Original scientific paper

https://doi.org/10.5562/cca2100

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

Tatjana Šumanovac Ramljak ; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, P. O. Box 180, 10 002 Zagreb, Croatia
Kata Mlinarić-Majerski orcid.org/0000-0001-6282-1662 ; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, P. O. Box 180, 10 002 Zagreb, Croatia
Branimir Bertoša ; Division of Physical Chemistry, Department of Chemistry, Faculty of Science, Horvatovac 102A, 10000 Zagreb, Croatia

Abstract

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, diazalariat
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.(doi: 10.5562/cca2100)

Keywords

diaza-bibracchial lariat ethers; adamantane functionalized crown ethers; metal ion complexation; metal ion transport; Monte Carlo conformational search

Hrčak ID:

107089

URI

https://hrcak.srce.hr/107089

Publication date:

17.12.2012.

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