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. 2005 Jun 1;127(21):7664-5.
doi: 10.1021/ja050401k.

The structure of the H3O+ hydronium ion in benzene

Evgenii S Stoyanov  1 , Stephan P Hoffmann, Kee-Chan Kim, Fook S Tham, Christopher A Reed
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Free article

The structure of the H3O+ hydronium ion in benzene

Evgenii S Stoyanov et al. J Am Chem Soc. .
Free article

Abstract

Infrared, X-ray structural, 1H NMR, and computational evidence for pi-solvation of H3O+ by benzene molecules is presented. A salt with a discrete [H3O.3benzene]+ cation can be isolated using a very weakly interacting carborane counterion, CHB11Cl11-. pi-Arene solvation of H3O+ explains the solubility of this salt in benzene solution. Similar results are indicated for the "Zundel-type" H5O2+ ion. These findings suggest structures for the active protonating species when strong acids are used as catalysts in arene solvents containing trace water. They are also relevant to structures that may be present in biological proton transport.

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