129786-07-8Relevant articles and documents
NMR studies of bond order in distorted aromatic systems
Gready, Jill E.,Hambley, Trevor W.,Kakiuchi, Kiyomi,Kobiro, Kazuya,Sternhell, Sever,Tansey, Charles W.,Tobe, Yoshito
, p. 7537 - 7540 (2007/10/02)
The 4JH-C=C-Me coupling constant has been previously established1,2 as a probe of bond order. This has now been used to examine the bond orders of compounds containing severely distorted benzene nuclei. In the case of 3,4-di-tert-butyltoluene, no electronic distortions in the aromatic ring can be detected by this method. A series of moderately to severely distorted paracyclophanes show no perturbation of electronic structure, with the possible exception of 8-methyl[6]paracyclophane, which exhibits a barely significant deviation from unstrained values. These conclusions are supported by the results of SCF-MO calculations.