Synthesis, crystal structure analysis, DFT calculations, antioxidant and antimicrobial activity of N,N-di-2,4-dimethoxybenzyl-N'-2-nitrobenzoylthiourea

Abstract

N,N-Di-2,4-dimethoxybenzyl-N'-2-nitrobenzoylthiourea (MBNBT) was synthesized and characterized by 1D and 2D NMR spectroscopy. The molecular structure of MBNBT was also confirmed by SCXRD study. The molecular structure of MBNBT was optimized using the theory level of B3LYP/6–311G(d,p). The obtained theoretical results were compared with experimental ones. Molecular parameters such as bond lengths and bond angles were compared with SCXRD data. Molecular characteristics such as the HOMO-LUMO energy, the energy gap between the LUMO and HOMO energies, and surface maps of molecular electrostatic potential were investigated. Hirshfeld surface analysis showed that H···H (42.5%), H···O/O···H (25.5%), H···C/C···H (17.6%), H···S/S···H (7.1%), and C···O/O···C (2.7%) interactions contact is the most significant contributors in crystal packing of compound. The visualization of 3D topology of molecular packing of the crystal packing for MBNBT is elucidated from energy-framework calculations which suggest that the intermolecular contacts formed between participating molecules are principally dispersive in nature. Furthermore, the antimicrobial and antioxidant activity properties of MBNBT were investigated. The in vitro antioxidant activity of MBNBT was tested by DPPH free radical scavenging activity, H2O2 scavenging activity, superoxide radical scavenging activity and ferric reducing antioxidant power methods. According to the results obtained from the experimental studies, it was determined that MBNBT has effective antioxidant and free radical scavenging activity, when compared with reference substances. At the same time, as a result of antimicrobial activity studies, it was determined that it was effective against C. parapsilosis and C. metapsilosis.