1022 J. Chin. Chem. Soc., Vol. 56, No. 5, 2009
Noroozi-Pesyan et al.
Table 2. Spectroscopic data of azo dyes (3a-3g and 8a-8c- 10a-10e)
Azo
dyes
IR, 1H NMR, 13C NMR
3a
IR (KBr, cm-1): 3413.57 (s), 3257.20 (s), 3096.67 (s), 2831.50 (w), 1738.83 (s), 1712.20 (s),
1668.12 (s), 1513.53 (s), 1433.56 (s), 1263.18 (s), 1196.93 (s), 1042.98 (s).
1H NMR (DMSO-d6): 14.13 (s, 1H), 11.49 (s, 1H), 11.29 (s, 1H), 7.66 (d, J = 8.4 Hz, 2H), 7.51 (d, J
= 8.4 Hz, 2H).
13C NMR: 162.50, 160.45, 150.24, 145.59, 141.82, 127.53, 118.44, 116.39.
IR (KBr, cm-1): 3428.04 (s), 3257.76 (s), 3096.46 (s), 1738.76 (s), 1710.24 (s), 1665.54 (s), 1509.09
(s), 1433.80 (s), 1261.14 (s), 1203.30 (s), 818.91 (m), 618.76 (m).
1H NMR (DMSO-d6): 14.24 (s, 1H), 14.15 (s, 1H), 12.58 (s, 1H), 12.41 (s, 1H), 11.50 (s, 1H), 11.28
(s, 1H), 7.68 (d, J = 8.7 Hz, 2H), 7.67 (d, J = 8.7 Hz, 2H), 7.55 (d, J = 8.7 Hz, 2H), 7.52 (d, J = 8.7
Hz, 2H).
3ba
13C NMR: 177.88, 162.50, 160.45, 160.34, 158.86, 150.24, 146.03, 145.58, 141.81, 141.65, 127.56,
127.52, 119.33, 118.44, 116.83, 116.39.
3c
IR (KBr, cm-1): 2600-3600 (bs), 1731.13 (s), 1682.62 (s), 1647.57 (s), 1525.84 (s), 1450.42 (s),
1384.66 (s), 1201.24 (s), 1123.72 (s), 651.38 (s).
1H NMR (DMSO-d6): 14.16 (s, 1H), 7.65 (d, J = 8.7 Hz, 2H), 7.21 (d, J = 8.7 Hz, 2H), 2.60-4.60
(bs, H2O), 3.22 (s, 3H), 3.21 (s, 3H).
13C NMR: 160.82, 159.28, 151.04, 145.65, 141.89, 134.64, 127.53, 127.46, 121.92, 118.12, 116.56.
IR (KBr, cm-1): 3486.44 (s), 3382.78 (s), 1629.21 (m), 1599.33 (s), 1224.05 (s), 1175.85 (s),
1122.18 (s), 1033.70 (s), 769.97 (m), 567.18 (s).
3d
1H NMR (DMSO-d6): 10.20 (bs, 1H), 8.18 (d, 4H, J = 8.2 Hz, phenyl sulfonate), 7.31-8.59 (m, 6H,
naphthyl).
13C NMR: 160.0, 157.70, 146.30, 143.90, 129.50, 128.62, 127.90, 126.80, 126.60, 126.50, 124.0,
121.70, 115.50, 109.70.
3e
IR (KBr, cm-1): 3420.81 (bs), 1618.32 (m), 1597.51 (m), 1507.51 (s), 1210.38 (s), 1120.49 (s),
1032.85 (s), 831.90 (m), 759.72 (m), 698.09 (m), 644.58 (m).
1H NMR (DMSO-d6): 15.81 (bs, 1H), 12.50 (bs, 1H), 8.54 (d, 1H, J = 8.4 Hz), 7.95 (d, 1H, J = 9.6
Hz), 7.73-7.83 (m, 5H), 7.61 (t, 1H, J = 7.45 Hz), 6.90 (d, 1H, J = 9.3 Hz).
13C NMR: 170.29, 147.91, 145.13, 140.76, 133.17, 129.86, 129.63, 129.40, 128.32, 127.61, 126.45,
124.58, 121.88, 118.56.
3f
IR (KBr, cm-1): 3487.75 (bs), 3384.88 (s), 1627.31 (m), 1604 48 (s), 1223.65 (s), 1176.39 (s),
1123.50 (s), 1034.72 (s), 573.23 (s).
1H NMR (DMSO-d6): 12.51 (bs, 1H), 10.35 (bs, 1H), 7.73-7.78 (m, 7H), 6.90-6.93 (m, 2H).
13C NMR: 161.54, 152.26, 150.17, 145.67, 127.06, 125.34, 122.01, 116.41.
IR (KBr, cm-1): 3460.67 (bs), 3385.48 (s), 1624.73 (s), 1604.81 (s), 1177.06 (s), 1122.80 (s), 1035
12 (s), 570.96 (m).
3g
1H NMR (DMSO-d6): 12.47 (s, 1H, -OH), 9.14 (s, 1H, -OH), 7.74-7.81 (m, 4H), 7.67 (d, 1H, J =
8.7 Hz), 6.51 (dd, 1H, J = 2.4 Hz), 6.36 (d, 1H, J = 2.7 Hz).
13C NMR: 163.66, 157.03, 150.97, 149.07, 132.82, 130.54, 127.19, 121.60, 109.81, 103.44.
IR: 3447.85 (m), 3072.32 (s), 1747.31 (s), 1679.78 (s), 1643.32 (m), 1488.16 (s), 1328.62 (s),
1229.67 (s), 813.81 (s).
8a
8b
8c
9a
1H NMR: 15.18 (s, 1H), 11.70 (s, 1H), 11.48 (s, 1H), 8.261 (dd, J3 = 8.4 Hz, J4 = 1.2 Hz, 1H), 8.08
(d, J = 7.8 Hz, 1H), 7.88 (t, J = 7.5 Hz, 1H), 7.38 (td, J3 = 7.8 Hz, J4 = 1.2 Hz).
IR: 3633.07 (m), 3504.99 (m), 3137.79 (s), 1720 (s), 1700 (s), 1668.53 (s), 1606.06 (s), 1583.33 (s),
1467.49 (s), 1217.17 (s).
1H NMR: 15.23 (s, 1H), 12.76 (s, 1H), 12.59 (s, 1H), 8.27 (dd, J3 = 8.4 Hz, J4 = 0.9 Hz, 1H), 8.08
(d, J = 8.4 Hz, 1H), 7.90 (t, J = 7.2 Hz, 1H), 7.41 (td, J3 = 7.8 Hz, J4 = 1.2 Hz).
IR: 3440.00 (bm), 3088.92 (m), 2950.00 (w), 2925.00 (w), 1736.95 (s), 1680.80 (s), 1647.45 (s),
1491.56 (s), 1337.86 (s), 1230.70 (s), 747.16 (s).
1H NMR: 15.23 (s, 1H), 8.29 (d, J = 8.4 Hz, 1H), 8.10 (d, J = 8.1 Hz, 1H), 7.91 (t, J = 7.8 Hz, 1H),
7.41 (t, J = 8.1 Hz, 1H), 3.24 (s, 3H), 3.23 (s, 3H).
IR: 3194.63 (s), 3074.07 (s), 1755.13 (s), 1729.67 (s), 1665.42 (s), 1519.42 (s), 1355.94 (s), 1249.74
(s), 814.03 (s).
1H NMR: 13.92 (bs, 1H), 11.39 (bs, 2H), 8.44 (t, J = 2.1 Hz, 1H), 8.03 (d, J = 2.1 Hz, 1H), 8.00 (d,
J = 2.1 Hz, 1H), 7.71 (t, J = 8.4 Hz).