Abstract

Dynamic feature of 1,8-dibenzoyl-2,7-dimethoxynaphthalene in solution is revealed through systematic comparison with the analogues
bearing p-carboxy group or p-amino one. (Carbonyl)C–C(naphthalene) bond rotation of aroyl group in amino group-bearing analogue is
slower than that of aroyl group in no substituent-bearing (i.e., benzoyl group or carboxy group) analogues. NMR study of unsymmetrically
substituted 1,8-dibenzoylnaphthalene analogues shows that (carbonyl)C–C(naphthalene) bond rotation of one benzoyl group is retarded by
the other aroyl group bearing p-amino group. These results strongly indicate that the bond rotation behaviour of two aroyl groups in the
1,8-diaroylnaphthalene analogue does not occur independently with each other but cooperatively.

Key words: peri-Aroylated naphthalene, Solution structure, Cooperative bond rotation, interconversion behaviour, 1H NMR study.