Intramolecular interactions in ortho-methoxyalkylphenylboronic acids and their catechol esters

Abstract

Catechol esters of ortho-methoxyalkylphenylboronic acids have been synthesized and characterized by (17)O NMR spectroscopy. The results were compared with the data for the parent acids. The influence of intramolecular and intermolecular hydrogen bonds on the properties of the boronic acids has been discussed. The (17)O NMR data for the boronic esters proved that there are no O → B interactions in the investigated compounds. This fact is connected with weak Lewis acidity of the parent acids and their low sugars' receptors activity. Crystal structure of ortho-methoxyphenylboronic acid catechol ester was determined.

Keywords: (17)O NMR; Boronic acids; Boronic esters; Hydrogen bond.