Aggregation of Ionic Liquids [Cnmim]Br (n = 4, 6, 8, 10, 12) in D2O:  A NMR Study

Zhao, Yang; Gao, Shanjiao; Wang, Jianji; Jing, Tang

doi:10.1021/jp076467e

Cited by 231 publications

(223 citation statements)

References 44 publications

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“…A similar observation has been previously reported for N-dodecyl-N,N-dimethyl-N-benzylammonium chloride in D 2 O, [19] and for 1-methyl-3-octylimidazolium bromide in D 2 O. [20] The presence of these cross-peaks seems to indicate that, at 298 K, the liquid structure of geminal IL 1 is governed not only by Coulomb interactions, but also by p-p stacking between imidazolium and the phenyl ring. The p-p interactions between aromatic motifs are well known.…”

Section: Nmr Spectroscopy Measurementssupporting

confidence: 86%

Geminal Ionic Liquids: A Combined Approach to Investigate Their Three‐Dimensional Organisation

D’Anna

Ferrante

Noto

2009

Chemistry A European J

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Different investigations, such as 1D and 2D NMR spectroscopy, resonance light scattering spectroscopy and molecular dynamics simulations, have been jointly used to achieve a deeper understanding of the degree of structural order in two geminal ionic liquids. In particular, 3,3'-di-n-butyl-1,1'-(1,3-phenylenedimethylene)diimidazolium and 3,3'-di-n-butyl-1,1'-(1,4-phenylenedimethylene)diimidazolium bis[bis(trifluoromethanesulfonyl)imide] have been studied. These geminal ionic liquids were chosen because of the presence of both a rigid phenylenedimethylene link between two imidazolium rings, which should give a high degree of order to the solvent system, and the different shapes of the two cations of the isomers, which could induce different properties and packing in the liquid state. Data collected here show that the two geminal ionic liquids are characterised by a different degree of structural order that induces, for example, a different sensitivity of the two solvent systems to temperature changes or to the presence of a co-solvent such as methanol.

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Section: Nmr Spectroscopy Measurementssupporting

confidence: 86%

Geminal Ionic Liquids: A Combined Approach to Investigate Their Three‐Dimensional Organisation

D’Anna

Ferrante

Noto

2009

Chemistry A European J

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“…Rollet et al demonstrated : 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, the existence of water molecules in the phase-separated IL aggregates on the microscopic scale changes the self-diffusion coefficients of each species. [23] In a similar manner to that report by Wang et al, [24] a characteristic shape of the plot of concentration versus chemical shift proves the emergence of conduction paths consisting of ZILs (see Figure S5, Supporting Information). The chemical compositions of IL and water are critical for formation of proton conduction networks.…”

supporting

confidence: 82%

Spectroscopic and Computational Insight into the Intermolecular Interactions between Zwitter‐Type Ionic Liquids and Water Molecules

Park¹,

Jung²,

Yang³

et al. 2010

ChemPhysChem

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Geometric and conformational changes of zwitter-type ionic liquids (ZILs) due to hydrogen-bonding interactions with water molecules are investigated by density functional theory (DFT), two-dimensional IR correlation spectroscopy (2D IR COS), and pulsed-gradient spin-echo NMR (PGSE NMR). Simulation results indicate that molecular structures in the optimized states are strongly influenced by hydrogen bonding of water molecules with the sulfonate group or imidazolium and pyrrolidinium rings of 3-(1-methyl-3-imidazolio)propanesulfonate (1) and 3-(1-methyl-1-pyrrolidinio)propanesulfonate (2), respectively. Concentration-dependent 2D IR COS reveals kinetic conformational changes of the two ZIL-H(2)O systems attributable to intermolecular interactions, as well as the interactions of sulfonate groups and imidazolium or pyrrolidinium rings with water molecules. The dramatic changes in the (1)H self-diffusion coefficients elucidate the formation of proton-conduction pathways consisting of ZIL networks. In ZIL domains, protons are transferred by a Grotthuss-type mechanism through formation, breaking, and restructuring of bonds between ZILs and H(2)O, leading to an energetically favorable state. The simulation and experimental investigations delineated herein provide a perspective to understanding the interactions with water from an academic point of view as well as to designing ILs with desired properties from the viewpoint of applications.

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“…ILs are designed to be chaotropic, and, thus, the aqueous and solution chemistries are only sparingly explored (42). Recent molecular dynamics simulation studies (43)(44)(45), as well as spectroscopic investigation via NMR techniques (46,47), suggest that ILs do not dissolve as independent ions but keep a nanostructured organization in aqueous media. After all, the inherent properties of ILs are not like traditional crystalline salts, and the very properties that make ILs low melting also make them behave differently both in the melt and in solution.…”

Section: Ion-pair Based Transportmentioning

confidence: 99%

Crystalline vs. Ionic Liquid Salt Forms of Active Pharmaceutical Ingredients: A Position Paper

et al. 2010

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Why not consider liquid salt forms of active pharmaceutical ingredients (APIs) as an alternative versatile tool in the pharmaceutical industry? Recent developments have shown that known APIs can be readily converted into ionic liquids and that these novel phases often possess different properties (e.g., improved solubilities and dissolution rates), which may have a direct impact on the pharmacokinetics and pharmacodynamics of the drug. They may also offer the potential of novel and more efficient delivery modes, as well as patent protection for each of the new forms of the drug. Since these pharmaceutically active ionic liquids represent a thermodynamically stable phase, they avoid the troublesome issues surrounding polymorphism and "polymorphic transformation." In some cases, an active cation and an active anion can be combined to produce a liquid possessing dual functionality. Here we examine and challenge the current industry reliance on crystalline APIs by discussing the breadth and potential impact of liquid salts as a possible approach to phase control.

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Aggregation of Ionic Liquids [C_nmim]Br (n = 4, 6, 8, 10, 12) in D₂O: A NMR Study

Cited by 231 publications

References 44 publications

Geminal Ionic Liquids: A Combined Approach to Investigate Their Three‐Dimensional Organisation

Geminal Ionic Liquids: A Combined Approach to Investigate Their Three‐Dimensional Organisation

Spectroscopic and Computational Insight into the Intermolecular Interactions between Zwitter‐Type Ionic Liquids and Water Molecules

Crystalline vs. Ionic Liquid Salt Forms of Active Pharmaceutical Ingredients: A Position Paper

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