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Prompt Formation of Organic Acids in Pulse Ozonation of Terpenes on Aqueous Surfaces

Enami, Shinichi and Hoffmann, Michael R. and Colussi, A. J. (2010) Prompt Formation of Organic Acids in Pulse Ozonation of Terpenes on Aqueous Surfaces. Journal of Physical Chemistry Letters, 1 (15). pp. 2374-2379. ISSN 1948-7185. https://resolver.caltech.edu/CaltechAUTHORS:20100831-155817688

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Abstract

A major atmospheric process, the gas-phase ozonation of terpenes yields suites of products via a cascade of chemically activated intermediates that ranges from primary ozonides to dioxiranes. If a similar mechanism operated in water, as it is generally assumed, such intermediates would be deactivated within picoseconds and, henceforth, be unable to produce carboxylic acids in microseconds. Herein, we report the online electrospray mass spectrometric detection of (M + 2O – H^+) and (M + 3O – H^+) carboxylates on the surface of aqueous β-caryophyllene (C_(15)H_(24), M = 204 Da) microjets exposed to a few ppmv of O_3(g) for < 10 μs. Since neither species is formed on dry solvent microjets and both incorporate deuterium from D_2O, we infer that carboxylates ensue from the interaction of nascent intermediates with interfacial water via heretofore unreported processes. These interfacial events proceed much faster than those in bulk liquids saturated with ozone.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/jz100847a DOIArticle
http://pubs.acs.org/doi/full/10.1021/jz100847aPublisherArticle
ORCID:
AuthorORCID
Enami, Shinichi0000-0002-2790-7361
Hoffmann, Michael R.0000-0001-6495-1946
Colussi, A. J.0000-0002-3400-4101
Additional Information:© 2010 American Chemical Society. Received Date: June 21, 2010. Accepted Date: July 9, 2010. Published on Web Date: July 15, 2010. S.E. appreciates the Japan Society for the Promotion of Sciences Postdoctoral Fellowships for Research Abroad. This work was supported by National Science Foundation Grant ATM-0714329.
Funders:
Funding AgencyGrant Number
Japan Society for the Promotion of Science (JSPS)UNSPECIFIED
NSFATM-0714329
Issue or Number:15
Record Number:CaltechAUTHORS:20100831-155817688
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20100831-155817688
Official Citation:Prompt Formation of Organic Acids in Pulse Ozonation of Terpenes on Aqueous Surfaces Shinichi Enami, Michael R. Hoffmann, A. J. Colussi The Journal of Physical Chemistry Letters 2010 1 (15), 2374-2379
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:19755
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:01 Sep 2010 18:05
Last Modified:03 Mar 2020 13:01

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