Nwachukwu Chideraa I, Bowling Nathan P, Bosch Eric
Chemistry, Missouri State University, 901 South National Avenue, Springfield, MO 65897, USA.
Department of Chemistry, University of Wisconsin-Stevens Point, 2001 Fourth Avenue, Stevens Point, WI 54481, USA.
Acta Crystallogr C Struct Chem. 2017 Jan 1;73(Pt 1):2-8. doi: 10.1107/S2053229616018702.
Halogen bonding is a well-established and intensively studied intermolecular interaction that has also been used in the preparation of functional materials. While polyfluoroiodo- and polyfluorobromobenzenes have been widely used as aromatic halogen-bond donors, there have been very few studies of iodoimidazoles with regard to halogen bonding. We describe here the X-ray structures of three iodoimidazole derivatives, namely 1-benzyl-2-iodo-1H-imidazole, CHIN, (1), 1-benzyl-4-iodo-1H-imidazole, CHIN, (2), and 1-benzyl-2-iodo-1H-benzimidazole, CHIN, (3), and the halogen bonds that dominate the intermolecular interactions in each of these three structures. The three-dimensional structure of (1) is dominated by a strong C-I...N halogen bond, with an N...I distance of 2.8765 (2) Å, that connects the molecules into one-dimensional zigzag ribbons of molecules. In contrast, the three-dimensional structures of (2) and (3) both feature C-I...π halogen-bonded dimers.
卤键是一种已被充分确立且得到深入研究的分子间相互作用，它也被用于功能材料的制备。虽然多氟碘苯和多氟溴苯已被广泛用作芳香族卤键供体，但关于碘代咪唑的卤键研究却非常少。我们在此描述三种碘代咪唑衍生物的X射线结构，即1-苄基-2-碘-1H-咪唑（CHIN，(1)）、1-苄基-4-碘-1H-咪唑（CHIN，(2)）和1-苄基-2-碘-1H-苯并咪唑（CHIN，(3)），以及在这三种结构中主导分子间相互作用的卤键。(1)的三维结构由一个强C-I...N卤键主导，N...I距离为2.8765 (2) Å，该卤键将分子连接成一维之字形分子链。相比之下，(2)和(3)的三维结构均以C-I...π卤键二聚体为特征。
