Noncovalent Functional‐Group–Arene Interactions

Hanging in the balance: A series of dibenzobicyclo[3,2,2]nonanes provides a delicate conformational balance for investigating weak interactions, such as OH⋅⋅⋅π(Ar) π-hydrogen bonding (see scheme, red O) and solvent–solute interactions. The models are designed to probe the effectiveness of replacing a hydroxy group by fluorine or to compare the arene affinities of sulfur and oxygen.