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Criegee Intermediates React with Levoglucosan on Water

Enami, Shinichi and Hoffmann, Michael R. and Colussi, A. J. (2017) Criegee Intermediates React with Levoglucosan on Water. Journal of Physical Chemistry Letters, 8 (16). pp. 3888-3894. ISSN 1948-7185.

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Levoglucosan (Levo), a C_6-anhydrosaccharide produced in the combustion of cellulosic materials, is the major component of aerosols produced from biomass burning over vast regions worldwide. Levo has long been considered chemically inert and thus has been used as a tracer of biomass burning sources. However, we now show that sugars including Levo, glucose, arabitol, and mannitol react rapidly with Criegee intermediates (CIs) generated during the ozonolysis of sesquiterpenes on the surface of water:acetonitrile microjets. Hydrophilic Levo reacts faster with CIs than with water or surface-active 1-octanol at air–aqueous interfaces. This unexpected phenomenon is likely associated with the relatively low water density at air–aqueous interfaces coupled with a higher gas-phase acidity of the saccharide hydroxyl groups (i.e., −OH) versus n-alkanols. Results presented herein show that aerosol saccharides are in fact reactive toward CIs. Given the abundance of saccharides in the atmosphere, they may be important contributors to the growth and mass loading of secondary organic aerosols.

Item Type:Article
Related URLs:
URLURL TypeDescription Information
Enami, Shinichi0000-0002-2790-7361
Hoffmann, Michael R.0000-0001-6495-1946
Colussi, A. J.0000-0002-3400-4101
Additional Information:© 2017 American Chemical Society. Received: June 29, 2017. Accepted: August 2, 2017. Published: August 2, 2017. We are grateful to Prof. Yosuke Sakamoto of Kyoto University, and Drs. Satoshi Inomata, Akihiro Fushimi, and Kei Sato of NIES for valuable discussions. This work is partly supported by the research foundation for opto-science and technology, JSPS KAKENHI Grant Numbers 15H05328 and 15K12188. Author Contributions: S.E. designed and performed research; S.E. and A.J.C. analyzed data; S.E., M.R.H., and A.J.C. wrote the paper. The authors declare no competing financial interest.
Funding AgencyGrant Number
Japan Society for the Promotion of Science (JSPS)15H05328
Japan Society for the Promotion of Science (JSPS)15K12188
Issue or Number:16
Record Number:CaltechAUTHORS:20170814-152742950
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Official Citation:Criegee Intermediates React with Levoglucosan on Water Shinichi Enami, Michael R. Hoffmann, and A. J. Colussi The Journal of Physical Chemistry Letters 2017 8 (16), 3888-3894 DOI: 10.1021/acs.jpclett.7b01665
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:80382
Deposited By: George Porter
Deposited On:14 Aug 2017 22:43
Last Modified:03 Mar 2020 13:01

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