Cyanohydridoborate Anions: Synthesis, Salts, and Low‐Viscosity Ionic Liquids
- Authors:
-
- Institut für nachhaltige Chemie &, Katalyse mit Bor (ICB), Institut für Anorganische Chemie Julius-Maximilians-Universität Würzburg Am Hubland 97074 Würzburg Germany
- Institut für Organische Chemie &, Center for Nanosystems Chemistry Julius-Maximilians-Universität Würzburg Am Hubland 97074 Würzburg Germany
- Physical Sciences Division Pacific Northwest National Laboratory 902 Battelle Boulevard, P.O. Box 999, MSIN K8-88 Richland WA 99352 USA
- Department of Chemistry Purdue University 560 Oval Drive West Lafayette IN 47907 USA
- Institut für nachhaltige Chemie &, Katalyse mit Bor (ICB), Institut für Anorganische Chemie Julius-Maximilians-Universität Würzburg Am Hubland 97074 Würzburg Germany, Consultant Merck KGaA 64293 Darmstadt Germany
- Publication Date:
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1494206
- Resource Type:
- Publisher's Accepted Manuscript
- Journal Name:
- Chemistry - A European Journal
- Additional Journal Information:
- Journal Name: Chemistry - A European Journal Journal Volume: 25 Journal Issue: 14; Journal ID: ISSN 0947-6539
- Publisher:
- Wiley Blackwell (John Wiley & Sons)
- Country of Publication:
- Germany
- Language:
- English
Citation Formats
Bischoff, Lisa A., Drisch, Michael, Kerpen, Christoph, Hennig, Philipp T., Landmann, Johannes, Sprenger, Jan A. P., Bertermann, Rüdiger, Grüne, Matthias, Yuan, Qinqin, Warneke, Jonas, Wang, Xue‐Bin, Ignat'ev, Nikolai V., and Finze, Maik. Cyanohydridoborate Anions: Synthesis, Salts, and Low‐Viscosity Ionic Liquids. Germany: N. p., 2019.
Web. doi:10.1002/chem.201804698.
Bischoff, Lisa A., Drisch, Michael, Kerpen, Christoph, Hennig, Philipp T., Landmann, Johannes, Sprenger, Jan A. P., Bertermann, Rüdiger, Grüne, Matthias, Yuan, Qinqin, Warneke, Jonas, Wang, Xue‐Bin, Ignat'ev, Nikolai V., & Finze, Maik. Cyanohydridoborate Anions: Synthesis, Salts, and Low‐Viscosity Ionic Liquids. Germany. https://doi.org/10.1002/chem.201804698
Bischoff, Lisa A., Drisch, Michael, Kerpen, Christoph, Hennig, Philipp T., Landmann, Johannes, Sprenger, Jan A. P., Bertermann, Rüdiger, Grüne, Matthias, Yuan, Qinqin, Warneke, Jonas, Wang, Xue‐Bin, Ignat'ev, Nikolai V., and Finze, Maik. Mon .
"Cyanohydridoborate Anions: Synthesis, Salts, and Low‐Viscosity Ionic Liquids". Germany. https://doi.org/10.1002/chem.201804698.
@article{osti_1494206,
title = {Cyanohydridoborate Anions: Synthesis, Salts, and Low‐Viscosity Ionic Liquids},
author = {Bischoff, Lisa A. and Drisch, Michael and Kerpen, Christoph and Hennig, Philipp T. and Landmann, Johannes and Sprenger, Jan A. P. and Bertermann, Rüdiger and Grüne, Matthias and Yuan, Qinqin and Warneke, Jonas and Wang, Xue‐Bin and Ignat'ev, Nikolai V. and Finze, Maik},
abstractNote = {},
doi = {10.1002/chem.201804698},
journal = {Chemistry - A European Journal},
number = 14,
volume = 25,
place = {Germany},
year = {2019},
month = {2}
}
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Cited by: 23 works
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Works referenced in this record:
Self-Diffusion Coefficients and Related Transport Properties for a Number of Fragile Ionic Liquids
journal, June 2016
- Harris, Kenneth R.; Kanakubo, Mitsuhiro
- Journal of Chemical & Engineering Data, Vol. 61, Issue 7
Deprotonation of a Hydridoborate Anion
journal, January 2017
- Landmann, Johannes; Keppner, Fabian; Hofmann, Daniel B.
- Angewandte Chemie International Edition, Vol. 56, Issue 10
New hydrophobic ionic liquids with perfluoroalkyl phosphate and cyanofluoroborate anions
journal, September 2015
- Ignat’ev, N. V.; Finze, M.; Sprenger, J. A. P.
- Journal of Fluorine Chemistry, Vol. 177
“Umpolung” von Bor im [B(CN)4]− Anion durch Reduktion zum Dianion [B(CN)3]2−
journal, October 2011
- Bernhardt, Eduard; Bernhardt-Pitchougina, Vera; Willner, Helge
- Angewandte Chemie, Vol. 123, Issue 50
Systematic Study of the Thermophysical Properties of Imidazolium-Based Ionic Liquids with Cyano-Functionalized Anions
journal, August 2013
- Neves, Catarina M. S. S.; Kurnia, Kiki Adi; Coutinho, João A. P.
- The Journal of Physical Chemistry B, Vol. 117, Issue 35
On the concept of ionicity in ionic liquids
journal, January 2009
- MacFarlane, Douglas R.; Forsyth, Maria; Izgorodina, Ekaterina I.
- Physical Chemistry Chemical Physics, Vol. 11, Issue 25
Density-functional exchange-energy approximation with correct asymptotic behavior
journal, September 1988
- Becke, A. D.
- Physical Review A, Vol. 38, Issue 6
NMR Chemical Shifts of Trace Impurities: Common Laboratory Solvents, Organics, and Gases in Deuterated Solvents Relevant to the Organometallic Chemist
journal, May 2010
- Fulmer, Gregory R.; Miller, Alexander J. M.; Sherden, Nathaniel H.
- Organometallics, Vol. 29, Issue 9
[H(OEt 2 ) 2 ] + and [Ph 3 C] + Salts of the Borate Anions [B(CF 3 ) 4 ] - , [(CF 3 ) 3 BCN] - , and [B(CN) 4 ] -
journal, October 2005
- Finze, Maik; Bernhardt, Eduard; Berkei, Michael
- Organometallics, Vol. 24, Issue 21
Synthesis of LiBC 4 N 4 , BC 3 N 3 , and Related C−N Compounds of Boron: New Precursors to Light Element Ceramics
journal, August 2000
- Williams, Darrick; Pleune, Brett; Kouvetakis, J.
- Journal of the American Chemical Society, Vol. 122, Issue 32
Application of Ionic Liquids Containing Tricyanomethanide [C(CN) 3 ] − or Tetracyanoborate [B(CN) 4 ] − Anions in Dye-Sensitized Solar Cells
journal, November 2011
- Marszalek, Magdalena; Fei, Zhaofu; Zhu, Dun-Ru
- Inorganic Chemistry, Vol. 50, Issue 22
Synthesis of Amine-dicyanohydroboranes, [Amine-bis(ethylnitrilium)hydroboron(2+)] Tetrafluoroborates, and Their Derivatives as Precursors of Amine-dicarboxyboranes
journal, November 1999
- Berente, Zoltán; Györi, Béla
- Inorganic Chemistry, Vol. 38, Issue 23
Borylation of fluorinated arenes using the boron-centred nucleophile B(CN) 3 2− – a unique entry to aryltricyanoborates
journal, January 2017
- Landmann, Johannes; Hennig, Philipp T.; Ignat’ev, Nikolai V.
- Chemical Science, Vol. 8, Issue 9
Physical properties of 3-methyl-N-butylpyridinium tetracyanoborate and 1-butyl-1-methylpyrrolidinium tetracyanoborate and ternary LLE data of [3-mebupy]B(CN)4 with an aromatic and an aliphatic hydrocarbon at T=303.2K and 328.2K and p=0.1MPa
journal, November 2011
- Meindersma, G. W.; Simons, Bart T. J.; de Haan, André B.
- The Journal of Chemical Thermodynamics, Vol. 43, Issue 11
Cyanoborohydride-Based Ionic Liquids as Green Aerospace Bipropellant Fuels
journal, April 2014
- Zhang, Qinghua; Yin, Ping; Zhang, Jiaheng
- Chemistry - A European Journal, Vol. 20, Issue 23
Development of a low-temperature photoelectron spectroscopy instrument using an electrospray ion source and a cryogenically controlled ion trap
journal, July 2008
- Wang, Xue-Bin; Wang, Lai-Sheng
- Review of Scientific Instruments, Vol. 79, Issue 7
NMR nomenclature. Nuclear spin properties and conventions for chemical shifts(IUPAC Recommendations 2001)
journal, January 2001
- Harris, Robin K.; Becker, Edwin D.; Cabral de Menezes, Sonia M.
- Pure and Applied Chemistry, Vol. 73, Issue 11
Stable Mesoscopic Dye-Sensitized Solar Cells Based on Tetracyanoborate Ionic Liquid Electrolyte
journal, June 2006
- Kuang, Daibin; Wang, Peng; Ito, Seigo
- Journal of the American Chemical Society, Vol. 128, Issue 24
Das Hexacyanodiboran(6)-Dianion [B 2 (CN) 6 ] 2−
journal, July 2015
- Landmann, Johannes; Sprenger, Jan A. P.; Hailmann, Michael
- Angewandte Chemie, Vol. 127, Issue 38
Synthesis of sodium and tetra-n-butylammonium dicyanodihydroborate
journal, September 1984
- Spielvogel, Bernard F.; Ahmed, Fahim U.; Das, Mrinal K.
- Inorganic Chemistry, Vol. 23, Issue 20
Brønsted Acid−Base Ionic Liquids as Proton-Conducting Nonaqueous Electrolytes
journal, May 2003
- Noda, Akihiro; Susan, Md. Abu Bin Hasan; Kudo, Kenji
- The Journal of Physical Chemistry B, Vol. 107, Issue 17
Avoiding Diffusion Limitations in Cobalt(III/II)-Tris(2,2′-Bipyridine)-Based Dye-Sensitized Solar Cells by Tuning the Mesoporous TiO2 Film Properties
journal, July 2012
- Tsao, Hoi Nok; Comte, Pascal; Yi, Chenyi
- ChemPhysChem, Vol. 13, Issue 12
Evidence of Significant Covalent Bonding in Au(CN) 2 −
journal, November 2009
- Wang, Xue-Bin; Wang, Yi-Lei; Yang, Jie
- Journal of the American Chemical Society, Vol. 131, Issue 45
Dynamic Viscosity of Tetracyanoborate- and Tricyanomethanide-Based Ionic Liquids by Dynamic Light Scattering
journal, March 2015
- Bi, Shengshan; Koller, Thomas M.; Rausch, Michael H.
- Industrial & Engineering Chemistry Research, Vol. 54, Issue 11
Development of a Manufacturing Process for 1-(1-Pyridin-2-yl methyl-piperidin-4-yl)-1 H -indole: A Key Intermediate for Protein Kinase C Inhibitor LY317615
journal, November 2006
- Boini, Sathish; Moder, Kenneth P.; Vaid, Radhe K.
- Organic Process Research & Development, Vol. 10, Issue 6
Reaction of the Tricyanoborate Dianion [B(CN) 3 ] 2– with HgCl 2
journal, April 2017
- Bernhardt, Eduard; Bernhardt-Pitchougina, Vera; Jenne, Carsten
- Inorganic Chemistry, Vol. 56, Issue 9
“Umpolung” at Boron by Reduction of [B(CN)4]− and Formation of the Dianion [B(CN)3]2−
journal, October 2011
- Bernhardt, Eduard; Bernhardt-Pitchougina, Vera; Willner, Helge
- Angewandte Chemie International Edition, Vol. 50, Issue 50
The Hexacyanodiborane(6) Dianion [B 2 (CN) 6 ] 2−
journal, July 2015
- Landmann, Johannes; Sprenger, Jan A. P.; Hailmann, Michael
- Angewandte Chemie International Edition, Vol. 54, Issue 38
The isomerization of HNCBH3 ⇌ HCNBH3
journal, June 1992
- Neogrády, Pavel; Černušák, Ivan; Urban, Miroslav
- Journal of Molecular Structure: THEOCHEM, Vol. 258, Issue 3-4
Self-Consistent Equations Including Exchange and Correlation Effects
journal, November 1965
- Kohn, W.; Sham, L. J.
- Physical Review, Vol. 140, Issue 4A, p. A1133-A1138
Sum Frequency Generation Spectroscopy of Imidazolium-Based Ionic Liquids with Cyano-Functionalized Anions at the Solid Salt–Liquid Interface
journal, May 2013
- Peñalber, Chariz Y.; Baker, Gary A.; Baldelli, Steven
- The Journal of Physical Chemistry B, Vol. 117, Issue 19
Eine effiziente Synthese von Tetracyanoboraten durch Sinterprozesse
journal, July 2003
- Bernhardt, E.; Finze, M.; Willner, Helge
- Zeitschrift für anorganische und allgemeine Chemie, Vol. 629, Issue 78
Density‐functional thermochemistry. III. The role of exact exchange
journal, April 1993
- Becke, Axel D.
- The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652
Thermodynamics and activity coefficients at infinite dilution measurements for organic solutes and water in the ionic liquid 1-butyl-1-methylpyrrolidinium tetracyanoborate
journal, December 2011
- Domańska, Urszula; Królikowski, Marek; Acree, William E.
- The Journal of Chemical Thermodynamics, Vol. 43, Issue 12
Ionic Liquids as Hypergolic Fuels
journal, September 2011
- Zhang, Yanqiang; Gao, Haixiang; Joo, Young-Hyuk
- Angewandte Chemie International Edition, Vol. 50, Issue 41
Boronium-Cation-Based Ionic Liquids as Hypergolic Fluids
journal, November 2012
- Wang, Kai; Zhang, Yanqiang; Chand, Deepak
- Chemistry - A European Journal, Vol. 18, Issue 52
A short history of SHELX
journal, December 2007
- Sheldrick, George M.
- Acta Crystallographica Section A Foundations of Crystallography, Vol. 64, Issue 1, p. 112-122
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density
journal, January 1988
- Lee, Chengteh; Yang, Weitao; Parr, Robert G.
- Physical Review B, Vol. 37, Issue 2
Perfluoroalkyltricyanoborate and Perfluoroalkylcyanofluoroborate Anions: Building Blocks for Low-Viscosity Ionic Liquids
journal, November 2017
- Landmann, Johannes; Sprenger, Jan A. P.; Hennig, Philipp T.
- Chemistry - A European Journal, Vol. 24, Issue 3
Hydrophobic, Highly Conductive Ambient-Temperature Molten Salts †
journal, January 1996
- Bonhôte, Pierre; Dias, Ana-Paula; Papageorgiou, Nicholas
- Inorganic Chemistry, Vol. 35, Issue 5
Dynamic Disorder and Electronic Structures of Electron-Precise Dianionic Diboranes: Insights from Solid-State Multinuclear Magnetic Resonance Spectroscopy
journal, June 2017
- Wong, Y. T. Angel; Landmann, Johannes; Finze, Maik
- Journal of the American Chemical Society, Vol. 139, Issue 24
Tetracyanoborate Salts M[B(CN) 4 ] with M = Singly Charged Cations: Properties and Structures
journal, February 2005
- Küppers, Torsten; Bernhardt, Eduard; Willner, Helge
- Inorganic Chemistry, Vol. 44, Issue 4
Viscosity, Interfacial Tension, Self-Diffusion Coefficient, Density, and Refractive Index of the Ionic Liquid 1-Ethyl-3-methylimidazolium Tetracyanoborate as a Function of Temperature at Atmospheric Pressure
journal, February 2012
- Koller, Thomas; Rausch, Michael H.; Schulz, Peter S.
- Journal of Chemical & Engineering Data, Vol. 57, Issue 3
Thermophysical Properties of the Ionic Liquids [EMIM][B(CN) 4 ] and [HMIM][B(CN) 4 ]
journal, July 2013
- Koller, Thomas M.; Rausch, Michael H.; Ramos, Javier
- The Journal of Physical Chemistry B, Vol. 117, Issue 28
Dicyanoborate-Based Ionic Liquids as Hypergolic Fluids
journal, November 2010
- Zhang, Yanqiang; Shreeve, Jean'ne M.
- Angewandte Chemie International Edition, Vol. 50, Issue 4
Ionicity in ionic liquids: correlation with ionic structure and physicochemical properties
journal, January 2010
- Ueno, Kazuhide; Tokuda, Hiroyuki; Watanabe, Masayoshi
- Physical Chemistry Chemical Physics, Vol. 12, Issue 8
Preparation and properties of novel cyano and isocyano derivatives of borane and the tetrahydroborate anion
journal, October 1983
- Györi, Béla; Emri, József; Fehér, István
- Journal of Organometallic Chemistry, Vol. 255, Issue 1
Convenient access to the tricyanoborate dianion B(CN) 3 2− and selected reactions as a boron-centred nucleophile
journal, January 2015
- Landmann, Johannes; Sprenger, Jan A. P.; Bertermann, Rüdiger
- Chemical Communications, Vol. 51, Issue 24
Development of low viscous ionic liquids: the dependence of the viscosity on the mass of the ions
journal, June 2014
- Barthen, Peter; Frank, Walter; Ignatiev, Nikolai
- Ionics, Vol. 21, Issue 1
Acidic 1-ethyl-3-methylimidazolium fluoride: a new room temperature ionic liquid
journal, October 1999
- Hagiwara, Rika; Hirashige, Takayuki; Tsuda, Tetsuya
- Journal of Fluorine Chemistry, Vol. 99, Issue 1
MBPT and coupled-cluster investigation of isomerization reactions: HCN .ltbbrac. = .rtbbrac. HNC, BH3CN- .ltbbrac. = .rtbbrac. BH3NC-, and HCNBH3 .ltbbrac. = .rtbbrac. HNCBH3
journal, July 1988
- Urban, Miroslav.; Bartlett, Rodney J.
- Journal of the American Chemical Society, Vol. 110, Issue 15
Die Tetracyanoborate M[B(CN)4], M = [Bu4N]+, Ag+, K+
journal, February 2000
- Bernhardt, E.; Henkel, G.; Willner, H.
- Zeitschrift für anorganische und allgemeine Chemie, Vol. 626, Issue 2
Physicochemical Properties of Three Ionic Liquids Containing a Tetracyanoborate Anion and Their Lithium Salt Mixtures
journal, July 2014
- Sanchez-Ramirez, Nédher; Martins, Vitor L.; Ando, Rômulo A.
- The Journal of Physical Chemistry B, Vol. 118, Issue 29
Ionische Flüssigkeiten als hypergole Treibstoffe
journal, September 2011
- Zhang, Yanqiang; Gao, Haixiang; Joo, Young-Hyuk
- Angewandte Chemie, Vol. 123, Issue 41
Deprotonierung eines Hydridoborat-Anions
journal, January 2017
- Landmann, Johannes; Keppner, Fabian; Hofmann, Daniel B.
- Angewandte Chemie, Vol. 129, Issue 10
On the origin of ionicity in ionic liquids. Ion pairing versus charge transfer
journal, January 2014
- Hollóczki, Oldamur; Malberg, Friedrich; Welton, Tom
- Phys. Chem. Chem. Phys., Vol. 16, Issue 32
A new method for the synthesis of cyanohydroborates and cyanoborane complexes
journal, January 1983
- Emri, József; Győri, Béla
- J. Chem. Soc., Chem. Commun., Issue 22
Hydroboration. XLI. Hydroboration of alkenes and alkynes with dichloroborane etherates. Convenient procedures for the preparation of alkyl- and alkenyldichloroboranes and their derivatives
journal, March 1976
- Brown, Herbert C.; Ravindran, N.
- Journal of the American Chemical Society, Vol. 98, Issue 7
Chlorocyanoborates: Synthesis, Spectroscopic and Structural Characterization, and Properties of Ionic Liquids: Chlorocyanoborates: Synthesis, Spectroscopic and Structural Characterization, and Properties of Ionic Liquids
journal, August 2018
- Bischoff, Lisa A.; Sprenger, Jan A. P.; Hennig, Philipp T.
- Zeitschrift für anorganische und allgemeine Chemie, Vol. 644, Issue 21
Dicyanoborate-Based Ionic Liquids as Hypergolic Fluids
journal, November 2010
- Zhang, Yanqiang; Shreeve, Jean'ne M.
- Angewandte Chemie, Vol. 123, Issue 4
Organo-Tricyanoborates as Tectons: Illustrative Coordination Polymers Based on Copper(I) Derivatives
journal, September 2005
- Yao, Haijun; Kuhlman, Matthew L.; Rauchfuss, Thomas B.
- Inorganic Chemistry, Vol. 44, Issue 18
Syntheses of Tricyanofluoroborates M[BF(CN) 3 ] (M = Na, K): (CH 3 ) 3 SiCl Catalysis, Countercation Effect, and Reaction Intermediates
journal, March 2015
- Sprenger, Jan A. P.; Landmann, Johannes; Drisch, Michael
- Inorganic Chemistry, Vol. 54, Issue 7
Determination of the electron affinity of iodine
journal, April 1992
- Hanstorp, D.; Gustafsson, M.
- Journal of Physics B: Atomic, Molecular and Optical Physics, Vol. 25, Issue 8