Synthesis, Molecular Structure, Thermal and Spectroscopic Analysis of a Novel Bromochalcone Derivative with Larvicidal Activity

Chalcones belong to the flavonoids family and are natural compounds which show promising larvicidal property against Aedes aegypti larvae. Aiming to obtain a synthetic chalcone derivative with high larvicidal activity, herein, a bromochalcone derivative, namely (E)-3-(4-butylphenyl)-1-(4-bromophenyl)-prop-2-en-1-one (BBP), was designed, synthesized and extensively characterized by H-1- and C-13- nuclear magnetic resonance (NMR), infrared (IR), Raman spectroscopy, mass spectrometry (MS), ultraviolet-visible spectroscopy (UV-Vis), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), and X-ray diffraction. Further, the quantum mechanics calculations implemented at the B3LYP/6-311+G(d)* level of the theory indicate that the supramolecular arrangement was stabilized by C-HMIDLINE HORIZONTAL ELLIPSISO and edge-to-face C-HMIDLINE HORIZONTAL ELLIPSIS pi interactions. The EGAP calculated (3.97 eV) indicates a good reactivity value compared with other similar chalcone derivatives. Furthermore, the synthesized bromochalcone derivative shows promising larvicidal activity (mortality up to 80% at 57.6 mg center dot L-1) against Ae. aegypti larvae.

Automated summary

In this study, a bromochalcone derivative with high larvicidal activity against Ae. aegypti larvae was successfully designed and synthesized. The compound's structure and properties were extensively characterized, and its reactivity value was found to be higher compared to similar derivatives through calculations.