title: First principles and DFT supported investigations on vibrational spectra and electronic structure of 2-((phenylamino)methyl)isoindoline-1,3-dione--an antioxidant active Mannich base.
abstract: The 2-((phenylamino)methyl)isoindoline-1,3-dione (PID) is a synthesized Mannich base which has significant antioxidant activity and biological importance. Quantum mechanical calculations on energy, geometry and vibrational wavenumber of PID were computed using ab initio HF and density functional theory (DFT/B3LYP) methods with 6-31+G/6-311++G(d,p) basis sets. Optimized geometrical parameters obtained by HF and DFT calculations were indicatively agreement with experimental crystal geometry. The experimental FT-Raman and FT-IR spectra of PID has been recorded and analyzed by comparing with simulated spectra. The (1)H and (13)C NMR spectra of title molecule records the chemical shift resulted from shielding and deshielding effects. Natural bond orbital (NBO) analysis has been carried out to calculate various intramolecular interactions that are accountable for the stabilization of this Mannich base. The predicted HOMO-LUMO gap offers interesting information on intramolecular charge transfer and reactivity of the molecular system. Molecular electrostatic potential (MEP) imprint visualize the reactive sites in PID, which is also supported by Mulliken, ESP, Hirshfeld and NBO charges. Thermodynamic properties of PID at various temperatures have been calculated at B3LYP/6-311++G(d,p) in gas phase and the correlations between standard entropies (S), internal energy (E or U) and standard heat capacity (C) with different temperatures.
authors.affiliation: Department of Chemistry, St. Joseph's College, Tiruchirapalli 620 002, Tamil Nadu, India. Electronic address: Jerry.Fedrick@gmail.com.
authors.forename: Maria susai
authors.initials: Ms
authors.lastname: Boobalan
authors.affiliation: Department of Chemistry, St. Joseph's College, Tiruchirapalli 620 002, Tamil Nadu, India.
authors.forename: M
authors.initials: M
authors.lastname: Amaladasan
authors.affiliation: Department of Physics, A.V.C. College, Mayiladuthurai 609 305, Tamil Nadu, India.
authors.forename: S
authors.initials: S
authors.lastname: Ramalingam
authors.affiliation: Department of Chemistry, National Institute of Technology, Tiruchirapalli 620 015, Tamil Nadu, India.
authors.forename: D
authors.initials: D
authors.lastname: Tamilvendan
authors.affiliation: Department of Chemistry, National Institute of Technology, Tiruchirapalli 620 015, Tamil Nadu, India.
authors.forename: G
authors.initials: G
authors.lastname: Venkatesa Prabhu
authors.affiliation: Nanotechnology Centre, University of Bahrain, Bahrain.
authors.forename: M
authors.initials: M
authors.lastname: Bououdina
mesh_terms: D000975:Antioxidants / Q000737:chemistry*; D003198:Computer Simulation; D003460:Crystallization; D004583:Electrons; D006863:Hydrogen-Ion Concentration; D007211:Indoles / Q000737:chemistry*; D054833:Isoindoles / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D012984:Software; D013053:Spectrophotometry; D017550:Spectroscopy, Fourier Transform Infrared; D055672:Static Electricity; D013696:Temperature; D013816:Thermodynamics; D014732:Vibration
chemical_list: C000600936:2-((phenylamino)methyl)isoindoline-1,3-dione; D000975:Antioxidants; D007211:Indoles; D054833:Isoindoles
keywords: 2-((Phenylamino)methyl)isoindoline-1,3-dione; MEP; Mannich base; NBO; NMR; Thermodynamic properties