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 Citations (Scopus)

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

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Bearings (structural)
Nitrobenzene
Ethers
Cations
Nitrogen
Positive ions
Ions
nitrobenzene
15-crown-5

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Gustowski, D. A., Echegoyen, L., Goli, D. M., Kaifer, A., Schultz, R. A., & Gokel, G. W. (1984). ELECTROCHEMICALLY SWITCHED CATION BINDING IN NITROBENZENE-SUBSTITUTED, NITROGEN-PIVOT LARIAT ETHERS. Journal of the American Chemical Society, 106(6), 1633-1635.

ELECTROCHEMICALLY SWITCHED CATION BINDING IN NITROBENZENE-SUBSTITUTED, NITROGEN-PIVOT LARIAT ETHERS. / Gustowski, Deborah A.; Echegoyen, Luis; Goli, Deepa M.; Kaifer, Angel; Schultz, Rose Ann; Gokel, George W.

In: Journal of the American Chemical Society, Vol. 106, No. 6, 01.03.1984, p. 1633-1635.

Research output: Contribution to journalArticle

Gustowski, DA, Echegoyen, L, Goli, DM, Kaifer, A, Schultz, RA & Gokel, GW 1984, 'ELECTROCHEMICALLY SWITCHED CATION BINDING IN NITROBENZENE-SUBSTITUTED, NITROGEN-PIVOT LARIAT ETHERS.', Journal of the American Chemical Society, vol. 106, no. 6, pp. 1633-1635.
Gustowski, Deborah A. ; Echegoyen, Luis ; Goli, Deepa M. ; Kaifer, Angel ; Schultz, Rose Ann ; Gokel, George W. / ELECTROCHEMICALLY SWITCHED CATION BINDING IN NITROBENZENE-SUBSTITUTED, NITROGEN-PIVOT LARIAT ETHERS. In: Journal of the American Chemical Society. 1984 ; Vol. 106, No. 6. pp. 1633-1635.
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