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Why, on Interaction of Urea-Based Receptors with Fluoride, Beautiful Colors Develop

David Esteban-Gómez, Luigi Fabbrizzi,* and Maurizio Licchelli

Dipartimento di Chimica Generale, Universit di Pavia, viale Taramelli 12, 27100 Pavia, Italy luigi.fabbrizzi@unipv.it

J. Org. Chem., 2005, 70 (14), pp 5717–5720

DOI: 10.1021/jo050528s

Publication Date (Web): June 15, 2005

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Abstract

Urea-based receptors, containing electron-withdrawing chromogenic substituents, in a DMSO solution, in the presence of varying excess of fluoride, do not form H-bond complexes, but undergo stepwise deprotonation of the two N−H fragments, an event which is signaled by the development of vivid colors. Double deprotonation is also observed in the presence of hydroxide. Less basic anions (CH₃COO^-, H₂PO₄^-) induce deprotonation of only one N−H.

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Published In Issue July 08, 2005
Received March 15, 2005

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Why, on Interaction of Urea-Based Receptors with Fluoride, Beautiful Colors Develop

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

What Anions Do to N−H-Containing Receptors

Signaling Recognition Events with Fluorescent Sensors and Switches

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