Effect of amino acid addition on the micelle formation of the surface-active ionic liquid 1-tetradecyl-3-methylimidazolium bromide in aqueous solution

Mabel Rojas, Z. Miskolczy, L. Biczók, Paulina Pavez

Research output: Contribution to journalArticle

Abstract

The effect of 3 amino acids on the self-assembly properties of the surface-active ionic liquid: 1-tetradecyl-3-methyl imidazolium bromide, [C14mim][Br], was studied in neutral and basic aqueous solution. The critical micelle concentrations were determined by different techniques, and the thermodynamic parameters of micellization (ΔG0 mic, ΔH0 mic, and ΔS0 mic) were measured by isothermal titration calorimetry. The critical micelle concentration values decrease in the presence of all the amino acids used in this study. The most substantial effect was observed in the presence of L-tryptophan at pH 12, due to the electrostatic and π-π interactions with the imidazolium headgroup of the surfactant. Always entropy-driven micellization occurred. Both the enthalpy and entropy changes upon association to micelles increased when the pH was enhanced from 7 to 12. 1H NMR measurements demonstrated that among the used amino acids, L-tryptophan interacts most strongly with the headgroup of the surfactant cation. The knowledge on the surfactant-amino acid interactions significantly contributes to the deeper understanding of the effect of surfactants on the properties of peptides.

Original languageEnglish
JournalJournal of Physical Organic Chemistry
DOIs
Publication statusAccepted/In press - Jan 1 2018

Fingerprint

Ionic Liquids
Micelles
Bromides
Surface-Active Agents
amino acids
bromides
micelles
surfactants
aqueous solutions
Amino Acids
Micellization
Critical micelle concentration
tryptophan
liquids
Tryptophan
Entropy
entropy
Calorimetry
Titration
titration

Keywords

  • Self-assembly properties
  • Surface-active ionic liquid

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

@article{211190337ac4475b9a3dfbfffc5bcaf4,
title = "Effect of amino acid addition on the micelle formation of the surface-active ionic liquid 1-tetradecyl-3-methylimidazolium bromide in aqueous solution",
abstract = "The effect of 3 amino acids on the self-assembly properties of the surface-active ionic liquid: 1-tetradecyl-3-methyl imidazolium bromide, [C14mim][Br], was studied in neutral and basic aqueous solution. The critical micelle concentrations were determined by different techniques, and the thermodynamic parameters of micellization (ΔG0 mic, ΔH0 mic, and ΔS0 mic) were measured by isothermal titration calorimetry. The critical micelle concentration values decrease in the presence of all the amino acids used in this study. The most substantial effect was observed in the presence of L-tryptophan at pH 12, due to the electrostatic and π-π interactions with the imidazolium headgroup of the surfactant. Always entropy-driven micellization occurred. Both the enthalpy and entropy changes upon association to micelles increased when the pH was enhanced from 7 to 12. 1H NMR measurements demonstrated that among the used amino acids, L-tryptophan interacts most strongly with the headgroup of the surfactant cation. The knowledge on the surfactant-amino acid interactions significantly contributes to the deeper understanding of the effect of surfactants on the properties of peptides.",
keywords = "Self-assembly properties, Surface-active ionic liquid",
author = "Mabel Rojas and Z. Miskolczy and L. Bicz{\'o}k and Paulina Pavez",
year = "2018",
month = "1",
day = "1",
doi = "10.1002/poc.3814",
language = "English",
journal = "Journal of Physical Organic Chemistry",
issn = "0894-3230",
publisher = "John Wiley and Sons Ltd",

}

TY - JOUR

T1 - Effect of amino acid addition on the micelle formation of the surface-active ionic liquid 1-tetradecyl-3-methylimidazolium bromide in aqueous solution

AU - Rojas, Mabel

AU - Miskolczy, Z.

AU - Biczók, L.

AU - Pavez, Paulina

PY - 2018/1/1

Y1 - 2018/1/1

N2 - The effect of 3 amino acids on the self-assembly properties of the surface-active ionic liquid: 1-tetradecyl-3-methyl imidazolium bromide, [C14mim][Br], was studied in neutral and basic aqueous solution. The critical micelle concentrations were determined by different techniques, and the thermodynamic parameters of micellization (ΔG0 mic, ΔH0 mic, and ΔS0 mic) were measured by isothermal titration calorimetry. The critical micelle concentration values decrease in the presence of all the amino acids used in this study. The most substantial effect was observed in the presence of L-tryptophan at pH 12, due to the electrostatic and π-π interactions with the imidazolium headgroup of the surfactant. Always entropy-driven micellization occurred. Both the enthalpy and entropy changes upon association to micelles increased when the pH was enhanced from 7 to 12. 1H NMR measurements demonstrated that among the used amino acids, L-tryptophan interacts most strongly with the headgroup of the surfactant cation. The knowledge on the surfactant-amino acid interactions significantly contributes to the deeper understanding of the effect of surfactants on the properties of peptides.

AB - The effect of 3 amino acids on the self-assembly properties of the surface-active ionic liquid: 1-tetradecyl-3-methyl imidazolium bromide, [C14mim][Br], was studied in neutral and basic aqueous solution. The critical micelle concentrations were determined by different techniques, and the thermodynamic parameters of micellization (ΔG0 mic, ΔH0 mic, and ΔS0 mic) were measured by isothermal titration calorimetry. The critical micelle concentration values decrease in the presence of all the amino acids used in this study. The most substantial effect was observed in the presence of L-tryptophan at pH 12, due to the electrostatic and π-π interactions with the imidazolium headgroup of the surfactant. Always entropy-driven micellization occurred. Both the enthalpy and entropy changes upon association to micelles increased when the pH was enhanced from 7 to 12. 1H NMR measurements demonstrated that among the used amino acids, L-tryptophan interacts most strongly with the headgroup of the surfactant cation. The knowledge on the surfactant-amino acid interactions significantly contributes to the deeper understanding of the effect of surfactants on the properties of peptides.

KW - Self-assembly properties

KW - Surface-active ionic liquid

UR - http://www.scopus.com/inward/record.url?scp=85041603182&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85041603182&partnerID=8YFLogxK

U2 - 10.1002/poc.3814

DO - 10.1002/poc.3814

M3 - Article

JO - Journal of Physical Organic Chemistry

JF - Journal of Physical Organic Chemistry

SN - 0894-3230

ER -