Table 6. The chemical shifts δ [ppm] from the experimental and theoretical 1H and 13C NMR spectra of studied ligands.
| Ring | Atom no. | Chromone | Flavone | 3-Hydroxyflavone | 3,7-Dihydroxyflavone | Galangin | Kaempferol | Quercetin | ||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Exp. | Calc. | Exp. | Calc. | Exp. | Calc. | Exp. | Calc. | Exp. | Calc. | Exp. | Calc. | Exp. | Calc. | |||
| C4 | 176.35 | 181.52 | 177.08 | 182.07 | 173.00 | 177.34 | 172.36 | 175.33 | 176.3 | 175.00 | 175.91 | 175.17 | 175.90 | 178.09 | C4 | |
| C9 | 155.95 | 163.13 | 162.55 | 163.14 | 154.56 | 161.68 | 162.57 | 163.29 | 164.24 | 164.98 | 163.89 | 164.74 | 163.94 | 164.86 | C9 | |
| C | C2 | 156.90 | 162.59 | 155.67 | 171.17 | 145.12 | 149.53 | 156.58 | 148.98 | 160.77 | 146.89 | 160.71 | 147.28 | 160.78 | 150.109 | C2 |
| C3 | 112.26 | 117.83 | 134.27 | 112.01 | 139.11 | 145.77 | 144.15 | 144.05 | 156.43 | 144.83 | 159.19 | 143.74 | 156.20 | 142.80 | C3 | |
| C10 | 124.91 | 30.28 | 118.51 | 129.58 | 121.30 | 124.90 | 114.28 | 119.18 | 98.34 | 108.89 | 98.20 | 108.58 | 98.25 | 108.85 | C10 | |
| H3/OH3 | 6.33 | 6.89 | 7.32 | 7.31 | 7.59 | 7.26 | 7.38 | |||||||||
| C1’ | - | - | 131.13 | 137.99 | 131.31 | 137.00 | 131.50 | 137.28 | 137.12 | 137.11 | 146.81 | 128.83 | 146.85 | 128.39 | C1’ | |
| C4’ | - | - | 129.09 | 137.27 | 129.83 | 135.45 | 129.54 | 134.94 | 130.96 | 135.30 | 135.66 | 164.42 | 145.11 | 153.35 | C4’ | |
| B | C3’ | - | - | 126.33 | 133.87 | 128.48 | 133.70 | 128.49 | 133.93 | 129.96 | 133.66 | 129.51 | 118.59 | 135.80 | 148.76 | C3’ |
| C5’ | - | - | 126.33 | 134.07 | 128.48 | 133.43 | 128.49 | 133.68 | 129.34 | 133.32 | 129.51 | 118.60 | 135.80 | 119.16 | C5’ | |
| C2’ | - | - | 125.49 | 131.69 | 127.65 | 130.27 | 127.39 | 130.44 | 128.54 | 130.14 | 121.67 | 132.38 | 120.05 | 114.59 | C2’ | |
| C6’ | 125.49 | 132.27 | 127.65 | 135.02 | 127.39 | 134.44 | 127.56 | 134.21 | 121.67 | 136.39 | 115.67 | 129.54 | C6’ | |||
| H2’ | 8.46 | 8.37 | 8.2 | 8.60 | 8.17 | 8.54 | 8.15 | 8.44 | 8.14 | 8.36 | 7.57 | 7.76 | ||||
| H3’/OH3’ | 7.52 | 7.70 | 7.53 | 7.80 | 7.52 | 7.82 | 7.52 | 7.76 | 6.92 | 7.18 | 6.89 | 4.65 | ||||
| H4’/OH4’ | 7.74 | 7.67 | 7.64 | 7.62 | 4.95 | 5.69 | ||||||||||
| H5’ | 7.76 | 7.76 | 7.69 | 7.68 | 9.98 | 7.17 | ||||||||||
| H6’ | 8.46 | 8.18 | 8.2 | 9.08 | 8.17 | 9.08 | 8.15 | 8.98 | 8.15 | 8.83 | 7.68 | 8.38 | ||||
| C9 | 155.95 | 163.13 | 162.55 | 163.14 | 154.56 | 161.68 | 162.57 | 163.29 | 164.24 | 164.98 | 163.89 | 164.74 | 163.94 | 162.45 | C9 | |
| C7 | 134.16 | 139.01 | 131.79 | 139.35 | 133.64 | 139.76 | 138.48 | 168.23 | 145.75 | 168.00 | 156.18 | 167.76 | 147.76 | 169.52 | C7 | |
| A | C5 | 124.23 | 130.66 | 124.77 | 129.69 | 127.79 | 129.91 | 126.60 | 131.68 | 114.05 | 164.73 | 115.44 | 164.60 | 115.13 | 168.06 | C5 |
| C6 | 125.42 | 130.28 | 123.32 | 130.28 | 124.49 | 129.95 | 114.94 | 117.37 | 103.24 | 102.11 | 103.05 | 101.84 | 103.08 | 101.61 | C6 | |
| C10 | 124.91 | 130.28 | 118.51 | 129.58 | 121.30 | 124.90 | 114.28 | 119.18 | 98.34 | 108.89 | 98.20 | 108.58 | 98.25 | 106.61 | C10 | |
| C8 | 118.42 | 123.45 | 106.94 | 122.83 | 118.36 | 122.98 | 102.01 | 106.23 | 93.59 | 96.64 | 93.48 | 98.63 | 93.42 | 96.69 | C8 | |
| H5/OH5 | 8.47 | 8.36 | 8.42 | 8.29 | 5.29 | 5.23 | 5.24 | |||||||||
| H6 | 7.58 | 7.88 | 7.67 | 7.42 | 7.69 | 6.93 | 7.00 | 6.21 | 6.22 | 6.19 | 6.19 | 6.19 | 6.18 | |||
| H7/OH7 | 7.87 | 7.95 | 7.98 | 5.01 | 4.90 | 4.86 | 4.86 | |||||||||
| H8 | 7.72 | 7.78 | 7.82 | 7.69 | 7.87 | 7.45 | 7.18 | 7.08 | 6.66 | 6.44 | 6.61 | 6.41 | 6.57 | |||