Synthesis, Characterization, Single Crystal Structural Studies, Antibacterial Activity and DFT Investigations of 2-Chloro-5-Ethoxy-3,6-Bis(Methylamino)-1,4-Benzoquinone

Abstract

A new compound 2-chloro-5-ethoxy-3,6-bis(methylamino)-1,4-benzoquinone (cemb) has been synthesized and characterized by various physicochemical techniques. The compound crystallizes in the triclinic system with the space group P-1 and contains extended hydrogen bonding interaction providing supramolecular architecture. The compound contains CH∙∙∙π and oxygen∙∙∙π interaction which stabilizes the crystal structure and is also responsible for the semiconducting behavior. The DFT calculations in the gaseous phase of cemb with B3LYP hybrid functional show good correlation with experimental results (single crystal XRD data) and are used to predict the molecular properties. Excluding the side ethyl group, the structure possesses Cs symmetry. The ring breathing mode of vibration is found to have frequency (551 cm-1) which is much lower as compared to the corresponding mode of benzene (991 cm-1). The bioefficacy of the compound has been examined against the growth of bacteria in vitro to evaluate antimicrobial potential. The pphotoluminescence properties indicate that the compound has characteristic fluorescence emissions. The HOMO and LUMO energy gap reveals that the energy gap reflects the chemical activity of the molecule.