Broensted superacidity of hydrochloric acid in a liquid chloroaluminate. Aluminum chloride - 1-ethyl-3-methyl-1H-imidazolium chloride (55.O m/o AlCl3)

Smith, G. Pedro; Dworkin, A. S.; Pagni, Richard M.; Zingg, S. P.

doi:10.1021/ja00184a020

Cited by 183 publications

(110 citation statements)

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“…HA and HD are likely to follow their P.A. values; so depending on the equilibrium constant of Equation (7) [63][64][65] analogous to the formation of ionic/molecular superacid systems from Brønsted and Lewis acid combinations such as SO 3 /SbF 5 /HSO 3 F. [49] …”

Section: Liquid Protic Saltsmentioning

confidence: 99%

Brønsted Acidity and the Medium: Fundamentals with a Focus on Ionic Liquids

2011

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Fundamental aspects of Brønsted acidity in ionic liquid systems, in relation to those of simple protic molecules in the gas phase, pure protic molecules in the condensed phase and solutions of protic molecules in molecular systems, are presented. The variety of acidities possible, beyond those observed in aqueous systems, is emphasised and discussed in terms of differences of solvent levelling, ionisation, dissociation, homo-/hetero-conjugate ion speciation and the stabilisation of proton-transfer products from solvent to solvent. It is argued that data regarding aqueous systems do not necessarily explain acid/base behaviour in other liquids satisfactorily. Methods of measuring acidity are reviewed, particularly by spectrophotometry and electrochemistry and recommendations proffered for estimating speciation and acidity of ionic liquids of various complexities.

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Section: Liquid Protic Saltsmentioning

confidence: 99%

Brønsted Acidity and the Medium: Fundamentals with a Focus on Ionic Liquids

2011

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“…19 All solution preparations were per- * Electrochemical Society Member. * * Electrochemical Society Fellow.…”

Section: Methodsmentioning

confidence: 99%

Cyclic Voltammetry and X-ray Absorption Spectroscopy of Nickel Oxide in the Ionic Liquid 1-Ethyl-3-Methyl Imidazolium Chloride/Aluminum Chloride

Roeper¹,

Cheek²,

Pandya³

et al. 2017

J. Electrochem. Soc.

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Transition metal chlorides have been examined in situ in ionic liquids (ILs) using cyclic voltammetry (CV) but the oxides of these metals have not received as much attention. In this study, the structure of nickel oxide in the ionic liquid, 1-ethyl-3-methyl imidazolium chloride (EMIC) and aluminum chloride has been investigated. The NiO in EMIC/AlCl3 IL was examined with CVs and Extended X-ray Absorption Fine Structure (EXAFS) in both Lewis acidic and basic IL solutions. The CV of NiO in both acidic and basic EMIC/AlCl3 ILs shows similarities with the CV of NiCl2 in these ILs. The EXAFS data for the NiO and anhydrous NiCl2 in these acidic and basic IL solutions are also analogous, indicating that some corresponding molecular structures may have formed and these are discussed in detail.

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“…BMPY TfO was prepared according to a standard literature method. 30 EMIm Cl was prepared 31 by reaction of chloroethane and 1-methylimidazole (Aldrich), and EMIm BF 4 was prepared by metathesis of EMIm Cl and NaBF 4 (Aldrich) in acetone, using purification method B. 32 1-Butyl-2,3-dimethylimidazolium tetrafluoroborate (BDMIm BF 4 ) was prepared by metathesis of BDMIm Cl and NaBF 4 .…”

Section: Methodsmentioning

confidence: 99%

Electrochemical Investigation of Benzil in Ionic Liquids

Cheek

2017

J. Electrochem. Soc.

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The voltammetric behavior of benzil (1,2-ethanedione, 1,2-diphenyl) has been investigated by cyclic voltammetry in the ionic liquids 1-ethyl-3-methylimidazolium tetrafluoroborate (EMImBF4), 1-butyl-2,3-dimethylimidazolium tetrafluoroborate (BDMIm BF4), and 1-butyl-1-methylpyrrolidinium trifluoromethanesulfonate BMPY TfO. At 100 mV/s, protonation of the radical anions of benzil by the EMIm cation is extensive and leads to complicated voltammetry; however, the protonation reaction is slow and is much less significant at 1000 mV/s. Use of BDMIm BF4, in which the acidic imidazolium 2-position is substituted, precludes protonation of these radical anions. It has been found that addition of BF3 etherate to solutions of benzil in EMImBF4 results in the complexation of benzil by BF3. Benzil has been found to undergo two successive reversible one-electron redox processes in the ionic liquid 1-butyl-1-methylpyrrolidinium trifluoromethanesulfonate (BMPY TfO). This behavior is observed due to the very low proton-donating ability of the BMPY cation. Upon addition of acetonitrile, however, the second redox process becomes irreversible as is observed in acetonitrile alone. The benzil dianion is evidently undergoing protonation by acetonitrile, and the resulting voltammogram is very similar to that in acetonitrile itself.

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Broensted superacidity of hydrochloric acid in a liquid chloroaluminate. Aluminum chloride - 1-ethyl-3-methyl-1H-imidazolium chloride (55.O m/o AlCl3)

Cited by 183 publications

References 0 publications

Brønsted Acidity and the Medium: Fundamentals with a Focus on Ionic Liquids

Brønsted Acidity and the Medium: Fundamentals with a Focus on Ionic Liquids

Cyclic Voltammetry and X-ray Absorption Spectroscopy of Nickel Oxide in the Ionic Liquid 1-Ethyl-3-Methyl Imidazolium Chloride/Aluminum Chloride

Electrochemical Investigation of Benzil in Ionic Liquids

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