2
018 Singh et al.
Asian J. Chem.
MS: [M+1] 473.56 (obs.), 472.76 (calcd.). UV-vis.: λmax in nm
(in DMSO, 2 × 10 M), 274 (π-π* transitions), 402 (n-π* transi-
tion), 575 (d-d transition).
+
1
31.39, 144.96, 154.35, 155.67, 155.80, 157.82, 159.60. Elem-
ental analysis (%) of C21 S calcd. (found): C, 69.79
70.95); H, 4.18 (4.63); N, 3.88 (3.96); S, 8.87 (8.98); ESI-
-4
H
15NO
3
(
+
MS: [M+1] 362.41 (obs.) 361.41 (calcd.). UV-vis.: λmax in nm
(E)-((4-((2-Aminophenyl)imino)-2-(4-chlorophenyl)-4H-
chromen-3-yl)oxy)cobalt dihydrate chloride (I-3): Colour:
-
4
(
in DMSO, 2 × 10 M), 268 (π-π* transitions), 365 (n-π* transi-
-1
tion).
brown; Yield 68 %, m. p. > 300 ºC. IR (KBr, νmax, cm ): 3486
(
E)-2-(4-Chlorophenyl)-4-((2-mercaptophenyl)imino)-
(OH), 3308 (NH), 3033 (CH), 1585 (C=N), 1624 (C=C), 1314
7
1
4
H-chromen-3-ol (L ):Yield: 68 % (0.26 g), colour: yellowish
(C-O), 538 (O-Co), 499 (N-Co), 367 (Co-Cl); H NMR (DMSO-
-
1
brown, m.p.: 132 ºC. IR (KBr,νmax, cm ): 3433 (OH), 2950 (CH),
d
6
, 400 MHz, 25 ºC, TMS), δ (ppm): 4.08 (2H, s), 7.3 (s, 2H),
1
565 (C=N), 1530 (C=C), 2580 (SH), 1239 (C-S), 1243 (C-O);
7.46-9.23 (m,Ar-H). Elemental analysis (%) of C21 Cl Co
H
17
N
2
O
4
2
1
H NMR (400 MHz, DMSO-d
6
), δ (ppm): 3.00(1H, s, SH),
calcd. (found): C, 51.35 (51.37); H, 3.49(3.50); N, 5.70 (5.69);
+
6
.90 (2H, d, J = 7.9, Hz), 7.00 (2H, d, J = 8.3, Hz), 7.14 (4H,
Cl, 14.43 (14.43); Co, 12.00 (11.98). ESI-MS: [M+1] 491.20
13
-4
m), 7.26 (4H, m), 9.57 (1H, s, OH); C NMR (100 MHz,
DMSO-d ), δ (ppm): 111.82, 113.72, 118.62, 120.51 124.78,
26.71, 126.72, 127.01, 127.49, 127.71, 128.10, 128.10, 128.96,
28.97, 131.34, 135.68, 144.98, 154.36, 155.66, 155.81, 159.60.
SCl calcd. (found): C,
6.40 (66.95); H, 3.71 (3.83); N, 3.69 (3.96); Cl, 9.33 (9.47);
(obs.), 491.21 (calcd.). UV-vis.: λmax innm (in DMSO, 2 × 10 M)
6
264 (π-π* transitions), 407 (n-π* transition), 527 (d-d transi-
tion).
1
1
(E)-((4-((2-Aminophenyl)imino)-2-(4-(dimethylamino)-
phenyl)-4H-chromen-3-yl)oxy)cobalt dihydrate chloride (I-4):
Elemental analysis (%) of C21
H14NO
2
-1
6
Colour: brown;Yield 58 %, m. p.: > 300 ºC. IR (KBr,νmax, cm ):
+
S, 8.44 (8.52); ESI-MS: [M+1] 380.86 (obs.) 379.86 (calcd.).
UV-vis.: λmax in nm (in DMSO, 2 × 10 M), 275 (π-π* transi-
tions), 355 (n-π* transition).
3526 (OH), 3326 (NH), 3021 (CH), 1585 (C=N), 1654 (C=C),
-4
1
1296 (C-O), 528 (O-Co), 495 (N-Co), 344 (Co-Cl); H NMR
(DMSO-d
(2H, s), 7.02 (s, 2H), 7.16-9.86 (m, Ar-H). Elemental analysis
ClCo calcd. (found): C, 55.27 (55.34); H,
6
, 400 MHz, 25 ºC, TMS), δ (ppm): 2.88 (6H, s), 3.96
(
E)-2-(4-(Dimethylamino)phenyl)-4-((2-mercapto-
8
phenyl)imino)-4H-chromen-3-ol (L ): Yield: 66 % (0.26 g),
colour: reddish brown, m.p.: 145 ºC. IR (KBr, νmax, cm ): 3464
(%) of C23
H
23
N O
3 4
-
1
4.64 (4.67); N, 8.41 (8.40), Cl, 7.09 (7.11); Co, 11.79 (11.75).
+
(
(
OH), 2897 (CH), 1593 (C=N), 1578 (C=C), 2571 (SH), 1235
C-S), 1206 (C-O), 1277 (C-N); H NMR (400 MHz, DMSO-
ESI-MS: [M+1] 500.64 (obs.), 499.83 (calcd.). UV-vis.: λmax
1
-4
innm(in DMSO, 2 × 10 M), 266 (π-π* transitions), 382 (n-π*
d
8
6
), δ (ppm): 2.89 (6H, s), 2.86 (1H, s, SH), 6.61 (2H, d, J =
transition), 562 (d-d transition).
.8 Hz), 7.04 (2H, d, J = 7.5Hz), 7.40-7.56 (4H, m), 7.31 (4H,
(E)-((4-((2-Aminophenyl)imino)-2-(4-(dimethylamino)-
phenyl)-4H-chromen-3-yl)oxy)cobalt dihydrate chloride (I-5):
Colour: yellow brown; Yield 72 %, m.p.: > 360 ºC. IR (KBr,
13
m), 9.93 (1H, s, OH); C NMR (100 MHz, DMSO-d
6
), δ (ppm):
4
1
1
0.31, 40.31, 111.78, 118.66, 113.77, 113.84, 113.84, 120.53,
24.75, 126.42, 126.44, 127.11, 127.49, 127.69, 128.09, 128.10,
31.34, 144.99, 151.40, 154.34, 155.68, 155.81, 159.59.
-
1
ν
max, cm ): 3545 (OH), 2890 (CH), 1590 (C=N), 1564 (C=C),
1293 (C-S), 1297 (C-O), 527 (O-Co), 498 (N-Co), 356 (Co-Cl),
1
Elemental analysis (%) of C23
H
20
N
2
O
2
S calcd. (found): C, 71.11
471(Co-S); H NMR (DMSO-d
3.95 (3H, s), 6.96-8.76 (m, Ar-H). Elemental analysis (%) of
SClCo calcd. (found): C, 52.44 (52.47); H, 3.80
6
, 400 MHz, 25 ºC,TMS), δ(ppm):
(
71.75); H, 5.19 (5.63); N, 7.21 (7.77); S, 8.25 (8.68). ESI-
+
MS: [M+1] 389.48 (obs.), 388.48 (calcd.). UV-vis.: λmax in nm
C
22
H
19NO
5
-4
(
in DMSO, 2 × 10 M), 273 (π-π* transitions), 347 (n-π* transi-
(3.83); Cl, 7.04 (7.03); N, 2.78 (2.77); S, 6.36 (6.35); Co, 11.70
+
tion).
(11.71). ESI-MS: [M+1] 504.32 (obs.), 503.84 (calcd.). UV-
-4
(E)-((4-((2-Aminophenyl)imino)-2-(4-methoxyphenyl)-
vis.: λmax in nm (in DMSO, 2 × 10 M), 270 (π-π* transitions),
390 (n-π* transition), 550 (d-d transition).
4
H-chromen-3-yl)oxy)cobalt dihydrate chloride (I-1):
-1
Colour: brown;Yield 73 %, m. p.: > 350 ºC. IR (KBr,νmax, cm ):
3
1
(E)-((4-((2-Mercaptophenyl)imino)-2-(4-methoxyphenyl)-
4H-chromen-3-yl)oxy)cobalt dihydrate chloride (I-6): Colour:
530 (OH), 3356 (NH), 2859 (CH), 1557 (C=N), 1548 (C=C),
298 (C-O), 527 (O-Co), 492 (N-Co), 352 (Co-Cl); H NMR
1
-1
reddish brown;Yield 69 %, m.p.: > 320 ºC. IR (KBr,νmax, cm ):
(
3
C
(
DMSO-d
6
, 400 MHz, 25 ºC, TMS), δ (ppm): 3.47 (3H, s),
.78 (2H, s), 7.00-9.80 (m, Ar-H). Elemental analysis (%) of
ClCo calcd. (found): C, 54.28 (54.76); H, 4.14
4.28); N, 5.75 (5.74); Cl, 7.28 (7.31); Co, 12.11 (12.12). ESI-
3547 (OH), 2990 (CH), 1576 (C=N), 1614 (C=C), 1281 (C-S),
1307 (C-O), 537 (O-Co), 502 (N-Co), 362 (Co-Cl), 478 (C-S);
1
22
H
20
2
N O
5
H NMR (DMSO-d
6
, 400MHz,25ºC,TMS), δ(ppm): 9.78 (s, OH),
SClCo
6.96-8.93 (m,Ar-H). Elemental analysis (%) of C21
H
17NO
5
+
MS: [M+1] 504.82 (obs.), 504.2 (calcd.). UV-vis.: λmax in nm
calcd. (found): C, 51.49 (51.51); H, 3.50 (3.52); Cl, 7.24 (7.23);
-4
+
(
in DMSO, 2 × 10 M), 257 (π-π* transitions), 402 (n-π* transi-
tion), 542 (d-d transition).
E)-((4-((2-Aminophenyl)imino)-2-(4-hydroxyphenyl)-
H-chromen-3-yl)oxy)cobalt dehydrate chloride (I-2): Colour:
N, 2.86 (2.84); S, 6.55 (6.53); Co, 12.03 (12.06); ESI-MS: [M+1]
490.58 (obs.), 489.81 (calcd.). UV-vis.: λmax innm (in DMSO, 2
-4
(
× 10 M), 269 (π-π* transitions), 372 (n-π* transition), 532
(d-d transition).
4
-1
blackish brown;Yield 65 %, m.p.: > 360 ºC. IR (KBr,νmax, cm ):
3
1
(E)-((2-(4-Hydroxyphenyl)-4-((2-mercaptophenyl)-
imino)-4H-chromen-3-yl)oxy)cobalt dihydrate chloride (I-7):
Colour: blackish brown;Yield 66 %, m.p.: > 300 ºC. IR (KBr,
523 (OH), 3327 (NH), 2837 (CH), 1563 (C=N), 1629 (C=C),
302 (C-O), 545 (O-Co), 497 (N-Co), 3364 (Co-Cl); H NMR
1
-1
(
DMSO-d
s, 2H), 6.86-8.96 (m, Ar-H). Elemental analysis (%) of
ClCo calcd. (found): C, 53.35 (53.37); H, 3.84
3.86); N, 5.93 (5.92), Cl, 7.50 (7.49); Co, 12.47 (12.46). ESI-
6
, 400 MHz, 25 ºC, TMS), δ (ppm): 3.88 (2H, s), 6.59
ν
max, cm ): 3507 (OH), 2870(CH), 1570 (C=N), 1627 (C=C),
(
C
(
1274 (C-S), 1316 (C-O), 525 (O-Co), 499 (N-Co), 372 (Co-Cl),
1
21
H
18
2
N O
5
486(C-S); H NMR (DMSO-d
6
, 400 MHz, 25 ºC, TMS), δ (ppm):
SCl Co
6.72-8.82 (m,Ar-H). Elemental analysis (%) of C21
H
16NO
4
2