H.D. Yin et al. / Journal of Organometallic Chemistry 690 (2005) 3714–3719
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Table 2
1H, 13C and 119Sn NMR signals for salicylaldehyde isonicotinylhydrazone (H2SalN) and its tin(IV) complexes in CDCl3
1H NMR (d)
13C NMR (d)
119Sn NMR (d)
H2SalN
11.25 (1H, s, OH), 8.32 (1H, s,
N@CH), 8.73 (2H, d, J = 5 Hz,
2,6-pyridine-H), 7.79 (2H, d,
J = 6 Hz, 3,5-pyridine-H), 7.41–
6.87 (4H, m, Haromatic), 3.71–3.74
(1H, m, NH)
150.3, 143.5, 126.2 (Cpyridine),
149.9, 135.9, 128.7, 121.0, 115.9,
112.0 (Caromatic), 164.6 (C@O),
155.2 (C@N)
1
2
3
8.86 (1H, m, N@CH), 7.93 (2H,
d, J = 6 Hz, 2,6-pyridine-H), 7.35
(2H, d, J = 7 Hz, 3,5-pyridine-
H), 7.26–6.70 (4H, m, Haromatic),
1.34 (18H, s, –C(CH3)3)
159.0, 143.7, 129.0 (Cpyridine),
142.3, 137.6, 129.7, 121.2, 115.3,
112.0 (Caromatic), 172.1 (C–O),
159.1 (C@N), 40.7, 29.9 (C–But,
1JSnC = 650 Hz)
À262.4
À323.2
À305.4
8.88 (1H, m, N@CH), 8.13 (2H,
d, J = 6 Hz, 2,6-pyridine-H), 7.65
(2H, d, J = 6 Hz, 3,5-pyridine-
160.3, 144.1, 122.3 (Cpyridine),
150.5, 143.2, 138.3, 136.9, 134.6,
130.5, 129.1, 127.3, 125.3, 114.4
(Caromatic,
1JSnC = 589 Hz), 171.3
H), 7.78–7.04 (14H, m, Haromatic
)
(C–O), 163.9 (C@N)
8.89 (1H, m, N@CH), 8.06 (2H,
161.2, 145.2, 127.7 (Cpyridine),
152.3, 148.5, 139.3, 137.4, 134.7,
131.3, 129.5, 127.4, 125.3, 111.5
(Caromatic), 169.4 (C–O), 157.8
(C@N), 38.3 (Sn–CH2,
d, J = 4 Hz, 2,6-pyridine-H), 7.52
(2H, d, J = 6 Hz, 3,5-pyridine-
H), 7.84–6.34 (14H, m, Haromatic),
3.13 (4H, t, JSn–H = 79 Hz,
PhCH2Sn)
1JSnC = 624 Hz)
4
5
6
7
8
8.95 (1H, m, N@CH), 7.99 (2H,
d, J = 6 Hz, 2,6-pyridine-H), 7.75
(2H, d, J = 5 Hz, 3,5-pyridine-
H), 7.64–6.63 (12H, m, Haromatic),
3.26 (4H, s, JSn–H = 86 Hz,
ArCH2Sn)
152.3, 146.3, 123.4 (Cpyridine),
151.8, 146.5, 140.2, 138.3, 136.5,
135.4, 133.6, 131.4, 129.2, 128.5,
127.3, 109.9 (Caromatic), 172.3
(C–O), 156.9 (C@N), 34.5
À310.5
À322.8
À297.9
À304.9
À317.6
1
(Sn–CH2, JSnC = 655 Hz)
8.86 (1H, m, N@CH), 8.10 (2H,
d, J = 6 Hz, 2,6-pyridine-H), 7.68
(2H, d, J = 6 Hz, 3,5-pyridine-
H), 7.81–6.89 (12H, m, Haromatic),
3.33 (4H, s, JSn–H = 89 Hz,
ArCH2Sn)
158.5, 142.4, 121.4 (Cpyridine),
152.0, 144.6, 136.5, 135.6, 132.6,
128.5, 127.6, 121.3, 115.6, 109.9
(Caromatic), 169.4 (C–O), 159.9
(C@N), 32.6 (Sn–CH2,
1JSnC = 623 Hz)
8.88 (1H, m, N = CH), 8.13 (2H,
d, J = 6 Hz, 2,6-pyridine-H), 7.65
(2H, d, J = 6 Hz, 3,5-pyridine-
H), 7.65–6.88 (12H, m, Haromatic),
3.31 (4H, s, JSn–H = 80 Hz,
ArCH2Sn)
155.1, 147.2, 123.7 (Cpyridine),
153.1, 147.5, 141.4, 138.1, 137.1,
135.2, 134.1, 131.8, 129.5, 128.5,
127.3, 107.4 (Caromatic), 172.8
(C–O), 157.3 (C@N), 34.9
1
(Sn–CH2, JSnC = 635 Hz)
8.98 (1H, m, N@CH), 8.04 (2H,
d, J = 6 Hz, 2,6-pyridine-H), 7.58
(2H, d, J = 4 Hz, 3,5-pyridine-
H), 7.98–7.21 (12H, m, Haromatic),
3.12 (4H, s, JSn–H = 79 Hz,
ArCH2Sn)
161.4, 147.4, 126.5 (Cpyridine),
154.3, 145.4, 139.5, 135.9, 134.4,
132.0, 127.6, 125.4, 124.7, 122.4,
112.6, 109.2 (Caromatic), 170.2
(C–O), 161.4 (C@N), 34.7
1
(Sn–CH2, JSnC = 642 Hz)
8.89 (1H, m, N@CH), 8.21 (2H,
d, J = 6 Hz, 2,6-pyridine-H), 7.72
(2H, d, J = 6 Hz, 3,5-pyridine-
H), 7.76–7.13 (12H, m, Haromatic),
3.28 (4H, s, JSn–H = 85 Hz,
ArCH2Sn)
160.1, 143.1, 121.6 (Cpyridine),
152.6, 145.1, 136.7, 135.4, 133.1,
128.2, 127.7, 121.6, 117.4, 110.2
(Caromatic), 170.2 (C–O), 159.6
(C@N), 32.7 (Sn–CH2,
1JSnC = 619 Hz)
bazone) moiety and the plane of the phenyl (or pyridine)
ring, which are 3.9ꢁ and 10.58(10)ꢁ in H2SalN and
H2Bz4Ph, respectively, and the angles between the acy-
lhydrazone (or thiosemicarbazone) chain and the pyri-
dine (or N(4)-phenyl) ring, which are 9.9ꢁ and
15.95(8)ꢁ, respectively. Such dissimilarities are pro-
bably responsible for the differences in the angles in
the acylhydrazone (or thiosemicarbazone) moiety of