Department of Chemistry, Lash Miller Laboratories, University of Toronto, 80 St George St., Toronto ON M5S 3H6, Canada.
Chemistry. 2013 Feb 4;19(6):2050-8. doi: 10.1002/chem.201202689. Epub 2012 Dec 28.
The interactions of iodoperfluoroarenes and -alkanes with anions in organic solvent were studied. The data indicates that favorable halogen-bonding interactions exist between halide anions and the monodentate model compounds C(6)F(5)I and C(8)F(17)I. These data served as a basis for the development of preorganized multidentate receptors capable of high-affinity anion recognition. Several new receptor architectures were prepared, and the multidentate-iodoperfluorobenzoate-ester design, as described in a preliminary communication, was evaluated in more detail. Computation was employed to better interpret the structure-activity relationships arising from these studies. Investigations of the thermodynamics of anion binding (by van't Hoff analysis) and solvent effects reveal details of these halogen bonding interactions.
研究了碘代全氟芳烃和 -烷烃与有机溶剂中阴离子的相互作用。数据表明，卤化物阴离子与单价模型化合物 C(6)F(5)I 和 C(8)F(17)I 之间存在有利的卤素键相互作用。这些数据为开发能够高亲和力识别阴离子的预组织多齿受体提供了依据。制备了几种新的受体结构，并更详细地评估了初步通讯中描述的多齿碘代全氟苯甲酸盐酯设计。计算被用来更好地解释这些研究中出现的结构-活性关系。通过范特霍夫分析研究阴离子结合的热力学和溶剂效应揭示了这些卤素键相互作用的细节。
