ortho-Borylated trifluoroacetanilides: synthesis and fluoride ion binding properties Academic Article

abstract

• 2006 Taylor and Francis. The o-(pinacolboryl)trifluoroacetanilide (1) has been synthesized and structurally characterized. As indicated by NMR spectroscopy, this novel derivative reacts with fluoride to afford the corresponding fluoroborate derivative [1-F]^- in which the boron-bound fluorine atom forms a hydrogen bond with the proton of the trifluoroacetamide functionality. Compound 1 reacts with KHF2 to afford the corresponding trifluoroborate derivative which has been isolated as a dibenzo-18-crown-6 potassium salt (2). The crystal structure and the ¹H NMR spectrum of this salt confirm the presence of a B-F H-N hydrogen bond.

authors

• Gabbai, Francois

published proceedings

• MAIN GROUP CHEMISTRY

author list (cited authors)

• Hudnall, T. W., Bondi, J. F., & Gabbai, F. P.

citation count

• 9

complete list of authors

• Hudnall, Todd W||Bondi, James F||Gabbaii, Francois P

publication date

• December 2007

publisher

• IOS Press  Publisher

published in

• Main Group Chemistry  Journal

keywords

• Boron
• Fluoride
• Hydrogen-bond

Digital Object Identifier (DOI)

• 10.1080/10241220701596753

start page

• 319

end page

• 327

volume

• 5

issue

• 4

URL

• http://dx.doi.org/10.1080/10241220701596753