Title

Water Deficient Environment Accelerates Proton Exchange: Acetone-Water Reaction Catalyzed By Calix[4]Hydroquinone Nanotubes

Abstract

Calix[4]hydroquinone nanotubes possess the unique property to catalyze proton exchange between water and acetone. Since concerted proton transfer mechanisms could be excluded previously, stepwise proton transfer via ionic intermediates created by predissociation of CHQ OH groups is studied using state-of-the-art quantum chemical methodology. In fact, the presence of charged species, protonated acetone or deprotonated hydroquinone, leads to a substantial decrease of the proton transfer energy barrier and to calculated reaction rates that provide an explanation for the experimentally observed proton exchange. Furthermore, our quantum chemical investigation demonstrates that the catalytic activity of CHQ aggregates is not based on a reduction of the energy barrier connected with proton transfer but on the desolvation of acetone and prevention of solvent water cluster formation. © 2009 American Chemical Society.

Publication Date

6-18-2009

Publication Title

Journal of Physical Chemistry C

Volume

113

Issue

24

Number of Pages

10395-10401

Document Type

Article

Personal Identifier

scopus

DOI Link

https://doi.org/10.1021/jp900223n

Socpus ID

67650711192 (Scopus)

Source API URL

https://api.elsevier.com/content/abstract/scopus_id/67650711192

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