Research Article

Hetarylazopyrazolone Dyes Based on Benzothiazole and Benzimidazole Ring Systems: Synthesis, Spectroscopic Investigation, and Computational Study

Table 2

Spectral data for dyes 3a–3f.

Dye number1H- (ppm, DMSO-d6)FT-IR (cm−1, KBr)MS (m/e)

3a2.30 (s, 3H, pyr CH3)3245 (N–H), 3070 (Ar C–H),393 [M]+ (%100)
7.35 (m, 2H, bth)
7.48 (m, 2H, bth)
7.59 (d, 1H, bth)
7.87 (t, 1H, bth)2915 (Al C–H), 1682 (C=O)258 (%33)
7.94 (d, 1H, bth)1595, 1523 (C=C, C=N)
8.05 (t, 1H, bth)
14.94 (b, NH)

3b2.30 (s, 3H, pyr CH3)3212 (N–H), 3062 (Ar C–H),427 [M]+ (%100)
7.33–8.14 (m, 7H, Ar CH)2994, 2978 (Al C–H)
15.00 (b, NH)1684 (C=O), 1597, 1523 (C=C, C=N)258 (%31)

2.40 (s, 3H, pyr CH3)3453 (N–H), 3070 (Ar C–H), 2940 (Al C–H)423 [M]+ (%100)
3.90 (s, 3H, bth OCH3)
7.00–8.10 (m, 7H, Ar CH)1670 (C=O), 1606, 1529 (C=C, C=N)79 (%10)

3d2.31 (s, 6H, dimetbth 2xCH3)3420 (N–H), 3060 (Ar C–H),421 [M]+ (%100)
2.47 (s, 3H, pyr CH3)2968, 2919 (Al C–H), 1638 (C=O)
7.42 (t, 1H, bth)1557, 1519 (C=C, C=N)258 (%16)
7.52 (s, 1H, dimetbth)
7.61 (s, 1H, dimetbth)
7.79 (d, 1H, bth)

3e2.41 (s, 3H, pyr CH3)3416 (N–H), 3194 (benzimidazole N–H),376 [M]+ (%100)
7.21–7.97 (m, 6H, Ar CH)3057 (Ar C–H), 2935 (Al C–H),
13.30 (b, bimi NH)1658 (C=O), 1621, 1570 (C=C, C=N)258 (%43)

3f2.33 (s, 6H, dimetbimi-2xCH3)3390 (N–H), 3147 (benzimidazole N–H),404 [M]+ (%100)
2.42 (s, 3H, pyr CH3)3021 (Ar C–H)
7.34–8.14 (m, 6H, Ar CH)2967 (Al C–H), 1669 (C=O),258 (%10)
13.23 (b, dimethylbenzimidazole NH)1616, 1529 (C=C, C=N)

, singlet; d, doublet; t, triplet; m, multiplet; b, broad.
pyr: pyrazolone, bth: benzothiazole, and dimetbth: dimethylbenzothiazole.
bimi: benzimidazole; dimetbimi: dimethylbenzimidazole.
-NMR in CHCl3.