Kinetics and Mechanism of Oxidation of Some Substituted Benzhydrols by N-Bromosuccinimide

Hiran, B. L.; Malkani, R. K.; Rathore, Narendra

doi:10.1007/s10975-005-0081-0

Cited by 10 publications

(8 citation statements)

References 6 publications

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“…Various N-halogeno compounds [1][2][3][4][5][6][7], such as Nbromoacetamide (NBA), N-bromosuccinimide (NBS), N-chlorosuccinimide (NCS) are reported to have diverse chemistry due to their ability to act as a source of halonium cations, hypohalite species, nitrogen anions, strong electrolytes in aqueous solution and strongly polarised N-linked halogens. NBA has been used as an oxidant for uncatalysed [8][9][10][11][12] and catalysed [13][14][15][16][17][18] reactions involving transition metals including Ru(III), Ir(III) and Pd(II) as homogeneous catalysts.…”

Section: Introductionmentioning

confidence: 99%

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: Introductionmentioning

confidence: 99%

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 benzhydrols has been studied by many reagents such as 2,2'-bipyridylCu(II) permanganate 11 , pyridinium chlorochromate 12 , chloramine-T 13 , N-bromo succinimide 14,15 , Tl(III) 16 and N-bromopthalimide 17 . However, the kinetics of oxidation of benzhydrol by TBABC, a Cr(VI) reagent has not yet been studied.…”

Section: Introductionmentioning

confidence: 99%

Kinetics and Thermodynamics of Oxidation of Benzhydrol by Tetrabutyl Ammonium Bromochromatein the Presence of Oxalic Acid

Hemalatha¹,

Asghar²,

Mansoor³

2016

Orient. J. Chem

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The kinetics of oxidation of benzhydrol (BH) by tetrabutylammonium bromochromate (TBABC) was described. Product analysis confirmed the formation of benzophenone. The reaction has been studied in the presence of oxalic acid (OA). The reaction was run under pseudo-first-order conditions. The rate of reaction is first order with respect to TBABC, BH and [H + ] in the presence of oxalic acid (OA). Rates of oxidation of BH were determined at different temperatures between 298 and 313 K and the activation parameters were calculated. Further, a suitable mechanism has been proposed based upon the experimental results.

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“…In the recent development, N-halo compounds are the source of positive halogen and have been exploited as oxidant for a variety of substrates in both acidic and alkaline media. The various N-halo compounds extensively used as reagents in organic chemistry are Nbromophthalimide 3 , N-bromoacetamide 4 , N-chloroacetamide 5 , N-chlorobenzenesulphonamide 6 , N-bromobenzenesulphonamide 7 , N-chlorobenzamide 8 , N-bromobenzamide 9 , N-chloro-ptoluensulphonamide 10 , N-chloronicotinamide 11 , N-chlorosuccinimide 12 , Nbromosaccharin 13 , N-bromo-3,5-dinitrobenzamide 14 , N-chlorosaccharin 15 , Nbromosuccinimide 16 and N-bromoanisamide 17 . Although a lot of works have been reported on the oxidation of organic compounds by N-halo compounds, it is to be noted that no systematic kinetic investigation on the oxidation of 4-oxo-4-phenylbutanoic acid by Nbromoanisamide has yet been reported in the literature.…”

Section: Introductionmentioning

confidence: 99%

Kinetics and Mechanism of Oxidation of 4-Oxo-4-phenylbutanoic Acid by N-Bromoanisamide in Aqueous Acetic Acid Medium

2016

Chem Sci Trans

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Kinetics and mechanism of oxidation of 4-oxo-4-phenylbutanoic acid (KA) by N-bromoanisamide (NBAS) in aqueous acetic acid medium have been studied potentiometrically. The reactions exhibit a first order rate dependence each with respect to oxidant, substrate and [H + ]. The reaction rate retarded by the addition of anisamide. The decrease in dielectric constant of the medium increases rate of the reaction. Increase in ionic strength, by the addition of sodium perchlorate has no effect on the rate constant. The effect of temperature on the reaction has been investigated in the temperature range 308-323 K. Based on the kinetic results and the product analysis, a suitable mechanism has been proposed for the reaction of NBAS with 4-oxo-4-phenylbutanoic acid.

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Kinetics and Mechanism of Oxidation of Some Substituted Benzhydrols by N-Bromosuccinimide

Cited by 10 publications

References 6 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 and Thermodynamics of Oxidation of Benzhydrol by Tetrabutyl Ammonium Bromochromatein the Presence of Oxalic Acid

Kinetics and Mechanism of Oxidation of 4-Oxo-4-phenylbutanoic Acid by N-Bromoanisamide in Aqueous Acetic Acid Medium

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