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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Anion-induced urea deprotonation.

The urea-based receptor 1 (1-(7-nitrobenzo[1,2,5]oxadiazol-4-yl)-3-(4-nitrophenyl)urea, L--H), interacts with X- ions in MeCN, according to two consecutive steps: 1) formation of a hydrogen-bond complex [L--H...X]-; 2) deprotonation of L--H to give L- and [HX2]-, as shown by spectrophotometric and 1H NMR titration experiments. Step 2) takes place with more basic anions (fluoride, carboxylates, dihydrogenphosphate), while less basic anions (Cl-, NO2-, NO3-) do not induce proton transfer. On crystallisation from a solution containing L--H and excess Bu4NF, the tetrabutylammonium salt of the deprotonated urea derivative (Bu4N[L]) was isolated and its crystal and molecular structure determined.[1]


  1. Anion-induced urea deprotonation. Boiocchi, M., Del Boca, L., Esteban-Gómez, D., Fabbrizzi, L., Licchelli, M., Monzani, E. Chemistry (Weinheim an der Bergstrasse, Germany) (2005) [Pubmed]
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