Análise conformacional e interações intramoleculares em ácidos aromáticos fluorados e derivados

Abstract

The conformational study allows understanding several factors related to changes in reactivity and biological activity of a structure, and many of these factors are related to intramolecular interactions. It is known that, in many cases, the fluorine atom in the C-F bond forms weak intramolecular hydrogen bonds or does not form such interaction with acidic hydrogens, due to geometric constraints. The great importance of aromatic organic acids for biological and pharmaceutical purposes, as well as for convenient methods to introduce acidic groups (carboxylic or boronic) to give performance organic molecules and corresponding precursors, is well recurrent in the literature. Some monosubstituted derivatives of phenylboranes/phenylboronic acids, aminofluorobenzoic acids and fluorosalicylic acid were studied to evaluate the strength of possible hydrogen bonds FH(O), XB interactions, as well as other interactions as driving forces of the conformational isomerism in these compounds. The study involves quantum chemical theoretical calculations and spectroscopic techniques, namely nuclear magnetic resonance and infrared.