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Nature of urea-fluoride interaction: incipient and definitive proton transfer

Boiocchi, Massimo, Del Boca, Laura, Gómez, David Esteban, Fabbrizzi, Luigi, Licchelli, Maurizio, Monzani, Enrico·2004·Journal of the American Chemical Society
DOI 10.1021/ja045936c
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Abstract

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.

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  • Some hits are structurally similar to known small molecule fluoride receptors.

    “Intriguingly, some of our hits are also structurally similar to known small molecule fluoride receptors (Boiocchi et al., 2004).”

    From Small Molecule Fluoride Toxicity Agonists (2015) · cites this paper as Boiocchi et al., 2004

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Research works printed but not linked: 22

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Metadata

Authors
Boiocchi, M., Del Boca, L., Gómez, D. E., Fabbrizzi, L., Licchelli, M., & Monzani, E.
Affiliations
Contribution from the Dipartimento di Chimica Generale, Università di Pavia, via Taramelli 12, 27100 Pavia, Italy, and Centro Grandi Strumenti, Università di Pavia, via Bassi 10, 27100 Pavia, Italy
Venue
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Published
2004-11-24
Volume
126
Issue
50
Pages
16507-16514
ISSN
  • 0002-7863
  • 1520-5126
DOI
10.1021/ja045936c
Cited by
815
References
0
Language
en

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