Naslov
Protonation and anion-binding properties of aromatic sulfonylurea derivatives

Autori
Barišić, Dajana ; Cindro, Nikola ; Vidović, Nikolina ; Bregović, Nikola ; Tomišić, Vladislav

Izvornik
RSC Advances (2046-2069) 11 (2021); 23992-24000

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Sulfonylurea ; protonation ; anion-binding ; NMR

Sažetak
In this work the anion-binding properties of three aromatic sulfonylurea derivatives in acetonitrile and dimethyl sulfoxide were explored by means of NMR titrations. It was found that the studied receptors effectively bind anions of low basicity (Cl−, Br−, I−, NO3− and HSO4−). The stoichiometry of the complexes with receptors containing one binding site was 1 : 1 exclusively, whereas in the case of the receptor containing two sulfonylurea groups 1 : 2 (receptor : anion) complexes were also detected in some cases. The presence of strongly basic anions (acetate and dihydrogen phosphate) led to the deprotonation of the sulfonylurea moiety. This completely hindered its anion-binding properties in DMSO and only proton transfer occurred upon the addition of basic anions to the studied receptors. In MeCN, a complex system of equilibria including both ligand deprotonation and anion binding was established. Since ionisation of receptors was proven to be a decisive factor defining the behaviour of the sulfonylurea receptors, their pKa values were determined using several deprotonation agents in both solvents. The results were interpreted in the context of receptor structures and solvent properties and applied for the identification of the interactions with basic anions.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA