Electrochemical reduction of 2-(arylideneamino)furans: an unexpected stable anion-radical

1992 ◽  
Vol 57 (15) ◽  
pp. 4287-4289
Author(s):  
F. Barba ◽  
J. R. Diaz ◽  
A. Sanchez ◽  
C. Seoane
Keyword(s):  
Electrochemical Reduction ◽  
Anion Radical ◽  
Stable Anion

Electrochemical reduction of para-substituted 2-acyl-5-phenylfuranes in dimethylformamide

1981 ◽  
Vol 46 (2) ◽  
pp. 498-502 ◽  
Author(s):  
Jozef Černák ◽  
František Tomanovič ◽  
Andrej Staško ◽  
Anna Fedosyevna Oleinikova ◽  
Jaroslav Kováč
Keyword(s):  
Electrochemical Reduction ◽  
Unpaired Electron ◽  
Anion Radical ◽  
Electron Wave ◽  
Epr Method ◽  
Electron Center ◽  
Nitrogen Nucleus ◽  
Nitro Derivatives ◽  
Stable Anion ◽  
Derivatives Of

para Substituted chloro, bromo, and nitro derivatives of 2-acyl-5-phenylfurane are reduced polarographically in a one-electron wave to the corresponding anion radicals, which were studied by the EPR method. The reduction of nitro derivatives, studied by the Kalousek switch, is reversible and leads to a stable anion radical with an unpaired electron center on the nitrogen nucleus; the reduction of the halogen derivatives is only partly reversible and leads to unstable ketyl radicals. The bromo derivatives give polarographic maxima typical for concurrent reactions.

Host–Guest interaction of pesticide bifenox with cyclodextrin molecules. An electrochemical study

2009 ◽  
Vol 74 (11-12) ◽  
pp. 1647-1664 ◽  
Author(s):  
Magdaléna Hromadová ◽  
Romana Sokolová ◽  
Lubomír Pospíšil ◽  
Štěpánka Lachmanová ◽  
Nicolangelo Fanelli ◽  
...  
Keyword(s):  
Complex Formation ◽  
Anion Radical ◽  
Formation Constants ◽  
Aprotic Solvents ◽  
Reduction Wave ◽  
Nitroaromatic Compound ◽  
Complex Formation Constants ◽  
Oh Groups ◽  
Stable Anion ◽  
Main Factor

The reduction of nitroaromatic compound bifenox (methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate) was studied in aprotic solvents in the absence or presence of cyclodextrin (CD) molecules of different cavity sizes. βCD and γCD form complexes with bifenox in DMSO with the complex formation constants (5 ± 2) × 102 M–1 [βCD–bifenox] and (3 ± 1) × 102 M–1 [γCD–bifenox], respectively. Bifenox yields a relatively stable anion radical in dimethyl sulfoxide, which is further reduced at more negative potentials by an overall addition of three electrons and four protons to the corresponding phenylhydroxylamine. In the presence of βCD the first reduction wave of bifenox becomes irreversible, it is shifted towards more positive potentials and the uptake of more than one electron is observed (up to four electrons during the exhaustive electrolysis). The first reduction wave of bifenox is not affected by the addition of glucose confirming that a simple availability of protons from the OH groups is not the main factor in further transformation of anion radical in the presence of βCD. The complex formation with βCD facilitates the protonation and additionally protects the molecule from disintegration into 2,4-dichlorophenol. A yield of 2,4-dichlorophenol decreases in the order βCD, γCD and αCD, respectively.

Properties of electrochemically generated primary anion radicals of 2,5-dimethyl-1-nitrophenylpyrroles

1981 ◽  
Vol 46 (10) ◽  
pp. 2494-2502 ◽  
Author(s):  
Pavel Kubáček
Keyword(s):  
Nitrogen Atom ◽  
Carbon Atom ◽  
Anion Radical ◽  
Platinum Electrode ◽  
Spin Population ◽  
Kinetics Of Decomposition ◽  
Primary Anion ◽  
Stable Anion ◽  
Kinetics Of ◽  
Anion Radicals

The first step of electrochemical reduction of 2,5-dimethyl-1-nitrophenylpyrroles on a platinum electrode in anhydrous acetonitrile consists in an one-electron process producing relatively stable anion radicals. The prediction based on HMO calculations concerning an almost complete localization of the LFMO in the nitrophenyl part of the studied molecules is fully confirmed by means of EPR spectroscopy. Magnitude of the found proton splitting constants is very close to the values found for anion radical of nitrobenzene. The splitting by nucleus of nitrogen atom of pyrrole cycle can be explained exclusively by the mechanism of π-σ spin polarization of σ C-N bond and by the spin population at the carbon atom. The EPR method has also been used for following the kinetics of decomposition of anion radicals of the molecules studied.

scholarly journals Reactions of Aromatic Anion Radicals and Dianions. IX. The Preparation of Stable Anion Radical Solutions Containing Tetra-alkylammonium Ions.

1978 ◽  
Vol 32b ◽  
pp. 510-514 ◽  
Author(s):  
Robert Lines ◽  
Bo Svensmark Jensen ◽  
Vernon D. Parker ◽  
Michael Sponholtz ◽  
Takao Matsuno
Keyword(s):  
Anion Radical ◽  
Stable Anion ◽  
Anion Radicals
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