title: Lewis acidity enhancement of triarylboranes via peripheral decoration with cationic groups.
abstract: The cationic boranes [Ar(N+)BMes(2)](+), [Ar(N+)(2)BMes](2+), and [Ar(N+)(3)B](3+) (Ar(N+) = [4-(Me(3)N)-2,6-Me(2)-C(6)H(2)](+); Mes = mesityl) have been synthesized and studied by cyclic voltammetry. The results obtained in this study show that the reduction potential of these derivatives in THF is increased by 0.36 V upon each substitution of a mesityl by a cationic Ar(N+) anilium group. Remarkably, the trication [3](3+), whose triflate salt is water soluble, complexes cyanide anions in pure water at pH 7. These properties underscore the dramatic effects caused by the increased number of cationic groups.
authors.affiliation: Department of Chemistry, Texas A&M University, College Station, Texas 77843, USA.
authors.forename: Ching-Wen
authors.initials: CW
authors.lastname: Chiu
authors.forename: Youngmin
authors.initials: Y
authors.lastname: Kim
authors.forename: François P
authors.initials: FP
authors.lastname: Gabbaï
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry; D001880:Boranes / Q000737:chemistry*; D002412:Cations; D003486:Cyanides / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy
chemical_list: D000814:Aniline Compounds; D001880:Boranes; D002412:Cations; D003486:Cyanides