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SYNTHESIS, SPECTRAL AND THEORETICAL CHARACTERIZATION OF 5,6-DICHLORO/DIMETHYL-2-(2´,3´/2´,4´/2´,5´/3´,4´/3´,5´-DIMETHOXYPHENYL)-1H-BENZIMIDAZOLES
Authors: Demet Gürbüz, Aydin Tavman, Adem Cinarli, Ismail Boz

Number of views: 511
5,6-Dichloro/dimethyl-2-(2´,3´/2´,4´/2´,5´/3´,4´/3´,5´-dimethoxyphenyl)-1H-benzimidazoles were
synthesized and characterized by using analytical data, FT-IR, FT-Raman, NMR, ESI-MS and fluorescence
spectroscopy. The optimized molecular geometry, zero point energy, dipole moment, ESE, band gap and charge
distributions were calculated by Gaussian 09 using Density Functional Theory (DFT, RB3LYP) with 6-31++G(d,p)
basis set. According to the calculations, the molecules have structures with various torsion angles between the
benzimidazole and benzene rings from 9.7º to 47.8º. The calculated energy values with ZPE correction and DFT
show that the methyl derivatives are more stable than the chloro forms. 3´,4´-Dimethoxy derivatives have higher
decomposition points in comparison with the other compounds in series. The chlorine atoms of 5,6-dichloro-2-(2´,3´/2´,4´/2´,5´/3´,4´/3´,5´-dimethoxyphenyl)-1H-benzimidazoles are positively charged whereas the C5 and
C6 carbon atoms are negatively charged due to the attached chlorine atoms, in virtue of the electron withdrawing characteristic of the imidazole part of the benzimidazole ring. Also, some calculated prominent bond lengths and bond angles were discussed.