Synthesis, characterization and DFT studies of 6-bis(2-(thiazol-4-yl)-benzimidazol-1-yl)hexane hemihydrate crystal: experimental and theoretical investigation
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Date
2019
Authors
El Bourakadi, Khadija
El Mehdi Mekhzoum, Mohamed
Boeré, René T.
El Kacem Qais, Abou
Bouhfid, Rachid
Journal Title
Journal ISSN
Volume Title
Publisher
Elsevier
Abstract
6-bis(2-(thiazol-4-yl)-benzimidazol-1-yl)hexane has been efficiently synthesized by direct
alkylation of 2-(4-thiazolyl)benzimidazole with 1,6-dibromohexane via phase-transfer
catalysis. The desired compound was obtained in high yield and its structural characterization
was performed by FTIR and NMR spectroscopies. A suitable single crystal of the compound
for X-ray structure analysis was obtained and analyzed. The organic salt 1,6-bis(2-(thiazol-4
yl)-benzimidazol-1-yl) hexane (Bis-TBZ 0.5H2O) crystallizes in the monoclinic space group I2/a (#15). The optimized geometries, IR frequencies, 1H and 13C-NMR chemical shifts and
frontier molecular orbital energies (HOMO, LUMO) of the compound have been calculated
by Density Functional Theory at the B3LYP/6-311G++(d,p) level of theory. All the available
theoretical results were compared with the experimental data. The X-ray parameters of the
title compound agree with the theoretically obtained values. The computed vibrational wavenumbers, 1H and 13C-NMR chemical shifts of the compound show good correlation with
the corresponding experimental ones. Finally, the calculated HOMO and LUMO energies
revealed that charge transfer occurs in the molecule.
Description
Sherpa Romeo green journal. Permission to archive accepted author manuscript
Keywords
Thiabendazole , 1,6-bis(2-(thiazol-4-yl)-benzimidazol-1-yl)hexane , X-ray structure , Spectroscopic analysis , DFT calculation , HOMO-LUMO
Citation
El Bourakadi, K., El Mehdi Mekhzoum, M., Boeré, R. T., El Kacem Qais, A., & Bouhfid, R. (2019). Synthesis, characterization and DFT studies of 6-bis(2-(thiazol-4-yl)-benzimidazol-1-yl)hexane hemihydrate crystal: Experimental and theoretical investigation. Journal of Molecular Structure, 1202, 127253. doi: https://doi.org/10.1016/j.molstruc.2019.127253.