Naslov
Dehydroacetic acid derivatives bearing amide and urea moieties as effective anion receptors

Autori
Bregović, Nikola ; Cindro, Nikola ; Bertoša, Branimir ; Barišić, Dajana ; Frkanec, Leo ; Užarević, Krunoslav ; Tomišić, Vladislav

Izvornik
Chemistry : a European journal (0947-6539) 23 (2017), 43; 10396-10406

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

Ključne riječi
anion binding ; amide and urea derivatives ; dehydroacetic acid ; solution thermodynamics ; Monte Carlo conformational search

Sažetak
Three novel derivatives of dehydroacetic acid comprising amide and urea subunits were synthesized and their anion binding properties investigated. The studied compounds selectively bind acetate and dihydrogen phosphate in acetonitrile and dimethyl sulfoxide among a series of halides and oxyanions. The corresponding complexation processes were characterized by means of 1H NMR titrations revealing the 1:1 complex stoichiometry in most cases, with the exception of dihydrogen phosphate which formed 2:1 (anion:ligand) complexes in acetonitrile. The complex stability constants were determined and discussed with respect to structural properties of the receptors, the hydrogen-bond forming potential of the anions and the characteristics of the solvents used. Based on the spectroscopic data and results of Monte Carlo simulations, the amide and urea groups were affirmed as the primary binding sites in all cases. The results of the computational methods indicated that an array of both inter- and intramolecular hydrogen bonds can be formed in the studied systems, which was shown to play an important role in defining the overall stability of the complexes. Solubility measurements were carried out in both solvents and thermodynamics of transfer from acetonitrile to dimethyl sulfoxide was characterized on a quantitative level. This afforded a detailed insight into the impact of the medium on the complexation reactions.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA