Boronate esters: Synthesis, characterization and molecular base receptor analysis

• Boronate esters formation in moderate yields.
• Donor–acceptor interactions.
• Modulation of boron acidity by changing the substituents of the aryl moiety substituents.
• Modulation on the donor capacity by changing the base nature.

The synthesis of three boronate esters obtained by reacting 4-fluorophenylboronic (1), 4-iodophenylboronic (2) and 3,4-chlorophenylboronic (3) acids with 2,4,5-trihidroxybenzaldehyde is reported. The structural characterization was determined by spectroscopic and spectrometric techniques. The boron atom was evaluated to acts as Lewis acid center in the reaction with pyridine (Py), triethylamine (TEA) and fluoride anion (F−). The titration method was followed by UV–Vis and 11B NMR spectroscopy; results indicate the good interaction with the fluoride ion but poor coordination towards pyridine in solution.