title: Hybrid Lewis acid/hydrogen-bond donor receptor for fluoride.
abstract: [reaction: see text] To verify if hydrogen-bond donor groups can assist fluoride binding at the boron center of triaryl boranes, o-(dimesitylboryl)trifluoroacetanilide has been synthesized. Reaction of this new borane with [n-Bu(4)N][F] in acetone affords the corresponding fluoroborate complex whose stability constant exceeds that of [Mes(3)BF](-) by at least 2 orders of magnitude. Presumably, the higher fluoride affinity of o-(dimesitylboryl)trifluoroacetanilide results from the cooperativity of the Lewis acidic boron center and the hydrogen-bond donor trifluoroacetamide group.
authors.affiliation: Department of Chemistry, Texas A&M University, College Station, 77843, USA.
authors.forename: Todd W
authors.initials: TW
authors.lastname: Hudnall
authors.forename: Mohand
authors.initials: M
authors.lastname: Melaïmi
authors.forename: François P
authors.initials: FP
authors.lastname: Gabbaï