کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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1406815 | 1501872 | 2008 | 8 صفحه PDF | دانلود رایگان |

Benzimidazole nucleus is present in many biologically active compounds. The synthesis and characterization of new benzimidazole derivatives is driven by the search for enhanced physiological activity. In this contribution, three 1-propenyl isomeric derivatives of 2-methylbenzimidazole (2-MBZM) prepared from the reaction of 2-MBZM with allyl chloride, using a strong base as a catalyst. Gas chromatography–mass spectrometry (GC–MS) was selected as the method of chemical analysis to identify and quantify the products of the reaction which allowed the characterization of two diastereomers: E-1-(1-propenyl)-2-methylbenzimidazole and Z-1-(1-propenyl)-2-methylbenzimidazole and one constitutional isomer: 1-(2-propenyl)-2-methylbenzimidazole. The structures of the compounds were confirmed by 1H and 13C Nuclear Magnetic Resonance. Also FT-Raman, FT-IR and UV–VIS spectral data in a condensed phase have been included. For the interpretation of the experimental results, the structural and spectral characteristics of 1-propenyl-2-methylbenzimidazole have been studied by performing DFT calculations for energies, geometries, vibrational frequencies and shieldings constants (GIAO method). Using the basis set 6-311+G∗∗ and the hybrid density functional B3LYP, the experimental and calculated results were consistent with each other.
Journal: Journal of Molecular Structure - Volume 892, Issues 1–3, 15 December 2008, Pages 477–484