title: Spectroscopic analysis and charge transfer interaction studies of 4-benzyloxy-2-nitroaniline insecticide: a density functional theoretical approach.
abstract: A widespread exploration on the intra-molecular charge transfer interaction through an efficient π-conjugated path from a strong electron-donor group (amino) to a strong electron-acceptor group (nitro) has been carried out using FTIR, FT-Raman, UV-Vis, fluorescence and NMR spectra on insecticide compound 4-benzyloxy-2-nitroaniline. Density functional theory method is used to determine optimized molecular geometry, harmonic vibrational wavenumbers and intensities using 6-311G(d,p) basis set by means of Gaussian 09W program suit. A comprehensive investigation on the sp(2) to sp(3) hybridization and non-planarity property has been performed. Natural bond orbital analysis is used to study the existence of C-H⋯O, N-H⋯O and C-H⋯π proper and improper hydrogen bonds. The HOMO and LUMO analysis reveals the possibility of charge transfer within the molecule. A complete assignment of the experimental absorption peaks in the ultraviolet region has also been performed. Isotropic chemical shifts of (13)C, (1)H, (15)N and (18)O NMR and nuclear spin-spin coupling constants have been computed using the gauge-invariant atomic orbital method. The biological activity of substituent amino and nitro groups are evident from the hydrogen bonds through which the target amino acids are linked to the drug as evidenced from molecular docking.
authors.affiliation: Department of Physics, Nesamony Memorial Christian College, Marthandam 629165, Tamil Nadu, India.
authors.forename: D
authors.initials: D
authors.lastname: Arul Dhas
authors.affiliation: Centre for Molecular and Biophysics Research, Department of Physics, Mar Ivanios College, Thiruvananthapuram 695015, Kerala, India.
authors.forename: I
authors.initials: I
authors.lastname: Hubert Joe
authors.affiliation: Department of Physics, Nesamony Memorial Christian College, Marthandam 629165, Tamil Nadu, India.
authors.forename: S D D
authors.initials: SD
authors.lastname: Roy
authors.affiliation: Department of Chemistry, M.G. College, Thiruvananthapuram 695004, Kerala, India.
authors.forename: S
authors.initials: S
authors.lastname: Balachandran
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry*; D001665:Binding Sites; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D019281:Dimerization; D004583:Electrons; D007306:Insecticides / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D056004:Molecular Dynamics Simulation; D066244:Proton Magnetic Resonance Spectroscopy; D011789:Quantum Theory; D012997:Solvents; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D013059:Spectrum Analysis, Raman; D055672:Static Electricity; D014732:Vibration; D014961:X-Ray Diffraction
chemical_list: C000598713:4-benzyloxy-2-nitroaniline; D000814:Aniline Compounds; D007306:Insecticides; D012997:Solvents; C578169:2-nitroaniline
keywords: DFT; Molecular docking; NMR; Raman; UV–Vis