H.A. Elagab, H.G. Alt / Polyhedron 115 (2016) 17–29
27
Table 4
NMR and mass spectroscopic data of free ligands 1–12 and complexes 13–44.
No. 1H NMR d (ppm) 13C NMR d (ppm)
Mass m/z (%)
+
1
2
3
8.69 (d, 1H), 8.29 (d, 1H), 7.95 (t, 1H), 7.59–7.57 (m, 2H), 7.48 (t, 151.3, 150.0, 149.1, 138.2, 125.4, 123.2, 122.1
195 M° (100)
1
H), 7.19–7.17 (m, 2H)
8.39 (d, 2H), 8.31 (t, 1H), 7.75–7.69 (m, 4H), 7.31–7.24 (m, 4H) 151.4, 148.5, 145.0, 140.1, 135.3, 124.4, 122.9,
22.0, 120.4, 112.6
7.88 (d, 1H), 7.80 (d, 1H), 7.69 (t, 2H), 7.64 (s, 2H, N–H), 7.61 (m, 151.6, 137.9, 133.5, 131.9, 129.4, 123.5, 115.5
H), 7.26 (m, 4H)
7.57 (d, 4H), 7.26 (t, 4H), 3.56 (s, 42H, 2CH
+
311 M° (100)
1
+
310 M° (100)
4
+
4
5
6
7
2
)
153.8, 135.4, 124.3, 114.6, 25.4
150.8, 138.4 122.9, 115.4, 29.8
156.0, 126.4, 123.8, 116.0
262 M° (100)
+
12.41 (s, 2H, NH), 7.46 (m, 4H), 7.11 (m, 4H), 4.43 (s, 2H, CH
7.11–6.99 (m, 8H)
2
)
248 M° (100)
+
234 M° (100)
+
8.64 (d, 1H), 8.38 (d, 1H), 7.83 (t, 1H), 7.75 (d, 1H), 7.42 (d, 1H), 150.9, 149.9, 148.8, 142.958, 137.4, 137.0, 133.9,
.37–7.23 (m, 3H), 6.12–6.02 (m, 1H), 5.52 (d, 2H), 5.11–5.02 124.7, 123.9, 123.4, 122.6, 120.1, 116.6, 110.7, 48.1
dd, 2H)
8.26 (d, 2H), 7.91 (t, 1H), 7.72 (d, 2H), 7.35 (d, 2H), 7.24 (t, 4H), 150.1, 150.0, 143.0, 138.21, 136.7, 133.2, 125.7,
.87–5.80 (m, 22H, 2CH), 5.01 (d, 4H), 4.81 (d, 4H) 123.71, 122.9, 120.2, 116.8, 111.1, 47.6
7.84 (d, 2H), 7.73–7.65 (m, 4H), 7.59–7.47 (m, 4H), 7.19 (t, 2H), 151.2, 132.9, 132.8, 131.8, 130.7, 130.3, 130.2,
.71–5.70 (m, 2H), 5.13–4.99 (dd, 4H), 4.60 (d, 4H) 129.7, 118.6, 66.2
7.67 (s, 2H), 7.18–7.17 (m, 6H), 5.86–5.83 (m, 2H, 2CH), 4.98 (d, 154.0, 142.7, 135.4, 132.0, 122.6, 122.2, 119.3,
H), 4.76 (s, 4H), 3.48 (s, 42H, 2CH 117.4, 109.7, 45.7, 24.9
7.58 (d, 2H), 7.50 (d, 2H), 7.20 (t, 4H), 5.99–5.92 (m, 22H, 2CH), 150.8, 142.9, 135.9, 133.8, 122.8, 122.3, 119.5,
.14 (d, 4,H), 5.00 (d, 4H), 4.61 (s, 2H, CH) 117.6, 111.1, 46.3, 25.6
7.19 (s, 8H), 5.90–5.84 (m, 2H, CH), 5.25–5.18 (m, 4H), 4.82 (s, 154.2, 130.6, 126.8, 124.4, 118.5, 115.9, 45.7
H)
8.93–8.90 (dd, 2H), 8.24 (t, 1H), 7,88–7.85 (dd, 2H), 7.80–7.75
dd, 1H), 7.61–7.58 (dd, 2H)
235 M° (100)
7
(
+
8
9
1
1
1
1
391 M° (100)
5
+
390 M° (100)
5
+
0
1
2
3
342 M° (100)
4
2
)
+
328 M° (100)
5
+
314 M° (100)
4
+
+
151.2, 147.8, 142.8, 139.1, 132.6, 128.3, 127.1,
124.8, 115.1
385 M° (5), 349 M° ÀCl (10), 312 M
+
+
(
° À2Cl (5), 276 M° À3Cl (15), 243 M
+
+
°
À4Cl (5) 195 M° ÀTiCl
4
(100)
+
+
1
4
8.79 (d, 1H), 8.50 (d, 1H), 8.08 (t, 1H), 7.71–7.68 (dd, 2H), 7.62– 150.8, 148.9, 144.2 138.8, 134.3, 127.3, 125.8,
428 M° (2), 392 M° ÀCl (15), 355 M
+
+
7.59 (dd, 1H), 7.38–7.36 (dd, 2H)
123.9, 115.5
° À2Cl (20), 320 M° À3Cl (5), 284 M
+
+
°
À4Cl (5), 195 M° ÀZrCl
4
(100)
+
+
1
5
7
n.d.
n.d.
352 M° (5), 316 M° ÀCl (20), 281 M
+
+
°
À2Cl (10), 195 M° ÀVCl
3
(100)
+
+
1
8.37 (d, 2H), 8.08 (t, 2H), 7.924–7.835 (m, 4H), 7.637–7.625 (m, 148.2, 134.0, 133.8, 133.6, 126.5, 125.1, 115.4
H)
500 M° (1), 463 M° ÀCl (2), 428 M
+
+
4
° À2Cl (3), 394 M° À3Cl (5), 357 M
+
+
°
À4Cl (2), 310 M° ÀTiCl
4
(100)
+
+
1
8
8.28–8.25 (dd, 2H), 7.94 (t, 2H), 7.71–7.67 (m, 4H), 7.45–7.42
m, 4H)
149.1, 135.0, 132.5, 126.2, 125.4, 115.3, 114.8
543 M° (1), 506 M° ÀCl (1), 437 M
+
+
(
° À3Cl (3), 400 M° À4Cl (5), 310 M
+
°
ÀZrCl
4
(100)
+
+
1
9
0
n.d.
n.d.
467 M° (1), 430 M° ÀCl (5), 393 M
+
+
°
À3Cl (2), 310 M° ÀVCl
3
(100)
+
+
2
7.76–7.70 (m, 4H), 7.50–7.43 (m, 4H), 3.95 (s, 42H, 2CH
2
)
152.5, 132.6, 125.6, 114.6, 24.5
452 M° (5), 416 M° ÀCl (2), 380 M
+
+
+
°
°
À2Cl (5), 343 M° À3Cl (10), 310 M
+
À4Cl (2), 262 M° ÀTiCl
4
(10)
+
+
2
1
2
7.73–7.71 (m, 4H), 7.45–7.42 (m, 4H), 3.84 (s, 42H, 2CH
n.d.
2
)
152.7, 133.3, 125.3, 114.7, 24.7
n.d.
495 M° (2), 458 M° ÀCl (2), 422 M
+
+
+
°
°
À2Cl (5), 387 M° À3Cl (3), 351 M
+
À4Cl (2), 262 M° ÀZrCl
4
(50)
+
+
2
420 M° (15), 385 M° ÀCl (15), 343 M
+
+
+
°
°
À2Cl (10), 310 M° À4Cl (2), 262 M
ÀVCl
3
(80)
+
+
2
3
4
7.52–7.49 (m, 4H), 7.52–7.14 (m, 4H), 4.55 (s, 2H, CH
2
)
)
149.0, 135.4, 124.4, 115.1, 27.5
150.6, 138.7, 122.6, 115.3, 29.6
438 M° (1), 402 M° ÀCl (2), 367 M
+
+
°
À2Cl (2), 248 M° ÀTiCl
4
(100)
+
+
2
7.63–7.62 (m, 4H), 7.33–7.30 (m, 4H), 4.91 (s, 2H, CH
2
481 M° (1), 444 M° ÀCl (2), 407 M
+
+
+
°
°
À2Cl (1), 370 M° À3Cl (2), 336 M
+
À4Cl (1), 248 M° ÀZrCl
4
(100)
+
+
2
5
n.d.
n.d.
406 M° (3), 368 M° ÀCl (7), 334 M
+
+
+
°
°
À2Cl (10), 299 M° À3Cl (20), 248 M
ÀVCl
3
(100)
+
+
+
2
2
2
2
6
7
8
9
7.40 (d, 4H), 7.15 (t, 4H)
7.18 (d, 4H), 7.04 (t, 4H)
n.d.
156.1, 126.6, 123.8, 116.2
156.2, 126.6, 124.0, 116.2
n.d.
425° (2), 352 M° À2Cl (2), 317 M° À3Cl
+
(
10), 234 M° ÀTiCl
4
(100)
+
+
+
467° (5), 397 M° À2Cl (2), 361 M° À3Cl
+
(
10), 234 M° ÀZrCl
4
(100)
+
+
+
392° (5), 323 M° À2Cl (2), 288 M° À3Cl
+
(
10), 234 M° ÀVCl
3
(50)
+
+
8.84 (d, 1H), 8.52 (d, 1H), 8.15 (t, 1H), 7.94–7.92 (m, 1H), 7.89– 150.8, 146.5, 144.0, 139.0, 133.8, 132.8, 132.3,
347 M° ÀCl-allyl (7), 312 M° À2Cl-allyl
+
7.87 (m, 1H), 7.70–7.67 (m, 1H), 7.58–7.54 (m, 2H), 6.09–6.02
127.7, 127.4, 127.1, 127.0, 119.3, 115.8 114.2, 49.1 (5), 235 M° ÀTiCl
4
, (100)
(
m, 1H, CH), 5.55 (d, 2H, CH ), 5.20–5.16 (dd, 2H, CH
2
2
)
+
+
3
3
3
3
0
1
2
3
8.69 (d, 1H), 8.41 (d, 1H), 7.75 (t, 1H), 7.69 (d, 1H), 7.46 (d, 1H), 150.9, 146.6, 144.0, 139.0, 134.0, 133.0, 132.4,
425 M° Àallyl (15), 396 M° À2Cl (10),
+
+
7
2
.35 (t, 1H), 7.28–7.22 (m, 2H), 6.18–6.01 (m, 1H, CH), 5.50 (d, 127.7 127.4, 127.1, 127.0, 119.5, 115.8, 114.3, 49.2 363 M° À3Cl (25), 235 M° ÀZrCl
4
, (100)
2 2
H, CH ), 5.12–5.02 (dd, 2H, CH )
+
+
n.d.
n.d.
n.d.
392 M° (1), 356 M° ÀCl (5), 3321 M
+
+
+
°
°
À2Cl (5), 315 M° ÀCl-allyl (5), 235 M
ÀVCl
3
, (100)
+
+
n.d.
548 M° (2), 512 M° ÀCl (5), 477 M
+
+
+
°
°
À2Cl (5), 441 M° À3Cl (2), 430 M
+
ÀCl-2allyl (3), 391 M° ÀVCl
3
(100)
+
+
8.13 (d, 2H), 7.91 (t, 2H), 7.82–7.81 (m, 4H), 7.59–7.56 (m, 4H), 149.7, 133.5, 132.8, 132.2, 131.5, 130.9, 125.7,
580 M° (1), 544 M° ÀCl (5), 507 M
(
continued on next page)