HIGH-FIELD NUCLEAR MAGNETIC RESONANCE SPECTRA OF SOME CARCINOGENIC POLYNUCLEAR HYDROCARBONS

High-resolution proton-magnetic-resonance spectra are described for seven carcinogenic polycyclic hydrocarbons: 1,2-benzanthracene, 10-methyl-1,2-benzanthracene, 9,10-dimethyl-1,2-benzanthracene, 20-methylcholanthrene, 1,2,5,6-dibenzanthracene, 1,2-benzpyrene, and 2,3-benzfluoranthene. For all compounds, spectra were recorded at 220 Mc s in CS2 solution; some measurements were also made at 100 Mc/s and some in acetone and in CS2/benzene-d6 solutions. Analyses were made of AB, AMX, and ABMX spin systems; assignments of chemical shifts were assisted by solvent variation, by predictions of shifts in parent hydrocarbons from MO theory, and by known substituent effects in other polycyclics. In the substituted 1,2-benzanthracenes, methyl groups appear to induce a downfield shift on peri protons and a small upfield shift on protons on the remote side of the ring. © 1969.