Polarographic Determination of Anthraquinone

Edsberg, R. L.; Eichlin, Dale; Garis, J. J.

doi:10.1021/ac60077a034

Cited by 26 publications

(6 citation statements)

References 11 publications

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“…The experimental half-wave potentials obtained for the reduction of our quiñones in dimethylformamide are listed in Table The polarograms that were obtained consisted in each case of two well-defined one-electron reduction waves. [14][15][16][17][18][19] The first wave is attributed to the addition of an electron to the quinone to produce a semiquinone radical anion and the second one to the subsequent addition of an electron to the radical anion producing a quinone dianion.…”

Section: Resultsmentioning

confidence: 99%

Electrochemical behavior of substituted polycyclic aromatic quinones

Klopman

Doddapaneni²

1974

J. Phys. Chem.

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In an attempt to find molecules exhibiting different electrochemical properties in the presence and absence of light, a series of phenyl-and mesityl-substituted benzoquinones were synthesized. The half-wave potentials of these and other quiñones were measured in aqueous dioxane and anhydrous DMF and correlated with theoretical values calculated by the Hiickel method. The photoisomers of the phenyl-and mesitylsubstituted quiñones were obtained under irradiation but, due to facile hydrogen migration, rapidly rearranged into unreducible hydroxy hydrocarbons.In an attempt to find organic systems capable of storing light energy and restoring it at a later time, we are investigating the electrochemical behavior of electrochemically reducible photochromic compounds. Such systems should be capable under light irradiation to reach a metastable structure of higher energy and return only under controlled conditions to their ground state.If the structure of both forms differ sufficiently, then a shift in the reduction potential of a suitable group attached to the system1 might allow us to take advantage of the energy gained in the process of irradiation.In this series of communications, we are specifically interested in the following process found to occur readily with stilbene derivatives2 and report here the synthesis and polarographic study of a series of phenyl-and mesityl-substituted benzoquinones and other polyphenyl-substituted quiñones. Some of these compounds contain a stilbene fragment and hence are susceptible to cyclize reversibly under irradiation.3 This produces a change in conjugation and may lead to a shift in the reduction half-wave potentials.4 The role of the quinoidic group is to provide the required reversible oxidation-reduction center.

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Section: Resultsmentioning

confidence: 99%

Electrochemical behavior of substituted polycyclic aromatic quinones

Klopman

Doddapaneni²

1974

J. Phys. Chem.

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“…Anthraquinone has been determined quantitatively in the presence of anthracene, phenanthrene, phthalic anhydride, and maleic anhydride in dimethvlformamide as a solvent. The reduction process in this medium is interesting in that it goes through the semiquinone anion to the red hydroquinone dianion which can be actually seen at the mercury drop (96).…”

Section: Illmentioning

confidence: 99%

“…The concept of acids and bases is undergoing a continuous change. De Morveau states, "teñir la définition des acides, c'est teñir la cié de la Chymie" (47), Mulliken (96) classified electron acceptors and donors into 25 types based on Lewis' broad conception of what should be meant by the words' 'acids' ' and "bases." Since the word acid is commonly used in a narrower meaning, he used an extension of Sidgwick's concept (118) of acceptors and donors.…”

Section: Anmentioning

confidence: 99%

Organic Polarography

Wawzonek¹

1954

Anal. Chem.

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“…The sodium cation-electron pair, (Na+, es~), has been observed in diglyme2,3 and in tetrahydrofuran. 4 The species Na~, formed by reaction of two solvated electrons with sodium cation, has been observed in ethylenedi-amine5™7 and in tetrahydrofuran.8•9 The ion pairs (K+,es_) and (Cs+,es~) in tetrahydrofuran have recently been reported.10 Optical absorption spectra have been determined. The kinetics4•7•10,11 of both the formation of such species and the reactions they undergo have been studied.…”

Section: Introductionmentioning

confidence: 99%

One-electron transfer equilibriums and redox potentials of radicals studied by pulse radiolysis

Meisel¹,

Czapski²

1975

J. Phys. Chem.

156

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The pulse radiolysis technique is utilized for measurements of the equilibrium constants for electron transfer between the durosemiquinone radical anion and oxygen, menadione, and indigodisulfonate. These equilibrium constants are in turn used for calculations of one-electron redox potentials for these systems. Each of these equilibrium constants was determined experimentally and independently and found to be selfconsistent. Only for the reactions of the semiquinone radical ions with oxygen could the electron transfer reaction be followed directly. For the reactions between the various quinone-semiquinone systems substantial indirect evidence is presented that these equilibria are achieved rapidly. In those cases equilibrium constants were determined from studies of the effect of quinone concentrations on the relative yields of the semiquinones. A method for distinguishing between kinetic competition and equilibrium is outlined and its usefulness is emphasized. The DQjDQ-(DQ = duroquinone) and IDS) IDS-(IDS = indigodisulfonate) systems were employed as reference couples as the redox potentials for those systems are either available in the literature (IDS) IDS-) or may be calculated from available data (DQ|DQ-). Taking 1, the redox potential for the first one-electron reduction step at pH 7, of DQjDQ-as -0.235 V or of IDSjIDSas -0.247 V both yield 1 = -0.325 V for the O2IO2-system (1 atm of O2) and 1 = -0.20 V for the menadione system.

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Polarographic Determination of Anthraquinone

Cited by 26 publications

References 11 publications

Electrochemical behavior of substituted polycyclic aromatic quinones

Electrochemical behavior of substituted polycyclic aromatic quinones

Organic Polarography

One-electron transfer equilibriums and redox potentials of radicals studied by pulse radiolysis

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