Oxidation of isoniazid by N‐haloarenesulfonamidates in alkaline medium: A kinetic and mechanistic study

Puttaswamy,; Anuradha, T. M.; Ramachandrappa, R.; Gowda, N. M. Made

doi:10.1002/(sici)1097-4601(2000)32:4<221::aid-kin4>3.3.co;2-t

Cited by 19 publications

(25 citation statements)

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“…The oxidation potential of CAT-PTS couple varies with the pH of the medium (1.139 V at pH 0.65, 0.778 V at pH 7.0 and 0.614 V at pH 9.7). The mechanistic aspects of CAT reactions have been well documented [7][8][9][10][11][12].…”

Section: Introductionmentioning

confidence: 85%

“…The reduction product of CAT, p-toluenesulfonamide (TsNH 2 ), among the reaction products was identified by paper chromatography [11] using benzyl alcohol saturated with water as the solvent system ascending irrigation and using 0.5 % vanillin in 1 % HCl in EtOH as the spray reagent (R f = 0.905). The oxidation products of catecholamines are corresponding o-benzoquinones under the kinetic conditions employed in the present work.…”

Section: Stoichiometry and Product Analysismentioning

confidence: 99%

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Oxidation of some catecholamines by sodium N-chloro-p-toluenesulfonamide in acid medium: A kinetic and mechanistic approach

Puttaswamy¹,

Jagadeesh

Vaz

2005

Open Chemistry

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The kinetics of the oxidation of five catecholamines viz., dopamine (A), Ldopa (B), methyldopa (C), epinephrine (D) and norepinephrine (E) by sodium N-chloro-ptoluenesulfonamide or chloramine-T (CAT) in presence of HClO 4 was studied at 30 ± 0.1 • C. The five reactions followed identical kinetics with a first-order dependence on [CAT] o , fractionalorder in [substrate] o , and inverse fractional-order in [H + ]. Under comparable experimental conditions, the rate of oxidation of catecholamines increases in the order D > E > A > B > C. The variation of ionic strength of the medium and the addition of p-toluenesulfonamide or halide ions had no significant effect on the reaction rate. The rate increased with decreasing dielectric constant of the medium. The solvent isotope effect was studied using D 2 O. A Michaelis-Menten type mechanism has been suggested to explain the results. Equilibrium and decomposition constants for CAT-catecholamine complexes have been evaluated. CH 3 C 6 H 4 SO 2 NHCl of the oxidant has been postulated as the reactive oxidizing species and oxidation products were identified. An isokinetic relationship is observed with β = 361 K, indicating that enthalpy factors control the reaction rate. The mechanism proposed and the derived rate law are consistent with the observed kinetics.

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Section: Introductionmentioning

confidence: 85%

Section: Stoichiometry and Product Analysismentioning

confidence: 99%

Oxidation of some catecholamines by sodium N-chloro-p-toluenesulfonamide in acid medium: A kinetic and mechanistic approach

Puttaswamy¹,

Jagadeesh

Vaz

2005

Open Chemistry

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“…A similar behaviour has been noted in the oxidation of several other substrates with CAT and BAT. [34][35][36][37] The facts furnished in this research and the literature reports led us to conclude that BAT is a stronger oxidant than CAT.…”

Section: Comparison Of Cat and Bat Reactivitiesmentioning

confidence: 99%

Mechanistic chemistry of oxidation of balsalazide with acidic chloramine-T and bromamine-T: A comparative spectrophotometric kinetic study

Puttaswamy

Dakshayani

2014

J Chem Sci

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Abstract. Balsalazide (BSZ) belongs to a class of non-steroidal anti-inflammatory drugs. Kinetics and mechanism of oxidation of BSZ with sodium N-halo-p-toluenesulfonamides viz., chloramine-T(CAT) and bromamine-T(BAT) in HClO 4 medium have been spectrophotometrically investigated (λ max =357nm) at 303 K. Under comparable experimental conditions, reactions with both the oxidants follow a first-order dependence of rate on [BSZ] and fractional-order dependence on each [oxidant] and [HClO 4 ]. Activation parameters and reaction constants have been computed. 2-hydroxy-5-nitroso-benzoic acid and 3-(4-nitroso-benzoylamino)-propionic acid are identified as the oxidation products of BSZ with both CAT and BAT. The rate of oxidation of BSZ is about five-fold faster with BAT than with CAT. Plausible mechanism and related rate law have been deduced for the observed kinetics.

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“…The versatile nature of N-haloamines is attributed to the presence of halonium cations and nitrogen anions in their structure, which can act as both a base and a nucleophile [1][2][3][4][5]. As a result, these compounds can react with a wide range of functional groups to cause numerous kinds of molecular changes.…”

Section: Introductionmentioning

confidence: 99%

Mechanistic Aspect of Iridium(III) Catalyzed Oxidation of Ethylene Glycol by Chloramine-T in Aqueous Acidic Medium: A Kinetic Model

Verma¹,

Pandey²,

Patel³

et al. 2018

ijcps

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Oxidation of isoniazid by N‐haloarenesulfonamidates in alkaline medium: A kinetic and mechanistic study

Cited by 19 publications

References 0 publications

Oxidation of some catecholamines by sodium N-chloro-p-toluenesulfonamide in acid medium: A kinetic and mechanistic approach

Oxidation of some catecholamines by sodium N-chloro-p-toluenesulfonamide in acid medium: A kinetic and mechanistic approach

Mechanistic chemistry of oxidation of balsalazide with acidic chloramine-T and bromamine-T: A comparative spectrophotometric kinetic study

Mechanistic Aspect of Iridium(III) Catalyzed Oxidation of Ethylene Glycol by Chloramine-T in Aqueous Acidic Medium: A Kinetic Model

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