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

doi:10.1021/ja00318a014

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 journal › Article

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 language	English (US)
Pages (from-to)	1633-1635
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	106
Issue number	6
DOIs	https://doi.org/10.1021/ja00318a014
State	Published - Mar 1 1984
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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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. https://doi.org/10.1021/ja00318a014

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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.",

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T1 - Electrochemically Switched Cation Binding in Nitrobenzene-Substituted, Nitrogen-Pivot Lariat Ethers

AU - Gustowski, Deborah A.

AU - Echegoyen, Luis

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AU - Kaifer, Angel

AU - Schultz, Rose Ann

AU - Gokel, George W.

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