Conformational exchange of 1,8-dibenzoyl-2,7-dimethoxynaphthalene analogues in solution

Akiko Okamoto, Shinji Ohisa, Sayaka Yoshiwaka, Noriyuki Yonezawa


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 (i.e., benzoyl group) or carboxy group-bearing 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.

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