Halogen bonding: An investigation of solvent and substituent effects in solution.

摘要

An investigation into solvent and substituent effects on halogen bonding strength in solution are described. Through initial investigations towards applications in catalysis, we quickly realized that information concerning halogen bonding interactions in solution are quite limited, and quantitative studies examining solvent and substituent effects are even more rare. Herein, an investigation as to the solvent effects on the halogen bond interaction of perfluorooctyliodide and triethylamine is reported. Also, an examination of para-substituent effects on the interaction of iodotetraflurobenzene analogs with triethylamine is discussed. Through 19F NMR binding isotherm experiments which involved varying the concentration of halogen bond acceptor (triethylamine), while keeping that of the donor constant, an association constant was calculated for all systems. Correlating the calculated association constants with various parameters of the system in question was attempted, with the goal of identifying trends and relationships in modeling the data.