Phosphate selective alkylenebisurea receptors: Structure-binding relationship

Blažek, Vesna; Bregović, Nikola; Mlinarić-Majerski, Kata; Basarić, Nikola

doi:10.1016/j.tet.2011.03.096

Pregled bibliografske jedinice broj: 508087

Phosphate selective alkylenebisurea receptors: Structure-binding relationship

Blažek, Vesna; Bregović, Nikola; Mlinarić-Majerski, Kata; Basarić, Nikola

Phosphate selective alkylenebisurea receptors: Structure-binding relationship // Tetrahedron, 67 (2011), 21; 3846-3857 doi:10.1016/j.tet.2011.03.096 (međunarodna recenzija, članak, znanstveni)

CROSBI ID: 508087 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Phosphate selective alkylenebisurea receptors: Structure-binding relationship

Autori
Blažek, Vesna ; Bregović, Nikola ; Mlinarić-Majerski, Kata ; Basarić, Nikola

Izvornik
Tetrahedron (0040-4020) 67 (2011), 21; 3846-3857

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

Ključne riječi
adamantanes ureas ; anion ; host molecules ; NMR titration ; UV-vis titration ;
(adamantanes ; ureas ; anion host molecules ; NMR titration ; UV-vis titration)

Sažetak
New host molecules for anions, adamantane and alkyl urea derivatives substituted by naphthalene chromophores, were synthesized. Their binding with F-, Cl-, Br-, OAc-, HSO4-, NO3- and H2PO4- was investigated by UV-Vis, fluorescence and NMR spectroscopy. The anion binding ability of adamantyl bisurea derivatives was compared with the analogous host molecules, wherein the urea moieties are separated by flexible alkyl linkers of the same length, and adamantane monourea derivative. The host molecules show the highest selectivity towards F- and H2PO4-. The binding stoichiometry and the values of the association constants depend on the basicity of anions, availability of H-bonding sites, preorganization and rigidity of the hosts, as well as solvent polarity and H-bonding availability. Rigid adamantane receptors, compared to flexible analogues show increased selectivity for H2PO4-, whereas binding of OAc- is better with flexible receptors. The binding of OAc- and H2PO4- was investigated by microcalorimetry. The stoichiometries and the stability constants of the corresponding complexes obtained by this method were in good agreement compared to those determined by UV-Vis titrations. In both cases the enthalpic contribution to the overall complex stability was predominant.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA

Projekti:
MZOS-098-0982933-2911 - Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima (Majerski, Kata, MZOS ) ( CroRIS)
MZOS-119-1191342-2960 - Elektroliti i koordinacijske reakcije u otopini (Tomišić, Vladislav, MZOS ) ( CroRIS)

Ustanove:
Institut "Ruđer Bošković", Zagreb,
Prirodoslovno-matematički fakultet, Zagreb

Profili:

Nikola Bregović (autor)