Preparation and characterization of ethane-1,2-diaminium trinitromethanide as a novel energetic ionic liquid

Jolodar, Omid Goli; Ghauri, Khatereh; Seddighi, Mohadeseh; Shirini, Farhad; Bayat, Yadollah

doi:10.1016/j.molstruc.2019.03.062

Cited by 9 publications

(3 citation statements)

References 50 publications

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“…Increasing the diversity of ionic liquid structures resulted in the adoption of new rules for labelling them, with reference to the special (dedicated) functional group that characterizes them, to the original features of a given salt-or regarding their use, e.g., as sweet [45], energetic [46], chiral [47], fluorescent [48], polymeric [49], magnetic [50] and many others. On the other hand, the possible methods of the structural combination of ionic liquids focusing on expanding their structure with The most common cationic parts include imidazolium (im, e.g., C 1 C 2 im, emim, EMIM: 1-ethyl-3-methylimidazolium), ammonium (N x x x x , e.g., N 1 8 8 8 : methyl(trioctyl)ammonium), pyridinium (py, e.g., C 6 py: 1-hexylpyridinium), phosphonium (P x x x , e.g., P 4 4 4 12 : tributyl(dodecyl)phosphonium), sulfonium (S x x x ), pyrrolidinium (pyrr), piperidinium (pip), morpholinium (morph), etc.…”

Section: Classification and Application Of Ilsmentioning

confidence: 99%

“…Increasing the diversity of ionic liquid structures resulted in the adoption of new rules for labelling them, with reference to the special (dedicated) functional group that characterizes them, to the original features of a given salt—or regarding their use, e.g., as sweet [ 45 ], energetic [ 46 ], chiral [ 47 ], fluorescent [ 48 ], polymeric [ 49 ], magnetic [ 50 ] and many others. On the other hand, the possible methods of the structural combination of ionic liquids focusing on expanding their structure with specific components resulted in the introduction of another term, namely task-specific ionic liquids (TSILs).…”

Section: Classification and Application Of Ilsmentioning

confidence: 99%

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Chiral Ionic Liquids: Structural Diversity, Properties and Applications in Selected Separation Techniques

Flieger

Feder‐Kubis

Tatarczak-Michalewska

2020

IJMS

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Ionic liquids (ILs) are chemical compounds composed of ions with melting points below 100 °C exhibiting a design feature. ILs are commonly used as the so-called green solvents, reagents or highly efficient catalysts in varied chemical processes. The huge application potential of ionic liquids (IL) justifies the growing interest in these compounds. In the last decade, increasing attention has been devoted to the development of new methods in the synthesis of stable chiral ionic liquids (CILs) and their application in various separation techniques. The beginnings of the successful use of CILs to separate enantiomers date back to the 1990 s. Most chiral ILs are based on chiral cations or chiral anions. There is also a limited number of CILs possessing both a chiral cation and a chiral anion. Due to the high molecular diversity of both ions, of which at least one has a chiral center, we have the possibility to design a large variety of optically active structures, thus expanding the range of CIL applications. Research utilizing chiral ionic liquids only recently has become more popular. However, it is the area that still has great potential for future development. This review aimed to describe the diversity of structures, properties and examples of applications of chiral ionic liquids as new chiral solid materials and chiral components of the anisotropic environment, providing chiral recognition of enantiomeric analytes, which is useful in liquid chromatography, countercurrent chromatography and other various CIL-based extraction techniques including aqueous biphasic (ABS) extraction systems, solid–liquid two-phase systems, liquid–liquid extraction systems with hydrophilic CILs, liquid–liquid extraction systems with hydrophobic CILs, solid-phase extraction and induced-precipitation techniques developed in the recent years. The growing demand for pure enantiomers in the pharmaceutical and food industries sparks further development in the field of extraction and separation systems modified with CILs highlighting them as affordable and environmentally friendly both chiral selectors and solvents.

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Section: Classification and Application Of Ilsmentioning

confidence: 99%

“…Increasing the diversity of ionic liquid structures resulted in the adoption of new rules for labelling them, with reference to the special (dedicated) functional group that characterizes them, to the original features of a given salt—or regarding their use, e.g., as sweet [ 45 ], energetic [ 46 ], chiral [ 47 ], fluorescent [ 48 ], polymeric [ 49 ], magnetic [ 50 ] and many others. On the other hand, the possible methods of the structural combination of ionic liquids focusing on expanding their structure with specific components resulted in the introduction of another term, namely task-specific ionic liquids (TSILs).…”

Section: Classification and Application Of Ilsmentioning

confidence: 99%

Chiral Ionic Liquids: Structural Diversity, Properties and Applications in Selected Separation Techniques

Flieger

Feder‐Kubis

Tatarczak-Michalewska

2020

IJMS

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“…Notably, they are used in ab initio molecular dynamics simulations of ionic liquids to account for electron correlation and charge transfer between ions. , These functionals as well as BP86 have been shown to improve greatly with the addition of empirical dispersion corrections, and their reduced cost gives them priority over higher-level functionals if they produce accurate geometries, especially moving toward a larger number of ion pairs . A meta-GGA functional, M06-2X, a hybrid functional, B3LYP, and a long-range corrected functional, ωB97X-D, are extremely popular functionals and have been used extensively for optimizations of ionic liquids in the literature. − The meta-GGA functional with D3 correction TPSS-D3 has been shown to perform well for single ion-paired systems …”

Section: Theoretical Calculationsmentioning

confidence: 99%

A Systematic Study of DFT Performance for Geometry Optimizations of Ionic Liquid Clusters

Seeger

Izgorodina

2020

J. Chem. Theory Comput.

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Clusters of two ion pairs of imidazolium-based ionic liquids were optimized with 43 different levels of theory, including DFT functionals and MP2-based methods combined with varying Dunning's basis sets, and added dispersion corrections. Better preforming DFT functionals were then applied to clusters consisting of four ion pairs. Excellent performance of some DFT functionals for the two ion pair clusters did not always match that of the four ion-paired clusters despite interionic distances remaining constant between the optimized two and four ion-paired clusters of the same ionic liquid. Combinations of DFT functional and basis set such as ωB97X-D/cc-pVDZ, M06-2X/aug-cc-pVDZ, B3LYP-D3/cc-pVTZ, and TPSS-D3/cc-pVTZ gave excellent results for geometry optimization of two ion-paired clusters of imidazolium ionic liquids but gave larger deviations when applied to the four ion-paired clusters of varying ionic liquids. Empirical dispersion corrections were seen to be crucial in correctly capturing correlation effects in the studied ionic liquid clusters, becoming more important in larger clusters. Dunning's double-ζ basis set, cc-pVDZ, is associated with the smallest root mean squared deviations for geometries; however, it also produces the largest deviations in total electronic energies. ωB97X-D and M06-2X produced the best performance with the augmented version of this basis set. The triple-ζ basis set, cc-pVTZ, leads to the best performance of most of the DFT functionals (especially the dispersion-corrected ones) used, whereas its augmented version, aug-cc-pVTZ, was not seen to improve results. The combinations of functional and basis set that gave the best geometry and energetics in both two and four ion-paired clusters were PBE-D3/cc-pVTZ, ωB97X-D/aug-cc-pVDZ, and BLYP-D3/cc-pVTZ. All three combinations are recommended for geometry optimizations of larger clusters of ionic liquids. PBE-D3/cc-pVTZ performed the best with an average deviation of 2.3 kJ mol −1 and a standard deviation of 3.4 kJ mol −1 for total electronic energy when applied to four ion-paired clusters. Geometries optimized with FMO2-SRS-MP2/cc-pVTZ produced total energy within 2.0 kJ mol −1 off the benchmark in two ion-paired clusters, with the cc-pVDZ basis set performing unsurprisingly poorly with the same method. The error increased to 4.8 kJ mol −1 on average in four ionpaired clusters, with the smallest RMSD deviations in geometries when compared to the benchmark ones. This study is the first report that investigated the performance of DFT functionals for two and four ion-paired clusters of a wide range of ionic liquids consisting of commonly used cations such as pyrrolidinium, imidazolium, pyridinium, and ammonium. It also identified the importance of assessing the performance of quantum chemical methods for ionic liquids on a variety of cation-anion combinations.

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One-Pot Synthesis of Pyrido[2,3-d]pyrimidines and 1,2,4-Triazolo[4,3−a]pyrimidines Using a Tropine-Based Dicationic Molten Salt as an Active Catalyst

Langroudi,

Mazloumi,

Shirini

et al. 2024

Iran J Sci

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Preparation and characterization of ethane-1,2-diaminium trinitromethanide as a novel energetic ionic liquid

Cited by 9 publications

References 50 publications

Chiral Ionic Liquids: Structural Diversity, Properties and Applications in Selected Separation Techniques

Chiral Ionic Liquids: Structural Diversity, Properties and Applications in Selected Separation Techniques

A Systematic Study of DFT Performance for Geometry Optimizations of Ionic Liquid Clusters

One-Pot Synthesis of Pyrido[2,3-d]pyrimidines and 1,2,4-Triazolo[4,3−a]pyrimidines Using a Tropine-Based Dicationic Molten Salt as an Active Catalyst

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