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

Abstract

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 1H- and 13C- 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–H⋯O and edge-to-face C–H⋯π 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·L−1) against Ae. aegypti larvae.

Insights into chalcone analogues with potential as antioxidant additives in diesel–biodiesel blends

“…Changing the substituent on aromatic ring 3 promotes a signicant improvement in the planarity, since the planarity in the chalcones is related to donor-acceptor interactions in a molecule, on position and the vicinity of the substituents. [76][77][78] Chalcones have structures that are generally identied with almost planar conformation, a conformational requirement that may be related to their potential for antifungal activity. [78][79][80][81][82] This activity is necessary to maintain the quality of fuels since the proliferation of microorganisms is harmful to the system.…”