Mechanistic study of the oxidation of catechol in the presence of secondary amines by digital simulation of cyclic voltammograms

Nematollahi, Davood; Tammari, Esmail; Sharifi, Sasan; Kazemi, Mohammad Hossein

doi:10.1016/j.electacta.2003.09.013

Cited by 30 publications

(27 citation statements)

References 16 publications

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“…Electrochemical oxidation of the catechol group has also been studied in the presence of secondary amines 36,37) and mercaptotriazole 38) as nucleophiles. Common to these reports is the presence of one anodic and a corresponding cathodic peak on the cyclic voltammetry record of the catechol in buffered solution.…”

Section: Discussionmentioning

confidence: 99%

“…These findings correspond to the transformation of the catechol to the corresponding o-benzoquinone and vice-versa, within a quasi reversible two electron transfer process. 36,37) The oxidation of the catechol in the presence of a nucleophile (secondary amines or thiols) results in a 1,4-Michael addition reaction. The resulting compounds (amines and thio substituted catechols) are more easily oxidized than the parent starting molecule by virtue of the presence of an extra electron-donating group.…”

Section: Discussionmentioning

confidence: 99%

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Synthesis and Cyclic Voltammetry Studies of 3,4-Methylenedioxymethamphetamine (MDMA) Human Metabolites

Macedo

Branco

Ferreira

et al. 2007

JOURNAL OF HEALTH SCIENCE

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3,4-Methylenedioxymethamphetamine (MDMA or "Ecstasy") is a widely abused, psychoactive recreational drug. There are growing evidences that the MDMA neurotoxic profile may be highly dependent on its hepatic metabolism. MDMA metabolism leads to the production of highly reactive derivates, namely catechols, catechol thioethers, and quinones. In this study the electrochemical oxidation-reduction processes of MDMA human metabolites, obtained by chemical synthesis, were evaluated by cyclic voltammetry based on an electrochemical cell with a glassy carbon working electrode. The toxicity of α-methyldopamine (α-MeDA), N-methyl-α-methyldopamine (N-Me-α-MeDA) and 5-(glutathion-S-yl)-α-methyldopamine [5-(GSH)-α-MeDA] to rat cortical neurons was then correlated with their redox potential. The obtained data demonstrated that the lower oxidation potential observed for the catecholic thioether of α-MeDA correlated with the higher toxicity of this adduct. This accounts for the use of voltammetry data in predicting the toxicity of MDMA metabolites.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Synthesis and Cyclic Voltammetry Studies of 3,4-Methylenedioxymethamphetamine (MDMA) Human Metabolites

Macedo

Branco

Ferreira

et al. 2007

JOURNAL OF HEALTH SCIENCE

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“…However to our best knowledge only a few papers have been published on electrochemical oxidation of catechols in the presence of amines [27] but because of importance of aminoquinones as biologically important compounds [28] in this direction we have investigated the anodic oxidation of catechol in the presence of diethylamine and dibuthylamine as representative of secondary aliphatic amines. Two electrochemical techniques, cyclic voltammetry and differential pulse voltammetry, were used in this work.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Study of Catechol in the Presence of Dibuthylamine and Diethylamine in Aqueous Media: Part 1. Electrochemical Investigation

Kiani¹,

Raoof²,

Nematollahi³

et al. 2005

Electroanalysis

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Electrochemical oxidation of catechol has been studied in the presence of secondary amines as nucleophiles in aqueous solution with various pH values using cyclic voltammetry and differential pulse voltammetry. Cyclic voltammetry of catechol in pure buffered solution (2.00 pH < 9.00) shows one anodic and corresponding cathodic peak which relates to the transformation of catechol to corresponding o-benzoquinone and vice versa within a quasireversible two electron transfer process. Also, a little amount of o-benzoquinone undergoes polymerization reaction. Cyclic voltammogram of catechol in the presence of nucleophilic amines, show one anodic peak in the first scan of potential but on the reverse scan the corresponding cathodic peak disappear and new peak is observed at less positive potential. In the second scan of potential also a new anodic peak is observed. On the other hand at high concentration of amines the redox peak attributable to formed polymer disappear showing that in this condition the polymerization reaction occurs at non-measurable extent. On the basis of these observations we propose an ECE mechanism for the electrochemical oxidation of catechol in the presence of secondary amines.

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“…1 H and 13 C, NMR spectra (DMSO-d 6 ) were recorded on JEOL JNM-EX90A spectrometer operating at 90 and 22.6 MHz, respectively and BRUKER DRX-500 AVANCE spectrometer at 500.1 and 125.8, MHz, respectively. Mass spectra were recorded on a QP-1100EX Shimadzu Mass spectrometer operating at an ionization potential of 70 eV.…”

Section: Methodsmentioning

confidence: 99%

“…3 1,2-Benzoquinone derivatives have been less extensively studied than the 1,4-benzoquinone derivatives because they are more difficult to prepare. 2,4,5 The importance of amino derivatives of quinones has encouraged us to study 6 and synthesize 7 a number of these compounds. However, no report has been published so far about the chemical or electrochemical synthesis of (dibenzylamino)dioxocyclohexadienecarboxylic acids.…”

Section: Introductionmentioning

confidence: 99%

Electro-organic synthesis of dibenzylaminodioxocyclohexa-dienecarboxylic acids

Nematollahi¹,

Hesari²,

Davarani³

2006

Arkivoc

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Electrochemical oxidation of dihydroxybenzoic acids 1a-c has been studied in the presence of dibenzylamine (3) as nucleophile in water/acetonitrile (90:10) solution using cyclic voltammetry and controlled-potential coulometry. The quinones 2a-c derived from dihydroxybenzoic acids participate in Michael addition reactions with dibenzylamine (3), and via ECE mechanism convert to the corresponding (dibenzylamino)dioxocyclohexadienecarboxylic acids 5a-c.

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Mechanistic study of the oxidation of catechol in the presence of secondary amines by digital simulation of cyclic voltammograms

Cited by 30 publications

References 16 publications

Synthesis and Cyclic Voltammetry Studies of 3,4-Methylenedioxymethamphetamine (MDMA) Human Metabolites

Synthesis and Cyclic Voltammetry Studies of 3,4-Methylenedioxymethamphetamine (MDMA) Human Metabolites

Electrochemical Study of Catechol in the Presence of Dibuthylamine and Diethylamine in Aqueous Media: Part 1. Electrochemical Investigation

Electro-organic synthesis of dibenzylaminodioxocyclohexa-dienecarboxylic acids

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