1048641-09-3Relevant academic research and scientific papers
On the synergy of Coulombic and chelate effects in bidentate diboranes: Synthesis and anion binding properties of a cationic 1,8-diborylnaphthalene
Zhao, Haiyan,Gabbai, Francois P.
scheme or table, p. 2327 - 2335 (2012/06/04)
As part of our investigation in the chemistry of bidentate Lewis acids for anion complexation, we have carried out the reaction of 1-(dimesitylboryl)-8- (1′-bora-9′-thia-anthryl)naphthalene (1) with methyltriflate. This reaction proceeds via alkylation of the sulfur atom to afford a bidentate diborane ([2]+) decorated by a peripheral sulfonium unit. This new diborane, which has been isolated as the triflate salt, reacts with both fluoride and azide anions to form the corresponding anion chelate complexes 2-μ2-F and 2-μ2-N3, respectively. Titration experiments carried out in chloroform indicate that the fluoride binding constant of [2]+ exceeds that of 1 by at least 4 orders of magnitude. These results, which are supported by spectroscopic, structural, and computational data, show that chelate and Coulombic effects are additive and can be combined to boost the anion affinity of bidentate Lewis acids.
Fluoride anion chelation by a bidentate stibonium-borane Lewis acid
Wade, Casey R.,Gabbai, Francois P.
scheme or table, p. 4479 - 4481 (2011/11/05)
The stibonium-borane [o-(Ph2MeSb)(Mes2B)C 6H4]+ (4+) has been synthesized and isolated as a triflate salt. Competition experiments carried out with [o-(Ph2MeP)(Mes2FB)C6H4] indicate that 4+ exhibits a much higher fluoride affinity than its lighter phosphorus congener. Structural studies show that the higher fluoride affinity of 4+ is correlated to the Lewis acidity of the stibonium center, which engages the boron-bound fluoride anion in the formation of a B-F→Sb bridge. These results illustrate that the Lewis acidity of main-group onium ions increases as the group is descended.
Azide ion recognition in water-CHCl3 using a chelating phosphonium borane as a receptor
Kim, Youngmin,Hudnall, Todd W.,Bouhadir, Ghenwa,Bourissou, Didier,Gabbai, Franois P.
supporting information; experimental part, p. 3729 - 3731 (2009/12/01)
In H2O-CHCl3, the phosphonium borane [ortho-(Mes 2B)C6H4(PMePh2)]+ selectively complexes azide anions to afford ortho-(Mes2(N 3)B)C6H4
