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Pregled bibliografske jedinice broj: 879228

Časopis

Autori: Bregović, Nikola; Cindro, Nikola; Bertoša, Branimir; Barišić, Dajana; Frkanec, Leo; Užarević, Krunoslav; Tomišić, Vladislav
Naslov: Dehydroacetic acid derivatives bearing amide and urea moieties as effective anion receptors
( Dehydroacetic acid derivatives bearing amide and urea moieties as effective anion receptors )
Izvornik: Chemistry : a European journal (0947-6539) 23 (2017), 43; 10396-10406
Vrsta rada: članak
Ključne riječi: anion binding ; amide and urea derivatives ; dehydroacetic acid ; solution thermodynamics ; Monte Carlo conformational search
( 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.
Projekt / tema: HRZZ-IP-2014-09-7309
Izvorni jezik: eng
Rad je indeksiran u
bazama podataka:
Current Contents Connect (CCC)
MEDLINE
Scopus
SCI-EXP, SSCI i/ili A&HCI
Science Citation Index Expanded (SCI-EXP) (sastavni dio Web of Science Core Collectiona)
Kategorija: Znanstveni
Znanstvena područja:
Kemija
URL Internet adrese: http://onlinelibrary.wiley.com/doi/10.1002/chem.201701677/abstract
Broj citata:
Altmetric:
DOI: 10.1002/chem.201701677
URL cjelovitog teksta:
Google Scholar: Dehydroacetic acid derivatives bearing amide and urea moieties as effective anion receptors
Upisao u CROSBI: Nikola Bregović (nbregovic@chem.pmf.hr:Nikola.Bregovic@chem.pmf.hr), 5. Lip. 2017. u 10:20 sati



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