Bis‐Selenoureas for Anion Binding: A 1H NMR and Theoretical Study. Issue 7 (1st July 2020)

• Record Type: Journal Article
• Authors: Picci, Giacomo; Mocci, Rita; Ciancaleoni, Gianluca; Lippolis, Vito; Zielińska‐Błajet, Mariola; Caltagirone, Claudia
• Is Part Of: ChemPlusChem. Volume 85:Issue 7(2020)
• Page Start: 1389
• Page End: 1395
• Publication Date: 2020-07-01
• Subjects: anion binding -- chalcogens -- density functional theory -- selenoureas -- supramolecular chemistry; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cplu.202000260
• Languages: English
• ISSNs: 2192-6506

Abstract

Abstract: The anion binding ability of a family of bis‐selenoureas L1 ‐L3 obtained by the reaction of 1, 3‐bis(aminomethyl)‐benzene and phenylisoselenocyanate, p ‐methoxyphenylisoselenocyanate and naphtylisoselenocyanate, for L1, L2, and L3, respectively, has been tested and compared to that of previously described bis‐urea analogues. Results suggest that the introduction of selenium leads to an increase in the acidity of the urea NH hydrogen atoms, and therefore to a stronger affinity (more than three‐fold higher) towards anion species, in particular dihydrogen phosphate, in DMSO‐ d 6 . Theoretical calculations allowed for the optimization of the adducts receptors corroborating the experimental results. Abstract : Family of bis‐selenoureas : The first examples of bis‐selenourea‐based receptors bearing different aryl substituents for anion binding are described. The introduction of selenium into the molecular skeleton of bis‐ureas improves the anion binding properties of these receptors, in particular towards dihydrogen phosphate, as a result of an increase in the acidity of the selenourea NH groups. Theoretical calculations confirmed the experimental results obtained in solution.