Derivatives of tetrahedral boronic acids

Article abstract of DOI:10.1016/0022-328X(92)83330-K

A series of aliphatic and benzylic bifunctional boronate esters have been prepared as potential ligands for affinity chromatography. α-Acetamido, picolino, thioureido and acetamidino boronates have the hetero atom coordinated with the boron, creating a tetrahedral structure.The 1H, 13C and 11B NMR for these compounds confirm the structure, as well as the hetero atom-boron coordination, and show that the bonding of the internal Lewis base with boron increases in order of coordination strength: pyridine < acetamido < thiourea < acetamidine.Bifunctional boronate esters containing these α-substituents and phenoxy ether or dimethylaminophenoxy ether groups, which can be coupled to a solid matrix via a diazonium bond, were prepared.