Table 1. GIAO/B3LYP/6-311++G(d,p)-Calculated 1H, 13C, and 15N NMR Chemical Shifts (δ in ppm) and Coupling Constants (J in Hz).
| 2a | 3a | 2b | 3b | 2c | 3c | 2d | 3d | 2e | 3e | |
|---|---|---|---|---|---|---|---|---|---|---|
| nuclei | H | H | 4-NO2 | 4-NO2 | 5-NO2 | 5-NO2 | 6-NO2 | 6-NO2 | 7-NO2 | 7-NO2 |
| 1H (ppm) | ||||||||||
| H3 | 7.83 | 7.82 | 8.79 | 8.70 | 8.00 | 8.05 | 7.94 | 7.88 | 7.96 | 7.97 |
| H4 | 7.65 | 7.62 | NO2 | NO2 | 8.70 | 8.78 | 7.64 | 7.61 | 7.87 | 7.92 |
| H5 | 7.16 | 7.06 | 8.26 | 8.25 | NO2 | NO2 | 8.16 | 8.05 | 7.15 | 7.08 |
| H6 | 7.37 | 7.26 | 7.35 | 7.29 | 8.40 | 8.23 | NO2 | NO2 | 8.17 | 8.49 |
| H7 | 7.48 | 7.72 | 7.77 | 8.03 | 7.40 | 7.64 | 8.55 | 8.82 | NO2 | NO2 |
| CH2 | 5.64 | 5.48 | 5.70 | 5.54 | 5.63 | 5.48 | 5.72 | 5.52 | 6.16 | 5.54 |
| OH | 1.59 | 2.15 | 1.74 | 2.29 | 1.79 | 2.33 | 1.80 | 2.28 | 1.42 | 2.59 |
| 13C (ppm) | ||||||||||
| C3 | 134.0 | 120.8 | 135.4 | 125.3 | 136.7 | 125.8 | 134.1 | 122.0 | 134.7 | 122.9 |
| C3a | 126.6 | 123.7 | 120.3 | 116.7 | 125.5 | 121.6 | 129.4 | 125.8 | 131.2 | 126.7 |
| C4 | 120.6 | 120.2 | 142.1 | 142.6 | 118.6 | 120.0 | 120.1 | 120.2 | 126.8 | 128.8 |
| C5 | 120.8 | 122.3 | 119.3 | 121.9 | 144.5 | 145.3 | 117.0 | 117.6 | 119.5 | 120.0 |
| C6 | 126.0 | 126.1 | 124.3 | 123.9 | 122.5 | 121.7 | 147.8 | 148.4 | 125.8 | 126.4 |
| C7 | 108.4 | 119.0 | 115.7 | 128.0 | 107.8 | 118.6 | 106.3 | 117.6 | 138.8 | 139.8 |
| C7a | 139.7 | 150.8 | 140.7 | 151.2 | 141.2 | 151.3 | 138.0 | 148.7 | 131.4 | 142.6 |
| CH2 | 72.4 | 76.7 | 73.0 | 77.0 | 72.8 | 77.0 | 72.7 | 77.2 | 76.5 | 77.2 |
| 15N (ppm) | ||||||||||
| N1 | –181.1 | –93.3 | –177.8 | –91.4 | –177.2 | –91.4 | –174.7 | –81.9 | –172.4 | –87.7 |
| N2 | –60.7 | –144.5 | –50.1 | –136.0 | –52.4 | –136.2 | –45.4 | –133.5 | –48.4 | –136.3 |
| NO2 | –15.8 | –16.1 | –17.3 | –16.7 | –16.8 | –16.2 | –14.1 | –17.6 | ||
| SSCC (Hz) | ||||||||||
| 3JCH2OH | –10.7 | –9.3 | –10.9 | –9.4 | –10.9 | –9.5 | –10.9 | –9.5 | –10.3 | –9.3 |
| 3JH4H5 | 7.4 | 7.8 | NO2 | NO2 | NO2 | NO2 | 8.2 | 8.6 | 7.2 | 7.6 |
| 3JH5H6 | 6.4 | 6.2 | 7.3 | 7.2 | NO2 | NO2 | NO2 | NO2 | 7.3 | 7.2 |
| 3JH6H7 | 7.7 | 8.1 | 7.6 | 7.9 | 8.6 | 8.5 | NO2 | NO2 | NO2 | NO2 |
| 4JH4H6 | 0.4 | 0.5 | 1.5 | 1.5 | 0.3 | 0.5 | ||||
| 4JH5H7 | 0.3 | 0.3 | 0.2 | 0.2 | 1.3 | 1.4 | ||||
| 5JH3H7 | 0.6 | 0.8 | 0.6 | 0.7 | 0.6 | 0.7 | 0.8 | 0.8 | NO2 | NO2 |