Studies of potential inversion in the electrochemical reduction of 11,11,12,12-tetracyano-9,10-anthraquinodimethane and 2,3,5,6-tetramethyl-7,7,8,8-tetracyano-1,4-benzoquinodimethane

The Journal of Physical Chemistry. B
Norma A Macías-Ruvalcaba, Dennis H Evans

Abstract

The electrochemical reduction of the title compounds, 2a and 3a, and 7,7,8,8-tetracyanoquinodimethane, 1a, was studied in acetonitrile. The reduction of 1a shows normal ordering of potentials, i.e., the potential for insertion of the first electron, E degrees1, is more positive than the potential for the second step of reduction, E degrees2. Thus, E degrees1 - E degrees2 > 0. By contrast, 2a and 3a show inversion of potentials where introduction of the second electron occurs with greater ease than the first (E degrees1 - E degrees2 < 0). The extent of inversion has been determined by simulation of the cyclic voltammograms obtained at 298 and 257 K. Electron paramagnetic resonance measurements at room temperature of solutions containing equimolar mixtures of the neutral and dianion allow determination of the concentration of anion radicals from which the disproportionation equilibrium constant and E degrees1 - E degrees2 can be calculated. The results were in good agreement with the voltammetric determinations. Calculations were conducted to characterize the structural changes accompanying reduction to the anion radical and dianion forms. Fast scan experiments at low temperatures (up to 10 000 V/s at 257 K; 500 V/s at 233 K) wer...Continue Reading

References

Apr 17, 2001·The Journal of Organic Chemistry·J J WolffM Würde
Feb 12, 2004·Journal of the American Chemical Society·Robert L Donkers, Mark S Workentin

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Citations

Mar 1, 2012·Physical Chemistry Chemical Physics : PCCP·Amy E MurschellTodd C Sutherland
May 1, 2007·Chemistry : a European Journal·Norma A Macías-Ruvalcaba, Dennis H Evans
Dec 20, 2014·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Zebing Zeng, Jishan Wu
Dec 9, 2017·Physical Chemistry Chemical Physics : PCCP·Chuhong LinRichard G Compton
Jun 15, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Ryota SakamotoHiroshi Nishihara

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