Tris(pentafluorophenyl)boron

Tris(pentafluorophenyl)boron

Chembox new
Name = Tris(pentafluorphenyl)boron
ImageFile = Tris(pentafluorophenyl)boron-3D-vdW.png ImageName = Tris(pentafluorphenyl)boron
IUPACName = Tris(pentafluorophenyl)boron
OtherNames = Perfluorotriphenylboron
Section1 = Chembox Identifiers
SMILES =
CASNo = 1109-15-5
RTECS =

Section2 = Chembox Properties
Formula = (C6F5)3B
C18F15B
MolarMass = 511.98 g/mol
Appearance = colorless solid
Density =
Solubility = forms adduct
MeltingPt = 126-131 °C
BoilingPt =
Viscosity =

Section3 = Chembox Structure
MolShape = trigonal planar
Dipole = 0 D

Section7 = Chembox Hazards
ExternalMSDS =
MainHazards =
RPhrases = 36/37/38
SPhrases = 26-36

Section8 = Chembox Related
OtherCpds = Triphenylboron (C6H5)3B
BF3

Tris(pentafluorophenyl)boron is the chemical compound (C6F5)3B. The molecule consists of three pentafluorophenyl groups attached in a "paddle-wheel" manner to a central boron atom; the BC3 core is planar. It has been described as the “ideal Lewis acid” because of its versatility and the relative inertness of the B-C bonds. Related fluoro-substituted boron compounds, such as those containing B-CF3 groups, decompose with formation of B-F bonds.

Preparation

(C6F5)3B is prepared using a Grignard reagent::3C6F5MgBr + BCl3 → (C6F5)3B + 3MgBrClOriginally the synthesis employed C6F5Li, but this reagent can detonate with elimination of LiF. [Piers, W. E.; Chivers, T. “Pentafluorophenylboranes: from Obscurity to Applications” Chemical Society Reviews volume 26, pages 345-354 (1997)]

Lewis acidity

The most noteworthy property of this molecule is its strong Lewis acidity: stronger than BF3 but weaker than BCl3. This property indicates that the electronegativity of the C6F5 group and a halide are similar. An most important application of (C6F5)3B is that it forms noncoordinating anions by removing anionic ligands from metal centers. [Fuhrmann, H.; Brenner, S.; Arndt, P.; Kempe, R. “Octahedral Group 4 Metal Complexes That Contain Amine, Amido, and Aminopyridinato Ligands: Synthesis, Structure, and Application in α-Olefin Oligo- and Polymerization” Inorganic Chemistry 1996, 35, 6742-6745.] Illustrative is a reaction that give rise to alkene polymerization catalyst::(C6F5)3B + (C5H5)2Zr(CH3)2 → [(C5H5)2ZrCH3+] [ C6F5)3BCH3] In this process, the strongly coordinating methyl group transfers to the boron to expose a reactive site on zirconium. Alkenes can bind to this site, whereupon they couple to the remaining methyl ligand to give a propyl ligand, thereby starting the growth of a chain of polyethylene.

(C6F5)3B is also capable of abstracting hydride to give [(C6F5)3BH] , and it catalyzes hydrosilylation of aldehydes. Otherwise (C6F5)3B binds to a wide range of Lewis bases, even weak ones. [Erker, G. "Tris(pentafluorophenyl)borane: A Special Boron Lewis Acid for Special Reactions" Dalton Transactions (2005), 1883-1890.] The compound is hygroscopic, forming the trihydrate [(C6F5)3BOH2] (H2O)2, wherein one water in coordinated to boron and the other two waters are hydrogen-bonded to the coordinated water.

Related compounds are Pentafluorophenylboron halides. [Chivers, T. “Pentafluorophenylboron halides: 40 years later” Journal of Fluorine Chemistry (2002), volume 115, page 1-8.]

Other reactions

(C6F5)3B was used to prepare a compound containing a Xe-C bond::(C6F5)3B + XeF2 → [C6F5Xe+] [(C6F5)2BF2]

One study ["Reversible, Metal-Free Hydrogen Activation" Gregory C. Welch, Ronan R. San Juan, Jason D. Masuda, Douglas W. Stephan Science (journal) 17 November 2006: Vol. 314. no. 5802, pp. 1124 - 1126 DOI|10.1126/science.1134230] reported a nucleophilic aromatic substitution on one of the pentafluorinephenyl rings by dimesityl phosphane:

:

The bulky mesityl groups prevent the phosphorus atom from coordinating directly to boron and instead the ring is attacked. When the fluorine atom on boron is replaced by hydrogen with dimethylchlorosilylhydride, the resulting phosphazenium borate is capable of reversible hydrogen storage [See also hydrogen storage]

References


Wikimedia Foundation. 2010.

Нужно сделать НИР?

Look at other dictionaries:

  • Non-coordinating anion — Anions that interact weakly with cations are termed non coordinating anions, although a more accurate term is weakly coordinating anion .[1] Non coordinating anions are useful in studying the reactivity of electrophilic cations. They are commonly …   Wikipedia

  • Organoboron chemistry — Organoboron Organoborane or organoboron compounds are chemical compounds that are organic derivatives of BH3, for example trialkyl boranes. Organoboron chemistry or organoborane chemistry is the chemistry of these compounds.[1] …   Wikipedia

  • Hydrogen storage — describes the methodologies for storing H2 for subsequent use. The methodologies span many approaches, including high pressures and cryogenics, but usually focus on chemical compounds that reversibly release H2 upon heating. Hydrogen storage is a …   Wikipedia

  • Organoborane — PropertiesThe C B bond has low polarity (the difference in electronegativity 2.55 for carbon and 2.04 for boron) and therefore alkyl boron compounds are in general stable though easily oxidized. Vinyl groups and aryl groups donate electrons and… …   Wikipedia

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”