Finding the Perfect Match: Halogen vs Hydrogen Bonding

The prediction of supramolecular structures involving different weak interactions is challenging. In this study, single-atom modifications to the molecular structure allow us to address their hierarchy. The resulting series of unimolecular assemblies are mainly based on halogen bonding (XB), hydrogen bonding (HB), or a combination of both. By varying the XB donor (F, Cl, Br, and I) and the XB and HB acceptors (pyridine vs pyridine-N-oxide) we can control the primary motifs directing the structure.