NMR Studies of Bond Order in Distorted Aromatic Systems

Jill E. Gready, Trevor W. Hambley, Kiyomi Kakiuchi, Kazuya Kobiro, Tobe Yoshito, Sever Sternhell*, Charles W. Tansey

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

24 Scopus citations

Abstract

The 4JH-C⩵C-Mecoupling constant has been previously established1,2as 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.

Original languageEnglish
Pages (from-to)7537-7540
Number of pages4
JournalJournal of the American Chemical Society
Volume112
Issue number21
DOIs
StatePublished - 1 Jan 1990

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