Complexes of 2,2',2 -Nitrilotriphenol. Part 1. A Study of Bimolecular Nucleophilic Substitution at the Boron Atom

Article abstract of DOI:10.1002/hlca.19870700303

The tetradentate ligand 2,2',2 -nitrilotriphenol forms a boron complex III with an intramolecular, transannular N->B dative bond of 1.68 Angstroem in astrained tricyclo<3.3.0>undecane chelating system.The complex reacts with nitrogen bases L, such as pyridine, quinuclidine and others, to form complexes III-L, in which the intramolecular B-N bond is replaced by one between B and the external nucleophile.In solution, this displacement reaction is reversible.It was studied by temperature-dependent NMR spectroscopy.The resulting reaction and activation parameters suggest that the reaction is a bimolecular nucleophilic substitution (S_N2).