Proton transfer in nonpolar solvents: an approach to generate electrolytes in aprotic media

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

Proton transfer in nonpolar solvents: an approach to generate electrolytes in aprotic media. / Smith, Gregory N.

In: Physical Chemistry Chemical Physics, Vol. 2018, No. 20, 25.06.2018, p. 18919-18923.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Smith, GN 2018, 'Proton transfer in nonpolar solvents: an approach to generate electrolytes in aprotic media', Physical Chemistry Chemical Physics, vol. 2018, no. 20, pp. 18919-18923. https://doi.org/10.1039/C8CP02349B

APA

Smith, G. N. (2018). Proton transfer in nonpolar solvents: an approach to generate electrolytes in aprotic media. Physical Chemistry Chemical Physics, 2018(20), 18919-18923. https://doi.org/10.1039/C8CP02349B

Vancouver

Smith GN. Proton transfer in nonpolar solvents: an approach to generate electrolytes in aprotic media. Physical Chemistry Chemical Physics. 2018 Jun 25;2018(20):18919-18923. https://doi.org/10.1039/C8CP02349B

Author

Smith, Gregory N. / Proton transfer in nonpolar solvents: an approach to generate electrolytes in aprotic media. In: Physical Chemistry Chemical Physics. 2018 ; Vol. 2018, No. 20. pp. 18919-18923.

Bibtex

@article{8052da2678fd4ffc954363cd02b2086e,
title = "Proton transfer in nonpolar solvents: an approach to generate electrolytes in aprotic media",
abstract = "Stabilizing charged species in nonpolar solvents is challenging due to their low dielectric constant. As a contrast to formally ionic electrolytes, two series of acidic “potential” electrolytes have been developed in this study. These can be ionized by combining them stoichiometrically with a small molecule base in a typical nonpolar solvent, n-dodecane. The electrolytic conductivity of solutions of bis(2-ethylhexyl)phosphoric acid as mixtures with linear and branched dioctylamines and trioctylamines was measured, and the solutions were found to become increasingly conductive as the concentration increased, demonstrating that proton transfer occurred between the two species. Linear octylamines were found to be most effective at deprotonation. An acid-tipped poly(lauryl methacrylate) polymer (PLMA48-COOH) was also studied to give a polymer soluble in n-dodecane with a single ionizable group located precisely at the end of the polymer chain. Trioctylamine could successfully deprotonate this acid group. Even in an aprotic solvent, the transfer of protons between acidic and basic moieties is a useful method for controlling the properties of dissolved molecules.",
author = "Smith, {Gregory N.}",
year = "2018",
month = jun,
day = "25",
doi = "10.1039/C8CP02349B",
language = "English",
volume = "2018",
pages = "18919--18923",
journal = "Physical Chemistry Chemical Physics",
issn = "1463-9076",
publisher = "Royal Society of Chemistry",
number = "20",

}

RIS

TY - JOUR

T1 - Proton transfer in nonpolar solvents: an approach to generate electrolytes in aprotic media

AU - Smith, Gregory N.

PY - 2018/6/25

Y1 - 2018/6/25

N2 - Stabilizing charged species in nonpolar solvents is challenging due to their low dielectric constant. As a contrast to formally ionic electrolytes, two series of acidic “potential” electrolytes have been developed in this study. These can be ionized by combining them stoichiometrically with a small molecule base in a typical nonpolar solvent, n-dodecane. The electrolytic conductivity of solutions of bis(2-ethylhexyl)phosphoric acid as mixtures with linear and branched dioctylamines and trioctylamines was measured, and the solutions were found to become increasingly conductive as the concentration increased, demonstrating that proton transfer occurred between the two species. Linear octylamines were found to be most effective at deprotonation. An acid-tipped poly(lauryl methacrylate) polymer (PLMA48-COOH) was also studied to give a polymer soluble in n-dodecane with a single ionizable group located precisely at the end of the polymer chain. Trioctylamine could successfully deprotonate this acid group. Even in an aprotic solvent, the transfer of protons between acidic and basic moieties is a useful method for controlling the properties of dissolved molecules.

AB - Stabilizing charged species in nonpolar solvents is challenging due to their low dielectric constant. As a contrast to formally ionic electrolytes, two series of acidic “potential” electrolytes have been developed in this study. These can be ionized by combining them stoichiometrically with a small molecule base in a typical nonpolar solvent, n-dodecane. The electrolytic conductivity of solutions of bis(2-ethylhexyl)phosphoric acid as mixtures with linear and branched dioctylamines and trioctylamines was measured, and the solutions were found to become increasingly conductive as the concentration increased, demonstrating that proton transfer occurred between the two species. Linear octylamines were found to be most effective at deprotonation. An acid-tipped poly(lauryl methacrylate) polymer (PLMA48-COOH) was also studied to give a polymer soluble in n-dodecane with a single ionizable group located precisely at the end of the polymer chain. Trioctylamine could successfully deprotonate this acid group. Even in an aprotic solvent, the transfer of protons between acidic and basic moieties is a useful method for controlling the properties of dissolved molecules.

U2 - 10.1039/C8CP02349B

DO - 10.1039/C8CP02349B

M3 - Journal article

VL - 2018

SP - 18919

EP - 18923

JO - Physical Chemistry Chemical Physics

JF - Physical Chemistry Chemical Physics

SN - 1463-9076

IS - 20

ER -

ID: 199679396