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Halogen-substituted ureas for anion binding: solid state and solution studies

Casula, Arianna; Fornasier, Marco; Montis, Riccardo; Bettoschi, Alexandre; Argent, Stephen P.; Blake, Alexander J.; Lippolis, Vito; Marongiu, Laura; Picci, Giacomo; Tidey, Jeremiah P.; Caltagirone, Claudia

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Arianna Casula

Marco Fornasier

Riccardo Montis

Alexandre Bettoschi

Alexander J. Blake

Vito Lippolis

Laura Marongiu

Giacomo Picci

Jeremiah P. Tidey

Claudia Caltagirone


Herein, we report the synthesis and the anion binding properties of a family of N,N′-diphenylureas L1-L15, bearing on the aromatic ring(s) halogens (chlorine and iodine) and/or nitro or trifluoromethyl electron-withdrawing groups. The analysis of the crystal structures obtained from single crystal X-ray diffraction experiments shows that self-assembled chains or tapes connected via N–H···O hydrogen bonds are the most commonly adopted arrangements for this type of molecules in the crystal lattice. In the presence of anion guests or solvent molecules with competing hydrogen bond donors and acceptors, other supramolecular arrangements can be observed. Solution studies conducted in DMSOd 6/0.5% H2O by means of 1H-NMR titrations show the formation of 1:1 adducts with all receptors. The different observed affinities of the receptors for the anion guests were rationalised in terms of steric hindrance of the substituents on the phenyl rings and their electron-withdrawing properties.


Casula, A., Fornasier, M., Montis, R., Bettoschi, A., Argent, S. P., Blake, A. J., …Caltagirone, C. (in press). Halogen-substituted ureas for anion binding: solid state and solution studies. Supramolecular Chemistry,

Journal Article Type Article
Acceptance Date Sep 2, 2017
Online Publication Date Sep 24, 2017
Deposit Date Oct 5, 2017
Publicly Available Date Sep 25, 2018
Journal Supramolecular Chemistry
Print ISSN 1061-0278
Electronic ISSN 1029-0478
Publisher Taylor and Francis
Peer Reviewed Peer Reviewed
Keywords anion binding, phenylurea
Public URL
Publisher URL
Additional Information This is an Accepted Manuscript of an article published by Taylor & Francis in Supramolecular Chemistry on 24.09.2017, available online:
Contract Date Oct 5, 2017


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