jo050651j_si_001.pdf (138.18 kB)
Planar and Pyramidal Tetracoordinate Carbon in Organoboron Compounds
journal contribution
posted on 2005-08-19, 00:00 authored by Ruslan M. Minyaev, Tatyana N. Gribanova, Vladimir I. Minkin, Andrey G. Starikov, Roald HoffmannUsing previously proposed C(BH)2(CH)2 (16, 17) and C(CH)2B2 (22) systems with a central planar
tetracoordinate carbon (ptC) atom linking two three-membered rings as building blocks, a series
of stable structures containing two and three ptC centers within a molecule have been designed
and computationally studied with the DFT (B3LYP/6-311+G**) method. Inclusion of a carbon atom
ligated with π-accepting and σ-donating boron centers into at least one aromatic ring is critical for
stabilization of a planar structure. A square pyramidal configuration at tetracoordinate carbon
may be achieved in appropriately strained molecules such as [3.3.3.3]tetraborafenestrane 45 and
others by surrounding the carbon with boron-centered ligands.