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Synthesis, characterization and DFT studies of 6-bis(2-(thiazol-4-yl)-benzimidazol-1-yl)hexane hemihydrate crystal: experimental and theoretical investigation
(Elsevier, 2019) El Bourakadi, Khadija; El Mehdi Mekhzoum, Mohamed; Boeré, René T.; El Kacem Qais, Abou; Bouhfid, Rachid
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.