Solvent-induced selectivity of Williamson etherification in the pursuit of amides resistant against oxidative degradation |
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| Authors: | James B. Derr John A. Clark Maryann Morales Eli M. Espinoza Sandra Vadhin Valentine I. Vullev |
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| Affiliation: | Department of Biochemistry, University of California, Riverside CA 92521 USA.; Department of Bioengineering, University of California, Riverside CA 92521 USA ; Department of Chemistry, University of California, Riverside CA 92521 USA ; Materials Science and Engineering Program, University of California, Riverside CA 92521 USA |
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| Abstract: | This article reports two discoveries. (1) 2-Methoxyethanol induces unprecedented selectivity for etherification of 5-hydroxy-2-nitrobenzic acids without forming undesired esters. (2) Such compounds are precursors for amides showing unusual robustness against oxidative degradation, essential for molecular electrets that transfer strongly oxidizing holes at about −6.4 eV vs. vacuum.Selective etherification produces precursors for amides resistant to oxidative degradation, i.e., showing reversible oxidation at 1.5 to 1.7 V vs. SCE. |
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