Cu(II)‐catalyzed hydrolysis of tris‐2‐pyridyl phosphate assisted by sodium dodecyl sulfate micelles

Wanderlind, Eduardo H.; Bittencourt, Catiunaiara R.; Manfredi, Alex M.; Gerola, Adriana P.; Souza, Bruno S.; Fiedler, Haidi D.; Nome, Faruk

doi:10.1002/poc.3837

Cited by 12 publications

(10 citation statements)

References 32 publications

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“…Together with counter ion binding ( β ), the values of the extent of micelle dissociation ( α ) were determined following the procedure described by other authors and us. [ 11,12 ] The values of α were estimated from the ratio S 2 / S 1 , where S 2 and S 1 are the slopes of the linear regions above and below the CMC in the κ versus (surfactant) plot. The values of β were evaluated by deducting the α values from unity, that is, β = (1 − α ).…”

Section: Resultsmentioning

confidence: 99%

“…[ 9,10 ] This unique micellar property of surfactants substantially boosts up the feebly water‐insoluble organic species by changing their microstructure: polarity, surface tension, viscosity, and so forth; surfactant micelle's solubility enhancement properties are widely employed in industrial, commercial, technological, and other applications. [ 11–17 ]…”

Section: Introductionmentioning

confidence: 99%

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Interaction of metformin hydrochloride with ionic surfactants in aqueous and NaCl solution: Effect of temperatures and compositions

Hoque

Alam

Khan

et al. 2020

J of Physical Organic Chem

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Herein, the interaction of metformin hydrochloride (MNH) with cetyltrimethylammonium bromide (CTAB) and sodium dodecyl sulfate (SDS) has been investigated by the conductometric technique in aqueous medium as well as in the existence of NaCl over a range of temperatures. MNH, an antidiabetic drug that belongs to the biguanide group, is generally prescribed for the patients to manage type II diabetes. The micellar parameters such as critical micelle concentration (CMC), the extent of counterion binding (β), and different thermodynamic properties for MNH + surfactant systems were estimated and discussed elaborately. The CMC values of CTAB + MNH and SDS + MNH systems are dependent on the concentrations of NaCl at different temperatures. The significant decrease of CMC values in NaCl solution indicates that NaCl stabilizes MNH‐mediated surfactant micelles. The CMC values versus T plots show a nonlinear pattern for the CTAB + MNH system, whereas the CMC values almost monotonically decrease with increasing temperature for the SDS + MNH system. The values of ∆G0m were negative for both systems in all cases. Both ∆G0m and ∆G0m,t values indicate that the aggregation processes of MNH + surfactants mixture are spontaneous, which is also manifested in NaCl solution and with the change of temperatures in most of the cases. The obtained results proposed that surfactants may assist as a proficient drug delivery agent for antidiabetic drug, enhancing their bioavailability.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Interaction of metformin hydrochloride with ionic surfactants in aqueous and NaCl solution: Effect of temperatures and compositions

Hoque

Alam

Khan

et al. 2020

J of Physical Organic Chem

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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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“…Self-assembly of colloidal systems maintained by hydrophobic effects has been reported for micellar and liposomal systems. They act as nanoreactors and increase the rate constants. ,− Regarding molecular self-assembly, hydrophobic forces are fundamental for the formation of colloidal systems. However, they alone are not efficient enough for the maintenance of the system, especially considering the great mobility of the monomers.…”

Section: Introductionmentioning

confidence: 99%

Self-Assembled Multifunctional Nanoreactors for Dephosphorylation Reactions

Demos

Bittencourt

Nardino

et al. 2021

ACS Appl. Nano Mater.

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Nature is a source of inspiration for the self-assembly of functional molecular nanoarchitectures based on intermolecular bonds. This work investigates the self-assembly of molecules (i) polyacrylic acid (PAA, COO– group), (ii) cetyltrimethylammonium (CTA+), and (iii) alkylimidazole (ImR, imidazole group) as building blocks with different properties and functionalities. For the dephosphorylation reaction of diethyl 2,4-dinitrophenyl phosphate (DEDNPP) in aqueous medium, the building blocks PAA, ImR, and CTA+ did not show relevant catalytic activity. An increase in the rate constant was observed from the critical aggregation concentration (CAC) between the polymer and surfactant. This result was related to the formation of hydrophobic pockets of the nanostructured supramolecular complexes. For the PAA/CTAB/ImR system, the formation of hydrophobic microenvironments made it possible to partition the DEDNPP to regions close to the catalytic site. The increase in the rate constant was up to 1.5 × 107-fold higher than that obtained with spontaneous hydrolysis. Thus, the extensive catalytic activity of the self-assembled multicomponent nanoreactor demonstrated potential because of its ease of obtainment and its variety of characteristics. Therefore, the combination of different functional macromolecules is a strategy for the development of inexpensive, efficient, and selective nanocatalysts with characteristics similar to enzymes, the best-known catalysts.

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Cu(II)‐catalyzed hydrolysis of tris‐2‐pyridyl phosphate assisted by sodium dodecyl sulfate micelles

Cited by 12 publications

References 32 publications

Interaction of metformin hydrochloride with ionic surfactants in aqueous and NaCl solution: Effect of temperatures and compositions

Interaction of metformin hydrochloride with ionic surfactants in aqueous and NaCl solution: Effect of temperatures and compositions

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

Self-Assembled Multifunctional Nanoreactors for Dephosphorylation Reactions

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