Influence of Highly Preorganised 7,7-Diphenylnorbornane in the Free Energy of Edge-to-Face Aromatic Interactions

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Abstract
The influence of preorganised 7,7‐diphenylnorbornane in the stability (Ka) of host–guest complexes as well as in the determination of the energy of edge‐to‐face aromatic interactions has been investigated. The guest molecules studied bind more strongly with hosts that contain the cofacial 7,7‐diphenylnorbornane subunit than with similar hosts that have a 1,1‐diphenylcyclohexane subunit. On the other hand, the value of the edge‐to‐face aromatic interactions calculated for our complexes (−0.2±0.6 kJ mol−1) is significantly lower (by a factor of seven) than the one previously reported in the literature. This result highlights the importance of entropic factors in the determination of weak noncovalent interactions.