Structural characterization and cytotoxicity of diorganotin complexes
Table 2. 13C NMR chemical shifts (d, ppm) of the Schiff base ligands and their corresponding diorganotin(IV) complexes
Compound
no.
C-1, C-3, C-4,
C-5, C-6
C-8
C-7
C-9, C-10, C-11, C-12, C-13, C-14,
C-15, C-16, C-17, C-18
C-2
Sn&ꢁ(Ca to Cd)
H2L1
1a
118.8, 126.0, 133.9, 171.2 156.5 121.3, 154.0, 110.9, 138.5, 124.2,
110.6, 136.0 124.0, 126.8, 128.5, 128.8, 130.5
117.7, 126.1, 135.8, 170.1 160.2 122.0, 155.4, 111.2, 138.3, 123.8,
108.5, 136.8 123.2, 127.3, 128.1, 128.8, 131.0
118.0, 126.4, 135.5, 170.3 160.0 121.8, 155.6, 111.1, 138.2, 123.8,
108.1, 136.6 123.3, 127.3, 128.0, 128.9, 130.9
163.8
165.5
—
1.9 (Ca, 1J(119/117Sn-13C) = 555, 525 Hz)
2b
166.1 22.8 (Ca, 1J(119/117Sn&ꢁ13C) = 565, 540 Hz), 26.9
(Cb, 2J(119Sn&ꢁ13C) = 28 Hz), 26.4 (Cg, 3J(119/
117Sn&ꢁ13C) = 77, 69 Hz), 13.6 (Cd)
3b
117.3, 126.2, 135.3, 169.7 160.2 121.4, 154.9, 110.9, 138.1, 123.7,
108.4, 136.4 123.1, 126.9, 127.9, 129.2, 131.0
167.7 137.5 (Ca, 1J(119/117Sn&ꢁ13C) = 510, 485 Hz), 130.4
(Cb, 2J(119Sn&ꢁ13C) = 22 Hz), 127.5 (Cg, J
3
(
119/117Sn&ꢁ13C) = 56, 50 Hz),
131.6 (Cd)
4a
117.8, 126.1, 135.5, 170.4 159.7 121.1, 155.5, 111.0, 138.1, 123.8,
107.8, 136.7 123.3, 127.3, 128.0, 128.8, 130.8
166.7 41.0 (Ca, 1J(119/117Sn&ꢁ13C) = 574, 548 Hz), 29.9
(Cb, 2J(119Sn&ꢁ13C) = 22 Hz), 28.4 (Cg, 3J(119/
117Sn&ꢁ13C) = 76, 69 Hz), 26.4 (Cd)
5c
117.9, 126.2, 135.4, 170.1 160.3 121.0, 155.2, 111.1, 138.3, 124.0,
110.1, 136.0 123.6, 126.9, 128.1, 129.0, 130.6
117.7, 126.4, 135.2, 169.8 160.0 121.1, 155.2, 110.9, 137.9, 123.9,
108.4, 136.7 123.3, 126.8, 128.0, 128.8, 130.2
117.4, 126.8, 135.0, 169.5 160.6 121.4, 155.5, 110.9, 138.0, 123.8,
109.2, 136.8 123.3, 127.2, 128.1, 128.8, 130.6
117.6, 126.6, 133.3, 171.9 157.2 121.3, 154.0, 117.4, 136.0, 124.0,
167.1 12.7 (Ca, 1J(119/117Sn&ꢁ13C) = 602, 580 Hz), 136.4,
125.3, 124.2, 129.6
6c
166.8 10.8 (Ca, 1J(119/117Sn&ꢁ13C) = 575, 550 Hz), 129.9,
134.8, 131.0 (Cb’), 125.0, 127.8 (Cg’), 128.5
167.6 10.9 (Ca, 1J(119/117Sn&ꢁ13C) = 596, 575 Hz), 133.3,
127.5, 124.9, 131.2
7c
H2L2
8a
163.8
—
110.6, 135.4
117.5, 126.1, 132.4
109.0, 135.6
123.2, 126.9, 128.4, 128.8, 130.5
170.1 160.3 121.8, 155.3, 116.9, 136.8, 123.4,
122.1, 127.2, 128.1, 128.8, 131.0
165.1
1.9 (Ca, 1J(119/117Sn-13C) = 590, 560 Hz)
9a
117.8, 126.0, 132.9, 170.3 160.0 121.7, 155.4, 117.0, 136.8, 123.8,
108.1, 135.5 122.4, 127.3, 128.0, 128.9, 130.9
165.7 22.8 (Ca, 1J(119/117Sn&ꢁ13C) = 593, 565 Hz), 26.7
(Cb, 2J(119Sn&ꢁ13C) = 31 Hz), 26.4 (Cg, 3J(119/
117Sn&ꢁ13C) = 78, 70 Hz), 13.5 (Cd)
10b
11a
117.9, 126.2, 132.7, 170.1 160.3 122.2, 155.7, 117.1, 136.5, 123.5,
108.4, 135.7 122.7, 127.4, 128.0, 128.3, 130.7
165.8 136.9 (Ca, 1J(119/117Sn&ꢁ13C) = 498, 475 Hz), 130.2
(Cb, 2J(119Sn&ꢁ13C) = 24 Hz), 128.7 (Cg, 3J(119/
117Sn&ꢁ13C) = 56, 50 Hz),
131.2 (Cd)
117.7, 126.2, 132.5, 169.9 162.0 121.3, 155.6, 117.1, 136.9, 123.5,
108.3, 135.8 122.0, 127.4, 128.3, 129.0, 131.2
168.4 43.8 (Ca, 1J(119/117Sn&ꢁ13C) = 530, 505 Hz), 29.9
(Cb, 2J(119Sn&ꢁ13C) = 22 Hz), 28.8 (Cg, 3J(119/
117Sn&ꢁ13C) = 78, 69 Hz), 26.5 (Cd)
12c
13c
14c
117.6, 126.0, 132.5, 170.2 162.4 121.7, 155.1, 117.3, 136.5, 123.6,
168.0 8.6 (Ca, 1J(119/117Sn&ꢁ13C) = 587, 565 Hz), 135.0,
128.2, 124.5, 129.9
108.8, 135.2
118.0, 126.2, 132.3
107.9, 135.1
122.5, 127.1, 128.5, 129.3, 131.0
172.0 162.6 120.7, 154.8, 116.8, 136.6, 123.4,
122.2, 127.0, 128.6, 130.2, 131.7
167.2 9.4 (Ca, 1J(119/117Sn&ꢁ13C) = 596, 570 Hz), 129.5,
138.1, 131.2(Cb’), 124.0, 127.5 (Cg’), 128.3
167.4 9.2 (Ca, 1J(119/117Sn&ꢁ13C) = 606, 589 Hz), 138.2,
128.4, 127.3, 129.5
117.9, 126.4, 132.0, 171.4 162.7 121.1, 155.0, 117.2, 136.3, 123.3,
108.5, 135.2 122.3, 126.8, 128.0, 130.0, 131.2
aSpectra recorded in CDCl3.
bSpectra recorded in DMSO-d6.
cSpectra recorded in 1,4-dioxane + 2–3 drops of CDCl3.
used as an indicator to predict the coordination environment of tin
in complexes.[38,39] The 119Sn NMR chemical shifts for the dimethyl-
tin complexes 1 and 8, dibutyltin complexes 2 and 9, and dicyclo-
hexyltin complexes 4 and 11 are found at ꢁ157 ppm, ꢁ196 ppm
and ꢁ262 ppm, respectively. The 119Sn NMR chemical shift for
diphenyltin complexes 3 and 10 are observed further upfield
at ꢁ340 ppm. The 119Sn NMR chemical shifts for dibenzyltin and
substituted dibenzyltin complexes are found in the range ꢁ217
to ꢁ296 ppm. The 119Sn NMR chemical shifts are found in the range
reported for five-coordinated diorganotin complexes.[40–45]
Appl. Organometal. Chem. 2012, 26, 310–319
Copyright © 2012 John Wiley & Sons, Ltd.
wileyonlinelibrary.com/journal/aoc