Halogen-substituted ureas for anion binding: solid state and solution studies
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...
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| Format: | Article |
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Taylor & Francis
2017
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| Online Access: | https://eprints.nottingham.ac.uk/46893/ |
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| author | 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 |
| author_facet | 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 |
| author_sort | Casula, Arianna |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T20:03:36Z |
| format | Article |
| id | nottingham-46893 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T20:03:36Z |
| publishDate | 2017 |
| publisher | Taylor & Francis |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-468932020-05-04T19:08:35Z https://eprints.nottingham.ac.uk/46893/ 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 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. Taylor & Francis 2017-09-24 Article PeerReviewed Casula, Arianna, Fornasier, Marco, Montis, Riccardo, Bettoschi, Alexandre, Argent, Stephen P., Blake, Alexander J., Lippolis, Vito, Marongiu, Laura, Picci, Giacomo, Tidey, Jeremiah P. and Caltagirone, Claudia (2017) Halogen-substituted ureas for anion binding: solid state and solution studies. Supramolecular Chemistry . pp. 1-12. ISSN 1029-0478 anion binding phenylurea http://www.tandfonline.com/doi/full/10.1080/10610278.2017.1377343 doi:10.1080/10610278.2017.1377343 doi:10.1080/10610278.2017.1377343 |
| spellingShingle | anion binding phenylurea 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 Halogen-substituted ureas for anion binding: solid state and solution studies |
| title | Halogen-substituted ureas for anion binding: solid state and solution studies |
| title_full | Halogen-substituted ureas for anion binding: solid state and solution studies |
| title_fullStr | Halogen-substituted ureas for anion binding: solid state and solution studies |
| title_full_unstemmed | Halogen-substituted ureas for anion binding: solid state and solution studies |
| title_short | Halogen-substituted ureas for anion binding: solid state and solution studies |
| title_sort | halogen-substituted ureas for anion binding: solid state and solution studies |
| topic | anion binding phenylurea |
| url | https://eprints.nottingham.ac.uk/46893/ https://eprints.nottingham.ac.uk/46893/ https://eprints.nottingham.ac.uk/46893/ |