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Table 2 Spectral interpretation of synthesized derivatives

From: 4-(2-(1H-Benzo[d]imidazol-2-ylthio)acetamido)-N-(substituted phenyl)benzamides: design, synthesis and biological evaluation

Comp. IR (KBr cm−1) 13C-NMR (DMSO-d6, δ ppm) 1H-NMR (DMSO-d6, δ ppm)
N1 [3104 (C–H str.), 1602 (C=C str.) pn(phenyl nucleus)], 1626 (–CONH str.), 1333 (N=CH str. (30 amine)), 1256 (C–N str. (20 amine)), 714 (C–S str., CH2–S), 2838 (C–H str., –CH2–), 1516 (C–NO2 str., C6H5NO2) 39.02, 113.68, 118.35, 122.48, 123.21, 128.54, 129.10, 137.44, 137.45, 142.67, 149.72, 166.25, 166.78 7.25–8.77 (m, 11H, Ar–H), 4.42 (s, 1H, NH of imidazole), 7.93 (s, 2H, (CONH)2)
N2 [3058 (C–H str.), 1599 (C=C str.) pn, 1684 (–CONH str.), 1332 (N=CH str.), 1293 (C–N str.), 716 (C–S str., CH2–S), 2931 (C–H str., –CH2–), 1513 (C–NO2 str., C6H5NO2) 3.6.41, 115.43, 118.44, 119.13, 122.59, 125.47, 130.25, 130.43, 135.62, 137.42, 142.72, 149.80, 166.28, 166.83 7.25–7.66 (m, 12H, Ar–H), 4.45 (s, 1H, NH of imidazole), 7.96 (s, 2H, (CONH)2)
N3 [3109 (C–H str.), 1599 (C=C str.) pn], 1666 (–CONH str.), 1331 (N=CH str.), 1299 (C–N str.), 713 (C–S str., CH2–S), 2833 (C–H str., –CH2–), 1540 (C–NO2 str., C6H5NO2) 36.42, 113.65, 118.42, 120.05, 122.48, 125.46, 129.83, 130.43, 137.43, 137.63, 142.74, 149.80, 166.32, 166.83 7.24–7.97 (m, 12H, Ar–H), 4.45 (s, 1H, NH of imidazole), 7.97 (s, 2H, (CONH)2)
N4 [3110 (C–H str.), 1600 (C=C str.) pn], 1681 (–CONH str.), 1301 (N=CH str.), 1280 (C–N str.), 712 (C–S str., CH2–S), 2934 (C–H str., –CH2–), 1542 (C–NO2 str., C6H5NO2) 113.63, 118.43, 118.55, 122.62, 125.47, 126.31, 130.43, 137.34, 142.73, 149.81, 166.27, 166.82; 7.26–7.97 (m, 12H, Ar–H), 4.47 (s, 1H, NH of imidazole), 7.97 (s, 2H, (CONH)2)
N5 3107 (C–H str.), 1598 (C=C str.)pn], 1669 (–CONH str.), 1330 (N=CH str.), 1313 (C–N str.), 711 (C–S str., CH2–S), 2944 (C–H str., –CH2–), 633 (C–Br str., C6H5Br) 39.02, 113.79, 118.38, 121.81, 125.42, 130.79, 149.72, 166.58, 166.84 7.19–7.97 (m, 12H, Ar–H), 4.38 (s, 1H, NH of imidazole), 4.34 (s, 1H, CH2), 7.97 (s, 2H, (CONH)2)
N6 [3101 (C–H str.), 1599 (C=C str.) pn], 1635 (–CONH str.), 1338 (N=CH str.), 1293 (C–N str.), 693 (C–S str., CH2–S), 2833 (C–H str., –CH2–),762 (C–Cl str., C6H5Cl), 1549 (C–NO2 str., C6H5NO2) 36.47, 113.56, 121.13, 122.84, 123.98, 125.41, 125.47, 129.95, 130.41, 130.43, 135.31, 136.81, 142.65, 142.70, 149.84, 166.15, 166.80 7.27–7.95 (m, 11H, Ar–H), 4.47 (s, 1H, NH of imidazole), 7.95 (s, 2H, (CONH)2)
N7 [3109 (C–H str.), 1599 (C=C str.) pn], 1686 (–CONH str.), 1318 (N=CH str.), 1293 (C–N str.), 694 (C–S str., CH2–S), 2870 (C–H str., –CH2–),750 (C–Cl str., C6H5Cl) 36.41, 115.59, 118.41, 122.56, 125.45, 125.56, 127.60, 128.92, 130.43, 137.29, 137.49, 142.73, 149.80, 166.27, 166.80 7.23–7.97 (m, 12H, Ar–H), 4.42 (s, 1H, NH of imidazole), 7.93 (s, 2H, (CONH)2)
N8 [3106 (C–H str.), 1598 (C=C str.) pn, 1683 (–CONH str.), 1331 (N=CH str.), 1293 (C–N str.), 694 (C–S str., CH2–S), 2868 (C–H str., –CH2–), 750 (C–Cl str., C6H5Cl) 36.38, 113.67, 118.44, 122.42, 125.46, 130.44, 135.62, 137.68, 142.73, 149.76, 166.38, 166.86; 7.19–7.94 (m, 12H, Ar–H), 4.41 (s, 1H, NH of imidazole), 7.94 (s, 2H, (CONH)2)
N9 [3018 (C–H str.), 1598 (C=C str.) pn], 1668 (–CONH str.), 1360 (N=CH str.), 1281 (C–N str.), 713 (C–S str., CH2–S), 2915 (C–H str., –CH2–), 2948 (C–H str., CH3) 39.01, 118.37, 121.64, 125.41, 130.46, 142.81, 149.71, 166.65, 166.85; 7.16–7.96 (m, 11H, Ar–H), 4.36 (s, 1H, NH of imidazole), 7.97 (s, 2H, (CONH)2), 2.53 (s, 6H, (–CH3)2)
N10 [3055 (C–H str.), 1599 (C=C str.)pn], 1667 (–CONH str.), 1331 (N=CH str.), 1298 (C–N str.), 714 (C–S str., CH2–S), 2934 (C–H str., –CH2–), 2888 (C–H str., CH3) 17.63, 20.37, 38.99, 113.78, 118.39, 121.82, 124.03, 125.42, 126.43, 130.46, 130.76, 138.78, 138.84, 142.79, 149.72, 166.59, 166.85 7.18–7.96 (m, 11H, Ar–H), 4.39 (s, 1H, NH of imidazole), 4.30 (s, 2H, CH2), 7.98 (s, 2H, (CONH)2), 2.23 (s, 6H, (–CH3)2)
N11 [3054 (C–H str.), 1597 (C=C str.) pn], 1667 (–CONH str.), 1360 (N=CH str.), 1311 (C–N str.), 713 (C–S str., CH2–S), 2834 (C–H str., –CH2–), 2877 (C–H str., CH3) 21.12, 39.01, 116.25, 118.45, 121.73, 124.18, 125.41, 128.59, 130.39, 130.46, 137.99, 138.72, 138.80, 138.92, 142.80, 149.73, 166.62, 166.85 7.17–7.96 (m, 12H, Ar–H), 4.39 (s, 1H, NH of imidazole), 4.33 (s, 2H, CH2), 7.97 (s, 2H, (CONH)2), 2.28 (s, 3H, –CH3)
N12 [3047 (C–H str.), 1604 (C=C str.) pn], 1650 (–CONH str.), 1318 (N=CH str.), 1253 (C–N str.), 692 (C–S str., CH2–S), 2905 (C–H str., –CH2–), 744 (C–Cl str., C6H5Cl), 1546 (C–NO2 str., C6H5NO2) 36.54, 115.49, 118.44, 123.23, 124.53, 125.50, 125.55, 130.40, 135.87, 142.68, 149.88, 166.02, 166.81 7.31–8.11 (m, 11H, Ar–H), 4.53 (s, 1H, NH of imidazole), 2.55 (s, 2H, CH2), 7.98 (s, 2H, (CONH)2)
N13 3051 (C–H str.), 1598 (C=C str.) pn], 1631 (–CONH str.), 1331 (N=CH str.), 1315 (C–N str.), 694 (C–S str., CH2–S), 2951 (C–H str., –CH2–), 749 (C–Cl str., C6H5Cl) 38.96, 113.67, 118.42, 122.39, 125.45, 130.44, 137.72, 142.74, 149.77, 166.37, 166.84 7.31–7.94 (m, 12H, Ar–H), 4.53 (s, 1H, NH of imidazole), 7.97 (s, 2H, (CONH)2)
N14 [3059 (C–H str.), 1599 (C=C str.) pn, 1683 (–CONH str.), 1333 (N=CH str.), 1315 (C–N str.), 692 (C–S str., CH2–S), 2921 (C–H str., –CH2–) 39.02, 113.67, 118.40, 122.31, 122.38, 123.52, 125.43, 128.77, 130.43, 137.85, 138.74, 142.75, 149.77, 166.79, 166.82; 7.07–7.93 (m, 13H, Ar–H), 4.41 (s, 1H, NH of imidazole), 4.38 (s, 2H, CH2), 7.94 (s, 2H, (CONH)2)
N15 [3053 (C–H str.), 1599 (C=C str.) pn], 1667 (–CONH str.), 1361 (N=CH str.), 1310 (C–N str.), 714 (C–S str., CH2–S), 2934 (C–H str., –CH2–), 2860 (C–H str., CH3) 36.26, 118.34, 119.02, 121.52, 125.37, 129.14, 130.45, 132.39, 136.32, 142.81, 149.68, 165.83, 166.82 7.11–7.92 (m, 12H, Ar–H), 4.34 (s, 1H, NH of imidazole), 4.28 (s, 2H, CH2), 7.94 (s, 2H, (CONH)2), 2.51 (s, 3H, –CH3)
N16 [3055 (C–H str.), 1599 (C=C str.) pn], 1683 (–CONH str.), 1332 (N=CH str.), 1315 (C–N str.), 694 (C–S str., CH2–S), 2941 (C–H str., –CH2–), 1250 (C–O–C str., phenyl ether), 2837 (C–H str., O-CH3) 38.87, 113.64, 118.46, 122.51, 125.48, 130.44, 137.50, 142.72, 149.77, 166.36, 166.88 7.26–7.82 (m, 12H, Ar–H), 4.49 (s, 1H, NH of imidazole), 4.38 (s, 2H, CH2), 8.00 (s, 2H, (CONH)2), 3.73 (s, 3H, –OCH3)
N17 [3107 (C–H str.), 1599 (C=C str.) pn], 1685 (–CONH str.), 1332 (N=CH str.), 1316 (C–N str.), 694 (C–S str., CH2–S), 2917 (C–H str., –CH2–), 1250 (C–O–C str., phenyl ether), 2837 (C–H str., O-CH3) 38.93, 113.67, 118.43, 122.38, 125.45, 130.44, 137.75, 142.74, 149.77, 166.39, 166.86 7.24–7.98 (m, 12H, Ar–H), 4.45 (s, 1H, NH of imidazole), 4.40 (s, 2H, CH2), 7.98 (s, 2H, (CONH)2), 3.74 (s, 3H, –OCH3)
N18 [3054 (C–H str.), 1600 (C=C str.) pn], 1679 (–CONH str.), 1334 (N=CH str.), 1314 (C–N str.), 691 (C–S str., CH2–S), 2933 (C–H str., –CH2–), 1248 (C–O–C str., phenyl ether), 2831 (C–H str., O-CH3) 38.95, 55.08, 113.89, 118.40, 120.66, 121.67, 125.43, 130.48, 131.92, 139.06, 149.72, 155.38, 165.61, 166.88; 6.92–7.99 (m, 12H, Ar–H), 4.40 (s, 1H, NH of imidazole), 4.33 (s, 2H, CH2), 7.99 (s, 2H, N(CONH)2), 3.74 (s, 3H, –OCH3)
N19 [3106 (C–H str.), 1597 (C=C str.) pn], 1667 (–CONH str.), 1361 (N=CH str.), 1313 (C–N str.), 692 (C–S str., CH2–S), 2934 (C–H str., –CH2–), 1117 (C–F str., C6H5F) 38.93, 113.64, 118.44, 122.52, 125.47, 130.44, 137.46, 142.74, 149.79, 166.34, 166.86 7.26–7.99 (m, 12H, Ar–H), 4.49 (s, 1H, NH of imidazole), 8.00 (s, 2H, (CONH)2)
N20 [3066 (C–H str.), 1598 (C=C str.) pn], 1667 (–CONH str.), 1361 (N=CH str.), 1310 (C–N str.), 713 (C–S str., CH2–S), 2937 (C–H str., –CH2–), 1116 (C–F str., C6H5F) 39.03, 118.36, 121.63, 125.39, 130.46, 142.80, 149.70, 166.64, 166.83 7.15–7.94 (m, 12H, Ar–H), 4.36 (s, 1H, NH of imidazole), 4.31 (s, 2H, CH2), 7.95 (s, 1H, CONH)
N21 [3103 (C–H str.), 1597 (C=C str.) pn], 1666 (–CONH str.), 1360 (N=CH str.), 1310 (C–N str.), 711 (C–S str., CH2–S), 2935 (C–H str., –CH2–), 2911 (C–H str., CH3) 39.03, 118.36, 121.63, 125.40, 130.46, 142.80, 149.70, 166.64, 166.83 7.16–7.96 (m, 13H, Ar–H), 4.36 (s, 1H, NH of imidazole), 7.96 (s, 1H, CONH)
N22 [3104 (C–H str.), 1599 (C=C str.) pn], 1684 (–CONH str.), 1331 (N=CH str.), 1316 (C–N str.), 695 (C–S str., CH2–S), 28,668 (C–H str., –CH2–), 616 (C–Br str., C6H5Br) 39.03, 113.68, 118.40, 122.36, 125.43, 130.43, 137.78, 142.75, 149.78, 166.36, 166.81 7.23–7.94 (m, 12H, Ar–H), 4.41 (s, 1H, NH of imidazole), 7.94 (s, 2H, (CONH)2)
N23 [3107 (C–H str.), 1602 (C=C str.) pn], 1650 (–CONH str.), 1350 (N=CH str.), 1316 (C–N str.), 691 (C–S str., CH2–S), 2840 (C–H str., –CH2–), 738 (C–Cl str., C6H5Cl) 39.02, 114.73, 118.53, 123.26, 125.50, 127.92, 130.41, 131.50, 136.04, 146.61, 166.02, 166.81 6.80–7.94 (m, 11H, Ar–H), 4.53 (s, 1H, NH of imidazole), 7.95 (s, 2H, (CONH)2)
N24 [3108 (C–H str.), 1599 (C=C str.) pn], 1685 (–CONH str.), 1332 (N=CH str.), 1316 (C–N str.), 694 (C–S str., CH2–S), 2916 (C–H str., –CH2–), 2874 (C–H str., CH3) 38.98, 113.61, 118.43, 122.64, 125.46, 130.42, 137.23, 142.72, 149.80, 166.27, 166.83 7.26–7.95 (m, 13H, Ar–H), 4.46 (s, 1H, NH of imidazole), 7.96 (s, 1H, CONH)
N25 [3109 (C–H str.), 1604 (C=C str.) pn], 1651 (–CONH str.), 1351 (N=CH str.), 1318 (C–N str.), 691 (C–S str., CH2–S), 2837 (C–H str., –CH2–), 771 (C–Cl str., C6H5Cl) 36.52, 115.62, 118.45, 123.13, 125.49, 130.18, 130.42, 131.91, 136.21, 136.27, 142.70, 149.87, 166.07, 166.82; 1H-NMR: 6.88–7.95 (m, 11H, Ar–H), 4.52 (s, 1H, NH of imidazole), 7.96 (s, 2H, (CONH)2)
N26 [3107 (C–H str.), 1600 (C=C str.) pn, 1650 (–CONH str.), 1351 (N=CH str.), 1316 (C–N str.), 689 (C–S str., CH2–S), 2839 (C–H str., –CH2–), 1650 (phenyl conjugation) 36.55, 116.67, 118.41, 119.57, 123.21, 125.48, 125.51, 129.07, 130.43, 136.15, 142.72, 143.38, 149.90, 166.05, 166.83 7.10–7.56 (m, 17H, Ar–H), 4.53 (s, 1H, NH of imidazole), 7.96 (s, 1H, CONH)