Formation of 5-Hydroxy-3-methoxy-1,4-naphthoquinone and 8-Hydroxy-4-methoxy-1,2-naphthoquinone from Juglone

Table 2

DFT-calculated ¹H NMR 𝛿_Hs (ppm) for compounds 2, 3, 6, 8, 11, and 12.

Compound	H-2/HO-2/CH3O-2	H-3/HO-3/CH3O-3	HO-5	H-6	H-7/CH3-7	H-8
2-Hydroxy juglone (2)	7.62	6.06	12.33	7.26	7.45	7.76
3-Hydroxy juglone (11)	6.09	7.42	11.04	7.11	7.59	7.77
2-Hydroxy-7-methyl juglone (3)	7.57	6.03	12.34	7.05	2.38	7.62
3-Hydroxy-7-methyl juglone (8)	6.05	7.44	11.05	6.91	2.40	7.62
3, observed [2]	no	6.08	11.69	7.01	2.41	7.42
2-Methoxy juglone (12)	3.68	5.78	12.19	7.17	7.45	7.72
3-Methoxy juglone (6)	5.80	3.69	11.76	7.11	7.51	7.73
6, observed (this work)	6.16	3.92	11.75	7.25	7.64	7.63

Legend: no: not observed.