Halogen bonding is the attraction between an electron donor and the electropositive region of a halogen. Designing molecules that exhibit intramolecular halogen bonding provides the opportunity to investigate this relatively weak interaction without entropic complications. In prior studies, “activated” halogen bond donors, with electron-withdrawing fluorine groups, have exhibited strong tendencies toward intramolecular halogen bonding. The purpose of this study is to investigate intramolecular halogen bonding in the absence of electron withdrawing groups, or non-activated systems. Intramolecular halogen bonds within activated systems (A) are formed from quinoline based molecules, where electron donor and acceptor units are linked by an aryldiyne bridge. Conversely, when electron-withdrawing groups are removed, the crystal structure of compound B reveals halogen bond driven dimer formation. Several factors, such as increased N...I distance or decreased π-π stacking propensity of non-fluorinated rings, that explain the differences in crystal behavior between A and B are currently being explored.

Testing the limits of intramolecular halogen bonding

251st National Meeting (2016)

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