Communication: Competition between ππ interaction and halogen bond in solution: A combined 13C NMR and density functional theory study

Abstract

Competition between ππ interaction and halogen bond in solution has been investigated by using carbon nuclear magnetic resonance spectroscopy ( 13C NMR) combined with density functional theory calculation. Both experimental and theoretical results clearly show that there are no C-Clπ or C-Brπ halogen bonds and only the ππ interactions exist in the binary liquid mixtures of C6D6 with C 6F 5Cl and C 6F 5Br, respectively. The case is totally different for the binary liquid mixtures of C6D6 with C6F5I in which the C-Iπ halogen bonds not the ππ interactions are present. The important role of entropy in the competition between ππ interaction and halogen bond in solution was also discussed. © 2012 American Institute of Physics.