Conformational profile, vibrational assignments, NLO properties and molecular docking of biologically active herbicide1,1-dimethyl-3-phenylurea

Abstract

1,1-Dimethyl-3-phenylurea (known as fenuron) which is a phenyl urea-based widely used herbicide exhibits interesting structural and conformational properties and a notable biological activity. A detailed analysis on the vibrational, molecular and electronic characteristics of fenuron has been carried out. Potential energy scans (PESs) performed at the B3LYP/6-311++G(d,p) level of theory predicted two possible minima corresponding to the optimized anti and synforms resulting from the internal rotation about the N-C bond. The presence of an auxochrome together with the interaction with DMSO solvent exhibited a blue shift corresponding to the C=O orbitals. Delocalization of HOMO and LUMO orbital facilitated the charge transfer effect in the molecule. The calculated HOMO-LUMO energies, chemical potential, energy gap and global hardness suggested a low softness value for the compound while its biological activity was described by the value of electrophilicity. Chlorine substitution in the phenyl ring influenced the orbital delocalization for ortho and para substitutions but that of meta remained unaffected. NLO properties were noticed to increase due to chlorine substitution in the parent molecule. The docking results suggested that the compound exhibits an inhibitory activity against mitochondrial ubiquinol-cytochrome-c reductase and can be developed as a potential anticancer agent.

Structural and physico-chemical evaluation of melatonin and its solution-state excited properties, with emphasis on its binding with novel coronavirus proteins

“…Such compounds find immense application in electronic displays, surveillance equipment, and consumer electronic gadgets. Computationally, the ability of a molecule to act as an NLO material can be determined from the polarizability and hyperpolarizability data [ [42] , [43] , [44] , [45] ]. The NLO properties of melatonin are shown in Table 2 .…”

“…Natural bond orbital analysis, which is a quantum mechanical method, is useful for this type of study. The molecular orbital properties of melatonin for the occupancy of the natural orbitals were performed by the NBO suite [ 43 ] embedded in the Gaussian software.…”

DFT and molecular docking investigations of oxicam derivatives

“…For that time dependent density functional theory, known as TDDFT is used to simulate the electronic spectra of the compounds. Long range corrected density functional- CAM-B3LYP is used in this study with the generic 6-31G(d) basis set in methanol solvent cage as provided in the PCM solvation model [19]. In the case of tenoxicam, the DOS spectra show no unusual overlap in the frontier molecular orbitals.…”

Excited-state electronic properties, structural studies, noncovalent interactions, and inhibition of the novel severe acute respiratory syndrome coronavirus 2 proteins in Ripretinib by first-principle simulations

“…Intramolecular electron displacements are very essential because they determine the inherent stability of a compound. The NBO analysis is an excellent tool for studying such interactions via hyperconjugations [ [58] , [59] , [60] , [61] ]. The occupancy values of NBOs and their delocalization energy avails valuable information on the aforementioned stabilities.…”