European Journal of Inorganic Chemistry
10.1002/ejic.201701100
FULL PAPER
7.5 Hz, 3JPtH = 90 Hz, 1H, CH
-CH), 1.19 (d, 3J(H,H) = 6.5, 6H, C-
): 172.9 (NCN), 168.7 (C=O),
m/z 707. Calcd for [M + Na] , C31
+
H
N
3
O
4
ClPtNa: m/z 765. Found (%):
1
2
34
). 13C NMR (125.8 MHz, acetone-d
m/z 765 (90). FT-IR (KBr pellet, cm ): ν� 1740 (C=O); 1585, 1535, 1489
-1
(
CH
3
)
2
6
1
1
47.4, 145.1, 144.4, 137.4, 136.9, 129.6, 129.5, 129.4, 129.1, 128.9,
28.8, 128.6, 128.3, 127.7, 122.3, 121.9, 121.8, 111.1 (Ar-C), 111.0
(C=C).
(
CH=CH
2
), 84.1 (CH=CH
2
), 68.3 (O-CH), 66.8 (OCH
2
), 55.9 (OCH
3
),
i
i
[
PtCl( PrEug)( Pr,Bn-bimy)] (5). Yield: 129 mg (0.174 mmol, 87%).
5
C
3
4.5/54.3 (NCH ), 38.7 (CH
2
2
-CH), 21.6/21.5 (C-(CH ). Anal. Calcd for
9
3 2
)
Yellow crystals were obtained by slow evaporation within 10 hours from a
32
H
35
N
2 4
O ClPt: C, 51.79; H, 4.72; N, 3.78. Found: C, 51.48; H, 4.30; N,
1
concentrated chloroform/isopropanol solution at ambient temperature. H
+
.95. MS (ESI) Calcd for [M − Cl] , C32
H
H
-
35
N
2
O
4
Pt: m/z 706. Found (%):
3
NMR (500 MHz, chloroform-d
1
): 5a: δ 7.67 (d, J(H,H) = 8 Hz, 1H, Ar−H),
+
m/z 706 (100). Calcd for [M + Na] , C32
35
N
2
O
4
ClPtNa: m/z 764. Found
7
6
.30–7.20 (m, 6H, Ar−H), 7.15−7.14 (m, 2H, Ar−H), 6.64 (s, 1H, Ar-H),
.14 (m, 1H, NCH), 6.08 (s, 1H, Ar−H), 5.98 (m, 2
PtH = 65 Hz, 1H,
), 5.00 (d, 3J(H,H) = 8
1
(
(
%): m/z 764 (8). FT-IR (KBr pellet, cm ): ν� 1748 (C=O); 1562, 1458
C=C).
J
CH=C), 5.74/5.42 (d, 2J(H,H) = 16 Hz, 2H, NCH
Hz, 2
PtH = 50 Hz, 1H, C=CH
1H, C=CH
OCH
2
J
2
), 4.72 (d, 3J(H,H) = 15 Hz, 2JPtH = 60 Hz,
), 4.60 (m, 1H, O-CH), 4.36/4.26 (d, 2J(H,H) = 16 Hz, 2H,
), 3.78−3.74 (ov, 4H, CH -CH, OCH
), 3.09 (d, 3J(H,H) = 17 Hz,
3JPtH = 90 Hz, 1H, CH -CH), 1.88/1.87 (d, 3J(H,H) = 7 Hz, 6H, NCH-
(CH
), 1.03/1.01 (d, 3J(H,H) = 6 Hz, 6H, C-(CH ). 5b: 1H NMR (500
MHz, chloroform-d ): δ 7.61−7.56 (ov, 2H, Ar−H), 7.40–7.33 (m, 4H,
Ar−H), 7.30−7.11 (ov, 3H, Ar−H), 6.65 (s, 1H, Ar−H), 6.23/5.84 (d,
2J(H,H) = 15.5 Hz, 2H, NCH ), 5.98 (m, 2JPtH = 65 Hz, 1H, CH=C), 5.66–
5.63 (ov, 2H, Ar−H, NCH), 4.99 (d, 3J(H,H) = 8 Hz, 2
PtH = 50 Hz, 1H,
C=CH
), 4.70 (d, 3J(H,H) = 15 Hz, 2JPtH = 60 Hz, 1H, C=CH
1H, O-CH), 4.20/4.01 (d, J(H,H) = 16 Hz, 2H, OCH
i
[
PtCl( PrEug)(Bn
2
-bimy)] (3). Yield: 143 mg (0,18 mmol, 90%).
2
Yellowish crystals were obtained by slow evaporation within 16 hours
from a concentrated acetone/water solution at RT. 1H NMR (500 MHz,
acetone-d
2
2
3
2
): δ 7.80 (d, 3J(H,H) = 7.5 Hz, 2H, Ar−H), 7.69 (d, J(H,H) =
.5 Hz, 1H, Ar−H), 7.56 (d, J(H,H) = 7.5 Hz, 2H, Ar−H), 7.43 (d, J(H,H)
7.5 Hz, 1H, Ar−H), 7.39 (t, 3J(H,H) = 7.5 Hz, 2H, Ar−H), 7.35–7.29 (m,
3
6
3
)
2
3 2
)
3
3
7
=
2
6
1
H, Ar−H), 7.29−7.25 (m, 4H, Ar−H), 6.72 (s, 1H, Ar-H),
2
2
), 5.92 (m, 2JPtH = 65
.34/6.05/5.80/5.41 (d, J(H,H) = 15 Hz, 4H, NCH
2
J
Hz, 1H, CH=C), 5.78 (s, 3JPtH = 65 Hz, 1H, Ar-H), 4.95 (d, 3J(H,H) = 8.5
Hz, 2 ), 4.67 (d, 3J(H,H) = 15 Hz, 2
PtH = 50 Hz, 1H, C=CH PtH = 60 Hz,
H, C=CH
), 4.30 (m, 1H, O-CH), 4.21/4.04 (d, 2J(H,H) = 16 Hz, 2H,
), 3.75 (dd, 2J(H,H) = 17 Hz, 3J(H,H) = 6.5 Hz, 1H, CH
-CH), 3.70
), 3.11 (d, 3J(H,H) = 17 Hz, 3
PtH = 90 Hz, 1H, CH -CH),
). C NMR (125.8 MHz,
): 184.2 (NCN), 169.4 (C=O), 148.2, 145.8, 145.0, 137.4,
36.8, 135.6, 135.1, 129.8, 129.7, 129.5, 129.2, 129.0, 128.9, 127.8,
24.8, 124.6, 122.9, 113.1, 112.6, 111.7 (Ar-C), 113.0 (CH=CH ), 86.4
), 53.0/52.7 (NCH ),
). Anal. Calc. for C36 ClPt:
), 4.52 (m,
), 3.86 (dd, J(H,H) =
2
2
2
2
J
2
J
2
1
OCH
2
16.5 Hz, 3J(H,H) = 6.5 Hz, 1H, CH
2
-CH), 3.75 (s, 3H, OCH
3
), 3.14 (d,
3J(H,H) = 16.5 Hz, 3JPtH = 90 Hz, 1H, CH
6H, NCH-(CH
(125.8 MHz, acetone-d
181.7 /181.6 (NCN), 168.7/168.5 (C=O), 147.4, 146.9, 145.1, 144.4,
144.0, 143.9, 135.7, 135.4, 135.2, 134.9, 132.6, 132.5, 128.9, 128.8,
128.7, 128.3 , 128.2 , 128.2, 128.0, 127.7, 125.9, 125.2, 123.4, 123.3,
123.1 , 123.1 , 122.9, 121.8, 112.2 , 112.1 , 112.1, 111.1, 110.4, 110.0
(Ar-C), 112.9 /112.9 (CH=CH ), 86.3/85.9 (CH=CH ), 68.4 /68.4 (O-
CH), 67.7/67.1 (OCH ), 56.0/55.9 (OCH ), 54.48/54.43 (NCH), 52.6/52.1
(NCH ), 38.5 /38.5 (CH -CH), 21.6 , 21.6, 21.5 , 21.4, 21.2 , 21.2 , 20.3
(CH-(CH
-CH), 1.64/1.29 (d, J(H,H) = 7,
3
2
2
2
(
s, 3H, OCH
3
J
2
3
)
2
), 1.05/0.94 (d, 3J(H,H) = 6, 6H, C-(CH
3 2
)
). 13C NMR
.97/0.87 (d, 3J(H,H) = 6.5, 6H, C-(CH
)
13
0
3
2
6
) for the mixture of 5a and 5b at the equilibrium:
acetone-d
1
1
6
5
9
2
4
9
(
CH=CH
2
), 68.8 (O-CH), 67.5 (OCH
2
), 56.4 (OCH
3
2
3
0
0
7
3
9.2 (CH
2
-CH), 21.9 /21.9 (C-(CH
6
5
3
)
2
37
H N
O
2 4
8
7
2
2
4
3
C, 54.58; H, 4.67; N, 3.54. Found: C, 54.87; H, 4.37; N, 3.85. MS (ESI)
Calcd for [M − Cl] , C36
Calcd for [M + Na] , C36
2
3
+
H
H
37
N
2
O
4
Pt: m/z 756. Found (%): m/z 756 (100).
ClPtNa: m/z 814. Found (%): m/z 814
2
7
3
2
3
6
8
5
+
37
2
N O
4
3
)
2
). Suitable elemental analysis could not be obtained despite
-
1
+
(
24). FT-IR (KBr pellet, cm ): ν� 1748 (C=O); 1590, 1562, 1485 (C=C).
several recrystallization attempts. MS (ESI) Calcd for [M
C
C
−
Cl] ,
+
32
H
H
37
N
N
2
O
4
Pt: m/z 708. Found (%): m/z 708 (100). Calcd for [M + Na] ,
i
-tazy)] (4). Yield: 134 mg (0.18 mmol, 90%). 1H
32
37
2 4
O ClPtNa: m/z 766. Found (%): m/z 766 (88). FT-IR (KBr pellet,
[
PtCl( PrEug)(Bn
2
-
1
3
cm ): ν� 1755 (C=O); 1562, 1485 (C=C).
NMR (500 MHz, acetone-d
8
6
): 4a: δ 8.81 (s, 1H, Htazy), 7.79 (dd, J(H,H) =
.5 Hz, J(H,H) = 1.5 Hz, 2H, Ar−H), 7.45–7.36 (m, 5H, Ar−H), 7.29–7.28
4
m, 3H, Ar−H), 6.73 (s, 1H, Ar-H), 6.01/5.61/5.39/5.05 (d, 2J(H,H) = 14.5
Hz, 4H, NCH PtH = 65 Hz, 1H, Ar-H),
), 5.92 (m, 1H, CH=C), 5.37 (s, 3
.98 (m, 1H, O-CH), 4.90 (d, 3J(H,H) = 8.5 Hz, 2
PtH = 50 Hz, 1H,
[PtBr( PrEug)(Bn
i
(
2
-bimy)] (6). Yield: 80 mg (0.095 mmol, 95%).
2
J
Yellow crystals were obtained by slow evaporation within 12 hours from a
concentrated acetone/water solution at ambient temperature. 1H NMR
4
J
C=CH
2
), 4.58 (d, 3J(H,H) = 15 Hz, 2
J
PtH = 60 Hz, 1H, C=CH
2
), 4.19/4.02
(500 MHz, acetone-d
J(H,H) = 7.5 Hz, 1H, Ar−H), 7.52 (d, J(H,H) = 7.5 Hz, 2H, Ar−H), 7.41–
7.37 (m, 3H, Ar−H), 7.33 (t, 3J(H,H) = 7.5, 2H, Ar−H), 7.28−7.23 (m, 4H,
6
): δ 7.80 (d, 3J(H,H) = 7.5 Hz, 2H, Ar−H), 7.68 (d,
d, 2J(H,H) = 16.5 Hz, 2H, OCH
), 3.82 (dd, 2J(H,H) = 17 Hz, J(H,H) =
3
3
3
(
2
3
3
6
9
8
.5 Hz, 1H, CH
0 Hz, 1H, CH
.63 (s, 1H, Htazy), 7.73 (dd, 3J(H,H) = 8.5 Hz, 4J(H,H) = 1.5 Hz, 2H,
2
-C), 3.72 (s, 3H, OCH
3
), 3.10 (d, J(H,H) = 17 Hz, JPtH
=
-C), 1.23/1.22 (d, 3J(H,H) = 5.5 Hz, 6H, C-(CH
Ar−H), 6.74 (s, 1H, Ar-H), 6.32/6.05/5.79/5.46 (d, J(H,H) = 15.5 Hz, 4H,
2
2
3
)
2
). 4b:
2
3
NCH
H), 5.05 (d, J(H,H) = 8.5 Hz, JPtH = 50 Hz, 1H, C=CH
= 15 Hz, 2JPtH = 60 Hz, 1H, C=CH
), 4.29 (m, 1H, O-CH), 4.21/4.04 (d,
2J(H,H) = 16.5 Hz, 2H, OCH
), 3.74 (dd, J(H,H) = 16.5 Hz, J(H,H) = 6.5
Hz, 1H, CH -CH), 3.70 (s, 3H, OCH
90 Hz, 1H, CH
-CH), 0.96/0.89 (d, 3J(H,H) = 6 Hz, 6H, C-(CH
NMR (125.8 MHz, acetone-d
143.9, 137.1, 136.5, 135.6, 135.1, 129.9, 129.6, 129.4, 129.1, 128.9,
128.7, 124.6, 124.4, 122.4, 112.9, 112.8, 111.5 (Ar-C), 112.1 (CH=CH ),
85.4 (CH=CH ), 68.7 (O-CH), 67.5 (OCH ), 56.2 (OCH ), 52.9 /52.8
(NCH ), 39.2 (CH -CH), 21.8 /21.8 (C-(CH ). Anal. Calc. for
2
), 5.93 (m, JPtH = 65 Hz, 1H, CH=C), 5.77 (s, JPtH = 65 Hz, 1H, Ar-
3
2
3
Ar−H), 7.45–7.40 (m, 5H, Ar−H), 7.32–7.31 (m, 3H, Ar−H), 6.73 (s, 1H,
2
), 4.73 (d, J(H,H)
2
Ar-H), 6.12/5.62/5.24/5.07 (d, J(H,H) = 14.5 Hz, 4H, NCH
2
), 5.85 (m, 1H,
2
CH=C), 5.45 (s, 3
J
PtH = 65 Hz, 1H, Ar-H), 4.98 (m, 1H, O-CH), 4.88 (d,
PtH = 50 Hz, 1H, C=CH
), 4.62 (d, 3J(H,H) = 15 Hz,
), 4.20/4.00 (d, 2J(H,H) = 16.5 Hz, 2H, OCH
),
.82 (dd, 2J(H,H) = 17 Hz, 3J(H,H) = 6.5 Hz, 1H, CH
-CH), 3.71 (s, 3H,
OCH -CH), 1.23/1.22
), 3.10 (d, 3J(H,H) = 17 Hz, 3JPtH = 90 Hz, 1H, CH
d, 3J(H,H) = 5.5 Hz, 6H, C-(CH ). 13C NMR (125.8 MHz, acetone-d
for the mixture of 4a and 4b at the equilibrium: 177.0 (NCN), 169.2/169.1
C=O), 148.0, 147.9, 145.6 , 145.5 , 144.8, 144.7, 144.5, 136.9, 136.7,
, 130.3, 129.8, 129.6, 129.5 , 129.4 , 129.4, 129.3,
29.2, 128.9, 127.7, 127.3, 122.0, 121.7, 111.6, 111.5
12.2 /112.1 (CH=CH ), 85.4/85.1 (CH=CH ), 68.8 /68.8
7.0/66.9 (OCH ), 57.0 /56.9 /52.6 /52.5 (NCH
9.1 /39.0 (CH -CH), 22.0 /22.0 /22.0 /22.0 (C-(CH
2
3
2
3
J(H,H) = 8.5 Hz, 2
2
3
J
2
2
3
), 3.13 (d, J(H,H) = 16.5 Hz, JPtH
). 13
=
C
2JPtH = 60 Hz, 1H, C=CH
2
2
2
3
)
2
3
2
6
): 184.3 (NCN), 169.2 (C=O), 148.2, 145.7,
3
2
(
3
)
2
6
)
2
2
2
3
4
6
(
3
9
2
2
5
2
3 2
)
1
1
1
6
3
36.2
3
, 136.1
7
, 130.3
3
2
8
C
36
H
37
N
2
O
4
BrPt: C, 51.67; H, 4.43; N, 3.36. Found: C, 52.10; H, 3.83; N,
+
6
(Ar-C),
3.48. MS (ESI) Calcd for [M − Br] , C36
m/z 756 (100). Calcd for [M + Na] , C36
(%): m/z 859 (30). FT-IR (KBr pellet, cm ): ν� 1755 (C=O); 1562, 1485
H
37
N
N
O
2 4
Pt: m/z 756. Found (%):
BrPtNa: m/z 859. Found
+
5
6
2
2
7
4
(O-CH),
H
37
O
2 4
-
1
2
3
8
3
2
), 56.3 (OCH
3
),
5
9
2
7
5
2
3
)
2
). Anal. Calc. for
(C=C).
C
31
H
34
N
3
O
4
ClPt: C, 50.10; H, 4.58; N, 5.66. Found: C, 50.11; H, 4.47; N,
+
5
.64. MS (ESI) Calcd for [M − Cl] , C31
34 3
H N O
4
Pt: m/z 707. Found (%):
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