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Adamantane bisurea derivatives: anion binding in the solution and in the solid state


Blažek, Vesna; Molčanov, Krešimir; Mlinarić-Majerski, Kata; Kojić-Prodić, Biserka; Basarić, Nikola
Adamantane bisurea derivatives: anion binding in the solution and in the solid state // Tetrahedron, 69 (2013), 2; 517-526 doi:10.1016/j.tet.2012.11.030 (međunarodna recenzija, članak, znanstveni)


Naslov
Adamantane bisurea derivatives: anion binding in the solution and in the solid state

Autori
Blažek, Vesna ; Molčanov, Krešimir ; Mlinarić-Majerski, Kata ; Kojić-Prodić, Biserka ; Basarić, Nikola

Izvornik
Tetrahedron (0040-4020) 69 (2013), 2; 517-526

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

Ključne riječi
Adamantanes; anion receptors; fluorescence titration; UV-vis titration; ureas; X-ray structural analysis

Sažetak
1, 3-Bis-(3-arylureido)adamantane receptors, bearing phenyl (5, 6), 1-naphthyl (7, 8) and 9-anthryl (9) fluorophore, were synthesized. Their ability for complexation with F-, Cl-, Br-, OAc-, NO3- HSO4-, and H2PO4- in solution was investigated by UV-vis and fluorescence spectrophotometry. The binding was compared to that of 2-naphthyl bisurea derivatives with flexible spacers (bearing propylene or pentalene, 2 and 4) and rigid adamantane analogues (1 and 3). In solution, the receptors form stable complexes with all anions except with NO3-. The complexation ability in CH3CN correlates with the basicity of anion and the acidity of the urea N-H, whereas in DMSO the complexes stability variations are less pronounced. The X-ray structure of receptor 1 indicates that incorporation of the adamantane moiety preorganizes the receptor in a tweezer-like conformation for the optimal formation of hydrogen bonding network and high selectivity for H2PO4- anion. Incorporation of the methylene spacers between the adamantane and the urea additionally increases stability of the complexes with anions. X-ray structural analysis was performed on the following complexes: 1∙Bu4NH2PO4, 3∙Bu4NH2PO4, 5∙Bu4NH2PO4∙4H2O, and 5∙Bu4NOAc∙3H2O. All H2PO4- complexes include extensive receptor•••H2PO4- hydrogen bonds, essential for the anion recognition, as well as H2PO4-•••H2PO4- hydrogen bonds.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
098-0982933-2911 - Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima (Kata Majerski, )
098-1191344-2943 - Protein-ligand međudjelovanja na atomnoj razini (Marija Luić, )

Ustanove
Institut "Ruđer Bošković", Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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