Sterically congested, geminal aryl-substituted, proton-ionizable sym-dibenzo-16-crown-5 lariat ethers: synthesis and alkali metal cation extraction

Abstract

Three series of proton-ionizable sym-dibenzo-16-crown-5 ethers with sterically demanding 1- naphthyl, 2-naphthyl, and 9-phenanthryl geminal groups are synthesized and characterized. Variation of the proton-ionizable group includes oxyacetic acid and N-(X)sulfonyl oxyacetamide units with X = Me, Ph, C6H4-4-NO2, and CF3. For the latter series, variation of X provides 'tunable' acidity of the ligand. The metal ion-complexing properties of the proton-ionizable sym- (aryl)dibenzo-16-crown-5 compounds are probed by competitive solvent extraction of alkali metal cations from aqueous solutions into chloroform.

Description

This work is licensed under a Creative Commons Attribution 4.0 International License.

Keywords

Lariat Ether, Solvent Extraction, Alkaline Metal Cations, Crown Ethers

Citation

Tu, C., Jang, Y., Bates, C. L., Gega, J., Surowiec, K., & Bartsch, R. A. (2010). Sterically congested, geminal aryl-substituted, proton-ionizable sym-dibenzo-16-crown-5 lariat ethers: synthesis and alkali metal cation extraction. ARKIVOC, 2010(7), 98-117. https://doi.org/10.3998/ark.5550190.0011.708

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