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Synthesis and alkali metal complexation studies of novel cage-functionalized cryptands


Šumanovac Ramljak, Tatjana; Despotović, Ines; Bertoša, Branimir; Mlinarić-Majerski, Kata
Synthesis and alkali metal complexation studies of novel cage-functionalized cryptands // Tetrahedron, 69 (2013), 49; 10610-10620 doi:10.1016/j.tet.2013.10.039 (međunarodna recenzija, članak, znanstveni)


Naslov
Synthesis and alkali metal complexation studies of novel cage-functionalized cryptands

Autori
Šumanovac Ramljak, Tatjana ; Despotović, Ines ; Bertoša, Branimir ; Mlinarić-Majerski, Kata

Izvornik
Tetrahedron (0040-4020) 69 (2013), 49; 10610-10620

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

Ključne riječi
Adamantane functionalized cryptands; metal ion complexation; metal ion transport; Monte Carlo conformational search; stability constant; quantum chemical calculations

Sažetak
The synthesis of novel cage-functionalized cryptands 1–5 containing adamantane-, 2-oxaadamantane- or noradamantane-moiety [i.e., 1, 3-diethyladamantano[2.2.0]cryptand (1), 1, 3-diethoxyadamantano[2.2.2]cryptand (2), 1, 3-di[(ethyloxy)methyl]adamantano[2.2.2]-cryptand (3), 1, 3-di[(ethyloxy)methyl]-2-oxaadamantano[2.2.3]cryptand (4), and 1, 2-diethyloxynoradamantano[2.2.2]cryptand (5)] and their alkali metal binding properties are reported. The results obtained by extraction experiments showed that all the cryptands displayed lower extraction capabilities than the parent [2.2.2]cryptand. However, cryptands 1 and 2 showed much higher selectivity toward K+ than the reference [2.2.2]cryptand. When the third bridge is enlarged by two additional CH2-groups as well as by two oxygen atoms, as in cryptands 3 and 4, the complexational abilities for bigger cations (K+, Rb+ and Cs+) are enhanced. Cryptand 5 displayed very good extraction capabilities of all cations, but showed practically no selectivity towards any of the alkali metal cation. The experimental findings are corroborated by calculation studies consisting of force field based conformational search using Monte Carlo method followed by investigation of the stabilities of the complexes of cryptands with Na+ and K+ metal ions in chloroform by means of quantum chemical calculations at the density functional theory level.

Izvorni jezik
Engleski

Znanstvena područja
Fizika, Kemija



POVEZANOST RADA


Projekt / tema
098-0982933-2911 - Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima (Kata Majerski, )
098-0982933-2932 - Broenstedove i Lewisove kiseline i baze u kemiji i biokemiji (Robert Vianello, )
098-1191344-2860 - Proučavanje biomakromolekula računalnim metodama i razvoj novih algoritama (Sanja Tomić, )

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