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Bis‐Selenoureas for Anion Binding: A 1H NMR and Theoretical Study

Bis‐Selenoureas for Anion Binding: A 1H NMR and Theoretical Study 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png ChemPlusChem Wiley

Bis‐Selenoureas for Anion Binding: A 1H NMR and Theoretical Study

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References (44)

Publisher
Wiley
Copyright
© 2020 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
eISSN
2192-6506
DOI
10.1002/cplu.202000260
Publisher site
See Article on Publisher Site

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.

Journal

ChemPlusChemWiley

Published: Jul 1, 2020

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