Synthesis, Spectroscopic, X-ray Diffraction and DFT Studies of Novel Benzimidazole Fused-1,4-Oxazepines.
A 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.
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia. almansor@ksu.edu.sa.
Abdulrahman I
AI
Almansour
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia. anatarajan@ksu.edu.sa.
Natarajan
N
Arumugam
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia. sraju@ksu.edu.sa.
Raju
R
Suresh Kumar
Department of Chemistry, College of Science &amp; Arts, King Abdulaziz University, P. O. Box 344, Rabigh 21911, Saudi Arabia. saied1soliman@yahoo.com.|Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt. saied1soliman@yahoo.com.
Saied M
SM
Soliman
Central Laboratory, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia. altafamu@gmail.com.
Mohammad
M
Altaf
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia. ghabbourh@yahoo.com.|Department of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt. ghabbourh@yahoo.com.
Hazem A
HA
Ghabbour
D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D004583:Electrons; D009682:Magnetic Resonance Spectroscopy; D055095:Optics and Photonics; D010077:Oxazepines / Q000138:chemical synthesis* / Q000737:chemistry; D011789:Quantum Theory; D013056:Spectrophotometry, Ultraviolet; D055672:Static Electricity; D014961:X-Ray Diffraction
D001562:Benzimidazoles; D010077:Oxazepines
1,4-oxazepine; DFT-calculation; X-ray diffraction studies; benzimidazole 2-carboxaldehyde