Trace Water Effects on Crystalline 1-Ethyl-3-methylimidazolium Acetate

Published

May 16, 2023

Author(s)

Ashlee Aiello, John Hoffman, Anthony Kotula, Lucas Flagg, Ruipeng Li, Jeremiah Woodcock

Abstract

Spontaneous room temperature crystallization of 1-ethyl-3-methylimidazolium acetate ([C2mim][OAc]) was observed upon removal of trace water. To ensure that this observation was not produced by trace water or other contaminants, sample purity was confirmed using analytical nuclear magnetic resonance spectroscopy. Raman spectroscopy and simultaneous quartz crystal microbalance/infrared spectroscopy measurements were used to study molecular reorganization that occurred during crystallization and decrystallization using trace water in the form of atmospheric moisture. These experimental results were supplemented with density functional theory calculations that indicate imidazolium cation ring stacking and side chain clustering with an exclusive arrangement of the acetate anion in the cation ring plane upon water removal, which is in agreement with other theoretical reports in the literature. Crystal structure formation was confirmed using two-dimensional wide angle X-ray scattering. This natural crystallization is attributed to removal of trace water over extended periods of time and calls attention to the molecular-level role of water in the structure of hydroscopic ionic liquid systems.

Citation

Journal of Physical Chemistry B

Volume

127

Issue

20

Pub Type

Journals

Download Paper

https://doi.org/10.1021/acs.jpcb.3c02735

Local Download

Keywords

ionic liquid, [EMIm][OAc], crystallization, water contamination

Citation

Aiello, A. , Hoffman, J. , Kotula, A. , Flagg, L. , Li, R. and Woodcock, J. (2023), Trace Water Effects on Crystalline 1-Ethyl-3-methylimidazolium Acetate, Journal of Physical Chemistry B, [online], https://doi.org/10.1021/acs.jpcb.3c02735, https://tsapps.nist.gov/publication/get_pdf.cfm?pub_id=936365 (Accessed February 5, 2025)