Catalytic Mechanism of Interfacial Water in the Cycloaddition of Quadricyclane and Diethyl Azodicarboxylate

Duy Nguyen, Sarah Casillas, Hnubci Vang, Anthony Garcia, Hikaru Mizuno, Erika J. Riffe, Richard J. Saykally, Son C. Nguyen

Research output: Contribution to journalArticlepeer-review

2 Scopus citations


“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.
Original languageEnglish (US)
Pages (from-to)3026-3030
Number of pages5
JournalThe Journal of Physical Chemistry Letters
StatePublished - Mar 18 2021
Externally publishedYes

ASJC Scopus subject areas

  • General Materials Science


Dive into the research topics of 'Catalytic Mechanism of Interfacial Water in the Cycloaddition of Quadricyclane and Diethyl Azodicarboxylate'. Together they form a unique fingerprint.

Cite this