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Alkali Metal Ion Complexation of Adamantane Functionalized Diaza-bibracchial Lariat Ethers

Šumanovac Ramljak, Tatjana; Majerski, Kata; Bertoša, Branimir (2012) Alkali Metal Ion Complexation of Adamantane Functionalized Diaza-bibracchial Lariat Ethers. Croatica Chemica Acta, 85 (4). pp. 559-568. ISSN 0011-1643

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A series of adamantane functionalized diaza-lariat ethers 1-6 have been prepared and alkali metal picrate extraction profiles determined. The ability of aza-crown ethers 1-6 to extract the alkali metal picrates was compared with that of diaza-18-crown-6 (7) and N,N'-dibenzodiaza-18-crown-6 (8). Na+ and K+ transport across bulk liquid membrane was also measured. The results of alkali metal cation extraction experiments showed that lariat ethers 2 and 3, in which the adamantane molecule is linked to the diaza-18-crown-6 by amine bond, have better complexation abilities for all cations compared to the parent crown ethers 7 and 8, as well as a significantly higher selectivity for K+ than diaza-18-crown-6. However, diaza-lariat ether 1 showed reduced, and 4-6 negligible extractability towards any of the alkali cations. Monte Carlo conformational analysis pointed to the importance of conformational flexibility of the investigated compounds for their extraction ability of alkali cations.

Item Type: Article
Uncontrolled Keywords: diaza-bibracchial lariat ethers; adamantane functionalized crown ethers; metal ion complexation; metal ion transport; Monte Carlo conformational search; crown-ethers; molecular-mechanics; binding-properties; macrocyclic carriers; liquid membranes; cation-binding; transport; design; mixtures; receptor
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Project titleProject leaderProject codeProject type
Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima[27342] Kata Majerski098-0982933-2911MZOS
Proučavanje biomakromolekula računalnim metodama i razvoj novih algoritama[113604] Sanja Tomić098-1191344-2860MZOS
Depositing User: Kata Majerski
Date Deposited: 11 Oct 2013 10:22
DOI: 10.5562/cca2100

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