Effect of structural variation within lipophilic N-(X)sulfonyl carbamoyl lariat ethers on the selectivity and efficiency of competitive alkali metal cation extraction into chloroform

Eun Kyung Lee, Bong Rae Cho, Hui Hu, Richard A. Bartsch

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Sixteen lipophilic N-(X)sulfonyl carbamoyl lariat ethers with polyether ring sizes of 12-crown-4, 14-crown-4, 15-crown-5, and 18-crown-6 are utilized for competitive alkali metal cation extractions from aqueous solutions into chloroform. Variation of the electron-withdrawing properties of X in the series of methyl, phenyl, 4-nitrophenyl, and trifluoromethyl allows the influence of the acidity of the C(O)NHSO2X group in the side arm upon extraction efficiency and selectivity to be assessed. With X = trifluoromethyl, effective alkali metal cation extractions from acidic, neutral, and basic aqueous solutions are achieved. When the crown ether rings are 14-crown-4, 15-crown-5, and 18-crown-6, selectivities for Li+, Na+, and K+, respectively, are observed. Results are compared with those reported for analogous lariat ether carboxylic acids and phosphonic acid monoethyl esters.

Original languageEnglish
Pages (from-to)2177-2183
Number of pages7
JournalAnalytical chemistry
Issue number9
Publication statusPublished - 2002 May 1


ASJC Scopus subject areas

  • Analytical Chemistry

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