Synthesis and anion affinity of a bidendate sulfonium fluorosilane Lewis acid. Academic Article

abstract

• The cationic fluorosilane [1-Ant(2)FSi-2-Me(2)S-(C(6)H(4))](+) (2(+)) readily complexes fluoride ions to afford the corresponding zwitterionic difluorosilicate complex 1-Ant(2)F(2)Si-2-Me(2)S-(C(6)H(4)) (2-F) with a binding constant in CHCl(3) of 7 (+/-1) x 10(6) M(-1). Structural and computational results indicate that the high fluorophilicity of 2(+) arises from both Coulombic and cooperative effects reflected by the formation of a Si-F-->S bridge with a F-->S distance of 2.741(3) A.

authors

• Gabbai, Francois

published proceedings

• Org Lett

author list (cited authors)

• Kim, Y., Kim, M., & Gabbai, F. P.

citation count

• 38

complete list of authors

• Kim, Youngmin||Kim, Mieock||Gabbaiï, François P

publication date

• February 2010

publisher

• American Chemical Society (ACS)  Publisher

published in

• Organic Letters  Journal

keywords

• Acids
• Anions
• Catalysis
• Crystallography, X-Ray
• Hydrocarbons, Fluorinated
• Molecular Conformation
• Molecular Structure
• Silanes

PubMed Central ID

• 20052988

Digital Object Identifier (DOI)

• 10.1021/ol902641v

start page

• 600

end page

• 602

volume

• 12

issue

• 3

URL

• http://dx.doi.org/10.1021/ol902641v