Complete assignment of 1H and 13C NMR spectra of benz[α]anthracene-7,12-dione and its nitro derivative

Benz[a]anthracene-7, 12-dione (1) was nitrated directly by nitric acid and a nitro-derivative (2) was obtained. Molecular orbital calculation predicted that the nitration reaction occurs in the C1 or C4 position of (1). To determine the position of the nitro group of(2), NMR chemical shifts were used. The absence of the chemical shift at delta9.7 in (2) clearly indicated that the nitro substituent issituated at the C1 position. The methodologies of FG-HOHAHA, FG-NOESY, FG-CH-COSY, and FG-HMBC were also used for detailed NMR spectral determination for their polycyclic aromatic ketons.