%0 Generic
%A Boiocchi, Massimo
%A Del Boca, Laura
%A Gómez, David Esteban
%A Fabbrizzi, Luigi
%A Licchelli, Maurizio
%A Monzani, Enrico
%D 2004
%T Nature of Urea−Fluoride Interaction: Incipient and Definitive
Proton Transfer
%U https://acs.figshare.com/articles/dataset/Nature_of_Urea_Fluoride_Interaction_Incipient_and_Definitive_Proton_Transfer/3311230
%R 10.1021/ja045936c.s001
%2 https://acs.figshare.com/ndownloader/files/5149963
%K Bu
%K urea deprotonation
%K tetrabutylammonium salt
%K CH 3 COO
%K H 2 PO 4
%K stability decreases
%K C 6 H 5 COO
%K formation
%K HF 2
%K HSO 4
%K HCO
%K MeCN solution
%X 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.
%I ACS Publications