Details

Autor(en) / Beteiligte

• Boiocchi, Massimo
• Del Boca, Laura
• Gómez, David Esteban
• Fabbrizzi, Luigi
• Licchelli, Maurizio
• Monzani, Enrico

Titel

Nature of Urea−Fluoride Interaction:  Incipient and Definitive Proton Transfer

Ist Teil von

• Journal of the American Chemical Society, 2004-12, Vol.126 (50), p.16507-16514

Ort / Verlag

Washington, DC: American Chemical Society

Erscheinungsjahr

2004

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 1,3-bis(4-nitrophenyl)urea (1) interacts through hydrogen bonding with a variety of oxoanions in an MeCN solution to give bright yellow 1:1 complexes, whose stability decreases with the decreasing basicity of the anion (CH3COO- > C6H5COO- > H2PO4 - > NO2 - > HSO4 - > NO3 -). The [Bu4N][1·CH3COO] complex salt has been isolated as a crystalline solid and its molecular structure determined, showing the formation of a discrete adduct held together by two N−H···O hydrogen bonds of moderate strength. On the other hand, the F- ion first establishes a hydrogen-bonding interaction with 1 to give the most stable 1:1 complex, and then on addition of a second equivalent, induces urea deprotonation, due to the formation of HF2 -. The orange-red deprotonated urea solution uptakes carbon dioxide from air to give the tetrabutylammonium salt of the hydrogencarbonate H-bond complex, [Bu4N][1·HCO3], whose crystal and molecular structures have been determined.