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Title: Structural evaluation and protium-deuterium exchange in 1-ethyl-3-methylimidazolium halide-ethylene glycol mixtures
Authors: Chen, Zhengfei
Tonouchi, Yuto
Matsumoto, Kazuhiko  kyouindb  KAKEN_id  orcid https://orcid.org/0000-0002-0770-9210 (unconfirmed)
Tsuzuki, Seiji
Nagata, Takashi  kyouindb  KAKEN_id  orcid https://orcid.org/0000-0002-3733-2709 (unconfirmed)
Katahira, Masato
Hagiwara, Rika
Author's alias: 松本, 一彦
永田, 崇
片平, 正人
萩原, 理加
Keywords: Solvate ionic liquids
NMR spectroscopy
Protium-deuterium exchange
Theoretical calculations
Issue Date: Nov-2020
Publisher: Elsevier BV
Journal title: Journal of Fluorine Chemistry
Volume: 239
Thesis number: 109637
Abstract: A series of equimolar mixtures of 1-ethyl-3-methylimidazolium halide ([C₂C₁im]X: X⁻ = F⁻, Cl⁻, Br and I⁻) and ethylene glycol (EG) are studied by ¹H NMR and IR spectroscopies. The chemical shifts for the protons in EG and imidazolium ring shift towards the downfield in the order of F⁻ >> Cl⁻ > Br⁻ > I⁻, owing to the strength of their respective X…H interactions. Amongst all the studied systems, the fluoride complex ([C₂C₁im]F·EG) shows extremely strong interactions between F⁻ and OH hydrogen of EG, resulting in no “free” EG in the mixture as reflected in the infrared spectra. Quantum chemical calculations suggest several possible geometries for all the halide systems, where the geometry with the EG molecule forming a chelate of halide ion gives the most stable structure. The calculated interaction energies of these geometries also confirm that the fluoride complex has a significantly higher interaction energy than those of the other halide systems. Furthermore, the halide anion affects the selectivity of protium-deuterium exchange site in these systems, and some imidazolium ring hydrogen atoms are activated only in the presence of F⁻.
Rights: © 2020. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/.
The full-text file will be made open to the public on 1 November 2022 in accordance with publisher's 'Terms and Conditions for Self-Archiving'.
This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
URI: http://hdl.handle.net/2433/255631
DOI(Published Version): 10.1016/j.jfluchem.2020.109637
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