Prediction of the Standard Gibbs Energy of Ion Transfer across the 1,2-Dichloroethane/Water Interface

Yamada, Akihiro; Yoshida, Erina; Eda, Kazuo; Osakai, Toshiyuki

doi:10.2116/analsci.18p088

Cited by 10 publications

(48 citation statements)

References 39 publications

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“…Therefore, the electrostatic ion-solvent interactions would contribute significantly to the Gibbs transfer energy. 15 On the other hand, PF6 -, C7F15COO -, C8F17SO3 -, and (CnF2n+1SO2)2Nare categorized to hydrophobic fluorinated ions. Their ΔG 0 tr, ′ MIX→W values are higher than those predicted from Eq.…”

Section: Resultsmentioning

confidence: 99%

Gibbs Transfer Energies of Ions from a Mixed Solvent of 2H,3H-Decafluoropentane and 1,2-Dichloroethane to Water

Katano¹,

Uematsu²,

Kuroda³

et al. 2019

ANAL. SCI.

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The transfer of hydrophilic, lipophilic, and fluorophilic ions at the interface between water (W) and a mixed solvent (MIX) of 2H,3H-decafluoropentane (DFP) and 1,2-dichloroethane (DCE) was studied voltammetrically and potentiometrically, and the formal Gibbs transfer energies of the ions from MIX to W, ΔG 0 tr, ′ MIX→W, were determined. The ΔG 0 tr, ′ MIX→W values of all the ions tested were higher than those from DFP to W. Namely, the ions would exist more stably in MIX than DFP, even for fluorophilic ions. This is due to the addition of DCE, which has a higher dielectric constant. A comparison of ΔG 0 tr, ′ MIX→W with that from DCE to W showed a superior affinity of fluorophilic ions to the fluorous solvent in spite of equivolume addition of DCE. Therefore, the mixed solvent would be a practically superior extraction medium for fluorophilic ions. In practice, the MIX | methylene blue + (W) system showed higher extractability of a fluorophilic ion C8F17SO3than the DFP | W and DCE | W systems.

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Section: Resultsmentioning

confidence: 99%

Gibbs Transfer Energies of Ions from a Mixed Solvent of 2H,3H-Decafluoropentane and 1,2-Dichloroethane to Water

Katano¹,

Uematsu²,

Kuroda³

et al. 2019

ANAL. SCI.

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“…8 b) Newly determined by ITV in a similar manner as reported previously. 27,35 c) Theoretical values obtained by using the non-Bornian solvation model. 35 d) Determined in this study.…”

Section: Determination Ofmentioning

confidence: 99%

“…27,35 c) Theoretical values obtained by using the non-Bornian solvation model. 35 d) Determined in this study. e) Estimated by using eq 7.…”

Section: Determination Ofmentioning

confidence: 99%

“…∘ and ) at the DCE|W interface were previously determined (or estimated) by ITV for the amine drugs. 27 Furthermore, we have optimized the measurement conditions as mentioned elsewhere, 35 and thus obtained more reliable data of ∆ -. ∘ and ) will be reported in this paper.…”

Section: Introductionmentioning

confidence: 99%

“…∘ can be estimated rather accurately by using the non-Bornian solvation model, which was recently proposed by our group. 35,36 Taking this into account, we have found a possibility of perfect in silico evaluation of the membrane permeability of drugs.…”

Section: Introductionmentioning

confidence: 99%

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A Strategy for in Silico Prediction of the Membrane Permeability of Drugs

Yoshida

Osakai

2018

Bulletin of the Chemical Society of Japan

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Parallel artificial membrane permeation assay (PAMPA) was performed for nine amine drugs and their permeability coefficient (log %&'%&) was determined at different pH's. The previously developed digital simulation method was successfully used to reproduce the sigmoid-like pH dependence of log %&'%& , and the distribution coefficient (log),+) to the lipid-containing dodecane membrane could be determined for all the amine drugs studied. The thus determined log),+ values showed a linear free-energy relationship with the standard ion-transfer potential (∆-. ∘ ; R 2 = 0.754) and the distribution coefficient (log) ; R 2 = 0.891), which were previously determined by ion-transfer voltammetry with the 1,2-dichloroethane|water interface. On the other side, we can predict ∆-. ∘ very accurately by a previously proposed solvation model called the "non-Bornian" model. These findings suggest a possible strategy for perfect in silico prediction of the membrane permeability of drugs.

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Computational Prediction of the Adsorption Equilibrium for Ionic Surfactants at the Electrified Oil/Water Interface

Yamauchi¹,

Eda²,

Osakai

2022

ChemElectroChem

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In a previous study (Somekawa et al., Langmuir 2019, 35, 11345–11350) a non‐Bornian solvation model was successfully applied to computational prediction of the adsorption equilibrium for nonionic surfactants at the oil (O)/water (W) interface. In this study, the method was extended to the adsorption of “ionic” surfactants at the polarized O/W interface. In this extension, the electrostatic potential of an ionic surfactant in the electric double layer formed at the O/W interface was taken into account together with the chemical potential estimated using the non‐Bornian solvation model. The calculation results clearly showed that a cationic surfactant (hexadecyltrimethylammonium ion) was adsorbed at the nitrobenzene/W interface, when the interfacial potential was negative. This prediction was consistent with the previous experimental observation using electrocapillary measurements.

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Prediction of the Standard Gibbs Energy of Ion Transfer across the 1,2-Dichloroethane/Water Interface

Cited by 10 publications

References 39 publications

Gibbs Transfer Energies of Ions from a Mixed Solvent of 2H,3H-Decafluoropentane and 1,2-Dichloroethane to Water

Gibbs Transfer Energies of Ions from a Mixed Solvent of 2H,3H-Decafluoropentane and 1,2-Dichloroethane to Water

A Strategy for in Silico Prediction of the Membrane Permeability of Drugs

Computational Prediction of the Adsorption Equilibrium for Ionic Surfactants at the Electrified Oil/Water Interface

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