Table 6.
The experimental and theoretical (6-311+G(d.p)) chemical shifts (δ/ppm) of protons and carbons in NMR spectra of rosmarinic acid and its alkali metal salts in DMSO solutions.
| Rosmarinic acid | Rosmarinates | ||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|
| Atom * | Exp. | Calc. | RA-Li | RA-Na | RA-K | RA-Rb | RA-Cs | ||||
| [8] | Exp. | Calc. | Exp. | Calc. | Exp. | Calc. | Exp. | Exp. | |||
| C1 | 127.6 | 125.36 | 132.75 | 125.48 | 132.86 | 125.48 | 133.07 | 125.45 | 133.20 | 125.45 | 125.41 |
| C2 | 114.5 | 113.26 | 115.54 | 114.73 | 115.47 | 114.73 | 115.19 | 114.68 | 114.88 | 114.21 | 114.62 |
| C3 | 146.8 | 145.93 | 150.95 | 146.07 | 151.38 | 146.00 | 151.19 | 146.09 | 150.95 | 145.88 | 146.15 |
| C4 | 149.7 | 148.63 | 153.46 | 148.86 | 153.02 | 148.73 | 152.75 | 148.73 | 152.25 | 148.71 | 148.85 |
| C5 | 116.2 | 116.70 | 117.72 | 116.81 | 118.13 | 116.70 | 118.08 | 116.70 | 117.76 | 116.73 | 116.77 |
| C6 | 123.1 | 121.58 | 132.56 | 120.90 | 131.59 | 120.82 | 131.45 | 120.57 | 131.20 | 121.05 | 120.58 |
| C7 | 147.6 | 144.94 | 156.96 | 144.47 | 154.15 | 144.39 | 152.48 | 144.39 | 153.42 | 144.93 | 144.47 |
| C8 | 115.2 | 115.40 | 113.42 | 115.58 | 116.60 | 115.49 | 117.16 | 115.47 | 116.75 | 115.50 | 115.54 |
| C9 | 168.5 | 165.92 | 171.03 | 166.33 | 170.56 | 166.30 | 170.56 | 166.32 | 170.39 | 166.16 | 166.38 |
| C1′ | 129.4 | 127.29 | 132.45 | 129.87 | 137.31 | 129.83 | 138.78 | 129.88 | 139.68 | 128.99 | 129.88 |
| C2′ | 117.5 | 115.77 | 119.00 | 116.17 | 119.55 | 116.06 | 118.98 | 116.00 | 119.11 | 116.03 | 116.04 |
| C3′ | 146.1 | 145.60 | 149.36 | 145.05 | 148.07 | 144.98 | 147.81 | 144.98 | 147.56 | 144.97 | 145.03 |
| C4′ | 145.2 | 144.02 | 150.28 | 143.71 | 148.58 | 143.63 | 148.13 | 143.61 | 148.28 | 143.78 | 143.66 |
| C5 | 116.5 | 114.90 | 119.00 | 115.17 | 119.10 | 115.11 | 119.10 | 115.23 | 118.83 | 115.16 | 115.29 |
| C6′ | 121.8 | 120.04 | 127.96 | 119.75 | 126.75 | 119.67 | 126.49 | 119.60 | 126.38 | 119.80 | 119.62 |
| C7′ | 37.9 | 36.11 | 41.07 | 37.23 | 35.83 | 37.25 | 36.02 | 37.26 | 35.83 | 36.84 | 37.25 |
| C8′ | 74.8 | 72.82 | 144.95 | 75.93 | 144.37 | 75.95 | 143.79 | 76.11 | 144.91 | 74.89 | 76.21 |
| C9′ | 167.4 | 170.83 | 165.08 | 172.88 | 183.49 | 173.07 | 179.28 | 172.51 | 175.57 | 172.11 | 172.52 |
| H2 | 6.88 | 7.06 | 7.65 | 7.05 | 7.65 | 7.05 | 7.61 | 7.05 | 7.50 | 7.06 | 7.06 |
| H3 | 9.64 | 5.47 | 5.41 | 5.35 | 5.30 | ||||||
| H4 | 8.79 | 4.99 | 4.86 | 4.84 | 4.91 | ||||||
| H5 | 6.61 | 6.77 | 7.00 | 6.76 | 6.95 | 6.76 | 6.98 | 6.74 | 7.03 | 6.76 | 6.74 |
| H6 | 6.79 | 7.01 | 7.03 | 6.92 | 7.04 | 6.92 | 7.05 | 6.90 | 6.96 | 6.95 | 6.90 |
| H7 | 7.39 | 7.47 | 7.74 | 7.38 | 7.98 | 7.38 | 7.84 | 7.38 | 7.73 | 7.41 | 7.39 |
| H8 | 6.11 | 6.24 | 6.54 | 6.19 | 6.42 | 6.19 | 6.40 | 6.18 | 6.38 | 6.21 | 6.19 |
| H2′ | 6.59 | 6.68 | 7.03 | 6.69 | 6.85 | 6.68 | 6.81 | 6.68 | 6.76 | 6.68 | 6.68 |
| H3′ | 8.73 | 4.50 | 4.35 | 4.30 | 4.30 | ||||||
| H4′ | 9.16 | 5.27 | 5.17 | 5.06 | 4.98 | ||||||
| H5′ | 6.54 | 6.64 | 6.97 | 6.61 | 6.97 | 6.61 | 6.96 | 6.60 | 6.94 | 6.62 | 6.60 |
| H6′ | 6.47 | 6.53 | 7.05 | 6.50 | 6.91 | 6.50 | 7.02 | 6.49 | 7.00 | 6.51 | 6.49 |
| H7′ | 2.85 | 2.99 | 4.34 | 3.05 | 4.81 | 3.03 | 4.83 | 3.01 | 4.10 | 3.02 | 3.00 |
| H7′’ | 2.93 | 2.90 | 3.56 | 2.77 | 4.30 | 2.78 | 4.24 | 2.77 | 5.31 | 2.81 | 2.77 |
| H8′ | 5.03 | 5.03 | 4.90 | 4.89 | 4.86 | 4.93 | 4.85 | ||||
| H9′ | 12.99 | 5.96 | |||||||||
* the numbering of atoms according to Figure 1.