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Complexes of 2,2′,2″‐Nitrilotriphenol. Part 1. A Study of Bimolecular Nucleophilic Substitution at the Boron Atom
Author(s) -
Müller Edgar,
Bürgi HansBeat
Publication year - 1987
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19870700303
Subject(s) - chemistry , intramolecular force , quinuclidine , nucleophilic substitution , nucleophile , pyridine , substitution reaction , medicinal chemistry , boron , ligand (biochemistry) , photochemistry , stereochemistry , organic chemistry , catalysis , biochemistry , receptor
The tetradentate ligand 2,2′,2″‐nitrilotriphenol forms a boron complex III with an intramolecular, transannular N→B dative bond of 1.68 Å in a strained tricyclo[3.3.3.0]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 N 2).