Mechanistic Description of Photochemical Oligomer Formation from Aqueous Pyruvic Acid

The Journal of Physical Chemistry. a
Rebecca J RapfVeronica Vaida

Abstract

The aqueous phase photochemistry of pyruvic acid, an important oxidation product of isoprene, is known to generate larger oligomeric species that may contribute to the formation of secondary organic aerosol in the atmosphere. Using high resolution negative mode electrospray ionization mass spectrometry, the aqueous photochemistry of dilute solutions of pyruvic acid (10, 1, and 0.5 mM) under anaerobic conditions was investigated. Even at the lowest concentration, covalently bonded dimers and trimers of pyruvic acid were observed as photochemical products. We calculate that it is energetically possible to photochemically generate parapyruvic acid, a dimer of pyruvic acid that is known to form via dark oligomerization processes. Subsequent photochemical reactions of parapyruvic acid with pyruvic acid form larger oligomeric products, such as 2,4-dihydroxy-2-methyl-5-oxohexanoic acid. A robust and relatively simple photochemical mechanism is discussed that explains both the conditional dependence and wide array of products that are observed.

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Citations

Jan 22, 2019·Physical Chemistry Chemical Physics : PCCP·Kateryna GrygoryevaMichal Fárník
Jan 22, 2021·The Journal of Physical Chemistry. a·Keaten J KappesVeronica Vaida
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Oct 17, 2017·The Journal of Physical Chemistry. a·Rebecca J RapfVeronica Vaida
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Oct 23, 2021·Atmospheric Chemistry and Physics·Andreas TilgnerV Faye McNeill

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