Synthesis and spectral studies of lariat ethers

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Texas Tech University

A series of highly lipophilic lariat ether esters based on 5>7w-dibenzo-16-crown-5 were synthesized for evaluation in ISFET (ion selective field effect transistor) electodes Both the substituent geminal to the functional side arm and the 0-alkyl group of the ester were varied.

A series of new N-(X)sulfonyl lariat ether carboxamides and their acid precursors based on 5>7w-dibenzo-16-crown-5 were synthesized for studies of the solvent extraction of alkali metal cations and their transport across polymeric inclusion membranes. These lariat ethers contain a 1-alkynyl group of varying length geminal to the functional side arm. The N-(X)sulfonyl carboxamides contain various electron-withdrawing and electron-donating X groups to "tune" the acidity of the proton-ionizable side arm.

IR and *H NMR spectra of the new jrv7w-dibenzo-16-crown-5 compounds were evaluated to obtain further information about bond characters, conformations, and chemical environments of diastereotopic methylene protons in solution.

Synthesis, Ethers