Synthesis, Spectroscopic, X-ray Diffraction and DFT Studies of Novel Benzimidazole Fused-1,4-Oxazepines
AbstractA series of benzimidazole-tethered oxazepine heterocyclic hybrids has been synthesized in good to excellent yields from an N-alkylated benzimidazole 2-carboxaldehyde, which in turn was accomplished from o-phenylenediamine in three good yielding steps. The calculated molecular structure of compounds 2-methyl-4-(2-((phenylimino)methyl)-1H-benzo-[d]imidazol-1-yl)-butan-2-ol 9 and 10 3,3-dimethyl-N-phenyl-1,2,3,5-tetrahydrobenzo-[4,5]imidazo[2,1-c][1,4]oxazepin-5-amine using the B3LYP/6–31 G(d, p) method were found to agree well with their X-ray structures. The charge distributions at the different atomic sites were computed using the natural bond orbital (NBO) method. The regions of electrophilic and nucleophilic reactivity were shown using a molecular electrostatic potential (MEP) map. In addition, the frontier molecular orbitals of these compounds were discussed at the same level of theory. Nonlinear optical (NLO) properties have also been investigated by computational hyperpolarizability studies, and it was found that Compound 9 is the best candidate for NLO applications. View Full-Text
- Supplementary File 1:
Supplementary (PDF, 6254 KB)
Share & Cite This Article
Almansour, A.I.; Arumugam, N.; Suresh Kumar, R.; Soliman, S.M.; Altaf, M.; Ghabbour, H.A. Synthesis, Spectroscopic, X-ray Diffraction and DFT Studies of Novel Benzimidazole Fused-1,4-Oxazepines. Molecules 2016, 21, 724.
Almansour AI, Arumugam N, Suresh Kumar R, Soliman SM, Altaf M, Ghabbour HA. Synthesis, Spectroscopic, X-ray Diffraction and DFT Studies of Novel Benzimidazole Fused-1,4-Oxazepines. Molecules. 2016; 21(6):724.Chicago/Turabian Style
Almansour, Abdulrahman I.; Arumugam, Natarajan; Suresh Kumar, Raju; Soliman, Saied M.; Altaf, Mohammad; Ghabbour, Hazem A. 2016. "Synthesis, Spectroscopic, X-ray Diffraction and DFT Studies of Novel Benzimidazole Fused-1,4-Oxazepines." Molecules 21, no. 6: 724.
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.