Studies in the tetraarylborates

Chao, Sherman; Moore, Carle E.

doi:10.1016/s0003-2670(01)93340-9

Cited by 23 publications

(16 citation statements)

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“…[1] Tetraphenylborate is an example of a simple organic precipitating reagent, but there have also been numerous studies of other substituted borates that form saltlike precipitates. [2] The investigation of borate complexes containing organic cations as guest molecules has not attracted a great deal of interest, although a variety of substituted borates bearing aryl groups have been synthesized. [3,4] Electrochemical sensors constitute an important group of chemical sensors that are attractive for practical applications allowing the use of small-size, portable, and low-cost instrumentation.…”

Section: Introductionmentioning

confidence: 99%

“…Additionally, we have studied the complexation of the N-methylpyridinium (6), 1-ethyl-4-(methoxycarbonyl)pyridinium (7), tropylium (8), imidazolium (9), and 1-methylimidazolium (10) cations with borates 1 and 2 (Scheme 1) by means of NMR and mass spectrometry and in some cases also by X-ray crystallography. Stability constants of complexes of N-methylpyridinium (6) and 1-ethyl-4-(methoxycarbonyl)pyridinium (7) (2), tetrakis(2-naphthyl)-borate (3), tetrakis(4-phenylphenol)borate (4), tetrakis(4-phenoxy)borate (5), N-methylpyridinium (iodide) (6), 1-ethyl-4-(methoxycarbonyl)pyridinium (iodide) (7), tropylium (tetrafluoroborate) (8), imidazolium (perchlorate) (9), and 1-methylimidazolium (perchlorate) (10).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterization, and Complexation of Tetraarylborates with Aromatic Cations and Their Use in Chemical Sensors

Alaviuhkola

Bobacka

Nissinen

et al. 2005

Chemistry A European J

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Five aromatic borate anions, namely tetrakis(4-phenoxyphenyl)borate (1), tetrakis(biphenyl)borate (2), tetrakis(2-naphthyl)borate (3), tetrakis(4-phenylphenol)borate (4), and tetrakis(4-phenoxy)borate (5), have been prepared and tested as ion-recognition sites in chemical sensors for certain aromatic cations and metal ions. To gain further insight into the complexation of the cations, some complexes have been prepared and structurally characterized. The complexation behavior of 1 and 2 towards N-methylpyridinium (6), 1-ethyl-4-(methoxycarbonyl)pyridinium (7), tropylium (8), imidazolium (9), and 1-methylimidazolium (10) cations has been studied, and the stability constants of the complexes of 1 with cations 6 and 8 have been measured to compare them with the values for the previously studied complexes of tetraphenylborate. The structures of the borate anions and their complexes have been characterized by NMR and mass spectrometric methods. X-ray crystal structures have been determined for potassium tetrakis(4-phenoxyphenyl)borate (K(+)1), N-methylpyridinium tetrakis(4-phenoxyphenyl)borate (61), 1-ethyl-4-(methoxycarbonyl)pyridinium tetrakis(4-phenoxyphenyl)borate (71), tropylium tetrakis(4-phenoxyphenyl)borate (81), and imidazolium tetrakis(biphenyl)borate (92). The results show that borate derivatives are potential candidates for a completely new family of charged carriers for use in cation-selective electrodes.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Complexation of Tetraarylborates with Aromatic Cations and Their Use in Chemical Sensors

Alaviuhkola

Bobacka

Nissinen

et al. 2005

Chemistry A European J

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“…Sodium tetrakis(1-imidazolyl) borate (1) was prepared according to [14] with slight modifications. In a Schlenk flask equipped with an air condenser sodium borohydride (3.64 g, 96 mmol) and imidazole (32.75 g, 481 mmol) were heated to 100…”

Section: Methodsmentioning

confidence: 99%

“…Since the first generation of tetrakis(1-pyrazolyl)borates in 1967, numerous derivatives with aromatic N-heterocycles have been reported such as tetrakis(1-pyrrolyl)borates, tetrakis(1-indolyl)borates and tetrakis(1-imidazolyl)borates (1) [13][14][15][16]. Generally, these compounds can be synthesized in a single step by conversion of borohydrides with the corresponding azole at elevated temperature under hydrogen evolution.…”

Section: Introductionmentioning

confidence: 99%

Azolylborates for Electrochemical Double Layer Capacitor Electrolytes

Francke

Cericola

Kötz

et al. 2011

Zeitschrift Für Physikalische Chemie

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Azolylborate / Alkylammonium Salt / Electrochemical Double Layer Capacitor / Supporting Electrolyte / Cyclic VoltammetryAsymmetric tetraalkylammonium salts of azolylborates were synthesized and studied with respect to their suitability as supporting electrolytes in electrochemical double layer capacitors. In contrast to current conducting salts used in this device, azolylborates exhibit an excellent stability towards thermal load and moisture. In addition to good conductivity and stability towards cathodic reduction we found certain limitations when more positive potentials were applied.

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“…This is the only nonhydrogen atom in the otherwise completely ordered TC structure that shows positional disorder, very likely dynamic. The hypothesis that the large Uij arise from a mixed MeOH,H,O occupancy was rejected as only marginally probable, as it did not lead to a significant reduction of the Uij(Cm 1) and the refined occupancy factor for C m l was 0.83 (2 (Table 2). However, there seems to be no clear-cut separation between the d(Li1"-N) and the corresponding bond lengths with Li in 3-or 5-coordination In Table 2.…”

Section: ~ mentioning

confidence: 99%

Crystal chemistry of tetraradial species. Part 7. Lithium tetrakis(1-imidazolyl)-borate solvate, Li^iv[Li^iv(H₂O)(MeOH)]-[B(C₃H₃N₂)4]₂•MeOH, a 3-dimensional polymer; with observations on the geometry of imidazole rings

Knop¹,

Bakshi²

1995

Can. J. Chem.

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Abstract:The title compound is a 3-dimensional polymer with a completely ordered triclinic structure ( P i , a = 12.380(2) A, b = 14.434(2) A, c = 9.683(3) A, ci = 90.36(2)", P = 105.44(2)", y = 90.75(2)", Z = 2). Every i 3 atom is tetrahedrally coordinated by N(1) atoms of the imidazole rings, every Li(1) atom is tetrahedrally coordinated by N(3) atoms, and every Li(2) atom is coordinated by two N(3) and two oxygen atoms, one from the H,O molecule and one from a MeOH molecule. The imidazole rings connected by the B-N(l) and Li-N(3) bonds thus generate a 3-dimensional covalent polymeric network. The MeOH molecules of coordination are hydrogen-bonded to unengaged N(3) atoms, thereby supplementing the covalent bonding system. The H 2 0 molecules are hydrogen-bonded to the MeOH molecules of solvation to form centrosymmetric [Ow...OMeOH], rings, which in turn are connected to the covalent network by OMeoH-H ... N(3) bonds to the remaining unengaged N(3) atoms. Every atom in the structure except the H(C) hydrogens is thus involved in the 3-dimensional bond system. The excellent consistency of the bond lengths and endocyclic bond angles + in the eight imidazole rings of the title compound has provided an opportunity for investigating the effect of substitution on the geometry of the imidazole ring in a sample of 17 substituted imidazoles. While the bond lengths have been found at most weakly correlated, the multilinear correlations of the + in this sample are highly significant. Among the substituents the NO, group is the most ipso-+-expanding and the anionic B (in the title compound) the most ipso-+-contracting. Protonation or deprotonation at the N atoms affect the ipso C-N-C angles considerably. Limited comparisons are drawn with the results of the classical investigations by Domenicano et al. on the effect of substitution on the geometry of the benzene ring.Ke.y words: hydrogen bond, imidazole, lithium compounds, polymers, tetrahedral boron ions.Resume : Le composC mentionnC dans le titre est un polymkre tridimensionnel avec une structure triclinique complktement ordonnCe ( p i , n = 12,380(2) A, O = 14,434(2) A, r = 9,683(3) A, ci = 90,36(2)", P = 105,44(2)",

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Studies in the tetraarylborates

Cited by 23 publications

References 9 publications

Synthesis, Characterization, and Complexation of Tetraarylborates with Aromatic Cations and Their Use in Chemical Sensors

Synthesis, Characterization, and Complexation of Tetraarylborates with Aromatic Cations and Their Use in Chemical Sensors

Azolylborates for Electrochemical Double Layer Capacitor Electrolytes

Crystal chemistry of tetraradial species. Part 7. Lithium tetrakis(1-imidazolyl)-borate solvate, Li^iv[Li^iv(H₂O)(MeOH)]-[B(C₃H₃N₂)4]₂•MeOH, a 3-dimensional polymer; with observations on the geometry of imidazole rings

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Studies in the tetraarylborates

Cited by 23 publications

References 9 publications

Synthesis, Characterization, and Complexation of Tetraarylborates with Aromatic Cations and Their Use in Chemical Sensors

Synthesis, Characterization, and Complexation of Tetraarylborates with Aromatic Cations and Their Use in Chemical Sensors

Azolylborates for Electrochemical Double Layer Capacitor Electrolytes

Crystal chemistry of tetraradial species. Part 7. Lithium tetrakis(1-imidazolyl)-borate solvate, Liiv[Liiv(H2O)(MeOH)]-[B(C3H3N2)4]2•MeOH, a 3-dimensional polymer; with observations on the geometry of imidazole rings

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Crystal chemistry of tetraradial species. Part 7. Lithium tetrakis(1-imidazolyl)-borate solvate, Li^iv[Li^iv(H₂O)(MeOH)]-[B(C₃H₃N₂)4]₂•MeOH, a 3-dimensional polymer; with observations on the geometry of imidazole rings