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Article

Choline Hydrogen Dicarboxylate Ionic Liquids by X-ray Scattering, Vibrational Spectroscopy and Molecular Dynamics: H-Fumarate and H-Maleate and Their Conformations

1
Department of Physical and Chemical Sciences, University of L’Aquila, Via Vetoio, I-67100 L’Aquila, Italy
2
Department of Chemistry, University of Rome La Sapienza, P.le A. Moro 5, 00185 Rome, Italy
3
INFN, Gran Sasso National Laboratories, I-67100 Assergi (AQ), Italy
*
Author to whom correspondence should be addressed.
Molecules 2020, 25(21), 4990; https://doi.org/10.3390/molecules25214990
Received: 23 September 2020 / Revised: 18 October 2020 / Accepted: 24 October 2020 / Published: 28 October 2020
(This article belongs to the Special Issue Theoretical Computational Description of Ionic Liquids)
We explore the structure of two ionic liquids based on the choline cation and the monoanion of the maleic acid. We consider two isomers of the anion (H-maleate, the cis-isomer and H-fumarate, the trans-isomer) having different physical chemical properties. H-maleate assumes a closed structure and forms a strong intramolecular hydrogen bond whereas H-fumarate has an open structure. X-ray diffraction, infrared and Raman spectroscopy and molecular dynamics have been used to provide a reliable picture of the interactions which characterize the structure of the fluids. All calculations indicate that the choline cation prefers to connect mainly to the carboxylate group through OH⋯O interactions in both the compounds and orient the charged head N(CH3)3+ toward the negative portion of the anion. However, the different structure of the two anions affects the distribution of the ionic components in the fluid. The trans conformation of H-fumarate allows further interactions between anions through COOH and CO2 groups whereas intramolecular hydrogen bonding in H-maleate prevents this association. Our theoretical findings have been validated by comparing them with experimental X-ray data and infrared and Raman spectra. View Full-Text
Keywords: ionic liquids; structure; molecular dynamics; X-ray diffraction; vibrational spectroscopy ionic liquids; structure; molecular dynamics; X-ray diffraction; vibrational spectroscopy
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MDPI and ACS Style

Di Muzio, S.; Ramondo, F.; Gontrani, L.; Ferella, F.; Nardone, M.; Benassi, P. Choline Hydrogen Dicarboxylate Ionic Liquids by X-ray Scattering, Vibrational Spectroscopy and Molecular Dynamics: H-Fumarate and H-Maleate and Their Conformations. Molecules 2020, 25, 4990. https://doi.org/10.3390/molecules25214990

AMA Style

Di Muzio S, Ramondo F, Gontrani L, Ferella F, Nardone M, Benassi P. Choline Hydrogen Dicarboxylate Ionic Liquids by X-ray Scattering, Vibrational Spectroscopy and Molecular Dynamics: H-Fumarate and H-Maleate and Their Conformations. Molecules. 2020; 25(21):4990. https://doi.org/10.3390/molecules25214990

Chicago/Turabian Style

Di Muzio, Simone, Fabio Ramondo, Lorenzo Gontrani, Francesco Ferella, Michele Nardone, and Paola Benassi. 2020. "Choline Hydrogen Dicarboxylate Ionic Liquids by X-ray Scattering, Vibrational Spectroscopy and Molecular Dynamics: H-Fumarate and H-Maleate and Their Conformations" Molecules 25, no. 21: 4990. https://doi.org/10.3390/molecules25214990

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