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

• Published in: Results in Chemistry 2022-01, Vol.4, p.100665, Article 100665
• Main Authors: Anila Raj, S., Vidya, V.G., Preethi, V., Viju Kumar, V.G.
• Format: Article
• Language: English
• Subjects: Aminoantipyrine; Antimicrobial activity; Benzil; Density Functional Theory; Schiff base; Single Crystal XRD
• ISSN: 2211-7156; 2211-7156
• DOI: 10.1016/j.rechem.2022.100665

[Display omitted] •DDAPDP, a novel single crystal synthesized using the standard crystal synthesis method.•SCXRD technique was used to determine crystal structure.•FTIR, UV visible, 13C NMR and 1H NMR analysis was used to investigate experimental and theoretical spectral analysis of DDAPDP.•Molecular electrostatic potentials, electronic properties, natural bond orbital analysis, atomic charge distribution and thermochemistry were investigated using DFT.•Innovative crystal structure developed to enhance luminescence property of pyrazolone derivatives. 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.