bis-(1H-Benzimidazol-2-yl)-methanone: New preparation method, crystal structure, vibrational spectroscopy and DFT calculations

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• 作者：Fabio da Silva Mir ; a ; Fabrí ; cio Gava Menezes ; Juliano Vicente ; Adailton J. Bortoluzzi ; Cé ; sar Zucco ; Ademir Neves ; Norberto Sanches Gonç ; alves
• 关键词：Benzimidazole ; B3LYP ; Vibrational spectroscopy
• 刊名：Journal of Molecular Structure
• 出版年：2009
• 出版时间：16 December 2009
• 年：2009
• 卷：938
• 期：1-3
• 页码：1-9
• 全文大小：590 K

文摘

This study reports a new preparation of bis-(1H-benzimidazol-2-yl)-methanone, 3, an interesting compound prepared by the oxidation of bis-(1H-benzimidazol-2-yl)-methane using two methods: (i) Fe(II)/O₂ in ethanol–water and (ii) hydrogen peroxide in acetic acid. Products of both methodologies were properly characterized by elemental analysis, IR, Raman, (¹H and ¹³C) NMR and X-ray crystallography. DFT calculations [B3LYP/6-31+G(d,p)] also showed good agreement between the theoretical and experimental values of optimized and X-ray structures as well as between the vibrational and NMR spectroscopy. The study of the conformational dynamics of 3 found a low energy barrier (0.41 kcal mol⁻¹) between the two conformations in the DMSO phase.