the calculated high-pressure limit reaction rate constants predict that p-benzoquinone is a major product from the unimolecular decomposition of the p-semiquinone radical, while the formation of o-benzoquinone from the o-semiquinone radical corresponds to a minor channel. This finding is consistent with the absence of o-benzoquinone from the thermal degradation of the 1,2-dihydroxybenzene isomer and the abundance of p-benzoquinone from the thermal decomposition of 1,4-dihydroxybenzene. Ring contraction/CO elimination is shown to be the dominant sink pathway for the o-semiquinone and m-semiquinone radicals. Thermochemical properties, in terms of enthalpies of formation, entropies, and heat capacities for dihydroxylated benzene isomers, semiquinone radicals, and benzoquinones, are evaluated by quantum chemical calculations. Values of the enthalpies of formation calculated by the B3LYP/GTLarge method show good agreement with those obtained at the G3B3 level of theory.

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Collaboration types
Domestic collaboration
International collaboration
Citation topics
2 Chemistry
2.15 Physical Chemistry
2.15.3 Quantum Chemistry
Web Of Science research areas
Chemistry, Physical
Physics, Atomic, Molecular & Chemical
ESI research areas
Chemistry
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