Aqueous Micelles as Catalytic Nanoreactors for Dephosphorylation Reactions

Wanderlind, Eduardo H.; Orth, Elisa S.; Medeiros, Michelle; Santos, Deise Menezes; Westphal, Eduard; Gallardo, Hugo; Fiedler, Haidi D.; Nome, Faruk

doi:10.5935/0103-5053.20140258

Cited by 9 publications

(9 citation statements)

References 2 publications

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“…For example, there has been a number of recent examples of catalytic systems for a variety of nucleophilic substitution reactions in phosphate esters in homogeneous, − microheterogeneous, − and heterogeneous − media. This collection of data available in the literature suggests that the best catalytic effects arise from the combination of several factors including, for example, the presence of at least one metal ion center.…”

Section: Introductionmentioning

confidence: 99%

Toward Heterogeneously Catalyzed Detoxification of Phosphotriesters: Insights from Kinetics and Theoretical Calculations

Zimmermann¹,

Almerindo

Medeiros³

et al. 2018

J. Phys. Chem. C

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A mixed Mg 2+ /Al 3+ oxide featuring an incipient spinel phase was employed in the catalytic decomposition of a range of phosphate triesters, including the neurotoxic biocide chlorpyrifos methyl O-analog, with estimated catalytic effects up to 10 4 -fold. The target reaction, namely, the transesterification with 1propanol, was conveniently chosen as a means to convert toxic organophosphorus substrates into trialkyl phosphates structurally related to a family of flame retardants. Catalytic efficiency depends upon the stereo-electronic properties of the substrate, with both leaving group ability and geometric factors displaying pivotal effects on the rate constants. To evaluate the adsorption of 1-propanol/ propoxide and the phosphotriester methyl paraoxon over the MgAl 2 O 4 (100) surface, density functional theory calculations with periodic boundary conditions were performed, which showed that the most probable reactants' conformation prior to the reaction is such that propoxide is bound to a Mg 2+ center with a juxtapositioned methyl paraoxon molecule at a close, neighboring Al 3+ site.

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Section: Introductionmentioning

confidence: 99%

Toward Heterogeneously Catalyzed Detoxification of Phosphotriesters: Insights from Kinetics and Theoretical Calculations

Zimmermann¹,

Almerindo

Medeiros³

et al. 2018

J. Phys. Chem. C

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“…Micellar catalysis (both chemical and enzymatic) for many years is demonstrated as a very effective tool for a number of diverse reactions. Formed micellar aggregates showed tremendous catalytic potential, also in carbohydrate chemistry . In the scientific literature only a few examples of the use of micellar catalysis for the synthesis of alkyl glucosides can be found.…”

Section: Methodsmentioning

confidence: 99%

Micellar Catalysis in Fischer Glycosidation: En Route to Diverse Functional Glycosides

et al. 2019

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We have demonstrated that direct Fischer glycosidation of carbohydrates with selected alcohols, glycols and chloroalcohols to corresponding glucosides in micellar reaction system can be a promising and effective route for the selective synthesis of a number of functional glucosides. The use of specific catalyst combining both surfactant and acid catalyst functions enables formation of the reactive micellar system. The formation of corresponding glucosides with spectacular high selectivity to monoglucosides is one of the most important phenomena of the application of micellar catalysis to functional glucosides synthesis.

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“…1,2 A related concern is the increasing prohibited/obsolete pesticide stockpiles-especially organophosphates (OPs)-which have required the development of efficient degradation processes. 3 For that matter, in the last few decades several systems have been proposed to mitigate the toxicity of OPs: nanocatalysts, 4 enzymes, 5,6 micelles, 7,8 nucleophiles, [9][10][11][12] etc. A major objective is centered on promoting the cleavage of a P-O bond of the OP, forming a quick hydrolysable intermediate, ideally leading to a non-toxic diester to complete the catalytic cycle.…”

Section: Introductionmentioning

confidence: 99%

Mechanistic insights into the amidolysis of a phosphate triester: the antagonistic role of water

et al. 2022

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Aqueous Micelles as Catalytic Nanoreactors for Dephosphorylation Reactions

Cited by 9 publications

References 2 publications

Toward Heterogeneously Catalyzed Detoxification of Phosphotriesters: Insights from Kinetics and Theoretical Calculations

Toward Heterogeneously Catalyzed Detoxification of Phosphotriesters: Insights from Kinetics and Theoretical Calculations

Micellar Catalysis in Fischer Glycosidation: En Route to Diverse Functional Glycosides

Mechanistic insights into the amidolysis of a phosphate triester: the antagonistic role of water

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