Experimental and theoretical study of a new functionalized derivative of 3-methyl-2-trifluoromethyl chromone

The research of new chemical compounds with medicinal potential is essential to address a wide range of diseases and pathogens that represent a significant challenge to human health and the optimal functioning of society. Among these compounds, chromones and their functionalized derivatives stand out due to their biological activity. The introduction of halogen substituents, such as difluoromethylene (-CF₂-) and trifluoromethyl (-CF₃) groups, can significantly enhance this activity due to their relevant properties such as high electronegativity, lipophilicity, metabolic stability, and bioavailability.

In this study, a derivative of 3-methyl-2-pentafluoroethylchromone substituted with a nitro group was synthesized through a nitration reaction in a controlled environment using a sulfuric acid and nitric acid (H₂SO₄/HNO₃) mixture. The characterization of the synthesized products was carried out using vibrational spectroscopic techniques (IR), electronic (UV-Visible) techniques, and nuclear magnetic resonance (NMR) of ¹H and ¹³C. Additionally, quantum chemical calculations were performed using different levels of theory to determine the lowest energy conformations, justify the stabilizing interactions through NBO calculations, and predict theoretical spectra to aid in the interpretation of the experimental results.

Preliminary results showed a 79% yield in the production of the compound through the nitration reaction and a good agreement between theoretical and experimental results.