Abstract
Five new azacrown ethers substituted on nitrogen with (2-naphthyl)methyl, (2quinolinyl)methyl, and (8-methoxy-2-quinolinyl)methyl groups are synthesized. Their complexation behavior towards a variety of mono- and divalent metal ions is assessed by picrate extraction.
Highlights
Pedersen on the synthesis of macrocyclic polyethers and their metal salt complexation behavior,[1,2] the influence of structural variation within such ligands has received ever-increasing attention.[3,4]. One such structural variation is the replacement of one ether oxygen with nitrogen to give an azacrown ether.[5]
If the side arm attachment site is a carbon atom of the macrocycle, the ligand is called a C-pivot lariat ether. If it is a nitrogen atom of an azacrown ether, the ligand is identified as a Npivot lariat ether
We report reactions of 2-(bromomethyl)-8methoxyquinoline with azacrown ethers to provide a series N-pivot lariat ethers in which the ring size of the macrocyclic ring is systematically varied from 12-crown-4 to 18-crown-6
Summary
The influence of structural variation within the N-pivot lariat ether upon the efficiency and selectivity of mono- and divalent metal ion complexation was determined by metal picrate extraction. To probe the influence of the quinolinyl nitrogen and methoxy groups in the side arm upon metal ion complexation, analogs were prepared (Scheme 2) in which one of these two structural units was missing from the N-substituted aza-15-crown-5 ligand.
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