A Theoretical Study of the Photoisomerization of Glycolaldehyde and Subsequent OH Radical-Initiated Oxidation of 1,2-Ethenediol

The Journal of Physical Chemistry. a
Sui SoGabriel da Silva

Abstract

It has recently been discovered that carbonyl compounds can undergo UV-induced isomerization to their enol counterparts under atmospheric conditions. This study investigates the photoisomerization of glycolaldehyde (HOCH2CHO) to 1,2-ethenediol (HOCH═CHOH) and the subsequent (•)OH-initiated oxidation chemistry of the latter using quantum chemical calculations and stochastic master equation simulations. The keto-enol tautomerization of glycolaldehyde to 1,2-ethenediol is associated with a barrier of 66 kcal mol(-1) and involves a double-hydrogen shift mechanism to give the lower-energy Z isomer. This barrier lies below the energy of the UV/vis absorption band of glycolaldehyde and is also considerably below the energy of the products resulting from photolytic decomposition. The subsequent atmospheric oxidation of 1,2-ethenediol by (•)OH is initiated by addition of the radical to the π system to give the (•)CH(OH)CH(OH)2 radical, which is subsequently trapped by O2 to form the peroxyl radical (•)O2CH(OH)CH(OH)2. According to kinetic simulations, collisional deactivation of the latter is negligible and cannot compete with rapid fragmentation reactions, which lead to (i) formation of glyoxal hydrate [CH(OH)2CHO] and HO2(•) through a...Continue Reading

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Citations

Nov 21, 2015·The Journal of Physical Chemistry. a·Gabriel da Silva
Mar 11, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Tao JiJunqing Hu
Jul 1, 2021·The Journal of Physical Chemistry. a·Parandaman ArathalaAmitabha Sinha
Aug 20, 2021·Journal of the American Chemical Society·N Fabian KleimeierRalf I Kaiser
Jun 30, 2018·The Journal of Physical Chemistry. a·Arathala ParandamanAmitabha Sinha

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