Hydrogen Bonding Features in Cholinium-Based Protic Ionic Liquids from Molecular Dynamics Simulations

Campetella, Marco; Donne, Andrea Le; Daniele, Maddalena; Gontrani, Lorenzo; Lupi, S.; Bodo, Enrico; Leonelli, Francesca

doi:10.1021/acs.jpcb.7b12455

Cited by 37 publications

(32 citation statements)

References 52 publications

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“…In the first investigation, Benedetto et al (Benedetto et al 2014) described in detail the cation-anion interaction with DFT methods in vacuo and in small clusters containing up to four ion pairs, for eight amino acid anions (Ala, Val, Ser, Cys, Asp, Asn, Phe, His). In some later reports (Campetella et al 2015a(Campetella et al , b, 2016a(Campetella et al , b, c, 2017(Campetella et al , 2018, the presence of strong ion pairing was confirmed in larger models of the liquid phase (32 ion pairs). In one of these studies on cholinealanine (Campetella et al 2015a(Campetella et al , 2015b, infrared spectroscopy was chosen as experimental technique to support the computational results.…”

Section: Structural Featuresmentioning

confidence: 75%

Choline-amino acid ionic liquids: past and recent achievements about the structure and properties of these really “green” chemicals

Gontrani

2018

Biophys Rev

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The structure of choline-amino acid ionic liquids, atoxic task-specific solvents composed of materials originated from renewable feedstocks, is reviewed in this letter. The varied and strong interactions that these liquids are capable of establishing are largely dependent on their structure and confer them outstanding solvating properties with respect to a large number of different solutes. Among the experimental methods capable of yielding structural insight, the energy-dispersive version of X-Ray diffraction, that uses the Bremsstrahlung radiation of the X-Ray tube, is a technique very well suited to investigate these liquid systems. The diffraction spectra of five choline-amino acid ionic liquids, recently measured, are reported and discussed; in particular, the presence or absence of the medium-range order pre-peak is related to the presence of polar groups within the amino acid side chain that destroys the hydrophobic interactions between aliphatic chains. In the final section, a recent example of choline-amino acid ionic liquids as for ancient paper preservation and two other interesting results are discussed at the end.

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Section: Structural Featuresmentioning

confidence: 75%

Choline-amino acid ionic liquids: past and recent achievements about the structure and properties of these really “green” chemicals

Gontrani

2018

Biophys Rev

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“…In the series of compounds that we shall present here, the clustering seems to take place between anions where, as we shall see, the cooperative effect of hydrogen bonds is sufficient to overcome the Coulomb repulsion. Here, we try to unravel the basic physics behind this surprising organization pattern that we have already proven to exist for some of the cholinium amino acid-based PILs (e.g., ref (11)).…”

Section: Introductionmentioning

confidence: 96%

Hydrogen Bonding as a Clustering Agent in Protic Ionic Liquids: Like-Charge vs Opposite-Charge Dimer Formation

et al. 2018

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The local structure of a series of homologous protic ionic liquids (PILs) is investigated using ab initio computations and ab initio-based molecular dynamics. The purpose of this work is to show that in PILs the network of hydrogen bonds may promote like-charge clustering between anionic species. We correlate the theoretical evidence of this possibility with viscosity experimental data. The homologous series of liquids is obtained by coupling choline with amino acid anions and varying the side chain. We find that the frictional properties of the liquids are clearly connected to the ability of the side chain to establish additional hydrogen bonds (other than the trivial cation–anion interaction). We also show that the large variation of bulk properties along the series of compounds can be explained by assuming that one of the sources of friction in the bulk liquid is the like-charge interaction between anions.

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“…A more extensive investigation of the structure and vibrational signatures of protic ILs has been presented very recently . The authors selected a series of ILs based on the choline cation and various aminoacid anions, with varying alkyl chain length and ramification: valine (Val − ), norvaline (Nva − ), leucine (Leu − ), and norleucine (Nle − ).…”

Section: Computational Vibrational Spectroscopymentioning

confidence: 99%

Section: Computational Vibrational Spectroscopymentioning

confidence: 99%

Computational Spectroscopy of Ionic Liquids for Bulk Structure Elucidation

Saielli

2018

Advcd Theory and Sims

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Computational spectroscopy" refers to quantum chemistry protocols capable of predicting the electronic and/or magnetic spectra of molecules. The most common techniques used for structural assignment are infrared, electronic, and NMR spectroscopies. Chemists can normally deduce the chemical structure of an unknown substance by using a vast collection of empirical relationships linking the spectral features with the presence or absence of functional groups and, this part mostly by NMR, the connectivity between them and the relative stereochemistry. Computational spectroscopy is a powerful aid for structural elucidation when empirical relationships do not suffice to unambiguously assign the structure. In these cases, the calculated spectrum of a putative structure is compared with the experimental one and the match, or lack thereof, between the two, measured by several statistical parameters, indicates whether or not that structure is the correct one. Is it possible to extend such protocols to bulk phases of complex fluids, such as ionic liquids, rather than covalent molecules, in order to get insights into the average structure of the fluid? It is the aim of this Progress Report to highlight recent advances in this field through the discussion of specific case studies.

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Hydrogen Bonding Features in Cholinium-Based Protic Ionic Liquids from Molecular Dynamics Simulations

Cited by 37 publications

References 52 publications

Choline-amino acid ionic liquids: past and recent achievements about the structure and properties of these really “green” chemicals

Choline-amino acid ionic liquids: past and recent achievements about the structure and properties of these really “green” chemicals

Hydrogen Bonding as a Clustering Agent in Protic Ionic Liquids: Like-Charge vs Opposite-Charge Dimer Formation

Computational Spectroscopy of Ionic Liquids for Bulk Structure Elucidation

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