Kinetics and mechanism of the oxidation of some aliphatic ketones by n-bromoacetamide in acidic media

Singh, Bharat; Saxena, B.B.L.; Samant, Amruta

doi:10.1016/0040-4020(84)85017-6

Cited by 16 publications

(10 citation statements)

References 11 publications

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“…The literature [8,11,[24][25][26][27][28] A report on the protonation of reducing sugars is available [29]. It was observed that the sugar participates in the reactions under investigation in its unprotonated form.…”

Section: Discussionmentioning

confidence: 98%

Kinetics of oxidation of d(+)melibiose and cellobiose by N-bromoacetamide using a rhodium(III) chloride catalyst

Singh

Srivastava

et al. 2010

Transition Met Chem

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The kinetics of oxidation of the sugars D(?)Melibiose (mel) and Cellobiose (cel) by N-bromoacetamide (NBA) in the presence of Rh(III) chloride as homogeneous catalyst in acidic medium at 45°C have been investigated. The reactions are first-order with respect to [NBA], [Rh(III)] and [substrate]. The rate is proportional to [H ? ]. No effects of [Hg(II)], [NHA] or [Cl -] on the rates were observed. Ionic strength and dielectric constant also have little effect. The observed kinetic data, available literature and spectroscopic evidence lead us to conclude that NBAH ? and [RhCl 5 (H 2 O)] 2-are the reactive species of NBA and Rh(III) chloride, respectively. The rate-determining step of the proposed reaction path common for both sugars gives an activated complex by the interaction of a charged complex species and neutral sugar molecule, which in the subsequent steps disproportionates into the reaction products with the regeneration of catalyst. The reactions have been studied at four different temperatures and with the help of first-order rate constant values, various activation parameters have been calculated. The main oxidation products of the reactions were identified as arabinonic acid, formic acid and lyxonic acid in the case of mel and arabinonic acid and formic acid in the case of cel.

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Section: Discussionmentioning

confidence: 98%

Kinetics of oxidation of d(+)melibiose and cellobiose by N-bromoacetamide using a rhodium(III) chloride catalyst

Singh

Srivastava

et al. 2010

Transition Met Chem

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“…It was reported 23,24,[34][35][36] that NBA existed in the following equilibrium in an acidic medium:…”

Section: Reactive Species Of Nbamentioning

confidence: 99%

Kinetics of the Oxidation of D‐Glucose and Cellobiose by Acidic Solution of N‐Bromoacetamide Using Transition Metal Complex Species, [RuCl₃(H₂O)₂OH] −, as Catalyst

et al. 2008

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“…The kinetics was studied under pseudo first order conditions where sufficiently large excess of concentration of ketone over that of the oxidant was maintained. Since the product analysis is an important aspect of the stoichiometry, the reactions both for ethylmethylketone and cyclohexanone [4] in excess over thallium (III) in acid perchlorate medium were allowed to occur in a thermostated water bath at 40 ± 0.1°C for ca. 8h.…”

Section: Stoichiometry and Product Analysismentioning

confidence: 99%

“…The mechanism of oxidation of ketones can not be considered to be completely established either for thallium (III) or other oxidants [1][2][3][4][5][6][7][8][9][10][11][12][13]. It is still an open question to settle whether it is nucleophilic addition or substitution on the -carbon atom which is associated with oxidation.…”

Section: Introductionmentioning

confidence: 99%

Kinetics and Mechanism of Electron-Transfer Reactions: Oxidation of Butanone and Cyclohexanone by Thallium (III) in Acid Perchlorate Medium- An Appraisal of Keto Form Reactivity

Hemkar¹

2013

AJPC

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The kinetics of oxidation of ketones by thallium (III) has been studied in acid perchlorate medium. The reaction does not indicate enolization to be the rate controlling step in the reaction mechanism. The kinetic rate law (1) has been observed.     Where K h is the hydrolysis constant of the oxidant. A plausible reaction mechanism is suggested conforming to the rate law (1). Activation parameters were evaluated.

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Kinetics and mechanism of the oxidation of some aliphatic ketones by n-bromoacetamide in acidic media

Cited by 16 publications

References 11 publications

Kinetics of oxidation of d(+)melibiose and cellobiose by N-bromoacetamide using a rhodium(III) chloride catalyst

Kinetics of oxidation of d(+)melibiose and cellobiose by N-bromoacetamide using a rhodium(III) chloride catalyst

Kinetics of the Oxidation of D‐Glucose and Cellobiose by Acidic Solution of N‐Bromoacetamide Using Transition Metal Complex Species, [RuCl₃(H₂O)₂OH] −, as Catalyst

Kinetics and Mechanism of Electron-Transfer Reactions: Oxidation of Butanone and Cyclohexanone by Thallium (III) in Acid Perchlorate Medium- An Appraisal of Keto Form Reactivity

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Kinetics and mechanism of the oxidation of some aliphatic ketones by n-bromoacetamide in acidic media

Cited by 16 publications

References 11 publications

Kinetics of oxidation of d(+)melibiose and cellobiose by N-bromoacetamide using a rhodium(III) chloride catalyst

Kinetics of oxidation of d(+)melibiose and cellobiose by N-bromoacetamide using a rhodium(III) chloride catalyst

Kinetics of the Oxidation of D‐Glucose and Cellobiose by Acidic Solution of N‐Bromoacetamide Using Transition Metal Complex Species, [RuCl3(H2O)2OH] −, as Catalyst

Kinetics and Mechanism of Electron-Transfer Reactions: Oxidation of Butanone and Cyclohexanone by Thallium (III) in Acid Perchlorate Medium- An Appraisal of Keto Form Reactivity

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Kinetics of the Oxidation of D‐Glucose and Cellobiose by Acidic Solution of N‐Bromoacetamide Using Transition Metal Complex Species, [RuCl₃(H₂O)₂OH] −, as Catalyst