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Issue 42, 2014
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Barrierless tautomerization of Criegee intermediates via acid catalysis

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Abstract

The tautomerization of Criegee intermediates via a 1,4 β-hydrogen atom transfer to yield a vinyl hydroperoxide has been examined in the absence and presence of carboxylic acids. Electronic structure calculations indicate that the organic acids catalyze the tautomerization reaction to such an extent that it becomes a barrierless process. In contrast, water produces only a nominal catalytic effect. Since organic acids are present in parts-per-billion concentrations in the troposphere, the present results suggest that the acid-catalyzed tautomerization, which can also result in formation of hydroxyl radicals, may be a significant pathway for Criegee intermediates.

Graphical abstract: Barrierless tautomerization of Criegee intermediates via acid catalysis

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Publication details

The article was received on 11 Jul 2014, accepted on 19 Sep 2014 and first published on 22 Sep 2014


Article type: Communication
DOI: 10.1039/C4CP03065F
Author version available: Download Author version (PDF)
Citation: Phys. Chem. Chem. Phys., 2014,16, 22968-22973
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    Barrierless tautomerization of Criegee intermediates via acid catalysis

    M. Kumar, D. H. Busch, B. Subramaniam and W. H. Thompson, Phys. Chem. Chem. Phys., 2014, 16, 22968
    DOI: 10.1039/C4CP03065F

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