Triaminocyclopropenium salts as ionic liquids

Self Cite

The octanuclear iodine‐chlorine interhalides [I4Cl4]2− and [I3Cl5]2− were prepared in two steps. Firstly, addition of ICl to the triaminocyclopropenium chloride salt [C3(NEt2)3]Cl forms the trihalide ICl2− salt, secondly, addition of half an equivalent of I2 or ICl, respectively, gave the desired products upon crystallization at low temperature. The non‐stoichiometric octahalide [I3.6Cl4.4]2− was obtained after heating a CH2Cl2 solution of the ICl2− salt to reflux for 2 hours followed crystallization. [I4Cl4]2− is best described as two ICl2− anions bridged by I2, whereas [I3Cl5]2− is best described as an [I2Cl3]− pentahalide with a weak halogen bond to an ICl2− trihalide. The octahalides were characterized by X‐ray crystallography, computational studies, Raman and Far‐IR spectroscopies, as well as by TGA and melting point.

Section: Methodsmentioning

confidence: 99%

The Binary Iodine‐Chlorine Octahalide Series [I_nCl_8−n]²⁻ (n=3, 3.6, 4)

Abdelbassit

Curnow

Dixon

et al. 2019

Self Cite

“…According to the general synthetic methods reported previously, four cyclopropane amine precursors were obtained and purified. Then, subsequent anion metathesis of these chlorine salts of sodium cyanoborate, silver dicyanamide, sodium azide, or sodium CIB efficiently yielded the desired ILs in high yields.…”

Section: Methodsmentioning

confidence: 99%

“…Interestingly, the lack of aromatic C−H groups in the cationic structure endowed TAC cations with aromaticity of three‐membered rings, with strong charge delocalization and reduced hydrogen‐bond‐donor capability than that of traditional imidazolium and pyridinium cations. Moreover, the TAC cations have high‐lying nonbonding HOMO orbitals, which weaken the cation–anion interactions . Therefore, TAC cations, as the component ions for ILs, are expected to yield unusual properties due to their weak ionic interactions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of Triaminocyclopropenium Cation Based Ionic Liquids as Hypergolic Fluids

Jin

Wang

Zhang

et al. 2018

A novel family of hydrophobic triaminocyclopropenium cation based ionic liquids have been synthesized, and their structures and physicochemical properties characterized by NMR and IR spectroscopy, elemental analysis, differential scanning calorimetry, and hypergolic tests. The experimental results showed that all of these ionic liquids exhibited the expected hypergolic reactivity with the oxidizer white fuming nitric acid. Among them, the hypergolic ionic liquid based on the cyanoimidazolylborohydride anion showed excellent integrated properties, including high decomposition temperature (194 °C), high density (0.95 g cm ), moderate viscosity (44 MPa s), ultrafast ignition delay time (6 ms), and high specific impulse (301.9 s); this demonstrates its potential as an environmentally friendly alternative to toxic hydrazine derivatives.

“…Many DCA-basedi onic liquidsa re commercially available fore nergy storage applications and are prized for their low viscosity and highc onductivity. [2][3][4][5][6] Transition-metaland rare-earth element-DCA complexes exhibit remarkable luminescent and magnetic properties thanks to the pseudohalide's small size and high degree of conjugation. [7][8][9][10][11][12][13][14][15][16][17][18][19] DCA has even been suspected of playing ar ole in primordial biogenesis due to its propensity to promotep eptide synthesis under conditions similar to those of primitive Earth.…”

mentioning

confidence: 99%

Synthesis of Heavy Dicyanamide Homologues from Air‐Stable Precursors

Binder

Kosnik

Onge

et al. 2018

A convenient synthesis of dicyanophosphide and dicyanoarsenide anions is reported. These heavy homologues of the long-known and fundamentally important dicyanamide anion were formed through the nucleophilic displacement of bis(diphenylphosphino)ethane (dppe) from the pnictogen transfer agents [dppePn][BPh ] (Pn=P, As) by exposure to cyanide salts. The protocol requires three synthetic steps from commercially available materials and the [dppePn][BPh ] salts are remarkably temperature, air, and moisture stable. All products have been fully characterized by spectroscopic methods and by single-crystal X-ray diffraction, and the electronic structures of the DCPn anions have been assessed computationally.