Bis-selenoureas for anion binding: A 1h nmr and theoretical study

Picci G.

Primo

;Mocci R.;Ciancaleoni G.;Lippolis V.;Zielinska-Blajet M.;Caltagirone C.

Ultimo

2020-01-01

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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-d6. Theoretical calculations allowed for the optimization of the adducts receptors corroborating the experimental results.