A highly Lewis acidic triarylborane bearing peripheral o-carborane cages

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A triarylborane (2) bearing three o-carborane cages at peripheral positions on the aryl groups was prepared and its crystal structure was determined from X-ray diffraction study. Treatment of 2 with KF in the presence of 18-crown-6 led to the potassium salt, [2F](-). A UV-vis titration experiment carried out in THF/H(2)O (9/1 v/v) showed that 2 binds fluoride ions with a binding constant (K) of 4.8 x 10(4) M(-1), which is an order-of-magnitude greater than K for the mono-carborane substituted triarylborane. The enhanced fluoride ion affinity of 2 indicates an apparent additive effect of multiple carborane substitutions on the Lewis acidity enhancement of the triarylborane. The highly Lewis acidic nature of 2 was further utilized in evaluating the fluoride ion affinity of tris(pentafluorophenyl) borane (B(C(6)F(5))3). A fluoride exchange reaction between [2F](-) and B(C(6)F(5))(3) resulted in 15 times higher fluorophilicity for B(C(6)F(5))(3) than for 2. The lower Lewis acidity of 2 compared with B(C(6)F(5))(3) was confirmed from its greater cathodic reduction potential.
Publisher
ROYAL SOC CHEMISTRY
Issue Date
2011
Language
English
Article Type
Article
Keywords

STEREOSPECIFIC OLEFIN POLYMERIZATION; WEAKLY COORDINATING ANIONS; FLUORIDE-ION COMPLEXATION; BIFUNCTIONAL PERFLUOROARYL BORANES; ELECTRON-ACCEPTING ABILITY; CHARGE-TRANSFER EMISSION; CATIONIC BORANE; METAL-FREE; 3-COORDINATE ORGANOBORON; SELECTIVE COMPLEXATION

Citation

DALTON TRANSACTIONS, v.40, no.44, pp.11758 - 11764

ISSN
1477-9226
URI
http://hdl.handle.net/10203/97992
Appears in Collection
CH-Journal Papers(저널논문)
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