Electrochemical switching of lariat ethers. Survey of cation binding by neutral and reduced forms of one- and two-armed carbon- and nitrogen-pivot lariat ethers

Kaifer, Ángel E.; Gustowski, Deborah A.; Echegoyen, Luis; Gatto, Vincent J.; Schultz, Rose Ann; Cleary, Thomas P.; Morgan, C. R.; Goli, Deepa M.; Rios, Angel M.; Gokel, George W.

doi:10.1021/ja00293a027

Cited by 96 publications

(30 citation statements)

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“…In aprotic media the cation of the supporting electrolyte or any added cation is known to form ion pairs with semiquinone and quinone dianion produced by the reduction of quinones [123,206,[209][210][211][212]. During the electrochemical reduction of anthraquinones in dimethylformamide the ion pairs of anthraquinone anions were examined where it was found that the ion-pairs were adsorbed on Hg electrodes in the presence of divalent metal ions while the same did not happen at the gold electrode surface.…”

Section: Role Of Cations and Anions Of Supporting Electrolytesmentioning

confidence: 99%

Electrochemical Reduction of Quinones in Different Media: A Review

Guin

Das

Mandal

2011

International Journal of Electrochemistry

339

246

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The electron transfer reactions involving quinones, hydroquinones, and catechols are very important in many areas of chemistry, especially in biological systems. The therapeutic efficiency as well as toxicity of anthracycline anticancer drugs, a class of anthraquinones, is governed by their electrochemical properties. Other quinones serve as important functional moiety in various biological systems like electron-proton carriers in the respiratory chain and their involvement in photosynthetic electron flow systems. The present paper summarizes literatures on the reduction of quinones in different solvents under various conditions using different electrochemical methods. The influence of different reaction conditions including pH of the media, nature of supporting electrolytes, nature of other additives, intramolecular or intermolecular hydrogen bonding, ion pair formation, polarity of the solvents, stabilization of the semiquinone and quinone dianion, catalytic property, and adsorption at the electrode surface, are discussed and relationships between reaction conditions and products formed have been presented.

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Section: Role Of Cations and Anions Of Supporting Electrolytesmentioning

confidence: 99%

Electrochemical Reduction of Quinones in Different Media: A Review

Guin

Das

Mandal

2011

International Journal of Electrochemistry

339

246

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“…It has been found that a donor atom in a side chain of lariat ethers increases the binding ability of the macrocycle. [7][8][9] Furthermore, structures with side arms attached at a nitrogen (N-pivot lariat ethers) instead of a carbon (C-pivot lariat ethers) have stronger binding properties because of greater flexibility, allowing the donor site to have the best binding position. 10…”

mentioning

confidence: 99%

Pyrazolic tripods synthesis and cation binding properties

Malek

Ramdani

Radi

2004

Journal of Chemical Research

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“…was synthesised according to the literature method [3]. All other chemicals were purchased from commercial sources and used without further purification.…”

Section: Reagents Nn%-bis(2-nitrobenzyl)-413-diaza-18-crown-6mentioning

confidence: 99%

Copper complexes with bibracchial lariat ethers: from mono- to binuclear structures

Rodrı́guez-Infante

Esteban‐Gómez

Avecilla

et al. 2001

Inorganica Chimica Acta

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Copper(II) complexes with a series of bibracchial lariat ethers are described. Independently of the nature of the counterion present (nitrate or perchlorate), the lariat ether N, N%-bis(2-aminobenzyl)-1,10-diaza-15-crown-5 (L 1 ) always forms mononuclear complexes, whereas the lariat ethers N, N%-bis(2-aminobenzyl)-4,13-diaza-18-crown-6 (L 2 ) and N,N%-bis(2-salicylaldiminobenzyl)-4,13-diaza-18-crown-6 (L 3 ) only give binuclear compounds. The X-ray crystal structure of [CuL 1 ](ClO 4 ) 2 shows a seven-coordinated copper(II) ion in a distorted (axially compressed) pentagonal-bipyramidal geometry. The X-ray crystal structure of [Cu 2 (L 3 -2H)](ClO 4 ) 2 confirms the binuclear nature of the compound with both metal ions having identical coordination environments and each one placed out of the crown hole but efficiently encapsulated by the corresponding pendant arm; each copper(II) ion is five-coordinated with an intermediate geometry between trigonal-bipyramidal and square-pyramidal (~= 0.40). The EPR spectra in frozen solution samples are in accordance with a stable coordinate pattern for the metal centre of ligand L 1 , yielding a rhombic distorted complex with axial compression in solution, in agreement with the X-ray crystal structure of [CuL 1 ](ClO 4 ) 2 . For the binuclear complexes of L 2 and L 3 , the Cu(II) centres in solution can be distorted from their tetragonally elongated structures via interaction with ethanol and/or the nitrate counterion, leading to more than one species.

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Electrochemical switching of lariat ethers. Survey of cation binding by neutral and reduced forms of one- and two-armed carbon- and nitrogen-pivot lariat ethers

Cited by 96 publications

References 1 publication

Electrochemical Reduction of Quinones in Different Media: A Review

Electrochemical Reduction of Quinones in Different Media: A Review

Pyrazolic tripods synthesis and cation binding properties

Copper complexes with bibracchial lariat ethers: from mono- to binuclear structures

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