Table 1.
Physical and select IR data of the synthesized azomethines 1-18.
| Compd. | Color | Moleculara formula (Mol. Mass) |
Mp (°C) (recryst. solvent)b | Yield (%) |
IR (cm−1) | ||
|---|---|---|---|---|---|---|---|
| N=C | Azomethine C-H |
Substituent | |||||
| 1 | Pale yellow | C13H10ClN [34] (215.05) |
72-4 (L.P) |
82 | 1621 | 2874, 1352 |
- |
| 2 | Yellow | C13H9ClN2O2 [35] (260.04) |
140-42 (L.P) |
74 | 1625 | 1333 | 1505, 1376(NO2) |
| 3 | Brown | C11H9NO [36] (171.07) |
106 d (B) |
79 | 1605 | 2850, 1328 | 3360(OH) |
| 4 | Brown | C11H8N2O3 [37] (216.05) |
196-98 (EtOH) |
68 | 1592 | 1285 | 1535, 1339(NO2) |
| 5 | Pale orange | C14H12N2OH (272.08) |
148-50 (L.P) |
64 | 1628 | 1325 | 3354–3480(OH) 1544, 1342 (NO2) |
| 6 | Pale yellow | C14H13NO2 (227.09) |
155-57 (L.P) |
72 | 1621 | 1388 | 3088 broad(OH) |
| 7 | Orange | C15H12N2O2 (252.09) |
133d (MeOH) |
65 | 1592 | 1300 | 1512, 1335(NO2) |
| 8 | Pale brown | C15H13N (207.10) |
100-02 (MeOH) |
66 | 1623 | 1375 | - |
| 9 | Orange | C13H10N2O3 (242.07) |
162-64 (L.P) |
59 | 1632 | 1338 | 1562, 1347 (NO2), 3150 (OH) |
| 10 | Pale brown | C17H12ClN (265.07) |
107-09 (MeOH) |
78 | 1637 | 1391 | - |
| 11 | Brown | C18H15NO2 (277.11) |
114-16 (B) |
76 | 1621 | 1381 | 3048(OH) |
| 12 | Pale Brown | C14H12ClNO (245.06) |
136-37 (MeOH) |
87 | 1629 | 2838, 1364 | 2838, 2895 (CH3) |
| 13 | Pale Brown | C15H15NO3 ( 257.11) |
257-59 (MeOH) |
70 | 1621 | 2954, 1378 | 3000 (broad OH), 2954, 2982 (CH3) |
| 14 | Greenish White | C14H13NO2 (227.09) |
85-87 (MeOH) |
67 | 1637 | 2964, 1362 | 3610(OH), 2964, 2996 (CH3) |
| 15 | White | C14H12ClN (229.07) |
127-29 (MeOH) |
79 | 1622 | 2929, 1354 | 2854, 2925 (CH3) |
| 16 | White | C14H13NO (211.10) |
96-98 (MeOH) |
67 | 1615 | 2920, 1366 | 3100 (OH), 2920 (CH3) |
| 17 | Pale Orange | C16H15N [38] (221.12) |
76-77 (MeOH) |
71 | 1627 | 2912, 1379 | 2912 (CH3) |
| 18 | Pale Yellow | C11H8N2O2S [39] (232.03) |
135-37 (MeOH) |
55 | 1612 | 1323 | 1543, 1341 (NO2) |
a references are given for known products, the others are new; b L.P = Light Petroleum b.p. 60–80 °C, B = benzene, EtOH = ethanol, MeOH = methanol.