Electrochemically Switched Cation Binding in Nitrobenzene-Substituted, Nitrogen-Pivot Lariat Ethers

Deborah A. Gustowski, Luis Echegoyen, Deepa M. Goli, Angel Kaifer, Rose Ann Schultz, George W. Gokel

Research output: Contribution to journalArticle

68 Scopus citations

Abstract

N-2-Nitrobenzylmonoaza-15-crown-5 (2) and N-4-Nitrobenzylmonoaza-15-crown-5, representatives of a new class of N-pivot lariat ethers bearing reducible nitroaromatic side arms, have been prepared and examined by cyclic voltammetric techniques. When the nitro group is sterically disposed to permit interaction with the ring-bound cation, intramolecular ion pairing occurs. This is not the case when the side arm is remote from the macroring nor when the side arm is detached. A thermochemical cycle is used to determine that the binding constant (K//s) enhancement in MeCN solution is 25,000-fold upon electrochemical switching.

Original languageEnglish (US)
Pages (from-to)1633-1635
Number of pages3
JournalJournal of the American Chemical Society
Volume106
Issue number6
DOIs
StatePublished - Mar 1 1984
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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