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Literature DB >> 15913341

The structure of the H3O+ hydronium ion in benzene.

Evgenii S Stoyanov¹, Stephan P Hoffmann, Kee-Chan Kim, Fook S Tham, Christopher A Reed.

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.

Entities: Chemical Gene

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Year: 2005 PMID： 15913341 DOI： 10.1021/ja050401k

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

7 in total

1. Myths about the proton. The nature of H+ in condensed media.

Authors: Christopher A Reed
Journal: Acc Chem Res Date: 2013-07-23 Impact factor: 22.384

2. The basicity of unsaturated hydrocarbons as probed by hydrogen-bond-acceptor ability: bifurcated N-H+ ...pi hydrogen bonding.

Authors: Evgenii S Stoyanov; Irina V Stoyanova; Christopher A Reed
Journal: Chemistry Date: 2008 Impact factor: 5.236

7. Generation and Applications of the Hydroxide Trihydrate Anion, [OH(OH₂ )₃ ]^- , Stabilized by a Weakly Coordinating Cation.

Authors: Robin F Weitkamp; Beate Neumann; Hans-Georg Stammler; Berthold Hoge
Journal: Angew Chem Int Ed Engl Date: 2019-09-09 Impact factor: 15.336

7 in total

The structure of the H3O+ hydronium ion in benzene.

1. Myths about the proton. The nature of H+ in condensed media.

2. The basicity of unsaturated hydrocarbons as probed by hydrogen-bond-acceptor ability: bifurcated N-H+ ...pi hydrogen bonding.

3. H(aq)+ structures in proton wires inside nanotubes.

4. Silylated Sulfuric Acid: Preparation of a Tris(trimethylsilyl)oxosulfonium [(Me₃ Si-O)₃ SO]⁺ Salt.

5. On Silylated Oxonium and Sulfonium Ions and Their Interaction with Weakly Coordinating Borate Anions.

6. Low-Temperature Isolation of a Labile Silylated Hydrazinium-yl Radical Cation, [(Me₃ Si)₂ N-N(H)SiMe₃ ]^.

7. Generation and Applications of the Hydroxide Trihydrate Anion, [OH(OH₂ )₃ ]^- , Stabilized by a Weakly Coordinating Cation.