Ab Initio Investigation of Cation Proton Affinity and Proton Transfer Energy for Energetic Ionic Liquids

Carlin, Caleb; Gordon, Mark S.

doi:10.1021/acs.jpca.6b02990

Cited by 16 publications

(21 citation statements)

References 35 publications

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“…prepared DHB ‐ILs from chloride‐ or bromide‐ILs and Ag[BH 2 (CN) 2 ] and tested these ILs as hypergolic fluids . The proton affinity of selected anions, including the DHB anion,, and proton transfer energies from organic cations to these anions in energetic ILs were investigated . A number of further properties of the DHB ion and DHB ‐ILs with respect to potential applications in the field of hypergolic ILs have been studied experimentally or by theoretical methods …”

Section: Cyanohydridoborateskt[bhn(cn)4–n] (N = 1–3)mentioning

confidence: 99%

Cyanoborates

Ignat’ev

Finze

2019

Eur J Inorg Chem

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Cyanoborate chemistry has emerged to an important topic during the last two decades, beginning with two independent reports on the successful synthesis of the tetracyanoborate anion [B(CN) 4 ]in 2000. A wealth of cyanoborate anions with different substituents in addition to CN group(s) bonded to boron, i.e. hydrogen, halogen, aryl, alkenyl, alkyl, perfluoroalkyl, and alkoxy, have been developed, which enable the tuning of properties of compounds and materials based on them. The readily accessible alkali metal cyanoborates are convenient starting materials for the preparation of cyanoborates with various organic, inorganic, and metal cations as well as cyanoborate coordination compounds. A focus has been on low-[a] Julius-Maximilians-Universität Würzburg,

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Section: Cyanohydridoborateskt[bhn(cn)4–n] (N = 1–3)mentioning

confidence: 99%

Cyanoborates

Ignat’ev

Finze

2019

Eur J Inorg Chem

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“…[148] Specifically,g uanidinium, dimethyltriazani-um, triethylammonium, N-ethyl-N-methylpyrrolidinium, N-ethylpyridinium, 1,4-dimethyl-1,2,4-triazolium, 1-ethyl-4-methyl-1,2,4-triazolium, and 1-butyl-4-methyl-1,2,4-triazoliumc ations were studied. To estimate the cation impact,a na binitio study of cation protona ffinity and proton transfer energy was performed for as et of cations at the MP2 level of theory.…”

Section: Hypergolic Ilsmentioning

confidence: 99%

“…To estimate the cation impact,a na binitio study of cation protona ffinity and proton transfer energy was performed for as et of cations at the MP2 level of theory. [148] Specifically,g uanidinium, dimethyltriazani-um, triethylammonium, N-ethyl-N-methylpyrrolidinium, N-ethylpyridinium, 1,4-dimethyl-1,2,4-triazolium, 1-ethyl-4-methyl-1,2,4-triazolium, and 1-butyl-4-methyl-1,2,4-triazoliumc ations were studied. The proton-transfer energiesf rom the cations to as et of anions studied previously were calculated;a ni nverse correlation between the latter and the likelihood thatt he cation/anion combination will react hypergolically with WFNA was found.…”

Section: Hypergolic Ilsmentioning

confidence: 99%

Prospective Symbiosis of Green Chemistry and Energetic Materials

et al. 2017

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A global increase in environmental pollution demands the development of new "cleaner" chemical processes. Among urgent improvements, the replacement of traditional hydrocarbon-derived toxic organic solvents with neoteric solvents less harmful for the environment is one of the most vital issues. As a result of the favorable combination of their unique properties, ionic liquids (ILs), dense gases, and supercritical fluids (SCFs) have gained considerable attention as suitable green chemistry media for the preparation and modification of important chemical compounds and materials. In particular, they have a significant potential in a specific and very important area of research associated with the manufacture and processing of high-energy materials (HEMs). These large-scale manufacturing processes, in which hazardous chemicals and extreme conditions are used, produce a huge amount of hard-to-dispose-of waste. Furthermore, they are risky to staff, and any improvements that would reduce the fire and explosion risks of the corresponding processes are highly desirable. In this Review, useful applications of almost nonflammable ILs, dense gases, and SCFs (first of all, CO ) for nitration and other reactions used for manufacturing HEMs are considered. Recent advances in the field of energetic (oxygen-balanced and hypergolic) ILs are summarized. Significant attention is paid to the SCF-based micronization techniques, which improve the energetic performance of HEMs through an efficient control of the morphology and particle size distribution of the HEM fine particles, and to useful applications of SCFs in HEM processing that makes them less hazardous.

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“…6, the first chemical reaction (i.e., the reaction that occurred at the lowest temperature) for both ILs was the deprotonation of the phosphonium cation by the salicylate/benzoate anion. Proton-transfer reactions between the cation and anion have been previously reported in phosphonium-based ILs 96,97 and in other systems, including native-like protein ions, 98,99 hypergolic fuels ILs, 100 and amino acid 101 ILs. It was also reported that the energy barriers for proton-transfer reactions are much lower than other reactions in thermal decomposition of hydrocarbons.…”

Section: Themogravimetric Experimentsmentioning

confidence: 85%