Colorimetric Test for Amides and Nitriles

Soloway, Saul; Lipschitz, Abraham

doi:10.1021/ac60065a041

Cited by 83 publications

(23 citation statements)

References 3 publications

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“…The main product of the oxidation, nitrile, was detected by a standard test (34). The reduced product of the oxidant was detected by thin-layer chromatography.…”

Section: Methodsmentioning

confidence: 99%

Kinetics of glycine oxidation by N‐bromophthalimide in the presence of sodium dodecyl sulfate

Joshi¹,

Katre²,

Singh³

2006

J Surfact & Detergents

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The kinetics of oxidation of glycine by N-bromophthalimide (NBP) were studied in the presence of an anionic surfactant, sodium dodecyl sulfate, in acidic medium at 308 K. The rate of reaction was found to have first-order dependence on [NBP] and fractional-order dependence on [glycine] and [H + ]. The addition of reduced product of the oxidant had no significant effect on the rate of reaction. Increasing [Hg(OAc) 2 ] and [Br -] increased the rate of reaction, whereas a change in ionic strength (µ) of the medium had no effect on oxidation velocity. The rate of reaction decreased with a decrease in dielectric constant of the medium. HCN was identified as the main oxidation product of the reactions. The various activation parameters have been computed. A suitable mechanism consistent with the experimental findings has been proposed. The index of cooperativity and the micelle binding constant have been calculated.Surfactants are amphipathic molecules with both hydrophobic and hydrophilic properties. When these molecules are dissolved in water they can achieve segregation of their hydrophobic portions from the solvent by self-aggregation. Aggregates of these surfactants, known as micelles, are responsible for altering the rates of organic reactions in aqueous surfactant solutions. Additions of surfactants to mixtures of chemical reactants are considered in view of the following: first, to further understand factors that influence the rates of reaction; second, to gain additional insight into the exceptional catalysis of enzymatic reactions; and third, to explore the utility of micellar systems for the purpose of synthesis. The micellar catalysis in chemical reactions is well reported (1-7). The hydrophobic and electrostatic forces in the presence of surfactants influence the rates of several redox reactions (8-17). The observed rate of reaction depends on the association between the reactants and micellar aggregates. Different models have been proposed to describe the reactions in the presence of micelles.Glycine occurs about every third amino acid in collagen, the most abundant protein in the body. It can be used directly as an energy source or for synthesis of glucose to supply blood sugar. It is required for porphyrin synthesis to initiate the pathway leading to heme formation. Every cell function involving formation of RNA or DNA is glycinedependent because of its role in purine biosynthesis. The importance of glycine in brain function is illustrated by the finding that nonketotic hyperglycinemia is associated with early myoclonic encephalopathy that may respond to vitamin B 6 (18).Previous work on the oxidation and halogenation of glycine by N-halo compounds has received considerable attention (19-28); however, very limited work on the kinetics of oxidation of glycine by N-halo compounds has been documented (29-31). A perusal of the literature shows that the reactivity of N-bromophthalimide (NBP) could be compared with that of other N-bromoimides such as N-bromosuccinimide (NBS) and N-bromosaccharin (NBSA). NB...

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“…The main product of the oxidation, nitrile, was detected by a standard test (34). The reduced product of the oxidant was detected by thin-layer chromatography.…”

Section: Methodsmentioning

confidence: 99%

Kinetics of glycine oxidation by N‐bromophthalimide in the presence of sodium dodecyl sulfate

Joshi¹,

Katre²,

Singh³

2006

J Surfact & Detergents

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show abstract

“…The products were identified as a mixture of nitrile, aldehyde, and trace of ammonia. Nitrile was identified by the color reaction with hydroxylamine and iron(III) chloride [26]. Presence of aldehyde was confirmed by Schiff , s reagent and ammonia was detected by Nessler , s reagent.…”

Section: Kinetic Proceduresmentioning

confidence: 99%

A Novel Oxidation of Valine by N-Bromophthalimide in the Presence of Ruthenium(III) Chloride as a Homogeneous Catalyst

Singh¹,

Jain²,

Negi³

et al. 2009

Catal Lett

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Kinetics of Ruthenium(III) [Ru(III)] chloride catalyzed oxidation of valine (Val) has been studied by N-bromophthalimide (NBP) in the acidic medium at 35°C. The reaction rate follows first-order and zero-order dependence with respect to [NBP] and [Val]. First-order kinetics was observed for Ru(III) chloride at low range of concentrations and tending towards zero-order at higher concentrations. A negative effect was observed for [H ? ] and [phthalimide], while a positive effect was observed for [Cl -] on the reaction rate. Hg(OAc) 2 , ionic strength (I), and dielectric constant (D) of the medium did not change significantly the reaction rate. The rate constants as a function of temperature (298-318 K) were used to calculate activation parameters of the oxidation of Val by NBP. A plausible mechanism was proposed to explain the results of kinetic studies, reaction stoichiometry and product analysis.

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“…Formation of BaCO 3 indicated the liberation of CO 2 in the oxidation of Gly by NBP. Initially, nitrile was identified by a conventional spot method [26,27] and was later confirmed by FT-IR and GC-MS. In the spot method, one drop of liquid sample was placed in a test tube and 2 cm 3 of 1 mol dm -3 hydroxyl ammonium chloride in propylene glycol plus 1 mL of potassium hydroxide in propylene glycol was added.…”

Section: Stoichiometry and Product Analysismentioning

confidence: 99%

Kinetic study of the ruthenium(III)-catalyzed oxidation of glycine by N-bromophthalimide in acidic medium

Singh¹,

Jain²,

Negi³

et al. 2010

Transition Met Chem

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The kinetics of ruthenium(III) chloridecatalyzed oxidation of glycine by N-bromophthalimide (NBP) was studied in aqueous perchloric acid at 35°C. The results showed first-and zero-order behavior with respect to NBP and Gly, respectively. Ru(III) showed a catalytic effect on the reaction which followed first-order kinetics with respect to [Ru(III)] at a low concentration range and tended to zero order at high concentration range. The rates decreased with increase in the proton concentration, while chloride positively influenced the rate of the reaction. Two moles of NBP were required to oxidize one mole of Gly, and the products were identified as phthalimide (NHP), HCN, CO 2 , and Br -. Neither added NHP nor Br -influenced the reaction rate. Ionic strength and dielectric constant of the medium had no significant effect on the rate. Activation parameters were determined by studying the reaction at different temperatures. A reaction scheme of the catalytic oxidation is proposed.

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Colorimetric Test for Amides and Nitriles

Cited by 83 publications

References 3 publications

Kinetics of glycine oxidation by N‐bromophthalimide in the presence of sodium dodecyl sulfate

Kinetics of glycine oxidation by N‐bromophthalimide in the presence of sodium dodecyl sulfate

A Novel Oxidation of Valine by N-Bromophthalimide in the Presence of Ruthenium(III) Chloride as a Homogeneous Catalyst

Kinetic study of the ruthenium(III)-catalyzed oxidation of glycine by N-bromophthalimide in acidic medium

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