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Table 2. 1H NMR and IR spectra of 2- and 4-(1H-indolylmethyl)phenols
Comp.
no.
IR spectrum, ν, cm–1
1H NMR spectrum, δ, ppm
3502, 3387 (NH/OH), 3051 (CHarom),
2893, 2835 (CH2), 1589 (C=C), 1501,
1454, 1431, 1335, 1261, 1219, 1188,
1169, 1095, 1049, 1007, 849, 760, 744,
613, 582, 501
4.08 s (2H, CH2), 6.78–6.88 m (3H, Harom), 7.02–7.17 m (5H, Harom), 7.42 d (1H, 4'-H,
J = 8.10 Hz), 7.55 d (1H, 7'-H, J = 8.10 Hz), 9.06 br. s (1H, NH)
Ia
3487, 3379 (NH/OH), 3040 (CHarom),
2900 (CH2), 1582 (C=C), 1501, 1454,
1366, 1331, 1261, 1227, 1167, 1095,
968, 824, 785, 766, 727, 579, 494, 447
4.07 s (2H, CH2), 6.80 t (1H, 4-H, J = 7.47 Hz), 6.85–6.93 m (3H, Harom), 6.99 t.d
(1H, Harom, J = 7.78, 4.98 Hz), 7.07–7.13 m (3H, Harom), 7.36 d (1H, 4'-H, J =
7.78 Hz), 9.35 br.s (1H, NH)
Ib
Ic
Id
3421, 3340 (OH/NH), 2924, 2854 (CH2), 4.00 s (2H, CH2), 6.81 d (1H, 6-H, J = 8.41 Hz), 7.09 d (1H, 2'-H, J = 2.18 Hz), 7.16 d
1585 (C=C), 1543, 1489, 1454, 1415, (1H, 3-H, J = 2.49 Hz), 7.20 d.d (1H, 5-H, J = 8.41, 2.49 Hz), 7.27 d (1H, 7'-H,
1385, 1265, 1223, 1169, 1103, 872, 813, J = 8.41 Hz), 7.41 d.d (1H, 6'-H, J = 8.41, 1.56 Hz), 7.63 br.s (1H, OH), 7.90 d (1H,
794, 737, 625, 579
4'-H, J = 0.94 Hz), 9.37 br. s (1H, NH)
3553, 3402 (NH/OH), 3055, 3028
(CHarom), 2908, 2851 (CHAd), 1582
(C=C), 1485, 1458, 1427, 1339, 1315,
1273, 1242, 1180, 1161, 1099, 1041,
752, 744, 702, 633
1.81 s (6H, CH2, Ad), 2.06 br.s (3H, CH, Ad), 2.14 s (6H, CH2, Ad), 4.26 s (2H, CH2),
6.65–6.68 m (2H, Harom, OH), 6.86–6.90 m (2H, Harom), 6.94 t.d (1H, 5'-H, J = 8.10,
0.93 Hz), 7.01–7.05 m (1H, Harom), 7.08 t. d (1H, 6'-H, J = 8.10, 0.93 Hz), 7.20 d (1H,
7'-H, J = 7.78 Hz), 7.39 d (1H, 4'- H, J = 8.10 Hz), 9.04 br.s (1H, NH)
3545, 3472, 3425, 3213 (NH/OH), 3047 1.82 s (6H, CH2, Ad), 2.07 br.s (3H, CH, Ad), 2.13 s (6H, CH2, Ad), 4.20 s (2H, CH2),
Ie
If
(CHarom), 2901, 2847 (CHAd), 1489,
1466, 1431, 1339, 1315, 1261, 1207,
1165, 1099, 1018, 806, 744, 609
6.69 d (1H, 3-H, J = 2.48 Hz), 6.82 d (1H, 6-H, J = 8.41 Hz), 6.96–6.99 m (1H, 6'-H),
7.11 t.d (1H, indole, J = 8.04, 1.24 Hz), 7.16 d.d (1H, 5-H, J = 8.41, 2.48 Hz), 7.20 s
(1H, OH), 7.25 d (1H, 5'- H, J = 7.81 Hz), 7.42 d (1H, 4'-H, J = 8.41 Hz), 9.12 br.s
(1H, NH)
3464 (NH/OH), 2912, 2847 (CHAd),
1589 (C=C), 1516 (NO2), 1493, 1462,
1435, 1335 (NO2), 1281, 1200, 1076,
829, 741
1.81 s (6H, CH2, Ad), 2.05 br.s (3H, CH, Ad), 2.13 s (6H, CH2, Ad), 4.29 s (2H, CH2),
6.98 t.d (1H, 5'- H, J = 7.76, 0.94 Hz), 7.03 d (1H, 6-H, J = 8.7 Hz), 7.13 t.d (1H, 6'-
H, J = 8.1, 0.94 Hz), 7.24 d (1H, 4'-H, J = 7.76 Hz), 7.44 d (1H, 7'-H, J = 8.1 Hz),
7.50 d (1H, 3-H, J = 2.8 Hz), 7.98 d.d (1H, 5-H, J = 8.7, 2.8 Hz), 8.65 br.s and 9.21
br.s (2H, OH, NH)
3517, 3398 (NH/OH), 2912, 2851
(CHAd), 1585 (C=C), 1485, 1458, 1317, 4.21 s (2H, CH2), 6.64–6.69 m (2H, 4-H, OH), 6.86 d (1H, 6-H, J = 7.78 Hz), 6.91 d
1198, 1184, 1165, 1040, 802, 752, 633
1.80 s (6H, CH2, Ad), 2.05 br.s (3H, CH, Ad), 2.12 s (6H, CH2, Ad), 2.33 s (3H, CH3),
Ig
Ih
(2H, 6'-H, 7'-H, J = 8.09 Hz), 7.00 s (1H, 4'- H), 7.04 m (1H, 5-H), 7.27 d (1H, 3-H,
J = 8.10 Hz), 8.94 br.s (1H, NH)
3491, 3383 (NH/OH), 3055, 3024
(CHarom), 2908, 2847 (CHAd), 1612
(C=C), 1512, 1462, 1435, 1339, 1315,
1.83 s (6H, CH2, Ad), 2.08 br.s (3H, CH, Ad), 2.16 s (6H, CH2, Ad), 4.26 s (2H, CH2),
6.63 br.s (1H, OH), 6.70 d (2H, 2-H, 6-H, J = 8.72 Hz), 6.93 t (1H, 5'-H, J = 7.48 Hz),
6.99 d (2H, 3-H, 5-H, J = 8.72 Hz), 7.08 t (1H, 6'- H, J = 7.48 Hz), 7.24 d (1H, 4'-H,
1250, 1177, 1099, 1014, 825, 744, 698, J = 8.10 Hz), 7.37 d (1H, 7'-H, J = 8.10 Hz), 9.01 br.s (1H, NH)
621
3364 (NH/OH), 2905, 2847 (CHAd),
1647 (CO), 1585 (C=C), 1485, 1458,
1439, 1369, 1339, 1312, 1277, 1242,
1207, 1146, 829, 771, 737, 687, 609
1.82 s (6H, CH2, Ad), 2.05 br. s (3H, CH, Ad), 2.14 s (6H, CH2, Ad), 4.22 s (2H, CH2),
6.87 s (1H, 6-H), 7.20–7.38 m (4H, Harom), 7.49 d (1H, Harom, J = 6.55 Hz), 7.72 d
(1H, Harom, J = 6.61 Hz), 9.61 s (1H, CHO), 9.74 br.s (2H, NH, OH)
Ii
3518, 3421 (NH/OH), 3020 (CHarom),
2901, 2847 (CHAd), 1616 (C=C), 1512, 4.23 s (2H, CH2), 6.64 br.s (1H, OH), 6.70 d (2H, 2-H, 6-H, J = 8.4 Hz), 6.90 d.d (1H,
1477, 1443, 1312, 1261, 1169, 1099,
984, 825, 806, 613
1.82 s (6H, CH2, Ad), 2.07 br.s (3H, CH, Ad), 2.13 s (6H, CH2, Ad), 2.34 s (3H, CH3),
Ij
Ik
6'-H, J = 8.10, 0.94 Hz), 6.98 d (2H, 3-H, 5-H, J = 8.40 Hz), 7.05 s (1H, 4'-H), 7.25 d
(1H, 7'- H, J = 8.10 Hz), 8.89 br.s (1H, NH)
3491, 3236 (ON/NH), 3051 (CHarom),
1.84 s (6H, CH2, Ad), 2.09 br.s (3H, CH, Ad), 2.21 s (6H, CH2, Ad), 2.53 s (3H, CH3),
2908, 2851 (CHAd), 1612, 1600 (C=C), 4.26 s (2H, CH2), 6.65 br.s (1H, OH), 6.70 d (2H, 2-H, 6-H, J = 8.71 Hz), 6.84–6.89
1508, 1450, 1407, 1365, 1315, 1234,
1169, 1103, 1018, 910, 845, 814, 791,
756, 741, 598
m (2H, 5'-H, 6'-H), 6.99 d (2H, 3-H, 5-H, J = 8.71 Hz), 7.11 d.d (1H, 4'-H, J = 6.70,
2.49 Hz), 8.56 br.s (1H, NH)
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 81 No. 1 2011