Ag. Martinez et al., Influence of highly preorganised 7,7-diphenylnorbornane in the free energyof edge-to-face aromatic interactions, CHEM-EUR J, 7(6), 2001, pp. 1171-1175
The influence of preorganised 7,7-diphenylnorbornane in the stability (K-a)
of host-guest complexes as well as in the determination of the energy of e
dge-to-face aromatic interactions has been investigated. The guest molecule
s studied bind more strongly with hosts that contain the cofacial 7,7-diphe
nylnorbornane subunit than with similar hosts that have a 1,1-diphenylcyclo
hexane subunit. On the other hand, the value of the edge-to-face aromatic i
nteractions calculated for our complexes (-0.2 +/-0.6 kJ mol(-1)) is signif
icantly lower (by a factor of seven) than the one previously reported in th
e literature. This result highlights the importance of entropic factors in
the determination of weak noncovalent interactions.