The Peculiar Nature of Molecular Interactions between an Imidazolium Ionic Liquid and Acetone

Kiefer, Johannes; Molina, Marta Martínez; Noack, Kristina

doi:10.1002/cphc.201100845

Cited by 68 publications

(52 citation statements)

References 36 publications

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“…In summary, the IR and Raman spectra of the C(2) protonated ILs show that the anion interacts with the cation via formation of a strong hydrogen bond at C(2)-H. Upon methylation, the anion moves to the C(4) and C(5) moiety, where it forms a new hydrogen bond with one of the two protons. The spectra do not suggest that other interaction mechanisms, such as those via the π-electron system of the aromatic ring (often referred to as the on-top position [37][38][39]), play a major role. Moreover, Endo et al [26] performed an experimental and computational study on methylated and nonmethylated butylimidazolium ILs with spherical anions.…”

Section: Vibrational Spectramentioning

confidence: 80%

Effects of C(2) Methylation on Thermal Behavior and Interionic Interactions in Imidazolium-Based Ionic Liquids with Highly Symmetric Anions

et al. 2018

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Featured Application: The study aims at making a step towards the rational design of ionic liquids for specific applications. The key to this rational design is to fully understand the structure-property relationships. In other words, knowing the links between the behavior at the molecular and the macroscopic scale will enable to develop materials/fluids with optimal properties for a given application, e.g., a chemical process or an electrochemical device. Abstract:The chemical and physical properties of imidazolium-based ionic liquids are determined by the interactions between the counter-ions. The C(2) position plays an important role in these interactions, as it represents the predominant site for interionic hydrogen bonding. This study shows that the directional hydrogen bonds between highly symmetrical anions (iodide, tetrafluoroborate, hexafluorophosphate) and the C(2)-H group of the 1-methyl-3-propylimidazolium cation determine the molecular and macroscopic behavior in terms of the thermal properties. Upon replacing the C(2) proton by a methyl group, the anion repositions itself at the C(4)/(5) moiety, where it forms a new hydrogen bond, apparently with only one of the two CH groups. In addition, the larger the anion is in diameter, the more likely it will establish further interactions with other parts of the cation, such as the propyl chain.

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Section: Vibrational Spectramentioning

confidence: 80%

Effects of C(2) Methylation on Thermal Behavior and Interionic Interactions in Imidazolium-Based Ionic Liquids with Highly Symmetric Anions

et al. 2018

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“…[18][19][20] It can be used to enhance the spectral resolution of the IR bands under study and look at changes in the dipole moment, reflecting changes in the charge distribution of the vibrating system. The procedure of calculating excess IR spectra was introduced by Li et al 18 lending the concept of thermodynamic excess properties.…”

Section: Excess Absorbance Spectramentioning

confidence: 99%

Characterization of gasoline/ethanol blends by infrared and excess infrared spectroscopy

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McGloin

et al. 2015

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Fuels for automotive propulsion are frequently blends of conventional gasoline and ethanol.However, the effects of adding an alcohol to a petrochemical fuel are yet to be fully understood. We report Fourier-transform infrared spectroscopy (FTIR) of ethanol/gasoline mixtures with systematically varied composition. Frequencies shifts and excess infrared absorbance are analyzed in order to investigate the mixture behavior at the molecular level.The spectroscopic data suggest that the hydrogen bonding between ethanol molecules is weakened upon gasoline addition, but the hydrogen bonds do not disappear. This can be explained by a formation of small ethanol clusters that interact via Van der Waals forces with the surrounding gasoline molecules. Furthermore, approaches for measuring the chemical composition of ethanol/gasoline blends by FTIR are discussed. For a simplistic approach based on the Beer-Lambert relation, an optimized set of parameters for quantitative measurements are determined. The best compromise between measurement sensitivity and accuracy is found for the CO stretching mode of the alcohol. For the traditional method of calibrating the ratio of integrated band intensities of the CH and OH stretching regions it is found that narrowing the spectral window of the CH stretch can significantly improve the measurement sensitivity.

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“…The IL was chosen as it has been characterized as a neat substance [38][39][40] as well as in combination with CuBTC 41 and molecular solvents. 42 In the second part of the study, the effects of extracting the IL from the MOF using the above organic solvents and water are investigated. In order to gain scientific insights and a comprehensive picture including molecular, crystallographic and macroscopic effects, infrared spectroscopy, powder x-ray diffraction, N 2 adsorption, scanning electron microscopy (SEM), and transmission electron microscopy (TEM) were employed.…”

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confidence: 99%

Removal of Confined Ionic Liquid from a Metal Organic Framework by Extraction with Molecular Solvents

et al. 2017

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Hybrid materials of ionic liquids (IL) confined in metal organic frameworks (MOF) are promising materials for energy storage. The effects of exposing or treating such composite materials with molecular solvents, e.g. with the aim to extract and replace the IL, have not been studied to date. In this study, acetone, isopropanol, methanol, and water were used to remove the IL 1-ethyl-3-methylimidazolium ethyl sulfate confined in a Cu-based metal organic framework (CuBTC). The consequences of the solvent extraction process were analyzed using vibrational spectroscopy (FTIR), powder X-ray diffraction (PXRD), N 2 adsorption, scanning electron microscopy (SEM), and transmission electron microscopy (TEM). Methanol was identified as the best solvent for IL removal as it shows high extraction efficiency without affecting the porous geometry and crystal structure of the MOF. On the other hand, acetone and isopropanol were not able to completely remove the IL from CuBTC under the conditions employed. Water effectively removed the IL, but it has a significant detrimental effect on the CuBTC structure.This impact manifests as changes in the infrared spectra and the PXRD patterns as well as in the electron micrographs. The degraded CuBTC exhibits a non-porous structure that presents itself as non-uniformly agglomerated micro-rods along with very few hexagonal/amorphous phases.The confinement of acetone, isopropanol, and methanol in the MOF was also investigated. The results show that CuBTC is stable in acetone, isopropanol, and methanol but unstable in water.

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The Peculiar Nature of Molecular Interactions between an Imidazolium Ionic Liquid and Acetone

Cited by 68 publications

References 36 publications

Effects of C(2) Methylation on Thermal Behavior and Interionic Interactions in Imidazolium-Based Ionic Liquids with Highly Symmetric Anions

Effects of C(2) Methylation on Thermal Behavior and Interionic Interactions in Imidazolium-Based Ionic Liquids with Highly Symmetric Anions

Characterization of gasoline/ethanol blends by infrared and excess infrared spectroscopy

Removal of Confined Ionic Liquid from a Metal Organic Framework by Extraction with Molecular Solvents

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