Titolo:  Halogenated isophthalamides and dipicolineamides: The role of the halogen substituents in the anion binding properties
Data di pubblicazione:  2020
Data di prima pubblicazione on-line:  2020
Autori:  Picci, G.; Bazzicalupi, C.; Coles, S. J.; Gratteri, P.; Isaia, F.; Lippolis, V.; Montis, R.; Murgia, S.; Nocentini, A.; Orton, J. B.; Caltagirone, C.
Numero degli autori:  11
Lingua:  Inglese
Presenza coautori internazionali: 
Volume:  49
Fascicolo:  27
Pagina iniziale:  9231
Pagina finale:  9238
Numero di pagine:  8
Digital Object Identifier (DOI):  http://dx.doi.org/10.1039/d0dt01492c
Codice identificativo Pubmed:  32500883
Codice identificativo Scopus:  2-s2.0-85088494098
Codice identificativo ISI:  WOS:000549100400008
Abstract:  A novel family of amide-based receptors is herein described. Specifically, the role of the halogen substituents at the aryl moieties in the anion binding properties of a series of halogenated isophthalamides and dipicolineamides (L1-L6) was investigated both in solution and in the solid state in order to evaluate the incidence of all possible different and combined weak host-guest interactions. Only L5 and L6 bearing pentafluorophenyl rings as substituents have some affinities for the set of anions studied. In particular, in the case of L5 an interesting behaviour with the formation of a non-symmetric adduct with benzoate and dihydrogen phosphate was hypothesised by 1H- A nd 19F-NMR spectroscopy studies in solution and confirmed by theoretical calculation. The study of the crystal structures of the receptors demonstrated that the steric hindrance determined by the halogen substituents in the receptor molecules influences the accessibility of the anions to the isophthalamide or dipicoline amide NH moieties, thus modulating the affinity for the anion guests.
Parole chiave:  pi interactions; receptor
Tipologia: 1.1 Articolo in rivista

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