Studies of Adiponitrile as an Electrochemical Solvent

Abstract

The usefulness of adiponitrile (ADN) as a solvent for electrochemical studies has been investigated using several solutes. In the present work, tetraethylammonium tetrafluorborate ( TEA BF 4 ) has been used as supporting electrolyte. Ferrocene undergoes reversible redox behavior in ADN/TEABF 4 , and the peak potential separation decreases markedly with increasing TEABF 4 concentration. The ketone 9-fluorenone undergoes two successive one-electron redox processes; however, the second process is not completely reversible at 100 mV/s in ADN. This behavior can be explained by the effect of a proton transfer between the fluorenone dianion and ADN. This proton transfer is not as extensive in acetonitrile, suggesting that intramolecular interactions in the ADN anion enhance the acidity of ADN.

Electrochemical Behavior of Toluene in Adiponitrile

“…A comparison study in acetonitrile, however, produced a shoulder on the background curve at platinum at a similar potential to that reported under somewhat similar conditions (9). These and previous studies (1)(2)(3)(4)(5) show that adiponitrile is a useful solvent system with a potential range similar to that of acetonitrile, although adiponitrile is considerably more viscous and has a much higher boiling point (295 o C) than does acetonitrile.…”

“…In a continuing study of adiponitrile (NCCH 2 CH 2 CH 2 CH 2 CN)/tetraethylammonium tetrafluoroborate (TEA BF 4 ) in this laboratory, this solvent system has been generally characterized (1) and used for organic electrochemistry (2,3), the electrodeposition of metals (4), and oxidation of hydrocarbons (5). Adiponitrile has also been used as a solvent for capacitors (6) due to its very wide potential range and other useful properties (7).…”

Investigations of the Electrochemical Behavior of Hydrocarbons in Adiponitrile

“…Recent work from this laboratory has shown that adiponitrile (NCCH 2 CH 2 CH 2 CH 2 CN) / tetraethylammonium tetrafluoroborate (TEABF 4 ) is a versatile solvent system for organic electrochemistry (1,2). The extraordinarily wide 8-Volt potential limit which has been observed in earlier work (3) has been confirmed and applied to measurement of water (1) and to the electrodeposition of metals (4).…”

Electrochemical Studies of 9,10-Anthraquinone in Adiponitrile

“…With this behavior in mind, it was thought to be of interest to compare the effect of added aluminum ions to AQ in a nitrile-based nonaqueous solvent. It has been found recently that adiponitrile possesses reasonably good characteristics as a solvent for electrochemical research (8-10) and produces typical voltammograms for reversible systems such as 9-fluorenone (11,12). The present paper reports the results of a study of AQ reduction in adiponitrile, including the effect of addition of aluminum(III) trifluoromethanesulfonate on the quinone electrochemistry.…”