ObjectivesMolecular structures, spectroscopic properties, charge distributions, frontier orbital energies, nonlinear optical (NLO) properties and molecular docking simulations were analyzed to examine the bio-usefulness of a series of (4-fluorophenyl)[5-(4-nitrophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]methanone derivatives.MethodsThe compounds were studied through computational methods. Equilibrium optimization of the compounds was performed at the B3LYP/6-31G(d,p) level of theory, and geometric parameters, frequency vibration, UV–vis spectroscopy and reactivity properties were predicted on the basis of density functional theory (DFT) calculations.ResultsThe energy gap (ΔEg), electron donating/accepting power (ω−/ω+) and electron density response toward electrophiles/nucleophiles calculated forM1andM2revealed the importance of substituent positioning on compound chemical behavior. In addition,ω−/ω+ and ΔEn/ΔEe indicated thatM6is more electrophilic because of the presence of two NO2groups, which enhanced its NLO properties. The hyperpolarizability (β0) of the compounds ranged from 5.21 × 10−30to 7.26 × 10−30esu and was greater than that of urea; thus,M1–M6were considered possible candidates for NLO applications. Docking simulation was also performed on the studied compounds and targets (PDB ID:5ADHand1RO6),and the calculated binding affinity and non-bonding interactions are reported.ConclusionThe calculated ω−and ω+indicated the electrophilic nature of the compounds;M6, a compound with two NO2groups, showed enhanced effects. Molecular electrostatic potential (MEP) analysis indicated that amide and nitro groups on the compounds were centers of electrophilic attacks. The magnitude of the molecular hyperpolarizability suggested that the entire compound had good NLO properties and therefore could be explored as a candidate NLO material. The docking results indicated that these compounds have excellent antioxidant and anti-inflammatory properties.