Comp | IR (KBr, cm−1) | 1H NMR (400 MHz, DMSO-d6) | 13C NMR (400 MHz, DMSO-d6) | C, H, N analyses calculated (found); MS, ES + (ToF): m/z—[M+ + 1] |
---|---|---|---|---|
Int-ii | 3319–3179 (N–H str.), 2920 (C–H str. aliphatic), 1739 (C=O str.) | 1.22–2.24 (m, 28H, CH2), 0.83 (s, 3H, CH3), 2.5 (s, 2H, NH2), 8.873 (s, 1H, NH) | 14.0, 19.4, 29.4, 39.1, 128.9, 149.9, 168.6, 189.4 | C, 71.06; H, 12.67; N, 10.36; (C, 71.01; H, 12.57; N, 10.26); 271 |
Int-iii | 3424 (N–H str.), 2921 (C–H str. aliphatic), 1372 (C=S str.), 1589 (C=N str.), 1115 (C–O str.) | 1.22–2.47 (m, 28H, CH2), 0.84 (s, 3H, CH3) | 15.7, 18.7, 29.8, 37.1, 124.1, 149.9, 160.6, 182.4 | C, 65.34; H, 10.32; N, 8.96; (C, 65.31; H, 10.29; N, 8.91); 313 |
Int-iv | 3319 (N–H str.), 2919 (C–H str., aliphatic), 1631 (C=N str.), 2572 (S–H str.) | 1.22–2.12 (m, 28H, CH2), 0.82 (s, 3H, CH3), 2.51 (s, 2H, NH2), 8.87 (s, 1H, NH) | 17.7, 18.4, 29.8, 39.6, 128.1, 124.98, 149.9, 168.6, 188.4 | C, 62.53; H, 10.49; N, 17.16; (C, 62.50; H, 10.42; N, 17.12); 327 |
T1 | 2925 (C–H str., aliphatic), 1625 (C=N str.), 3100 (C=C str., aromatic), 1719 (C–H str., aromatic.), 2568 (S–H str.) | 1.24–2.45 (m, 28H, CH2), 0.84 (s, 3H, CH3), 7.41–7.93 (m, 5H, Ar–H), 3.37 (s, H, SH) | 15.0, 18.4, 29.1, 39.1, 124.1, 128.98, 148.9, 160.6, 182.4 | C, 69.52; H, 9.24; N, 13.51; (C, 69.49; H, 9.22; N, 13.49); 415 |
T2 | 2990 (C–H str., aliphatic), 1646 (C=N str.), 1751 (C=O, str.), 1641 (C=C str., aromatic), 3073 (C–H str., aromatic), 2572 (S–H str.) | 1.32–2.51 (m, 28H, CH2), 0.86 (s, 3H, CH3), 2.51 (s, 2H, CH2), 7.08–7.91 (m, 4H, Ar–H), 3.37 (s, H, SH), 10.02 (s, H, CHO) | 13.8, 22.0, 28.5–28.9, 31.2, 129.8, 139.8, 140.9, 174.6, 192.4 | C, 67.83; H, 8.65; N, 12.66; (C, 67.80; H, 8.61; N, 12.62); 443 |
T3 | 2922 (C–H str., aliphatic), 1649 (C=N str.), 1646 (C=C str., aromatic), 3098 (C–H str., aromatic), 1790 (ring, str.), 2560 (S–H str.) | 1.29–2.51 (m, 24H, CH2), 0.87 (s, 3H, CH3), 7.30 (s, H, =CH), 7.51–7.62 (m, 4H, Ar–H), 3.37 (s, H, SH), 2.34 (s, 3H, Ar–CH3) | 13.8, 22.0, 24.4, 28.5–28.8, 31.2, 128.6, 129.7, 142.3, 161.11 | C, 70.05; H, 9.41; N, 13.07 (C, 70.00; H, 9.38; N, 13.02); 429 |
T4 | 2920 (C–H str., aliphatic), 1631 (C=N str.), 2856 (C–O–C str.), 1647 (C=C str., aromatic), 3105 (C–H str., aromatic), 2593 (S–H str) | 1.26–2.51 (m, 28H, CH2), 0.86 (s, 3H, CH3), 7.90 (s, H, =CH), 7.01–7.61 (m, 3H, Ar–H), 3.11 (s, H, SH), 3.76 (s, 6H, Ar–OCH3) | 13.8, 22.0, 28.3–28.9, 31.2, 55.1, 111.1, 149.1, 176.0 | C, 65.78; H, 8.92; N, 11.80; (C, 65.72; H, 8.89; N, 11.78; O, 6.70); 475 |
T5 | 2923 (C–H str., aliphatic), 1639 (C=N str.), 2860 (C–O–C str.), 1450 (C=C str., aromatic), 3078 (C–H str., aromatic), 2572 (S–H str.) | 1.23–2.47 (m, 28H, CH2), 0.85 (s, 3H, CH3), 7.21 (s, H, =CH), 7.10–7.27 (m, 2H, Ar–H), 3.52 (s, H, SH), 3.76 (s, 9H, Ar–OCH3) | 14.0, 39.1, 105.6, 129.2, 140.2, 153.1, 161.1 | C, 64.25; H, 8.79; N, 11.10; (C, 64.21; H, 8.75; N, 11.08); 505 |
T6 | 2988 (C–H str., aliphatic), 1677 (C=N str.), 1715 (ring, str.), 3400 (O–H str.), 2843 (C–O–C str.), 1636 (C=C str., aromatic), 3154 (C–H str., aromatic), 2555 (S–H str.) | 1.21–2.46 (m, 28H, CH2), 0.96 (s, 3H, CH3), 8.0 (s, H,CH), 7.51–7.69 (m, 3H, Ar–H), 3.37 (s, H, SH), 6.71 (s, H, OH), 3.79 (s, H, Ar–OCH3) | 13.8, 22.0, 28.5–28.9, 31.8, 55.5, 115.3, 120.7, 128.7, 142.7, 146.2, 168.2 | C, 65.18; H, 8.75; N, 12.16; (C, 65.13; H, 8.78; N, 12.15); 461 |
T7 | 2923 (C–H str., aliphatic), 1617 (C=N str.), 3401(O–H, str.), 1632 (C=C str., aromatic), 3101 (C–H str., aromatic), 2695 (S–H str.) | 1.27–2.52 (m, 28H, CH2), 0.85 (s, 3H, CH3), 8.35 (s, H, =CH), 7.31–7.79 m, 4H, Ar–H), 3.37 (s, H, SH), 4.05 (s, H, OH) | 14.0, 15.0, 24.4, 29.0, 31.2, 33.9, 39.9, 59.9, 61.1, 116.6, 129.4, 157.06, 162.7 | C, 66.94; H, 8.89; N, 13.01; (C, 66.90; H, 8.83; N, 12.9); 431 |
T8 | 2919 (C–H str., aliphatic), 1686 (C=N str.), 3483 (O–H, str.), 1665 (C=C str., aromatic), 3098 (C–H str., aromatic), 2572 (S–H str.) | 1.28–2.53 (m, 28H, CH2), 0.88 (s, 3H, CH3), 8.10 (s, H, =CH), 6.43–7.49 (m, 4H, Ar–H), 3.37 (s, H, SH), 5.01 (s, H, OH) | 14.3, 24.7, 29.0, 31.6, 34.1, 39.9, 46.2, 116.2, 129.1, 160, 175, 191.5 | C, 66.94; H, 8.89; N, 13.01; (C, 66.90; H, 8.85; N, 12.89); 431 |
T9 | 2925 (C–H str., aliphatic), 1684 (C=N str.), 1645 (C=C str., aromatic), 3097 (C–H str., aromatic), 3431 (N–H amine, str.) 2572 (S–H str.) | 1.21–2.51 (m, 28H, CH2), 0.85 (s, 3H, CH3), 7.11–7.48 (m, 4H, Ar–H), 8.12 (s, H, =CH), 3.01 (s, H, SH), 2.99 (s, 6H, N–(CH3)2) | 13.8, 22.0, 24.4, 29.0, 31.2, 46.3, 57.6, 118.7, 124.9, 128.1, 130.1, 134.9, 168.1, 114.4 | C, 68.23; H, 9.47; N, 15.30 (C, 68.20; H, 9.42; N, 15.27);458 |
T10 | 2916 (C–H str., aliphatic), 1650 (C=N str.), 1456 (C=C str., aromatic), 3065 (C–H str., aromatic), 750 (C–Cl str.), 2567 (S–H str.) | 1.24–2.45 (m, 28H, CH2), 0.85 (s, 3H, CH3), 8.01 (s, H, =CH), 6.80–7.61 (m, 4H, Ar–H), 3.0 (s, H, SH) | 14.2, 22.2, 24.5, 29.4, 31.0, 46.3, 57.6, 118.7, 128.1, 130.1, 134.9, 148, 168.1 | C, 64.19; H, 8.30; N, 12.48; (C, 64.15; H, 8.28; N, 12.43); 449 |
T11 | 2916 (C–H str., aliphatic), 1650 (C=N str.), 1635 (C=C str., aromatic), 3105 (C–H str., aromatic), 767 (C–Cl str.), 2572 (S–H str.) | 1.26–2.56 (s, 28H, CH2), 0.87 (s, 3H, CH3), 8.01 (s, H, =CH), 6.90–7.68 (m, 4H, Ar–H), 3.2 (s, H, SH) | 14.1, 22.0, 24.2, 29.9, 31.9, 40.3, 55.6, 118.7, 128.1, 131.1, 137.9, 148.9, 168.8 | C, 64.19; H, 8.30; N, 12.48; (C, 64.15; H, 8.27; N, 12.43); 449 |
T12 | 2905 (C–H str., aliphatic), 1678.98 (C=N str.), 1604 (C=C str., aromatic), 3087 (C–H str., aromatic), 767 (C–Cl str.), 2505 (S–H str.) | 1.23–2.51 (m, 28H, CH2), 0.86 (s, 3H, CH3), 8.10 (s, H, =CH), 6.60–7.57 (m, 3H, Ar–H), 3.07 (s, H, SH) | 13.9, 22.5, 24.4, 29.9, 31.5, 44.3, 57.6, 119.7, 127.1, 131.9, 139.9, 148.9, 168.9 | C, 59.61; H, 7.50; N, 11.59; (C, 59.58; H, 7.48; N, 11.53); 483 |
T13 | 2919 (C–H str., aliphatic), 1648 (C=N str.), 1624 (C=C str., aromatic), 3109 (C–H str., aromatic), 699 (C–Br str.), 2505 (S–H str)] | 1.29–0.55 (m, 28H, CH2), 0.87 (s, 3H, CH3), 8.12 (s, H, =CH), 6.98–7.65 (m, 4H, Ar–H), 3.02 (s, H, SH) | 14.4, 23.2, 24.0, 29.9, 33.3, 48.3, 59.6, 118.7, 128.9, 130.9, 134.8, 148.7, 168.6 | C, 58.41; H, 7.56; N, 11.35; (C, 58.41; H, 7.56; N, 11.35); 495 |
T14 | 2919 (C–H str., aliphatic), 1648 (C=N str.), 1498 (C=C str., aromatic), 3054 (C–H str., aromatic), 699 (C–Br str.), 2505 (S–H str) | 1.29–2.59 (m, 28H, CH2), 0.88 (s, 3H, CH3), 8.98 (s, H, =CH), 6.50–7.68 (m, 4H, Ar–H), 3.09 (s, H, SH) | 15.4, 23.8, 24.9, 29.9, 33.0, 47.3, 56.6, 116.7, 129.9, 131.2, 134.8, 148.8, 168.9 | C, 58.41; H, 7.56; N, 11.35; (C, 58.39; H, 7.53; N, 11.30); 495 |
T15 | 2921 (C–H str., aliphatic), 1698 (C=N str.), 1445 (C=C str., aromatic), 3100 (C–H str., aromatic), 1545 (NO2 str.), 2529 (S–H str.) | 1.29–2.67 (m, 28H, CH2), 0.87 (s, 3H, CH3), 8.02 (s, H, =CH), 7.51–7.64 (m, 4H, Ar–H), 3.07 (s, H, SH), | 13.4, 23.7, 24.5, 29.9, 32.3, 48.6, 59.8, 118.9, 127.9, 131.9, 134.9, 148.7, 168.5 | C, 62.71; H, 8.11; N, 15.24; (C, 62.69; H, 8.09; N, 15.20); 460 |
T16 | 2878 (C–H str., aliphatic), 1648 (C=N str.), 1646 (C=C str., aromatic), 3045 (C–H str., aromatic), 1424 (NO2 str.), 2572 (S–H str.) | 1.29–2.51 (m, 28H, CH2), 0.87 (s, 3H, CH3), 8.01 (s, H, CH), 7.51–7.96 (m, 4H, Ar–H), 3.37 (s, H, SH), 2.34 (s, 3H, Ar–CH3) | 13.4, 23.7, 24.5, 29.9, 32.3, 48.6, 59.8, 118.9, 127.9, 131.9, 134.9, 148.7 | C, 62.71; H, 8.11; N, 15.24; (C, 62.68; H, 8.07; N, 15.19); 460 |
T17 | 2880 (C–H str., aliphatic), 1647 (C=N str.), 1498 (C=C str., aromatic), 3076 (C–H str., aromatic), 1520 (NO2 str.), 2572(S–H str.) | 1.24–2.56 (m, 28H, CH2), 0.86 (s, 3H, CH3), 8.31 (s, H, =CH), 6.90–7.76 (m, 4H, Ar–H), 3.07 (s, H, SH) | 14.4, 23.9, 24.7, 29.8, 31.3, 48.6, 57.8, 116.9, 127.9, 131.7, 135.9, 148.9, 168.3 | C, 62.71; H, 8.11; N, 15.24; (C, 62.68; H, 8.10; N, 15.22); 460 |
T18 | 2880 (C–H str., aliphatic), 1650 (C=N str.), 1608 (C=C str., aromatic), 3109 (C–H str., aromatic), 3401 (O–H str.), 2572 (S–H str.) | 1.29–2.98 (m, 28H, CH2), 0.87 (s, 3H, CH3), 8.01 (s, H, =CH), 6.88–8.08 (m, 6H, Ar–H), 3.07 (s, H, SH), 5.01 (s, H, Ar–OH) | 13.4, 22.9, 24.8, 29.8, 31.3, 46.6, 54.8, 116.9, 126.9, 130.7, 135.9, 148.9, 169.3, 189.9 | C, 69.96; H, 8.39; N, 11.66; (C, 69.91; H, 8.32; N, 11.64); 481 |
T19 | 2985 (C–H str., aliphatic), 1650 (C=N str.), 1490 (C=C str., aromatic), 3099 (C–H str., aromatic), 2572 (S–H str.) | 1.29–2.98 (s, 28H, CH2), 0.87 (s, 3H, CH3), 5.60–7.06 (m, 3H, =CH),6.01–7.69 (m, 6H, Ar–H), 3.07 (s, H, SH) | 14.4, 22.1, 29.5, 31.2, 54.8, 116.9, 126.9, 130.7, 135.9, 148.6, 164.3, 189.6 | C, 70.86; H, 9.15; N, 12.71; (C, 70.82; H, 9.12; N, 12.62); 441 |
T20 | 2879 (C–H str., aliphatic), 1648 (C=N str.), 2879 (C–O–C, str.), 1678 (C=C str., aromatic), 3156 (C–H str., aromatic), 2572 (S–H str) | 1.29–2.52 (m, 28H, CH2), 0.84 (s, 3H, CH3), 6.30–7.40 (m, 3H, Ar–H), 3.07 (s, H, SH), | 14.7, 21.9, 25.8, 26.8, 31.1, 47.6, 54.5, 119.9, 130.1, 135.5, 158.9, 179.3, 188.9 | C, 65.31; H, 8.97; N, 13.85; (C, 65.28; H, 8.91; N, 13.80); 405 |