Next Article in Journal
Biologically Synthesized Gold Nanoparticles Ameliorate Cold and Heat Stress-Induced Oxidative Stress in Escherichia coli
Next Article in Special Issue
Design, Synthesis and Antifungal Activity of Novel Benzofuran-Triazole Hybrids
Previous Article in Journal
Four New Monoterpenoid Glycosides from the Flower Buds of Magnolia biondii
Previous Article in Special Issue
Synthesis of Novel UV Absorbers Bisindolylmethanes and Investigation of Their Applications on Cotton-Based Textile Materials
Article Menu
Issue 6 (June) cover image

Export Article

Open AccessArticle
Molecules 2016, 21(6), 724; doi:10.3390/molecules21060724

Synthesis, Spectroscopic, X-ray Diffraction and DFT Studies of Novel Benzimidazole Fused-1,4-Oxazepines

Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
Department of Chemistry, College of Science & Arts, King Abdulaziz University, P. O. Box 344, Rabigh 21911, Saudi Arabia
Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt
Central Laboratory, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
Department of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt
Author to whom correspondence should be addressed.
Academic Editor: Eugene Babaev
Received: 16 April 2016 / Revised: 22 May 2016 / Accepted: 27 May 2016 / Published: 3 June 2016
(This article belongs to the Collection Heterocyclic Compounds)
View Full-Text   |   Download PDF [4851 KB, uploaded 3 June 2016]   |  


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. View Full-Text
Keywords: 1,4-oxazepine; benzimidazole 2-carboxaldehyde; X-ray diffraction studies; DFT-calculation 1,4-oxazepine; benzimidazole 2-carboxaldehyde; X-ray diffraction studies; DFT-calculation

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top