Monitoring Micelle Breakdown by Chemical Trapping

Pazo‐Llorente, Roman; Bravo‐Díaz, Carlos; González-Romero, Elisa

doi:10.1021/la034879i

Cited by 17 publications

(17 citation statements)

References 41 publications

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“…However, the 3MBD ions will be mainly located in the aqueous pseudophase because of their positive charge, as demonstrated previously by Cuccovia et al [57] and by Bravo-Díaz and co-workers [58]. Thus, one would expect a similar inhibition of the reactions when employing CTAX micelles.…”

supporting

confidence: 59%

Micellar Effects on the Reaction between an Arenediazonium Ion and the Antioxidants Gallic Acid and Octyl Gallate

Losada‐Barreiro

Sánchez-Paz

Pastoriza-Gallego

et al. 2008

Helvetica Chimica Acta

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The effect of sodium dodecyl sulfate (SDS) micelles on the reaction between the 3-methylbenzenediazonium (3MBD) ion and either the hydrophilic antioxidant gallic acid (GA) or the hydrophobic analogue octyl gallate (OG) have been investigated as a function of pH. Titration of GA in the absence and presence of SDS micelles showed that the micelles do not alter the first ionization equilibrium of GA. Analysis of the dependence of the observed rate constant (k obs ) with pH shows that the reactive species are GA 2À and OG À. Kinetics results in the absence and presence of SDS micelles suggest that SDS aggregates do not alter the expected reaction pathway. SDS Micelles inhibit the spontaneous decomposition of 3MBD as well as the reaction between 3MBD and either GA or OG, and upon increasing the SDS concentration, with k obs approaching the value for the thermal decomposition of 3MBD in the presence of SDS. Our results are consistent with the prediction of the pseudophase model and show that the origin of the inhibition for the reaction with GA is different to that for the reaction with OG; in the former case, the observed inhibition can be rationalized in terms of the micelle-induced electrostatic separation of reactants in the micellar Stern layer, whereas the observed inhibition in the reaction with OG is a consequence of the dilution effect caused by increasing SDS concentration, decreasing the local OG À concentration in the Stern layer.

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supporting

confidence: 59%

Micellar Effects on the Reaction between an Arenediazonium Ion and the Antioxidants Gallic Acid and Octyl Gallate

Losada‐Barreiro

Sánchez-Paz

Pastoriza-Gallego

et al. 2008

Helvetica Chimica Acta

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“…2,4,6-benzeneacetamide (1-ArNHAc) and 2,6-dimethy-4-hexadecyl-benzeneacetamide, 16-ArNHAc, were synthesized as described. 18,19 Synthesis of 2,4,6-trimethylanisole (1-ArOMe) and 2,6-dimethyl-4-hexadecylanisole (16-ArOMe): 500 mg of 1-ArN 2 + or 16-ArN 2 + , were added to 100 mL of methanol containing 50 μL of an aqueous solution of HCl 1.0 mol dm −3 and maintained at 30°C for 24 h. After solvent evaporation, water was added, and the product extracted with chloroform. Na 2 SO 4 was added to the chloroform to remove traces of water and filtered.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Molecular Dynamics Simulations of the Initial-State Predict Product Distributions of Dediazoniation of Aryldiazonium in Binary Solvents

Cruz¹,

Lima²,

Dias³

et al. 2015

J. Org. Chem.

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The dediazoniation of aryldiazonium salts in mixed solvents proceeds by a borderline SN1 and SN2 pathway, and product distribution should be proportional to the composition of the solvation shell of the carbon attached to the -N2 group (ipso carbon). The rates of dediazoniation of 2,4,6-trimethylbenzenediazonium in water, methanol, ethanol, propanol, and acetonitrile were similar, but measured product distributions were noticeably dependent on the nature of the water/cosolvent mixture. Here we demonstrated that solvent distribution in the first solvation shell of the ipso carbon, calculated from classical molecular dynamics simulations, is equal to the measured product distribution. Furthermore, we showed that regardless of the charge distribution of the initial state, i.e., whether the positive charge is smeared over the molecule or localized on phenyl moiety, the solvent distribution around the reaction center is nearly the same.

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“…A variety of electron donors reduce arenediazonium ions [13,15]. Electrochemical reductions of arenediazonium ions have been studied in aqueous, nonaqueous, and micellar solutions [16][17][18][19][20]. Polarographic techniques were used to estimate partitioning of electroactive compounds [21][22][23], but the models used to fit the results did not explicitly include a separate interfacial region.…”

Section: Introductionmentioning

confidence: 99%

Determining α-tocopherol distributions between the oil, water, and interfacial regions of macroemulsions: Novel applications of electroanalytical chemistry and the pseudophase kinetic model

Gunaseelan

Romsted

Pastoriza-Gallego

et al. 2006

Advances in Colloid and Interface Science

110

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Monitoring Micelle Breakdown by Chemical Trapping

Cited by 17 publications

References 41 publications

Micellar Effects on the Reaction between an Arenediazonium Ion and the Antioxidants Gallic Acid and Octyl Gallate

Micellar Effects on the Reaction between an Arenediazonium Ion and the Antioxidants Gallic Acid and Octyl Gallate

Molecular Dynamics Simulations of the Initial-State Predict Product Distributions of Dediazoniation of Aryldiazonium in Binary Solvents

Determining α-tocopherol distributions between the oil, water, and interfacial regions of macroemulsions: Novel applications of electroanalytical chemistry and the pseudophase kinetic model

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