Electrochemical oxidation of some phenethylamines

Portis, Louis C.; Klug, J. T.; Mann, Charles K.

doi:10.1021/jo00938a007

Cited by 27 publications

(10 citation statements)

References 6 publications

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“…The former apparently exhibit only one JAT~ vs APH relationship [9] while the latter show several [1,2]; this paper). An analogous difference might exist between chloroplasts [5] and bacterial chromatophores [3,4]. Scrutiny of these variations from system to system could hopefully offer clues as to the reasons for the multiplicity of flow-force relationships.…”

Section: Discussionmentioning

confidence: 99%

“…Results at variance with this latter expectation have however been reported for rat liver 11) and ~e~~~~~~~ tuberosus ]2] mitochondria and for R~~d~ps~udomon~~ capsulata chromatophores [3,4]. In these systems (but not in chloroplasts [5]) different JATP vs APH relationships have been obtained depending on the Abbreviations: AflH, transmembrane electrochemical proton gradient; A$, transmembrane electrical potentia1 difference; JATP, rate of ATP synthesis; J,, rate of oxygen consumption;…”

Section: Introductionmentioning

confidence: 98%

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Multiple relationships between rate of oxidative phosphorylation and Δµ̃H in rat liver mitochondria

Zoratti¹,

Petronilli²

1985

FEBS Letters

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

Multiple relationships between rate of oxidative phosphorylation and Δµ̃H in rat liver mitochondria

Zoratti¹,

Petronilli²

1985

FEBS Letters

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“…26 In studies of amine oxidation in non-aqueous electrolytes, the first electron transfer has been determined to be the rate-determining step (RDS). 11,15,16,27 If we assume that the first electron transfer is rate-limiting, we could determine the corresponding transfer coefficient. The Tafel slope at standard conditions is related to the transfer coefficient as:…”

Section: Outer-sphere Mechanismmentioning

confidence: 99%

Nature of the First Electron Transfer in Electrochemical Ammonia Activation in a Nonaqueous Medium

et al. 2019

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Decreasing costs of renewable sources of electricity will increase the viability of electrochemical processes in chemical manufacturing. To this end, improved understanding of electrochemical N-H bond activation is essential to develop electrochemical routes for nitrogen-containing chemicals. In this work, we investigate electrochemical ammonia activation in acetonitrile, a prototypical non-aqueous solvent for electro-organic syntheses. Non-aqueous environments are desirable for electroorganic syntheses due to large electrochemical stability windows and high solubility for organic products. We find that ammonia oxidation in acetonitrile proceeds through an outer-sphere mechanism involving an initial electron transfer as the rate-determining step, likely producing an ammonia radical cation. Density functional theory calculations explain a low transfer coefficient and suggest possible subsequent reaction steps. Structural factors involved in lowering of the transfer coefficient provide insights that are applicable to wider range of small-molecule activation chemistries.

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“…Perhaps the most definitive evidence against the SET mechanism is the finding that the covalent flavin of MAO B exhibits one electron oxidation-reduction potentials of +0.043 V. for the Ox/Sq couple and + 0.037 V for the Sq/Hq couple [34]. Since the potential required for one-electron oxidation of primary or secondary amines is in the range of +1.0 to +1.5 V ( [35], the possibility of 1 electron amine oxidation by a ground state flavin is quite remote. Recent theoretical calculations on MAO catalysis have demonstrated the plausibility of the polar nucleophilic mechanism for MAO catalysis shown in Fig.…”

Section: Proposed Mechanism Of C-h Bond Cleavage In Mao Catalysismentioning

confidence: 99%

Structural insights into the mechanism of amine oxidation by monoamine oxidases A and B

Edmondson¹,

Binda²,

Mattevi³

2007

Archives of Biochemistry and Biophysics

184

144

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Due to their pharmacological importance in the oxidation of amine neurotransmitters, the membrane-bound flavoenzymes monoamine oxidase A and monoamine oxidase B have attracted numerous investigations and, as a result, two different mechanisms; the single electron transfer and the polar nucleophilic mechanisms, have been proposed to describe their catalytic mechanisms. This review compiles the recently available structural data on both enzymes with available mechanistic data as well as current NMR data on flavin systems to provide an integration of the approaches. These conclusions support the proposal that a polar nucleophilic mechanism for amine oxidation is the most consistent mechanistic scheme as compared with the single electron transfer mechanism.

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Electrochemical oxidation of some phenethylamines

Cited by 27 publications

References 6 publications

Multiple relationships between rate of oxidative phosphorylation and Δµ̃H in rat liver mitochondria

Multiple relationships between rate of oxidative phosphorylation and Δµ̃H in rat liver mitochondria

Nature of the First Electron Transfer in Electrochemical Ammonia Activation in a Nonaqueous Medium

Structural insights into the mechanism of amine oxidation by monoamine oxidases A and B

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