Encyclopedia of Electrochemistry. Organic Electrochemistry by Marvin Antelman

By Marvin Antelman

This booklet is an try and assemble the main entire directory of chemical electrode potentials up to now. In compiling this encyclopedia, many papers, articles, and publi­ cations-often with contradictory data-were consulted. Of the entire par­ released fabric on hand, the authors came upon the subsequent of ticular curiosity: G. Milazzo and S. Caroli, Tables of ordinary Electrode Poten­ tials, John Wiley and Sons, Inc. (1978). A. J. deBethune and N. A. Swendeman Loud, common Aque­ ous Electrode Potentials and Temperature Coefficients at 25°C, Clifford A. Hempel (1964). W. Mansfield Clark, Oxidation-Reduction Potentials of - ganic structures, The Williams and Wilkins Co. (1960). despite the fact that, it was once our rationale additionally to incorporate unpublished advanced forma­ tion EMF info. moreover, after we consulted released EMF info, we came across that the compilations frequently paid no realization to disparate stipulations and ranging pressures and electrolyte concentrations. to accomplish an invaluable compilation, we resorted to Nernst equation thermodynamic calculations to reconcile disparate information. We additionally uti­ lized the following relationships to calculate EMF values for inclusion in our tables from organization constants: In okay = nFE log okay = -nE(16. nine) RT As a realistic instance, ponder the response three Ca + Nta- - 2e = Ca(Ntar We may perhaps write 2 Ca - 2e = Ca+ EO = -2. 87 2 three Ca+ + Nta- = Ca(Ntar E, = ? three Ca - 2e + Nta- = Ca(Ntar E2 = ? xl xII advent Given log ok Ca(Ntaf = 6. forty-one, 6. forty-one = -(2)(16.

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A standard aprotic electrolyte system with general applicability for electroorganic syntheses is acetonitrile with Bu4 NBF4 as supporting electrolyte. 7 V, a low reactivity (nucleophily and electrophily) and a relatively high dielectric constant and conductivity. The low boiling point allows an easy separation after the reaction. The toxicity of acetonitrile has to be considered, however (maximum allowable concentration at the working place 20 ppm). The application of aprotic electrolytes usually requires that water traces are carefully removed and therefore needs much effort for purification steps in an inert gas atmosphere.

Advantages of the SPE technology have been verified for different reactions using cation- and anion-exchange membranes in combination with various electrode materials in aqueous and nonaqueous media. A successful example is the methoxylation of amides, such as N ,N -dimethylformamide (DMF), which runs nearly perfectly with graphite felt electrodes, pressed on the surfaces of a cation-exchange membrane (Nafion ) in a pure mixture of methanol and DMF without any additive. Approximately 100% selectivity and current efficiency at a low cell voltage [68] is better than reported for Bu4 NBF4 as supporting electrolyte [69].

The low boiling point simplifies the product separation by distillation. Especially interesting is methanol simultaneously as reactant and solvent, for example, for methoxylations (see Chapter 6). The dual methoxylation, for example, of toluene derivatives, results in the selective synthesis of acetals, which can be hydrolyzed to aldehydes, under recycling of the methanol. g. [3b, 63]). 4 Solvents Electrolytes Based on Aprotic Aprotic electrolytes are usually needed if reactants or especially basic intermediates would be protonated by a protic solvent.

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