Molecular Structure of 4,16-dichloro- and 4,16-dibromo[2.2]-Paracyclophanes
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science
An x-ray diffraction structural analysis showed that the distortions in the geometries of sterically strained 4,16-dichloro- and 4,16-dibromo[2.2]paracyclophanes are similar to those found in unsubstituted [2.2]paracyclophane. The introduction of bulky halogen atoms at C4 and C16 in the [2.2]paracyclophane molecule does not lead to a marked increase in the steric repulsion of the benzene rings. The polar nature of the halogen atoms leads to dipole-dipole attraction of the antiparallel benzene rings which are drawn somewhat closer to each other and to the halogen atom of the other ring.
Lindeman, Sergey; Struchkov, Yu T.; and Guryshev, Vyacheslav N., "Molecular Structure of 4,16-dichloro- and 4,16-dibromo[2.2]-Paracyclophanes" (1986). Chemistry Faculty Research and Publications. 735.