Effect of cetyltrimethylammonium bromide micelles on the ionic equilibrium and the reactivity of hydrogen peroxide toward electrophilic substrates

Vakhitova, L. N.; Bogutskaya, K. V.; Taran, N. A.; Razumova, N. G.; Savëlova, V. A.; Popov, A. F.

doi:10.1007/s11237-008-9014-0

Cited by 2 publications

(2 citation statements)

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“…These data clearly demonstrate that the absolute value of the observed micellar effect increases more than twofold as pH decreases from 12.5 to 8.5. Change of pK a value of hydrogen peroxide in going to micellar solution [42] (which is especially appreciable in weakly alkaline medium) in combination with micellar catalytic effect (up to 15-fold) makes the rate of decomposition according to nucleophilic mechanism at pH 8.5 comparable to the rate of analogous process at pH ~10.2 at a constant concentration of hydrogen peroxide.…”

Section: Methodsmentioning

confidence: 99%

Nucleophilic oxidizing systems based on hydrogen peroxide for decomposition of ecotoxicants

et al. 2011

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The kinetics of oxidation of methylsulfanylbenzene and nucleophilic decomposition of diethyl 4-nitrophenyl phosphate with hydrogen peroxide in the presence of ammonium hydrogen carbonate or boric acid in aqueous, aqueous-alcoholic, micellar, and microemulsion media were studied. Quantitative parameters of the examined processes were determined, and the possibility of using hydrogen peroxide for the design of oxidative nucleophilic decontaminating systems was demonstrated.Taking into account huge worldwide stocks of chemical weapons [1-6], the problem implying utilization of highly toxic chemical agents has recently become especially important. The most common chemical weapons may be divided into three main groups: (1) phosphorus acid esters (neurotoxins and structurally similar pesticides, e.g., GB, GD, and Metaphos); (2) organosulfur compounds (blister agents, e.g., Yperite or HD); and (3) compounds with combined (neuroparalytic) action (VX).The optimal system for decontamination of toxic chemical agents should ensure their solubilization and simultaneously high rate of decomposition. Therefore, organized nanosize systems such as micellar solutions and microemulsions are promising from the viewpoint of development of ecologically safe decontaminating compositions [11,12,[15][16][17][18][19][20][21]; these systems provide increased reagent concentration at the phase boundary between micelles (oil drop) and water and create favorable conditions for nucleophilic attack on electrophilic centers of toxic substrates [21,22].While searching for chemically active components capable of rapidly and irreversibly decomposing toxic chemicals, specific attention is now given to the design of universal oxidative nucleophilic systems for degradation of chemical agents of different natures. For example, nucleophilic reagents are efficient toward phosphorus acid esters and halides (GB) [23,24], dialkyl sulfides like HD are decomposed by the action of oxidants [16,25,26], whereas oxidative nucleophilic systems containing an HOX-OX -couple (X = OH, Hlg, etc.) are preferred for decontamination of chemical agents like VX or mixtures of compounds belonging to the above three types (GB, HD, VX) [20,27]. In this respect, hydrogen peroxide due to its dual nature (it is an effective oxidant toward HD analogs [15,25] and reactive α-nucleophile toward phosphorus acid esters [1,24,28]) may be regarded as universal agent in the design of mild and ecologically safe decontami-

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Section: Methodsmentioning

confidence: 99%

Nucleophilic oxidizing systems based on hydrogen peroxide for decomposition of ecotoxicants

et al. 2011

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“…Vakhitova et al 21 studied the rate-enhancing effect of CTAB on the nucleophilic reactions of HO À and HOO À with 4-nitrophenyl diethylphosphate (NPDEP) and 4-nitrophenyl toluenesulfonate (NPTS). CTAB was found to increase the apparent acid dissociation constant (K 0 a ) for H 2 O 2 by up to three-fold.…”

Section: Methodsmentioning

confidence: 99%

Reactivity in organised assemblies

Onel

Buurma

2009

Annu. Rep. Prog. Chem., Sect. B: Org. Chem.

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This report reviews the 2008 literature on reactivity in organised assemblies. The report is subdivided in sections discussing (1) reactivity in micelles, including medium effects and compartmentalisation, enzymatic catalysis in micellar media and metallomicellar catalysis, (2) reactivity in vesicles, (3) reactivity in emulsions, (4) reactions in assemblies resulting from dynamic combinatorial chemistry and template approaches, (5) DNA-based approaches to influence reactivity including catalysis by DNA, DNA-templated synthesis and DNA-based asymmetric synthesis, (6) reactivity in nanoparticleimmobilised assemblies and (7) modulation of nanoparticle catalysis through the use of thermoresponsive polymers. We have chosen to interpret ''organised assemblies'' in a rather more liberal way than in previous years. [1][2][3] now including assemblies such as those involving DNA as well as constructions resulting from dynamic combinatorial self assembly which were turned into covalent ''non dynamic assemblies''. In all cases, however, (self) organisation and (self) assembly are crucial to the results discussed. Related to the liberal interpretation of organised assemblies, this report does not (and cannot) aim to present an exhaustive review.

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Effect of cetyltrimethylammonium bromide micelles on the ionic equilibrium and the reactivity of hydrogen peroxide toward electrophilic substrates

Cited by 2 publications

References 4 publications

Nucleophilic oxidizing systems based on hydrogen peroxide for decomposition of ecotoxicants

Nucleophilic oxidizing systems based on hydrogen peroxide for decomposition of ecotoxicants

Reactivity in organised assemblies

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