Lewis acidity enhancement of triarylboranes via peripheral decoration with cationic groups.
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.
Chiu
Ching-Wen
CW
Department of Chemistry, Texas A&M University, College Station, Texas 77843, USA.
Kim
Youngmin
Y
Gabbaï
François P
FP
D000814:Aniline Compounds / Q000737:chemistry; D001880:Boranes / Q000737:chemistry*; D002412:Cations; D003486:Cyanides / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy
D000814:Aniline Compounds; D001880:Boranes; D002412:Cations; D003486:Cyanides