Departments of Chemical Biology and Structural Biology, Leibniz-Institut fϋr Molekulare Pharmakologie (FMP), Campus Berlin-Buch, Robert-Roessle-Strasse 10, 13125, Berlin, Germany.
Drug Discovery and Development Centre (H3D), Department of Chemistry, University of Cape Town, Rondebosch, 7701, South Africa.
Angew Chem Int Ed Engl. 2017 Jun 1;56(23):6454-6458. doi: 10.1002/anie.201700520. Epub 2017 Apr 28.
We dissected halogen-aryl π interactions experimentally using a bicyclic N-arylimide based molecular torsion balances system, which is based on the influence of the non-bonded interaction on the equilibria between folded and unfolded states. Through comparison of balances modulated by higher halogens with fluorine balances, we determined the magnitude of the halogen-aryl π interactions in our unimolecular systems to be larger than -5.0 kJ mol , which is comparable with the magnitude estimated in the biomolecular systems. Our study provides direct experimental evidence of halogen-aryl π interactions in solution, which until now have only been revealed in the solid state and evaluated theoretically by quantum-mechanical calculations.
我们使用基于双环 N-芳基酰亚胺的分子扭转平衡系统，通过实验对卤代芳烃π 相互作用进行了剖析，该系统基于非键相互作用对折叠态和展开态平衡的影响。通过比较由较高卤素调制的平衡与氟平衡，我们确定了我们单分子体系中卤代芳烃π相互作用的大小大于-5.0kJ/mol，这与生物分子体系中估计的大小相当。我们的研究提供了卤代芳烃π相互作用在溶液中的直接实验证据，这些相互作用迄今为止仅在固态中被揭示，并通过量子力学计算进行了理论评估。
