Photoinduced oligomerization of aqueous pyruvic acid

The Journal of Physical Chemistry. a
M I GuzmanM R Hoffmann

Abstract

The 320 nm-band photodecarboxylation of aqueous pyruvic acid (PA), a representative of the alpha-oxocarboxylic acids widely found in the atmospheric aerosol, yields 2,3-dimethyltartaric (A) and 2-(3-oxobutan-2-yloxy)-2-hydroxypropanoic (B) acids, rather than 3-hydroxy-2-oxobutanone as previously reported. A and B are identified by liquid chromatography with UV and ESI-MS detection, complemented by collisionally induced dissociation and 2H and 13C isotope labeling experiments. The multifunctional ether B gives rise to characteristic delta approximately 80 ppm 13C NMR resonances. Product quantum yields are proportional to [PA](a + [PA])(-1) in the range [PA] = 5-100 mM. CO2(g) release rates are halved, while A and B are suppressed by the addition of >1.5 mM TEMPO. A and B are only partially quenched in air-saturated solutions. These observations are shown to be consistent with an oligomerization process initiated by a bimolecular reaction between 3PA and PA producing ketyl, CH3C(OH)C(O)OH, and acetyl, CH3C(O)*, radicals, rather than by the unimolecular decomposition of 3PA into 1-hydroxyethylidene, 3HO(CH3)C: (+CO2), or [CH(3)C(O)* + *C(O)OH] pairs. A arises from the dimerization of ketyl radicals, while B ensues the facile decar...Continue Reading

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