Meltable Stannaborate Salts

Ronig, Benno; Pantenburg, Ingo; Wesemann, Lars

doi:10.1002/1099-0682(20022)2002:2<319::aid-ejic319>3.3.co;2-s

Cited by 7 publications

(13 citation statements)

References 5 publications

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“…The salt containing the chloro cluster shows the slightly lower melting point and the slightly higher decomposition temperature (Table ). In general the melting points of all compounds are in good agreement with those of other imidazolium salts containing monovalent boron clusters ,, but lower than those of salts containing related dianions. , In conclusion, longer alkyl chains attached to the ammonio group significantly lower the melting points of the respective imidazolium salts, while the influence of the halogen atoms is small.…”

Section: Resultssupporting

confidence: 70%

Improving the Solubility of Halogenated 1-Ammonio-closo-dodecaborate Anions

et al. 2017

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The partly halogenated and N-alkylated closo-dodecaborates [BClHN(propyl)] and [BBrHNR] (R = ethyl-pentyl) were prepared by alkylation of [BHNH] and subsequent halogenation with elemental chlorine or N-bromosuccinimide. Simple metathesis reactions yielded the [HNMe], [Cmim], [NBu], and Na salts, which were characterized by heteronuclear NMR and IR spectroscopy as well as electrospray ionization mass spectrometry. The crystal structures of the salts [HNMe][BBrHN(ethyl)]·CHCN, [HNMe][BBrHN(propyl)], Na[BBrHN(butyl)], and [HNMe][BClHN(propyl)]·CHCN were determined by single-crystal X-ray diffraction. The [Cmim] salts are thermally stable to temperatures higher than 300 °C. The melting points are between 57 and 80 °C, which classify the [Cmim] salts of [BClHN(propyl)] and [BBrHNR] (R = propyl-pentyl) as ionic liquids. The anions are oxidized only at potentials higher than 2 V versus Fc as determined by cyclic voltammetry. The solubility of the sodium salts in CHCl solution was determined by NMR spectroscopy. With the increasing length of the alkyl chain attached to the ammonio group the solubility is significantly enhanced. A solubility up to 125 mmol/L for Na[BBrHN(pentyl)] in dichloromethane was determined. In addition, the trialkylation of the perchlorinated anion [BClNH] was investigated in detail. A Hofmann elimination was observed to occur at higher temperatures, when alkyl groups with β-hydrogen atoms were introduced. Organic substituents without β-hydrogen atoms gave more stable compounds; however, trialkylation proved to be difficult presumably due to steric hindrance. The crystal structure of the byproduct [PPh][BClN(propargyl)] was determined.

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Section: Resultssupporting

confidence: 70%

Improving the Solubility of Halogenated 1-Ammonio-closo-dodecaborate Anions

et al. 2017

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“…3 Despite the still increasing importance of ionic liquids, 4 the number of boron cluster-based ionic liquids is still limited. Salts containing carborates 5 and stannaborates 6 show quite low melting points. In contrast, the melting points of salts based on the dianionic perchlorinated dodecaborate [B 12 Cl 12 ] 2− , 5e,7 which has been introduced by us as a weakly coordinating anion, 8 are higher.…”

Section: Introductionmentioning

confidence: 99%

Alkoxy substituted halogenated closo-dodecaborates as anions for ionic liquids

Jenne

Kirsch

2015

Dalton Trans.

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Halogenated and alkoxylated closo-dodecaborates [B12X11OR](2-) (X = Cl, Br; R = propyl, octyl, dodecyl) have been synthesized by halogenation of the known [B12H11OH](2-) anion followed by alkylation in the superbasic medium DMSO/KOH. The obtained sodium salts were transformed by simple metathesis reactions in aqueous solution to the tetrabutylammonium ([NBu4](+)) and 1-hexyl-3-methylimidazolium ([C6mim](+)) salts. All compounds were fully characterized by heteronuclear NMR, IR and Raman spectroscopy, ESI mass spectrometry, and thermal analytical measurements. Selected anions were also structurally characterized as their [Ph4P](+) salts by single crystal X-ray diffraction. The [C6mim](+) salts are thermally stable up to more than 300 °C and show clear melting points. Surprisingly, the compound [C6mim]2[B12Cl11O-propyl] having the short propyl group bound to the boron cluster shows the lowest melting point (96 °C) of all the investigated compounds. Thus this compound is a rare member of the class of ionic liquids consisting of dianions.

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“…As with [BMIM][BF 4 ], the melting points of carborane‐based ILs are also highly dependent upon the nature of cations and anions. Various cations and carborane‐based anions, shown in Figure , have been investigated , . The commonly used cations are N , N′ ‐dialkylimidazolium, N ‐alkylpyridinium, tetraalkylammonium, and tetraalkylphosphonium moieties, while the anions incorporate both the closo ‐ and nido ‐carborane clusters.…”

Section: Introductionmentioning

confidence: 99%

“…Ionic liquids containing boron clusters can be conveniently prepared by metathesis reactions as described above. In these procedures, either an ammonium (e.g., [NH 4 ] + or [Me 3 NH] + ) or a metal (Li, Na, K, or Cs) salt of a boron‐cluster‐based anion reacts with the corresponding cation precursor to form a crude product, which is further subjected to purification to provide the pure ionic liquid , . Ionic liquid [C 2 MIM][ closo ‐1,2‐C 2 B 10 H 11 ] (Table , entry 34) was prepared by the reaction of imidazolylidene carbene, which was generated in situ by reaction of n BuLi and 1‐ethyl‐3‐methylimidazolium bromide with ortho ‐carborane in an isolated yield of 91 % …”

Section: Introductionmentioning

confidence: 99%

Ionic Liquids: Recent Advances and Applications in Boron Chemistry

Zhu

Hosmane

2017

Eur J Inorg Chem

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Ionic liquids (ILs) are a type of low‐melting salts, which are generally nonvolatile, have low vapor pressure, very high boiling point, and excellent thermal stability. In addition, they have unique physical and chemical properties including highly variable viscosity, in contrast to common inorganic salts and organic liquids. Consequently, they have found potential applications in the broad area of green chemistry and as electrolytes. Recently, advances have been made in the use of ILs in boron chemistry, and as such various boron‐containing ILs have been reported and their applications in classic organic synthesis have been explored. Interestingly, many boron‐related reactions, such as hydroboration, were explored in ionic liquid media. This microreview mainly focuses on the progress of boron‐containing ILs and reactions involving boron compounds in ILs.

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Meltable Stannaborate Salts

Abstract: In a one-pot procedure, four imidazolium salts of alkylated stanna-closo-dodecaborate anions were synthesized. Alkyl substituents at the stannaborate anion and imidazolium cation were varied between ethyl and butyl, resulting in a range [a]

Cited by 7 publications

References 5 publications

Improving the Solubility of Halogenated 1-Ammonio-closo-dodecaborate Anions

Improving the Solubility of Halogenated 1-Ammonio-closo-dodecaborate Anions

Alkoxy substituted halogenated closo-dodecaborates as anions for ionic liquids

Ionic Liquids: Recent Advances and Applications in Boron Chemistry

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