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3.1.11. 1-[[(2,3,6-Trifluorophenyl)imino]methylenyl]-2-
naphthalenol (L11)
washed with cold ethanol and dried. Yield 0.81 g (91.6%),
m.p. 190–191 °C. 1H NMR (CDCl3, 300 MHz): d 5.34 (s,
2H), 6.82–8.10 (m, 14H), 9.78 (d, J ¼ 10:5 Hz, 1H), 15.38
(s, 1H) ppm. 13C NMR (CDCl3, 75 MHz): d 70.5, 109.0,
119.1, 120.0, 120.5, 123.8, 126.6, 126.7, 126.8, 128.2,
128.5, 128.8, 129.3, 134.4, 135.7, 139.8, 140.0, 142.4,
144.1, 145.2, 183.1 ppm. IR (KBr): 3438, 3059, 1618,
1570, 1536, 1496, 1460, 1405, 1384, 1314, 1280, 621, 430
cmꢀ1. Anal. Calc. for C23H18N2O2: C, 77.95; H, 5.12; N,
7.90. Found: C, 77.83; H, 5.09; N, 7.83%.
Ligand L11 was prepared with the above protocol for
L1 except that 2,3,6-trifluoroaniline was used in place of
2-isopropylaniline, and was obtained as yellow micro-
crystals. Yield 0.66 g (87.8%), m.p. 164–165 °C. 1H
NMR (CDCl3, 300 MHz): d 6.97–8.12 (m, 8H), 9.77 (s,
1H), 14.79 (d, J ¼ 1:2 Hz, 1H) ppm. 13C NMR (CDCl3,
75 MHz): d 109.5, 110.6, 110.7, 110.8, 111.0, 111.1,
112.7, 112.9, 113.0, 113.1, 119.2, 120.2, 123.9, 126.4,
127.7, 128.3, 129.3, 132.8, 136.6, 146.0, 149.4, 149.9,
153.1, 163.9, 165.2 ppm. IR (KBr): 3443, 3067, 1620,
1570, 1498, 1475, 1423, 1391, 1331 cmꢀ1. Anal. Calc. for
C17H10F3NO: C, 67.78; H, 3.35; N, 4.65. Found: C,
67.60; H, 3.30; N, 4.38%.
3.1.15. 1-[[(2-Pyridinyl)imino]methylenyl]-2-naphthale-
nol (L15)
Ligand L15 was prepared from the condensation of
2-hydroxy-1-naphthaldehyde with 2-aminopyridine us-
ing the above protocol for L14 as yellow solid. Yield
0.60 g (96.3%). Its characteristic data are consistent with
reported paper [29].
3.1.12. 1-[[(2,4,5-Trichlorophenyl)imino]methylenyl]-2-
naphthalenol (L12)
Ligand L12 was prepared from the condensation of
2,4,5-trichloroaniline with 2-hydroxy-1-naphthaldehyde
using the protocol described for L1 and was obtained as
yellow crystals. Yield 0.58 g (66.5%), m.p. 204–206 °C.
1H NMR (CDCl3, 300 MHz): d 7.16–8.19 (m, 8H), 9.43
3.1.16. 1-[[(4-Methyl-2-pyridinyl)imino]methylenyl]-2-
naphthalenol (L16)
Ligand L16 was prepared with a protocol described
in the literature [30], and was obtained as yellow mi-
crocrystals. Yield 0.58 g (89.0%).
(d, J ¼ 1:8 Hz, 1H), 14.96 (d, J ¼ 1:5 Hz, 1H) ppm. 13
C
NMR (CDCl3, 75 MHz): d 108.9, 118.7, 119.6, 120.1,
123.4, 123.5, 127.2, 127.9, 129.0, 129.8, 130.8, 131.5,
132.3, 136.5, 143.3, 157.3, 166.1, 200.2 ppm. IR (KBr):
3481, 3059, 1603, 1584, 1559, 1453, 1422, 1393, 1349,
1322 cmꢀ1. Anal. Calc. for C17H10Cl3NO: C, 58.23; H,
2.87; N, 3.99. Found: C, 58.20; H, 2.86; N, 3.84%.
3.1.17. 1-[[(4,6-Dimethyl-2-pyridinyl)imino]methylenyl]-
2-naphthalenol (L17) [30]
Ligand L17 was prepared from the condensation of
2-hydroxy-1-naphthaldehyde with 2-amino-4,6-dimeth-
ylpyridine using the above protocol for L14, and was
obtained as yellow crystals. Yield 0.58 g (83.7%), m.p.
1
3.1.13. 1-[[(2,4,6-Trichlorophenyl)imino]methylenyl]-2-
naphthalenol (L13)
196–198 °C. H NMR (CDCl3, 300 MHz): d 2.36 (s,
3H), 2.55 (s, 3H), 6.77–8.12 (m, 8H), 9.91 (d, J ¼ 8:4 Hz,
1H), 15.39 (s, 1H) ppm. 13C NMR (CDCl3, 75 MHz): d
20.8, 24.1 108.3, 112.9, 119.1, 121.6, 123.6, 125.3, 126.6,
128.3, 129.2, 134.2, 139.1, 149.0, 150.0, 151.4, 157.8,
179.8 ppm. IR (KBr): 3438, 3036, 1617, 1541, 1451,
1404, 1294, 611, 432 cmꢀ1. Anal. Calc. for C18H16N2O:
C, 78.24; H, 5.84; N, 10.14. Found: C, 78.11; H, 5.90; N,
10.08%.
Ligand L13 was prepared from the condensation of
2,4,6-trichloroaniline with 2-hydroxy-1-naphthaldehyde
using the protocol described for L1, and was obtained as
yellow microcrystals. Yield 0.49 g (56.2%), m.p. 158–160
1
°C. H NMR (CDCl3, 300 MHz): d 7.23–8.09 (m, 8H),
9.49 (s, 1H), 14.20 (s, 1H) ppm. 13C NMR (CDCl3, 75
MHz): d 108.9, 118.5, 119.1, 119.3, 119.8, 123.9, 124.4,
127.8, 128.1, 128.3, 128.6, 129.1, 129.3, 129.4, 130.6,
132.9, 136.3, 139.1, 142.9, 163.8, 165.7, 193.2 ppm. IR
(KBr): 3424, 3072, 1608, 1583, 1450, 1321 cmꢀ1. Anal.
Calc. for C17H10Cl3NO: C, 58.23; H, 2.87; N, 3.99.
Found: C, 57.93; H, 2.79; N, 3.74%.
3.1.18. 1-[[(3,5-Dibromo-6-methyl-2-pyridinyl)imino]-
methylenyl]-2-naphthalenol (L18)
Ligand L18 was prepared by using the above
protocol for L14 except that 2-amino-3,5-dibromo-6-
methylpyridine was used in place of 2-amino-3-benzyl-
oxypyridine, and was obtained as yellow crystals. Yield
0.93 g (88.8%), m.p. 217–218 °C. 1H NMR (CDCl3, 300
MHz): d 2.66 (s, 3H), 6.93–8.14 (m, 7H), 9.91 (d, J ¼ 6:6
Hz, 1H), 15.55 (d, J ¼ 6:4 Hz, 1H) ppm. 13C NMR
(CDCl3, 75 MHz): d 24.4, 109.4, 109.6, 116.7, 119.4,
124.0, 124.2, 127.2, 128.6, 129.4, 133.7, 139.5, 144.0,
149.2, 150.6, 155.6, 177.2 ppm. IR (KBr): 3435, 3057,
1621, 1609, 1540, 1437, 1407, 1379, 1319, 1291, 600, 435
cmꢀ1. Anal. Calc. for C17H12Br2N2O: C, 48.60; H, 2.88;
N, 6.67. Found: C, 48.69; H, 2.91; N, 6.48%.
3.1.14. 1-[[(3-Benzyloxy-2-pyridinyl)imino]methylenyl]-
2-naphthalenol (L14)
An ethanol (20 mL) solution of 2-amino-3-benzyl-
oxypyridine (0.50 g, 2.5 mmol) was added slowly over 30
min into a solution of 2-hydroxy-1-naphthaldehyde (0.43
g, 2.5 mmol) in ethanol (10 mL) at room temperature.
The reaction mixture was stirred for 5 h at 40–45 °C, and
the solution was then evaporated into 10 mL under
vacuum. The product was recrystallized from ethanol,
and, after filtration, the yellow crystals were collected,