Lipophilicity of acetylcholine and related ions examined by ion transfer voltammetry at a polarized room-temperature ionic liquid membrane
Ion transfer voltammetry at a polarized room-temperature ionic liquid (IL) membrane was used to evaluate the standard Gibbs energy of ion transfer from water to IL. This quantity was considered to be a measure of the ion lipophilicity, which is one of the factors playing a role in the extraction and...
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| Vydáno v: | Journal of electroanalytical chemistry (Lausanne, Switzerland) Ročník 815; s. 183 - 188 |
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| Médium: | Journal Article |
| Jazyk: | angličtina |
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Amsterdam
Elsevier B.V
15.04.2018
Elsevier Science Ltd |
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| ISSN: | 1572-6657, 1873-2569 |
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| Abstract | Ion transfer voltammetry at a polarized room-temperature ionic liquid (IL) membrane was used to evaluate the standard Gibbs energy of ion transfer from water to IL. This quantity was considered to be a measure of the ion lipophilicity, which is one of the factors playing a role in the extraction and transport processes in the two-phase liquid and liquid membrane systems. On this basis, the lipophilicity of several biologically active ions was compared, namely of neurotransmitter acetylcholine (ACH+) and several related ions including choline (CH+, precursor for ACH+), muscarine (MUS+, agonist of the muscarinic ACH+ receptors), protonated atropine (ATH+, antagonist of the muscarinic ACH+ receptors), protonated scopolamine (SAH+, antagonist of the muscarinic ACH+), and the tetramethylammonium ion (TMA+) representing their charged moiety. Cyclic voltammetric measurements were carried out using a 4-electrode cell with the IL membrane composed of highly hydrophobic tridodecylmethylammonium tetrakis[3,5-bis(trifluoromethyl)phenyl] borate. Analysis of the voltammetric data provided the values of the standard Gibbs energy of ion transfer (in kJ mol−1 in parentheses), which follow the order of ions TMA+ (14.6) < ACH+ (16.2) ~ ATH+ (16.4) < MUS+ (20.3) ~ SAH+ (20.4) < CH+ (24.1) indicating their rather weak and similar lipophilicity. An analysis of the effect of pH on the voltammetric behavior of ATH+ and SAH+ suggested that the partition coefficient for the neutral bases AT and SA is likely to be fairly small and, hence, that the lipophilicity of these neutral bases is also rather weak. Comparable theoretical values of the electrostatic contribution to the theoretical standard Gibbs energy of ion transfer were obtained by the density functional theory calculations, which accounted for the solvent effect by using the polarizable continuum model (PCM). On the other hand, an estimate of the (neutral) solvophobic contributions to the standard Gibbs energy of ion transfer that is based on the empirical Uhlig formula predicts a significant lipophilic effect increasing with the ion size. This effect is likely to be compensated by the strong dipole-dipole and specific (e.g., H-bond) interactions stabilizing most of the studied ions in the water environment. These conclusions are supported by an analysis based on the voltammetric data reported in literature for the ion transfer across the water/nitrobenzene interface, and the DFT calculations performed in the present study.
[Display omitted]
•Ion transfer voltammetry at a polarized ionic liquid (IL) membrane is used to evaluate the standard Gibbs energy of ion transfer.•Voltammetric data point to a weak and similar lipophilicity of studied ions.•Experimental data are compared with the Gibbs transfer energies obtained by the DFT calculations.•Lipophilic effect is compensated by strong dipole-dipole and specific interactions stabilizing ions in the water environment. |
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| AbstractList | Ion transfer voltammetry at a polarized room-temperature ionic liquid (IL) membrane was used to evaluate the standard Gibbs energy of ion transfer from water to IL. This quantity was considered to be a measure of the ion lipophilicity, which is one of the factors playing a role in the extraction and transport processes in the two-phase liquid and liquid membrane systems. On this basis, the lipophilicity of several biologically active ions was compared, namely of neurotransmitter acetylcholine (ACH+) and several related ions including choline (CH+, precursor for ACH+), muscarine (MUS+, agonist of the muscarinic ACH+ receptors), protonated atropine (ATH+, antagonist of the muscarinic ACH+ receptors), protonated scopolamine (SAH+, antagonist of the muscarinic ACH+), and the tetramethylammonium ion (TMA+) representing their charged moiety. Cyclic voltammetric measurements were carried out using a 4-electrode cell with the IL membrane composed of highly hydrophobic tridodecylmethylammonium tetrakis[3,5-bis(trifluoromethyl)phenyl] borate. Analysis of the voltammetric data provided the values of the standard Gibbs energy of ion transfer (in kJ mol−1 in parentheses), which follow the order of ions TMA+ (14.6) < ACH+ (16.2) ~ ATH+ (16.4) < MUS+ (20.3) ~ SAH+ (20.4) < CH+ (24.1) indicating their rather weak and similar lipophilicity. An analysis of the effect of pH on the voltammetric behavior of ATH+ and SAH+ suggested that the partition coefficient for the neutral bases AT and SA is likely to be fairly small and, hence, that the lipophilicity of these neutral bases is also rather weak. Comparable theoretical values of the electrostatic contribution to the theoretical standard Gibbs energy of ion transfer were obtained by the density functional theory calculations, which accounted for the solvent effect by using the polarizable continuum model (PCM). On the other hand, an estimate of the (neutral) solvophobic contributions to the standard Gibbs energy of ion transfer that is based on the empirical Uhlig formula predicts a significant lipophilic effect increasing with the ion size. This effect is likely to be compensated by the strong dipole-dipole and specific (e.g., H-bond) interactions stabilizing most of the studied ions in the water environment. These conclusions are supported by an analysis based on the voltammetric data reported in literature for the ion transfer across the water/nitrobenzene interface, and the DFT calculations performed in the present study. Ion transfer voltammetry at a polarized room-temperature ionic liquid (IL) membrane was used to evaluate the standard Gibbs energy of ion transfer from water to IL. This quantity was considered to be a measure of the ion lipophilicity, which is one of the factors playing a role in the extraction and transport processes in the two-phase liquid and liquid membrane systems. On this basis, the lipophilicity of several biologically active ions was compared, namely of neurotransmitter acetylcholine (ACH+) and several related ions including choline (CH+, precursor for ACH+), muscarine (MUS+, agonist of the muscarinic ACH+ receptors), protonated atropine (ATH+, antagonist of the muscarinic ACH+ receptors), protonated scopolamine (SAH+, antagonist of the muscarinic ACH+), and the tetramethylammonium ion (TMA+) representing their charged moiety. Cyclic voltammetric measurements were carried out using a 4-electrode cell with the IL membrane composed of highly hydrophobic tridodecylmethylammonium tetrakis[3,5-bis(trifluoromethyl)phenyl] borate. Analysis of the voltammetric data provided the values of the standard Gibbs energy of ion transfer (in kJ mol−1 in parentheses), which follow the order of ions TMA+ (14.6) < ACH+ (16.2) ~ ATH+ (16.4) < MUS+ (20.3) ~ SAH+ (20.4) < CH+ (24.1) indicating their rather weak and similar lipophilicity. An analysis of the effect of pH on the voltammetric behavior of ATH+ and SAH+ suggested that the partition coefficient for the neutral bases AT and SA is likely to be fairly small and, hence, that the lipophilicity of these neutral bases is also rather weak. Comparable theoretical values of the electrostatic contribution to the theoretical standard Gibbs energy of ion transfer were obtained by the density functional theory calculations, which accounted for the solvent effect by using the polarizable continuum model (PCM). On the other hand, an estimate of the (neutral) solvophobic contributions to the standard Gibbs energy of ion transfer that is based on the empirical Uhlig formula predicts a significant lipophilic effect increasing with the ion size. This effect is likely to be compensated by the strong dipole-dipole and specific (e.g., H-bond) interactions stabilizing most of the studied ions in the water environment. These conclusions are supported by an analysis based on the voltammetric data reported in literature for the ion transfer across the water/nitrobenzene interface, and the DFT calculations performed in the present study. [Display omitted] •Ion transfer voltammetry at a polarized ionic liquid (IL) membrane is used to evaluate the standard Gibbs energy of ion transfer.•Voltammetric data point to a weak and similar lipophilicity of studied ions.•Experimental data are compared with the Gibbs transfer energies obtained by the DFT calculations.•Lipophilic effect is compensated by strong dipole-dipole and specific interactions stabilizing ions in the water environment. |
| Author | Záliš, Stanislav Langmaier, Jan Samec, Zdeněk |
| Author_xml | – sequence: 1 givenname: Jan surname: Langmaier fullname: Langmaier, Jan – sequence: 2 givenname: Stanislav surname: Záliš fullname: Záliš, Stanislav – sequence: 3 givenname: Zdeněk surname: Samec fullname: Samec, Zdeněk email: zdenek.samec@jh-inst.cas.cz |
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| CitedBy_id | crossref_primary_10_1016_j_electacta_2023_141848 crossref_primary_10_1002_celc_202100701 crossref_primary_10_1016_j_jelechem_2018_05_001 crossref_primary_10_1016_j_jelechem_2020_113948 crossref_primary_10_1134_S0023158420050079 crossref_primary_10_1016_j_electacta_2019_02_086 crossref_primary_10_1002_elan_201900116 crossref_primary_10_1016_j_electacta_2019_135180 crossref_primary_10_1039_C8RA09118H |
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| Keywords | Room-temperature ionic liquid membrane Acetylcholine Choline Ion transfer voltammetry Lipophilicity DFT calculations |
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| SubjectTerms | Acetylcholine Atropine Choline Computational chemistry Continuum modeling Density functional theory DFT calculations Dipoles Electrolytes Empirical analysis Fourier transforms Ion transfer voltammetry Ionic liquids Lipophilicity Mathematical analysis Mineral solubility Neurotransmitters Receptors Room temperature Room-temperature ionic liquid membrane Solvation Solvent effect Voltammetry |
| Title | Lipophilicity of acetylcholine and related ions examined by ion transfer voltammetry at a polarized room-temperature ionic liquid membrane |
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