Fluoride ion capture from water with a cationic borane. Academic Article

abstract

• The reaction of the [Li(THF)4]+ salt of dimesityl-1,8-naphthalenediylborate with [Me2NCH2]I affords a borane (1-(Mes2B)-8-(Me2NCH2)-C10H6) which can be converted into a cationic borane [3]+ ([1-(Mes2B)-8-(Me3NCH2)-C10H6]+) by methylation with MeOTf. This cationic borane promptly complexes fluoride to afford the corresponding zwitterionic ammonium/fluoroborate 3-F (1-(Mes2FB)-8-(Me3NCH2)-C10H6). Cation [3]+ fails to react with chloride, bromide, and iodide indicating that fluoride complexation is selective. Structural, spectroscopic, and computational studies carried out on 3-F show the existence of an unusual C-H...F-B hydrogen bond. Remarkably, [3]+ captures fluoride from water under biphasic conditions (H2O/CHCl3) to form 3-F. The high fluoride affinity of [3]+ can be correlated to the Coulombic forces which stabilize the B-F bond against heterolysis.

authors

• Gabbai, Francois

published proceedings

• J Am Chem Soc

altmetric score

• 3

author list (cited authors)

• Chiu, C., & Gabbai, F. P.

citation count

• 199

complete list of authors

• Chiu, Ching-Wen||Gabbaiï, François P

publication date

• November 2006

publisher

• American Chemical Society (ACS)  Publisher

published in

• Journal of the American Chemical Society  Journal

keywords

• 0306 Physical Chemistry (incl. Structural)

PubMed Central ID

• 17076485

Digital Object Identifier (DOI)

• 10.1021/ja0658463

start page

• 14248

end page

• 14249

volume

• 128

issue

• 44

URL

• http://dx.doi.org/10.1021/ja0658463