Interaction of molecular oxygen with aminophenols mediated by copper metal and copper compounds

Prati, Laura; Rossi, M.; Ravasio, Nicoletta

doi:10.1016/0304-5102(92)80136-5

Cited by 19 publications

(16 citation statements)

References 14 publications

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“…The possible mechanisms reported in the literature for the catalytic and enzymatic oxidation of OAP [17] take into account two pathways:…”

Section: Resultsmentioning

confidence: 99%

“…Some metalloproteins like hemoglobin, tyrosinase [15] and catalase were found to be e±cient catalysts. A kinetic model involving the so-called OAP \oxidative cascade" was also suggested and discussed [16,17,18]. According to this model, APX formation was preceded by the appearance of some active intermediates resulting in successive oxidation, conjugate addition, and tautomerisation reactions.…”

Section: Introductionmentioning

confidence: 99%

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Temperature and pH effects on the kinetics of 2-aminophenol auto-oxidation in aqueous solution

Oancea

Puiu

2003

Open Chemistry

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The kinetics of the auto-oxidation of 2-aminophenol (OAP) to 2-amino-phenoxazin-3-one (APX) was followed in air-saturated aqueous solutions and the in®uence of temperature and pH on the auto-oxidation rate was studied. The kinetic analysis was based on a spectrophotometric method following the increase of the absorbance of APX. The process follows rst order kinetics according to the rate law. The experimental data, within the pH range 4{9.85, were analyzed using both di¬erential and incremental methods. The temperature variation of the overall rate constant was studied at pH = 9.85 within the range 25{50¸C and the corresponding activation energy was evaluated.

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“…The possible mechanisms reported in the literature for the catalytic and enzymatic oxidation of OAP [17] take into account two pathways:…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Temperature and pH effects on the kinetics of 2-aminophenol auto-oxidation in aqueous solution

Oancea

Puiu

2003

Open Chemistry

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“…1037 Para -aminophenol undergoes additions and oxidations to form a complex mixture of products; the only identifiable product is shown in Scheme 476. meta -Substituted aminophenol gives an unsymmetrically substituted quinone formed by oxygenation para to the phenol followed by oxidative nucleophilic addition to the quinone (cf., Sections VII.F.1 and VII.D.2).…”

Section: Reactions Of Phenols and Naphtholsmentioning

confidence: 99%

Aerobic Copper-Catalyzed Organic Reactions

et al. 2013

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24 peroxide [Cu I (pyr)(tpb)] 10 mol % TBHP, 1 atm O 2 , 1:2 AcOH/pyr, rt, 24 h ∼2.5 26 74 g 35 25 n-hexane aldehyde CuCl 2 , 18-crown-6 1 atm O 2 , MeCHO, CH 2 Cl 2 , 70 °C, 24 h 2.4 91 h 9 34a 26 n-decane aldehyde Cu II Cl 16 Pc-AM(PS) 3 equiv of PhCHO, MeCN, 1 atm O 2 , 50 °C 15.4 100 i 61 a See Chart 2 for ligand structures. b Also 28% cyclohexene. c Also 26% cyclohexene. d Mixture of alcohol and hydroperoxide. e Remainder of product is cyclohexene. f Approximately 93:7 of 1-adamantol/2-adamantol. g Approximately 98:2 of 1-adamantol/2-adamantol. h Afforded oxidation products in an approximately 1:1 ratio at the 2-and 3-positions. i Mixture of decanones.

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“…The step 6 includes several fast elementary steps (disproportionation, additions and oxidations occurring without catalyst assistance [40]); therefore, it can be treated as a single step in the specified working conditions, i.e. in oxygen saturated solution.…”

Section: Kinetic Modellingmentioning

confidence: 99%

Oxidase–peroxidase reaction: kinetics of peroxidase-catalysed oxidation of 2-aminophenol

Puiu

Răducan

Babaligea

et al. 2008

Bioprocess Biosyst Eng

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Possible reaction pathways that may lead to horseradish peroxidase inactivation during the aerobic oxidation of 2-aminophenol were investigated using extended kinetic curves. A kinetic model involving the formation of a low-reactive species, Compound III, was proposed and several rate constants were calculated using an optimisation computing program. Sensitivity analysis allowed to conclude that both oxidase and peroxidase cycles occur in 2-aminophenol oxidation.

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Interaction of molecular oxygen with aminophenols mediated by copper metal and copper compounds

Cited by 19 publications

References 14 publications

Temperature and pH effects on the kinetics of 2-aminophenol auto-oxidation in aqueous solution

Temperature and pH effects on the kinetics of 2-aminophenol auto-oxidation in aqueous solution

Aerobic Copper-Catalyzed Organic Reactions

Oxidase–peroxidase reaction: kinetics of peroxidase-catalysed oxidation of 2-aminophenol

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