Single crystal XRD and DFT investigation of 1,5-dimethyl-4-[(2-oxo-1,2-diphenylethylidene) amino]-2-phenyl-1,2-dihydro-3H-pyrazol-3-one

Abstract

The single crystal 1,5-dimethyl-4-[(2-oxo-1,2-diphenylethylidene) amine]-2-phenyl-1,2-dihydro-3H-pyrazol-3-one [DDAPDP] was designed to enhance luminescence property using benzil and 4-aminoantipyrine. DFT calculations of DDAPDP were done with Gaussian 16 W program employing hybrid functional B3LYP with 6–311++G (d,p) basis set for geometry optimization without symmetry constraints. The single crystal was studied based on theoretical aspects such as Frontier Molecular Orbital (FMO), Natural Bond Orbital (NBO), Mullikan atomic charge and Molecular Electrostatic Potential (MEP) using density functional method. The experimental and theoretical spectral analysis of the single crystal system was investigated using FTIR, Raman, UV –visible, 1H NMR and 13C NMR techniques. Positive electrostatic potential regions dispersed throughout the rings and represent possible nucleophilic attack sites, whereas negative electrostatic potential regions are typically grouped around the CO group. Energy gap −3.776391 eV, confirmed by the estimated HOMO and LUMO energies. Natural bond orbital analysis (NBO) was used to assess the molecule's stability as a result of charge delocalization and hyper conjugation. Electron population of each atom was calculated by Mulliken atomic charge distribution analysis. The bacterium E. coli (Gram negative) and the organism S. aureus, together with a standard medication, were used to study and assess the compounds' antimicrobial activity in vitro, which reveals the antibacterial and antifungal activities of DDAPDP.

Keywords

• Aminoantipyrine
• Benzil
• Density Functional Theory
• Schiff base
• Single Crystal XRD
• Antimicrobial activity