TRIORGANOTIN(IV) DERIVATIVES OF SCHIFF BASES
1043
Salicylidene-4-methyl-1-aminobenzene (p-smabH) bright yellow crystal; m.p.: 60
C. Yield: 85%; Anal. Found: C, 79.43; H, 6.03; N, 6.45%. Calc. For C14H13NO: C, 79.59;
◦
−1
1
H, 6.20; N, 6.63%. IR (KBr pellets, cm ): 3458(νO-H), 1616 (νC N), 1268(νC-O). H-NMR
CDCl3, δH): 12.76(H, s, Ph-OH), 8.23(H, s, CH N), 6.82-7.26(m, 8H, Ar-H), 2.36(3H, s,
(
13
Ar-CH3) ppm. C NMR (CDCl3, δC): 151.1 (s, CO, C-10), 156.5 (s, CN, C-8), 119.2 (C-1,
ꢀ
C-5), 129.9 (C-2, C-4), 132.8 (C-3), 18.5 (C-3 ), 145.8 (C-6), 117.1 (C-9), 132.0 (C-11),
1
20.9 (C-12), 118.9 (C-13), 133.8(C-14) ppm.
Salicylidene-1-aminobenzene (sabH) yellow crystal m.p.: 52 C. Yield: 75%; Anal.
Found: C, 78.95; H, 5.49; N, 6.93%. Calc. For C13H11NO: C, 79.16; H, 5.62; N, 7.10%. IR
◦
−1
1
(KBr pellets, cm ): 3426(νO-H), 1635(νC N), 1262(νC-O). H-NMR (CDCl3, δH): 12.40(H,
13
s, Ph-OH), 8.40(H, s, CH N), 6.62–7.91(m, 9H, Ar-H) ppm. C NMR (CDCl3, δC): 150.8
(
(
s, CO, C-10), 159.9 (s, CN, C-8), 118.6 (C-1, C-5), 126.6 (C-2, C-4), 130.2 (C-3), 142.7
C-6), 110.4 (C-9), 137.2 (C-11), 112.4 (C-12), 117.3 (C-13), 131.8 (C-14) ppm.
◦
Salicylidene-3-nitro-1-aminobenzene (snabH) yellow solid; m.p.: 121 C. Yield:
7
8%; Anal. Found: C, 64.28; H, 3.97; N, 11.38%. Calc. For C13H10N2O3: C, 64.46; H,
−1
1
4.16; N, 11.56%. IR (KBr pellets, cm ): 3350(νO-H), 1638(νC N), 1261(νC-O). H NMR
13
(CDCl3, δH): 12.67(H, s, Ph-OH), 8.44(H, s, CH N), 6.61–7.79(m, 8H, Ar-H) ppm.
C
NMR (CDCl3, δC): 148.2 (s, CO, C-10), 159.7 (s, CN, C-8), 132.0 (C-1), 137.1 (C-2), 121.2
(C-3), 139.4 (C-4), 117.3 (C-5), 147.4 (C-6), 115.8 (C-9), 139.4 (C-11), 118.2 (C-12), 120.2
(
C-13), 132.2 (C-14) ppm
n
[
Bu Sn(sap)] (1): Yield: 74%; Anal. Found: C, 59.07; H, 7.36; N, 5.69; Sn, 24.28%.
3
Calc. For C24H36N2OSn: C, 59.16; H, 7.45; N, 5.75; Sn, 24.36%. IR (KBr pellets,
−
1
1
cm ): 1608 (νC N), 1294(νC-O), 549(νSn-O), 519(νSn-C), 461(νSn-N). H NMR (CDCl3,
δH): 9.43(H, s, CH N), 6.56–7.96(m, 8H, Ar-H, Py-H), 1.05–1.81(m, 18H, (CH2)3-Sn),
0
3
13
.94(t, 9H, H3C-, JH-H = 7.4 Hz) ppm. C NMR (CDCl3, δC): 161.7 (s, CO, C-10), 157.7
(
s, CN, C-8), 138.9 (C-2), 130.7 (C-3), 138.6 (C-4), 109.8 (C-5), 145.5 (C-6), 113.7 (C-9),
1
33.2 (C-11), 119.9 (C-12), 132.2 (C-13), 132.4 (C-14), 26.7 (C-α), 27.3 (C-β), 27.2 (C-γ ),
119
13.7 (C-δ) ppm. Sn NMR (DMSO-d6, δSn): −140.8 ppm.
n
3
[
Bu Sn(sapic)] (2): Yield: 71%; Anal. Found: C, 59.82; H, 7.56; N, 5.51; Sn,
2
3.59%. Calc. For C25H38N2OSn: C, 59.90; H, 7.64; N, 5.59; Sn, 23.68%. IR (KBr pel-
−1
1
lets, cm ): 1610 (νC N), 1289(νC-O), 547(νSn-O), 522(νSn-C), 464(νSn-N). H NMR (CDCl3,
δH): 9.45(H, s, CH N), 6.54-7.99 (m, 7H, Ar-H, Py-H), 2.32(s, 3H, Py-CH3), 1.06-1.79(m,
3
13
1
8H, (CH2)3-Sn), 0.91(t, 9H, H3C-, JH-H = 7.3 Hz) ppm. C NMR (CDCl3, δC): 161.9 (s,
ꢀ
CO, C-10), 157.6 (s, CN, C-8), 138.7 (C-2), 133.5 (C-3), 138.5 (C-4), 20.4 (C-4 ), 109.5
(
2
C-5), 146.1 (C-6), 113.8 (C-9), 133.9 (C-11), 119.9 (C-12), 122.6 (C-13), 133.8 (C-14),
6.7 (C-α), 27.3 (C-β), 27.1(C-γ ), 13.6(C-δ) ppm. Sn NMR (DMSO-d6, δSn): −128.0
119
ppm.
n
[
Bu Sn(o-smab)] (3): Yield: 68%; Anal. Found: C, 62.38; H, 7.82; N, 2.77; Sn,
3
2
3.73%. Calc. For C26H39NOSn: C, 62.42; H, 7.86; N, 2.80; Sn, 23.73%. IR (KBr pellets,
−1
1
cm ): 1601 (νC N), 1292(νC-O), 532(νSn-O), 512(νSn-C), 470(νSn-N). H NMR (CDCl3,
δH): 8.58(H, s, CH N), 6.95-7.41(m, 8H, Ar-H), 2.40(3H, s, Ar-CH3), 1.37-1.85(m, 18H,
3
13
(
CH2)3-Sn), 0.96(t, 9H, H3C-, JH-H = 7.1 Hz) ppm. C NMR (CDCl3, δC): 161.3 (s, CO,
C-10), 158.3 (s, CN, C-8), 117.3 (C-1), 126.9 (C-2), 127.1 (C-3), 132.2 (C-4), 130.8 (C-5),
ꢀ
1
8.3 (C-5 ), 147.5 (C-6), 117.8 (C-9), 133.2 (C-11), 119.1 (C-12), 119.4 (C-13), 132.4
119
(C-14), 26.9 (C-α), 27.4 (C-β), 27.2 (C-γ ), 13.7 (C-δ) ppm. Sn NMR (DMSO-d6, δSn):
−
137.3 ppm.
n
[
Bu Sn(p-smab)] (4): Yield: 66%; Anal. Found: C, 62.37; H, 7.69; N, 2.76; Sn,
3
23.65%. Calc. For C26H39NOSn: C, 62.42; H, 7.86; N, 2.80; Sn, 23.73%. IR (KBr pellets,