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Table 2 Main characteristic values of infrared (IR) and 1 H and 13 C Nuclear Magnetic Resonance (NMR) of synthesized mesoionic compounds

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).