"Frozen" transition States: pentavalent carbon et Al.

Organic ligands have been designed for the stabilization of specific geometries of compounds of nonmetallic elements. These ligands have made possible the isolation, or direct observation, of large numbers of trigonal bipyramidal organo-nonmetallic species. Many of these species are analogs of transition states for nucleophilic displacement reactions and have been stabilized by the ligands to such a degree that they have become ground-state energy minima. Ideas derived from research on these species have been applied to carbon species to generate a molecule that is an analog of the transition state for the associative nucleophilic displacement reaction. The molecule is a pentavalent carbon species that has been observed by nuclear magnetic resonance spectroscopy.