Acta Chimica Sinica ›› 2011, Vol. 69 ›› Issue (05): 596-600. Previous Articles     Next Articles




  1. (西北大学合成与天然功能分子化学教育部重点实验室 西北大学化学与材料科学学院 陕西省物理无机化学
    重点实验室 西安 710069)
  • 投稿日期:2010-09-28 修回日期:2010-12-07 发布日期:2011-02-12
  • 通讯作者: 岳可芬
  • 基金资助:


Synthesis, Crystal Structure and Theoretical Calculation of 1,3-Bis(1-ferrocenesulfonyl-2-benzimidazolyl)propane

YUE Ke-Fen, ZHUO Fei, HOU Lei, JIANG Yan-Mei, DI Gao-Hong, YIN Bing, WANG Yao-Yu, WEN Zhen-Yi   

  1. (Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, Shaanxi Key Laboratory of Physico-Inorganic Chemistry, College of Chemistry and Materials Science, Northwest University, Xi an 710069)
  • Received:2010-09-28 Revised:2010-12-07 Published:2011-02-12
  • Contact: YUE Ke-Fen

A new compound, 1,3-bis(1-ferrocenesulfonyl-2-benzimidazolyl)propane, has been prepared, and characterized by 1H NMR, IR, MS and X-ray single crystal diffraction. Its crystal structure belongs to orthorhombic system, space group Pnma, with a=1.30079(13) nm, b=2.9627(3) nm, c=1.01257(10) nm, V=3.9023(7) nm3, Dc=1.492 g/cm3, µ=0.907 mm-1, Z=4, F(000)=1816, R1=0.0506, wR2=0.1583. The crystal structure shows that the title compound is cis-configuration, and not trans-configuration. The cis-configuration and the trans-configuration of the title compound are fully optimized by B3LYP/6-31G method in Gaussian 03 package, and the optimized structures in theory are α-BFBP (cis-configuration) and β-BFBP (trans-configuration), respectively. The results show that the bond lengths and bond angles obtained by quantum chemical calculation are almost the same with those of the experiment, suggesting that the molecular geometry optimization of the structures are reliable and the calculation method used is reliable. Especially, α-BFBP is in accordance with the crystal structure in the main. The molecular total energy of α-BFBP is far lower than that of β-BFBP, indicating that the cis-configuration of the title compound is more stable than the trans-configuration from the thermodynamic point of view. The HOMO energy of α-BFBP is lower than that of β-BFBP, suggesting that antioxidative potential of α-BFBP is superior than β-BFBP. The energy gap of frontier molecular orbits of α-BFBP is bigger than that of β-BFBP, indicating that the ground state of α-BFBP has better stability. In a word, the quantum chemical calculation of the title compound provides a good testimony for the crystal structure. The cis-configuration of the title compound is attributed to terminal direction of zigzag propyl between two benzimidazolyl.

Key words: 1,3-bis(1-ferrocenesulfonyl-2-benzimidazolyl)propane, crystal structure, theoretical calculation, optimized structure, frontier molecular orbit