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dc.contributor.authorNguyen, Duy
dc.contributor.authorCasillas, Sarah
dc.contributor.authorVang, Hnubci
dc.contributor.authorGarcia, Anthony
dc.contributor.authorMizuno, Hikaru
dc.contributor.authorRiffe, Erika J.
dc.contributor.authorSaykally, Richard J.
dc.contributor.authorNguyen, Son C.
dc.date.accessioned2021-03-21T07:09:41Z
dc.date.available2021-03-21T07:09:41Z
dc.date.issued2021-03-18
dc.identifier.citationNguyen, D., Casillas, S., Vang, H., Garcia, A., Mizuno, H., Riffe, E. J., … Nguyen, S. C. (2021). Catalytic Mechanism of Interfacial Water in the Cycloaddition of Quadricyclane and Diethyl Azodicarboxylate. The Journal of Physical Chemistry Letters, 3026–3030. doi:10.1021/acs.jpclett.1c00565
dc.identifier.issn1948-7185
dc.identifier.issn1948-7185
dc.identifier.doi10.1021/acs.jpclett.1c00565
dc.identifier.urihttp://hdl.handle.net/10754/668146
dc.description.abstract“On-water” catalysis, the unusual activity of water molecules at the organic solvent–water interface, has been demonstrated in many organic reactions. However, the catalytic mechanism has remained unclear, largely because of the irreproducibility of the organic–water interface under the common stirring condition. Here, the interfacial area was controlled by employing adsorbed water on mesoporous silica nanoparticles as the catalyst. Reliable kinetics of the cycloaddition reaction of quadricyclane and diethyl azodicarboxylate (DEAD) at the toluene–water interface within the nanoparticle pores were measured. Data reveal an Eley–Rideal mechanism, wherein DEAD adsorbs at the toluene–water interface via hydrogen bonds formed with interfacial water, which lower the activation energy of the cycloaddition reaction. The mechanistic insights gained and preparation of surface water in silica pores described herein may facilitate the future design of improved “on-water” catalysts.
dc.description.sponsorshipWe thank Dr. Ziliang Mao for the fruitful discussion. This work was supported by the UC Office of the President within the Multicampus Research Programs and Initiatives (M21PL3263) (S.C.N., R.J.S.), Director, Office of Basic Energy Sciences, Office of Science, U.S. Department of Energy under Contract No. DEAC02-05CH11231 through the Chemical Sciences Division of the Lawrence Berkeley National Laboratory (R.J.S., H.M.), the King Abdullah University of Science and Technology (E.R.), and the University of California’s Leadership Excellence through Advanced Degrees program (A.G.).
dc.publisherAmerican Chemical Society (ACS)
dc.relation.urlhttps://pubs.acs.org/doi/10.1021/acs.jpclett.1c00565
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Physical Chemistry Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.jpclett.1c00565.
dc.titleCatalytic Mechanism of Interfacial Water in the Cycloaddition of Quadricyclane and Diethyl Azodicarboxylate
dc.typeArticle
dc.identifier.journalThe Journal of Physical Chemistry Letters
dc.rights.embargodate2022-03-18
dc.eprint.versionPost-print
dc.contributor.institutionDepartment of Chemistry and Biochemistry, University of California, Merced, California 95343, United States
dc.contributor.institutionDepartment of Chemistry, University of California, Berkeley, California 94720, United States
dc.contributor.institutionChemical Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, California 94720, United States
dc.identifier.pages3026-3030


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