A hybrid Lewis acid/hydrogen bond donor receptor for fluoride

INOR 35

Todd W. Hudnall, thudnall@mail.chem.tamu.edu and François P. Gabbaï, gabbai@mail.chem.tamu.edu. Department of Chemistry, Texas A&M University, MS 3255, College Station, TX 77843-3255
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-Bu4N][F] in acetone affords the corresponding fluoroborate complex whose stability constant exceeds that of [Mes3BF]- by at least two 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.
 

Main Group
9:00 AM-11:20 AM, Sunday, 10 September 2006 Moscone Center -- Room 307, Oral

Division of Inorganic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006