Please confirm you are human
(Sign Up for free to never see this)
← Back to Search
Some data provided by SemanticScholar
Boratabenzene Anions C5B(CN)6(-) And C5B(CF3)6(-) And The Superacidic Properties Of Their Conjugate Acids.
Agnes Kütt, I. Koppel, I. Koppel, I. Leito
Published 2009 · Chemistry, Medicine
Twitter
Facebook
LinkedIn
Email Designing superacids: A computational study of protonated boratabenzenes and the gas-phase acidity of their conjugate acids is presented. Conjugate acids of boratabenzenes substituted with CN or CF(3) groups (see figure) are highly acidic species; the protonated hexacyanoboratabenzene and hexakis(trifluoromethyl)boratabenzene have computational gas-phase acidities of 250.5 and 276.8 kcal mol(-1), respectively.
This paper references
10.1021/JA060714V
An infrared nuNH scale for weakly basic anions. Implications for single-molecule acidity and superacidity.
E. Stoyanov (2006)
10.1016/S0022-328X(00)84487-3
Attempted synthesis of dibenzo[b,e]borin (9-boraanthracene) and its formation under electron impact
R. V. Veen (1970)
10.1002/EJOC.200500153
Strong Acidity of Some Polycyclic Aromatic Compounds Annulated to a Cyclopentadiene Moiety and Their Cyano Derivatives – A Density Functional B3LYP Study
R. Vianello (2005)
10.1002/CBER.19851180431
Synthese und Strukturuntersuchung von Pyridin‐Borabenzol und Pyridin‐2‐Boranaphthalin
R. Boese (1985)
10.1039/B502448J
Cyclic boronium and borenium cations derived from borabenzene-pyridine complexes.
Ioan Ghesner (2005)
10.1021/jo702513w
Pentakis(trifluoromethyl)phenyl, a sterically crowded and electron-withdrawing group: synthesis and acidity of pentakis(trifluoromethyl)benzene, -toluene, -phenol, and -aniline.
Agnes Kütt (2008)
10.1021/JA960938L
Nucleophilic Aromatic Substitution Reactions of Borabenzene-Trimethylphosphine: A Versatile Route to 1-Substituted Boratabenzenes
S. Qiao (1996)
10.1021/JA00137A030
A Boron Analogue of Benzene: Synthesis, Structure, and Reactivity of 1-H-Boratabenzene
D. A. Hoic (1995)
10.1002/CHEM.200400087
Relative stabilities of weakly coordinating anions: a computational study.
I. Krossing (2004)
10.1021/OM00032A008
Borabenzene derivatives. 21. 2,4-Pentadienylboranes as key intermediates of a novel route to boracyclohexadienes and boratabenzenes. Structure of [Li(TMPDA)](C5H5BNMe2)
G. Herberich (1993)
10.1021/CR00088A005
Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint
A. Reed (1988)
10.1021/JA058581L
The structure of the strongest Brønsted acid: the carborane acid H(CHB11Cl11).
E. Stoyanov (2006)
10.1002/1521-3765(20011105)7:21<4696::AID-CHEM4696>3.0.CO;2-5
Synthesis and properties of the tetrakis(trifluoromethyl)borate anion, [b(CF3)4]-: structure determination of Cs[B(CF3)4] by single-crystal X-ray diffraction.
E. Bernhardt (2001)
10.1021/JA0000753
Gas-Phase Acidities of Some Neutral Brønsted Superacids: A DFT and ab Initio Study
I. Koppel (2000)
10.1021/JA0255958
Generalized principle of designing neutral superstrong Brønsted acids.
I. Koppel (2002)
10.1039/B713173A
Rees polycyanated hydrocarbons and related compounds are extremely powerful Brønsted superacids in the gas-phase and DMSO—a density functional B3LYP study
R. Vianello (2008)
10.1021/OM9505569
Chemistry of Borabenzene: Efficient and General Synthesis of New Neutral Borabenzene−Ligand Complexes
D. A. Hoic (1996)
10.1002/(SICI)1096-987X(19960115)17:1<30::AID-JCC3>3.0.CO;2-1
Superacidity of neutral Brönsted acids in gas phase
P. Burk (1996)
10.1016/J.THEOCHEM.2007.03.017
Anions N[C(CN)2]3- and P[C(CN)2]3- and the superacidic properties of their conjugate acids
I. Leito (2007)
10.1039/B316122F
Exploration of the pentacyano-cyclo-pentadienide ion, C(5)(CN)(5)(-), as a weakly coordinating anion and potential superacid conjugate base. Silylation and protonation.
C. Richardson (2004)
10.1002/POLA.10087
Cyanocarbons: A classic example of discovery‐driven research
O. Webster (2002)
10.1007/BF01841234
Molecular conformation of hexakis(trifluoromethyl)benzene
M. H. Couldwell (1976)
10.1021/OM011081Q
Borabenzene Adducts of Ylidic Lewis Bases. Syntheses and Structures of 3,5-Me2C5H3BCH2PPh3, 3,5-Me2C5H3BCH(SiMe3)PPh3, and C5H5BN(Ph)PPh31
Xiaolai Zheng (2002)
10.1021/OM00001A064
Borabenzene Derivatives. 22. Synthesis of Boratabenzene Salts from 2,4-Pentadienylboranes. Structure of [NMe3Ph][C5H5BMe]
G. Herberich (1995)
10.1021/JA0440497
Anhydrous tetrabutylammonium fluoride.
Haoran Sun (2005)
This paper is referenced by
10.1007/978-1-4939-0302-3_1
Nonaqueous Electrolytes: Advances in Lithium Salts
W. A. Henderson (2014)
10.1039/c1dt10849b
1-Borabenzonitrile (B-cyanoboratabenzene).
Ian A. Cade (2011)
10.1002/chem.201104025
Bulk gas-phase acidity.
D. Himmel (2012)
10.1039/b906045f
Enhanced acidity of cyclopenta-2,4-dienylborane and its Al and Ga analogues. The role of aromatization.
M. Hurtado (2009)
10.1002/chem.201405391
Fluoro- and perfluoralkylsulfonylpentafluoroanilides: synthesis and characterization of NH acids for weakly coordinating anions and their gas-phase and solution acidities.
J. Kögel (2015)
10.1016/S0065-2725(10)09903-4
Monocyclic Hetarenes with π-Electron Aromatic Sextet
A. Balaban (2010)
10.1007/s00894-012-1682-y
Enhancing and modulating the intrinsic acidity of imidazole and pyrazole through beryllium bonds
O. Mó (2013)
10.1039/c8cp07313a
Constructing organic superacids from superhalogens is a rational route as verified by DFT calculations.
F. Zhou (2019)
Some data provided by SemanticScholar