Effect of Structure and Hydrogen Bonding on the Stereochemistry of Electrode Reactions. The α,α'-Dibromosuccinates

Elving, Philip J.; Rosenthal, Isadore; Martin, Andrew

doi:10.1021/ja01625a005

Cited by 39 publications

(17 citation statements)

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“…Such plots for trisethylenediaminecobalt (12) (the reduced product is soluble in the solution phase and it was assumed that Do = DR) do give straight lines, whose slopes of 0.93 do not agree too well with the theoretical slope of 0.87. 2 Since the planar electrode theory prediction of the fl function is in accord with that of the expanding spherical electrode, both theories will be in accord regarding current dependence on the mercury head. Thus, plots of (ilia) vs. (hl/2/ ho 1/2) would be expected to give a series of lines of ever increasing slope as the limiting current is approached.…”

Section: Electrochemical Processes Involving One Electrochemical Reacmentioning

confidence: 88%

“…[2] and [4] become identical, and the slopes of plots of (i/io) vs. (hl/S/ho l/s) would be expected to be nearly constant at 0.87 at all points along the wave. [2] and [4] become identical, and the slopes of plots of (i/io) vs. (hl/S/ho l/s) would be expected to be nearly constant at 0.87 at all points along the wave.…”

Section: Electrochemical Processes Involving One Electrochemical Reacmentioning

confidence: 99%

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Polarographic Reduction of the Phenyl-Substituted Ethenes

Grodzka

Elving²

1963

J. Electrochem. Soc.

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The theoretically expected variations of the criteria of reversibility for electrochemical reduction, which have been proposed for inorganic systems on the basis of direct current polarography, have been developed for the various possible mechanisms, which might be expected for the reduction of the phenylsubstituted ethenes at the dropping mercury electrode. These criteria of reversibility include the beta function (ratio of mean current to instantaneous current), the dependence of the current on the drop-time (mercury column ) unless CC License in place (see abstract). ecsdl.org/site/terms_use address. Redistribution subject to ECS terms of use (see 128.210.126.199 Downloaded on 2015-05-29 to IP ) unless CC License in place (see abstract). ecsdl.org/site/terms_use address. Redistribution subject to ECS terms of use (see 128.210.126.199 Downloaded on 2015-05-29 to IP ) unless CC License in place (see abstract). ecsdl.org/site/terms_use address. Redistribution subject to ECS terms of use (see 128.210.126.199 Downloaded on 2015-05-29 to IP

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Section: Electrochemical Processes Involving One Electrochemical Reacmentioning

confidence: 88%

Section: Electrochemical Processes Involving One Electrochemical Reacmentioning

confidence: 99%

Polarographic Reduction of the Phenyl-Substituted Ethenes

Grodzka

Elving²

1963

J. Electrochem. Soc.

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“…In eleetroehemieal proeesses at the mereury eleetrode involving organie eompounds, hydrogen ion addition or release usually takes plaee (an example of the very few eleetrode proeesses in whieh hydrogen ions do not take part is the reduetion of aliphatie derivatives of vieinal dihalogen eompounds: after the transfer of two eleetrons, two halogen ions are released and a multiple bond is formed between the earbon atoms [468][469][470][471][472]). On eleetrodes having a small hydrogen overvoltage the hydrogen atoms adsorbed on the eleetrode ean take part in the eleetrode proeess (see, for example, [473]).…”

Section: General Remarksmentioning

confidence: 99%

Catalytic and Kinetic Waves in Polarography

Mairanovskii¹

1968

129

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“…Control of product structure by external conditions is indicated by the effect of pH on reduction of meso-and racemic-%a'-dibromosuccinic acids (72).…”

Section: Steric Control Of Productsmentioning

confidence: 99%

Organic electrode processes: generalized reduction mechanisms

Elving¹

1977

Can. J. Chem.

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PHILIP J. ELVING. Can. J. Chem. 55,3392 (1977). Prototype formulations are considered for the reaction pathways commonly encountered for the electrolytic reduction of organic compounds in aqueous and nonaqueous media on the basis that the essential feature is severance of a chemical bond which requires transfer into the reaction site of one or two electrons; multiple electron processes result from instability at the applied potential of initially produced species or their chemically altered products. To obtain electrical neutrality, uptake of electrons may have to be accompanied by that of a cation, generally a proton. Pertinent factors in the path followed in the overall electrode process may include a sequence of free radical or radical anion going to dimeric or carbanion species (depending on the relative rates of chemical and charge-transfer steps), possible interaction of intermediate products with their progenitors, proton donor activities, medium properties (e.g in respect to rates of chemical reactions accompanying charge-transfer and control of the chemical states of reactants and intermediates), stereochemical factors inherent in reactant and intermediate species, and chemical interaction with the electrode material. Application of the general mechanistic considerations are illustrated by various types of electrolytic reductions: aromatic hydrocarbon, nitrogen heterocycle, carbon-halogen bond, ketone carbonyl group, and beta halogenated and/or unsaturated acids. PHILIP J. ELVING. Can. J. Chem. 55,3392 (1977). Des formules modkles sont considerees pour des chemins rkactionnels souvent rencontres dans la reduction tlectrolytique de composks organiques en milieu aqueux et non aqueux. On se base sur le fait que la rupture du lien chimique exige le transfert d'un ou deux Blectrons au site rtactionnel. Les processus multi-electroniques resultent de I'instabilite au potentiel appliquk des espkces initialement produites ou de leurs produits transformks. Afin d'obtenir une neutralitk Blectrique, le transfert d'un Blectron doit &tre accompagne par celui d'un cation, gknkralement un proton. Les facteurs appropriks dans ce chemin rkactionnel suivi, tout au long du processus prenant place aux klectrodes, peut impliquer : (a) la sequence d'un radical libre ou d'un radical anionique donnant des dim&res ou carbanions (dkpendant des vitesses relatives des Btapes chimiques et celles de transfert de charge) ; (b) I'interaction possible des intermkdiaires avec les produits initiaux, (c) des activitks proton-donneur; (d) des propriktes de milieu (i.e. par rapport aux reactions chimiques accompagnant le transfert de charge ainsi que du contrBle des Btats chimiques des rkactifs et intermkdiaires); (e) des facteurs stkrtochimiques propres aux rtactifs et intermkdiaires; (f) l'interaction chimique avec I'klectrode. L'application des considkrations mkcanistiques generales est illustrte par diffkrents types de reduction tlectrolytique, un hydrocarbure aromatique, un hkterocycle contenant un atome d'azote, un lien carbone-haloghe...

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Effect of Structure and Hydrogen Bonding on the Stereochemistry of Electrode Reactions. The α,α'-Dibromosuccinates

Cited by 39 publications

References 0 publications

Polarographic Reduction of the Phenyl-Substituted Ethenes

Polarographic Reduction of the Phenyl-Substituted Ethenes

Catalytic and Kinetic Waves in Polarography

Organic electrode processes: generalized reduction mechanisms

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