A complete and unambiguous assignment of 1H and 13C nuclear magnetic resonance (NMR) signals of 29 naphthoquinones is reported on the basis of one- and two-dimensional NMR techniques (1H, 13C, 1H-1H correlated spectroscopy (COSY) and 1H-13C heteronuclear multiple-bond correlation (HMBC)). This is the first report distinguishing data between para-naphthoquinones, ortho- and para-furanonaphthoquinones isomers.
Keywords:
1D and 2D NMR; 1H NMR and 13C NMR; naphthoquinones; furanonaphthoquinones
| 1H (δ, multiplicity, 3JH,H / Hz) | 3J13C (δ / ppm) | 2J13C (δ / ppm) |
|---|---|---|
| H-5 (8.11, d, J7.60) | C-4 (184.50); C-7 (133.16); C-9 (129.62) | - |
| H-6 (7.73, t, J7.40) | C-8 (126.08); C-10 (132.87) | - |
| H-7 (7.64, t, J7.40) | C-5 (127.19); C-9 (129.62) | - |
| H-8 (8.04, d, J7.60) | C-1 (181.56); C-10 (132.87) | - |
| H-1' (6.60, d, J16.00) | C-2 (151.47); C-3'(34.95); C-4 (184.50) | - |
| H-2' (7.10-7.03, m) | C-4'(31.45) | C-3 (120.18) |
| H-3' (2.30, q, J7.00) | C-1'(118.80); C-5'(22.55) | C2'(144.40); C4'(31.45) |
| H-4' (1.49, quint, J 7.20) | C-2' (144.40); C-6'(14.14) | C-3'(34.95); C-5'(22.55) |
| H-5' (1.38, st, J7.20) | C-3'(34.95) | C-6' (14.14) |
| H-6' (0.93, t, J7.20) | C-4'(31.45) | C-5' (22.55) |
| 1H (δ, multiplicity, 3JH,H / Hz) | 3J13C (δ / ppm) | 2J13C (δ / ppm) |
|---|---|---|
| H-7 (7.40, at, J7.70) | C-5 (122.15); C-9 (128.92) | - |
| H-8 (8.00, ad, J7.57) | C-1 (180.89); C-6 (135.46); C-10 (128.78) | C-7 (130.55) |
| H-1' (6.42, s) | C-2 (174.60); C-4 (159.65) | C-3 (122.68) |
| H-3' (2.71, t, J7.60) | C-1'(103.84); C-5'(22.28) | C-2' (160.49); C-4'(29.71) |
| H-4' (1.70, quint, J7.60) | C-2' (160.49); C-6'(13.85) | C-3'(27.70); C-5'(22.28) |
| H-5' (1.44, st, J7.60) | - | C-4'(29.71); C-6'(13.85) |
| H-6' (0.97, t, J 7.60) | C-4'(29.71) | C-5'(22.28) |
| 1H (δ, multiplicity, 3JH,H / Hz) | 3J13C (δ / ppm) | 2J13C (δ / ppm) |
|---|---|---|
| H-5 (8.20-8.17, m) | C-4 (181.06) | - |
| H-8 (8.15-8.13, m) | C-1 (173.23) | - |
| H-1' (6.60, s) | C-2 (151.72); C-4 (181.06) | C-2' (164.99); C-3 (131.95) |
| H-3' (2.81, t, J7.60) | C-1'(104.30); C-5'(22.34) | C-4'(29.68); C-2' (164.99) |
| H-4' (1.75, quint, J7.60) | C-2' (164.99); C-6'(13.83) | C-3'(28.20); C-5'(22.34) |
| H-5' (1.43, st, J7.50) | C-3' (29.20) | C-6'(13.83) |
| H-6' (0.96, t, J7.50) | C-4'(29.68) | C-5'(22.34) |
