74. Polarographic reduction of aromatic hydrocarbons and carbonyl compounds in dimethylformamide in the presence of proton-donors

Use of multivariate curve resolution analysis in the spectroelectrochemistry of 9,10-anthraquinone reduction in dimethylformamide solution

“…In order to show the predominance of the above mechanism of anthraquinone reduction, researchers have used some different electrochemical techniques including polarography [26], cyclic voltammetry [29], and spectroelectrochemistry [27,28]. In spectroelectrochemical experiments, there was increasing interest in viewing the pure spectrum of the reduced species.…”

“…In recent years, we have conducted widespread studies on some new derivatives of 9,10-anthraquinone and 9-anthrone, including pK a determination [3][4][5][6], solubility determination in supercritical CO 2 [7][8][9], electrochemical behavior [10][11][12][13][14], and some of their applications in solid phase extraction [15][16][17] and in preparation of ion selective electrodes [18][19][20][21]. The important role of anthraquinones in biological electron transport [2,22] and in industrial processes as redox catalysts [23] have led to extensive studies of their electrochemical behavior [10][11][12][13][14][24][25][26][27][28][29].…”

Mechanism of electroreduction of 9-anthraldehyde

“…The reactivitv of the \ , radical anions of the aromatic aldehydes depends strongly on the structure of the aldehydes and increases in the order: l-naphthaldehyde S 2-naphthaldehyde S 3-benzaldehyde S 9-anthraldehyde (9). The structure of the dimer was studied in detail in the case of benzaldehyde which, upon one-electron reduction, forms hydrobenzoin (4,5). The structure of a dimer formed by 9-anthraldehyde (ANCHO) has not been studied chemically but it has been suggested (without proof) that it does not form a glycol but instead forms a dimer by coupling in position 10 (10, 11).…”

“…In aprotic solvents aromatic aldehydes form two one-electron polarographic waves (1,3). The most detailed studies have been carried out for benzaldehyde (4)(5)(6)(7)(8) and it was found that the product of the one-electron reduction of aldehydes is a radical ion which is not stable and undergoes subsequent dimerization (9)(10)(11)(12). The reactivity of the ion radicals in aprotic solvents is influenced by the ion-pair formation with the supporting electrolyte cations and the rate of the dimerization reaction increases with the decrease in the radius of the cation (9).…”

QSPR correlations of half-wave reduction potentials of cata-condensed benzenoid hydrocarbons

“…[6][7][8][9][10][11][12][13][14][15][16][17][18] In both cases the lowest unoccupied molecular orbital (LUMO) is involved, and electron affinities or other quantum-chemical parameters are also derived from such experimental data. [19][20][21][22][23][24][25][26][27][28] So far, practically all quantitative structure-property relationships (QSPR) involving E ½ (including ref. 1 ) have resulted in correlations in terms of E LUMO .…”