From: Mesoionic compounds with antifungal activity against Fusarium verticillioides
Compound | IR | 1 H NMR | 13 C NMR |
---|---|---|---|
ν (cm −1 ) | (δ) | (δ) | |
MI-1 | 3432 (N-H); 3056 (C-H); 2670 (C = NH+); 1567 (C = N); 1330 (C-S) | 7.95 (d, H-α), 7.83-7.19 (m, 15 H), 7.06 (d, H-β) | 159.2 (C-5), 147.8 (C-2), 137.0 (C-α), 133.9-118.7 (18 C), 111.6 (C-β) |
MI-2 | 3432 (N-H); 3025 (C-H); 2969 (C-H); 2696 (C = NH+); 1567 (C = N); 1311 (C-S) | 7.89 (d, H-α), 7.76-7.01 (m, 14 H), 6.97 (d, H-β), 3.84 (s, 3H, OCH3) | 163.3 (C-4’), 162.5 (C-5), 158.4 (C-2), 148.3 ( C-α), 138.7-114.8 (17 C), 108.8 (C-β), 55.6 (OCH3) |
MI-3 | 3432 (N-H); 3048 (C-H); 2721 (C = NH+); 1571 (C = N); 1519 (C-NO2); 1342 (C-S) | 8.04 (d, H-α), 7.80-7.39 (m, 14 H), 7.33 (d, H-β) | 162.0 (C-5), 159.7 (C-2), 148.6 (C-4’), 144.7 ( C-α), 140.0-118.7 (17 C), 115.5 (C-β) |
MI-4 | 3423 (N-H); 3054 (C-H); 2925 (C-H); 2786 (C = NH+); 1565 (C = N); 1295 (C-S) | 7.92 (d, H-α), 7.77-7.10 (m, 14 H), 7.05 (d, H-β), 3.81 (s, 3H, OCH3) | 162.3 (C-4’), 159.2 (C-5), 158.6 (C-2), 144.6 (C-α), 138.3-118.9 (17 C), 111.40 (C-β), 55.5 (OCH3) |
MI-5 | 3425 (N-H); 3062 (C-H); 2923 (C-H); 2852 (C = NH+); 1565 (C = N); 1378 (C-S) | 10.24 (s, 1H, N-H), 7.90 (d, H-α), 7.73-7.13 (m, 14 H), 6.74 (d, H-β), 3.05–2.94 (m, 6H, NCH3) | 164.9 (C-4’), 155.1 (C-5), 151.8 (C-2), 140.0 (C-α), 138.7-113.1 (17 C), 104.0 (C-β), 40.2 (N-CH3) |
MI-6 | 3435 (N-H); 2997 (C-H); 2582 (C = NH+); 1541 (C = N); 1338 (NO2); 1627, 1585, 1338 (C-S) | 12.58 (s, 1H, N-H), 8.25-7.22 (m, 14 H), 8.10 (d, 1H, H-α), 7.25 (d, 1H, H-β) | 159.8 (C-5), 148.5 (C-2), 144.5 (C-α), 139.9-118.8 (17 C), 115.5 (C-β) |
MI-7 | 3431 (N-H); 3043 (C-H); 2929 (C-H); 2717 (C = NH+); 1512 (C = N); 1342 (C-S); 1109 (O-CH3) | 12.73 (s, 1H, N-H), 8.24-6.99 (m, 14 H), 8.09 (d, 1H, H-α), 7.24 (d, 1H, H-β), 3.73 (s, 3H, OCH3) | 161.3 (C-5), 156.0 (C-2), 148.5-114.6 (17 C), 144.2 (C-α), 115.5 (C-β), 55.3 (OCH3) |
MI-8 | 3431 (N-H); 3039 (C-H); 2922 (C-H); 2746 (C = NH+); 1523 (C = N); 1340 (C-S) | 12.58 (s, 1H, N-H), 8.25-7.22 (m, 14 H), 8.10 (d, 1H, H-α), 7.25 (d, 1H, H- β), 2.27 (s, 3H, CH3) | 159.8 (C-5), 148.5 (C-2), 144.5 (C-α), 139.9-118.8 (17 C), 115.5 (C-β), 20.5 (CH3) |
MI-9 | 3432 (N-H); 3037 (C-H); 2663 (C = NH+); 1540 (C = N); 1309 (C-S); 948, 669 (C-Br) | 12.58 (s, 1H, N-H), 8.25-7.22 (m, 14 H), 8.10 (d, 1H, Hα), 7.25 (d, 1H, Hβ) | 159.8 (C-5), 148.5 (C-2), 144.5 (C-α), 139.9-118.8 (17 C), 115.5 (C-β) |
MI-10 | 3419 (N-H); 3047 (C-H); 2723 (C = NH+); 1569 (C = N); 1319 (C-S) | 7.72-7.08 (m, 15 H) | 163.8 (C-5), 160.5 (C-2), 138,6-118.3 (18 C). |
MI-11 | 3425 (N-H); 3048 (C-H); 2935 (C-H); 2665 (C = NH+); 1567 (C = N); 1309 (C-S) | 12.90 (s, 1H, N-H), 7.70-7.25 (m, 14 H), 3.86 (s, 3H, OCH3) | 163.0 (C-5), 159.5 (C-2), 138.3- 114.7 (17 C), 55,5 (OCH3) |
MI-12 | 3434 (N-H); 3043 (C-H); 2721 (C = NH+); 1573 (C = N); 1537 (C-NO2); 1348 (C-S) | 7.71-7.00 (m, 14 H) | 160.8 (C-5), 149.2 (C-2), 138.0 (C-4’), 137.0-118.2 (17 C) |
MI-13 | 3438 (N-H); 3050 (C-H); 2902 (C-H); 2642 (C = NH+); 1567 (C = N); 1311 (C-S) | 9.76 (s, 1H, N-H), 7.62-6.60 (m, 13 H), 6.08 (s, 2H, OCH2O) | 165.1 (C-5), 161.5 (C-2), 152.7-110.4 (17 C), 149.0 (C-4’), 103.9 (OCH2O) |
MI-14 | 3435 (N-H); 3055 (C-H); 2719 (C = NH+); 1579 (C = N); 1543 (C-NO2); 1340 (C-S) | 13.62 (s, 1H, N-H), 8.32-7.52 (m, 14 H) | 165.8 (C-5), 160.4 (C-2), 144.0 (C-4”’), 142.5-118.7 (17 C) |
MI-15 | 3435 (N-H); 3184 (C-H); 3039 (C-H); 2736 (C = NH+); 1508 (C = N); 1249 (C-S) | 12.30 (s, 1H, N-H), 7.66-7.00 (m, 14 H), 3.73 (s, 3H, OCH3) | 161.3 (C-5), 156.1 (C-2), 148.5 (C-4”’), 144.2-114.6 (17 C), 55.3 (OCH3) |
MI-16 | 3433 (N-H); 3041 (C-H); 2914 (C-H); 2767 (C = NH+); 1562 (C = N); 1220 (C-S) | 12.73 (s, 1H, N-H), 7.67-7.21 (m, 14 H), 2.49 (s, 3H, CH3) | 163.9 (C-5), 160.4 (C-2), 137.7-118;4 (17 C), 133.2 (C-4”’), 20.5 (CH3). |