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Gold Bull (2012) 45:23–34
(0.11 cm3), ethanol (3 cm3), H2O (5 cm3), brown solid.
Yield: 86%; mp: 182°C. (Found: C 22.8, H 1.4, S 8.5%.
Calc. for C7H5O3SAu: C 23.0, H 1.4, S 8.8%). IR
(cm−1): 1,663 vs, ν(C0O); 1,466 vs, δ(OH); 1,281 vs
br, ν(C–O). NMR (DMSO-d6): 1H, δ 12.97 (brs, 1H, C
(1)OH), 7.61 (s, 1H, C(3)H), 7.25 (d, 1H, C(5)H), 6.68
(m, 1H, C(6)H), 7.89 (d, 1H, C(7)H); 13C, δ 165.9 C(1),
124.0 C(2), 131.5 C(3), 149.4 C(4), 118.4 C(5), 113.0
C(6), 146.3 C(7).
[Au(Htspa)] (3). H2tspa (0.07 g, 0.38 mmol),
NaAuCl4·3H2O (0.15 g, 0.38 mmol), thiodiglycol
(0.11 cm3), ethanol (3 cm3), H2O (5 cm3), green solid.
Yield: 85%; mp: 207°C. (Found: C 22.3, H 1.2, S
16.5%. Calc. for C7H5O2S2Au: C 22.0, H 1.3, S
16.8%). IR (cm−1): 1,674 vs, ν(C0O); 1,408 s, δ(OH);
1,270 vs, ν(C–O). NMR (DMSO-d6): 1H, δ 12.57 (brs,
1H, C(1)OH), 8.19 (s, 1H, C(3)H), 7.67 (d, 1H, C(5)H),
7.17 (pst, 1H, C(6)H), 7.89 (d, 1H, C(7)H); 13C, δ
166.1 C(1), 123.0 C(2), 137.6 C(3), 137.6 C(4), 140.3
C(5), 127.1 C(6), 134.2 C(7).
[Au(H-o-pyspa)] (4). H2-o-pyspa (0.07 g, 0.38 mmol),
NaAuCl4·3H2O (0.15 g, 0.38 mmol), thiodiglycol
(0.11 cm3), ethanol (3 cm3), H2O (5 cm3), pale yellow
solid. Yield: 85%; mp: 190°C. (Found: C 25.4, H 1.5, N
3.4, S 8.3%. Calc. for C8H6O2SNAu: C 25.5, H 1.6, N
3.7, S 8.5%). IR (cm−1): 1,694 s, ν(C0O); 1,466 m br,
δ(OH); 1,250 vs, ν(C–O). NMR (DMSO-d6): 1H, δ 7.00
(s, 1H, C(3)H), 8.30 (d, 1H, C(5)H), 8.10 (pst t, 1H, C(6)
H), 7.22 (pst, 1H, C(7)H), 8.55 (d, 1H, C(8)H); 13C, δ
165.1 C(1), 136.0 C(2), 134.1 C(3), 154.5 C(4), 150.0 C
(5), 134.0 C(6), 121.0 C(7), 124.0 C(8).
139.4 C(3), 122.3 C(4), 157.5 C(5), 111.1 C(6), 131.6
C(7), 119.8 C(8), 130.3 C(9), 55.5 C(OCH3).
[Au(H-p-mpspa)] (7). H2-p-mpspa (0.08 g, 0.38 mmol),
NaAuCl4·3H2O (0.15 g, 0.38 mmol), thiodiglycol
(0.11 cm3), ethanol (3 cm3), H2O (5 cm3), yellow solid.
Yield: 92%; mp: 215°C. (Found: C 29.5, H 2.2, S 7.5%.
Calc. for C10H9O3SAu: C 29.6, H 2.2, S 7.9%). IR
(cm−1): 1,674 vs, ν (C0O); 1,438 m, δ(OH); 1,256 vs
br, ν(C–O). NMR (DMSO-d6): 1H, δ 13.10 (brs, 1H, C
(1)OH), 7.79 (s, 1H, C(3)H), 7.83 (d, 2H, C(5)H, C(9)
H), 6.95 (d, 2H, C(6)H, C(8)H), 3.80 (s, 3H, OCH3);
13C, δ 166.5 C(1), 125.1 C(2), 144.8 C(3), 126.2 C(4),
133.0 C(5) and C(9), 113.8 C(6) and C(8), 160.7 C(7),
55.3 C(OCH3).
[Au(H-o-hpspa)] (8). H2-o-hpspa (0.07 g, 0.38 mmol),
AuCl4Na·3H2O (0.15 g, 0.38 mmol), thiodiglycol
(0.11 cm3), ethanol (3 cm3), H2O (5 cm3), orange
solid. Yield: 91%; mp: 190°C. (Found: C 27.6, H
1.8, S 8.6%. Calc. for C9H7O3SAu: C 27.6, H 1.8,
S 8.2%). IR (cm−1) 1,686 vs, ν(C0O); 1,452 s,
δ(OH); 1,250 vs, ν(C–O). NMR (DMSO-d6): 1H,
δ 13.16 (brs, 1H, C(1)OH), 7.97 (s, 1H, C(3)H),
9.99 (s, 1H, C(5)OH), 7.84 (d, 1H, C(6)H), 7.10
(pst, 1H, C(7)H), 6.82 (pst, 1H, C(8)H), 7.75 (d,
1H, C(9)H); 13C, δ 167.5 C(1), 121.4 C(2), 139.0
C(3), 123.2 C(4), 156.0 C(5), 115.4 C(6), 131.1 C(7),
118.2 C(8), 130.9 C(9).
[Au(H-p-hpspa)] (9). H2-p-hpspa (0.07 g, 0.38 mmol),
NaAuCl4·3H2O (0.15 g, 0.38 mmol), thiodiglycol
(0.11 cm3), ethanol (3 cm3), H2O (5 cm3), orange solid.
Yield: 65%; mp: 205°C. (Found: C 27.5, H 2.0, S 8.2%.
Calc. for C9H7O3SAu: C 27.6, H 1.8, S 8.2%). IR
(cm−1): 1,675 vs, ν(C0O); 1,433 m, δ(OH); 1,245 s
br, ν(C–O). NMR (DMSO-d6): 1H, δ 12.91 (brs, 1H, C
(1)OH), 7.74 (s, 1H, C(3)H), 7.77 (d, 2H, C(5)H, C(9)
H), 6.77 (d, 2H, C(6)H, C(8)H), 10.18 (s, 1H, C(7)OH);
13C, δ 166.7 C(1), 123.6 C(2), 145.4 C(3), 124.7 C(4),
133.4 C(5) and C(9), 115.3 C(6) and C(8), 159.7 C(7).
[Au(H-diBr-o-hpspa)] (10). H2diBr-o-hpspa (0.13 g,
0.38 mmol), NaAuCl4·3H2O (0.15 g, 0.38 mmol), thi-
odiglycol (0.11 cm3), ethanol (3 cm3), H2O (5 cm3),
yellow solid. Yield: 83%; mp: 238°C. (Found: C 19.8,
H 0.8, S 5.5%. Calc. for C9H5O3SBr2Au: C 19.6, H 0.9,
S 5.8%). IR (cm−1): 1,690 vs, ν(C0O); 1,448 vs,
[Au(HClpspa)] (5). H2Clpspa (0.08 g, 0.38 mmol),
NaAuCl4·3H2O (0.15 g, 0.38 mmol), thiodiglycol
(0.11 cm3), ethanol (3 cm3), H2O (5 cm3), yellow solid.
Yield: 84%; mp: 183°C. (Found: C 26.6, H 1.3, S 7.5%.
Calc. for C9H6O2SClAu: C 26.3, H 1.5, S 7.8%). IR
(cm−1): 1,689 vs, ν(C0O); 1,436 s, δ(OH); 1,247 s,
1
ν(C–O). NMR (DMSO-d6): H, δ 13.53 (brs, 1H, C
(1)OH), 7.86 (s, 1H, C(3)H), 7.46 (d, 1H, C(6)H), 7.31
(pst t, 2H, C(7)H), 7.38 (pst, 2H, C(8)H), 7.61 (d, 1H, C
(9)H); 13C, δ 166.6 C(1), 127.8 C(2), 139.7 C(3), 132.5
C(4), 133.5 C(5), 130.7 C(6), 131.3 C(7), 126.9 C(8),
129.3 C(9).
[Au(H-o-mpspa)] (6). H2-o-mpspa (0.08 g, 0.38 mmol),
NaAuCl4·3H2O (0.15 g, 0.38 mmol), thiodiglycol
(0.11 cm3), ethanol (3 cm3), H2O (5 cm3), pale yellow
solid. Yield: 77%; mp: 203°C. (Found: C 29.2, H 2.5, S
8.0%. Calc. for C10H9O3SAu: C 29.6, H 2.2, S 7.9%).
IR (cm−1): 1,685 vs, ν(C0O); 1,463 s, δ(OH); 1,249 vs,
ν(C–O). NMR (DMSO-d6): 1H, δ 13.15 (brs, 1H, C(1)
OH), 8.00 (s, 1H, C(3)H), 7.70 (d, 1H, C(6)H), 6.97
(pst, 1H, C(7)H), 7.40 (t, 1H, C(8)H), 7.05 (d, 1H, C(9)
H), 3.79 (s, 3H, OCH3); 13C, δ 167.1 C(1), 128.8 C(2),
1
δ(OH); 1,255 vs, ν(C–O). NMR (DMSO-d6): H, δ
13.30 (brs, 1H, C(1)OH), 7.87 (s, 1H, C(3)H), 9.95
(brs, 1H, C(5)OH), 7.75 (s, 1H, C(7)H), 7.59 (s, 1H,
C(9)H); 13C, δ 166.7 C(1), 126.5 C(2), 132.1 C(3),
127.0 C(4), 151.3 C(5), 112.8 C(6), 137.4 C(7), 110.6
C(8), 135.1 C(9).
[Au(Hcpa)] (11). H2cpa (0.06 g, 0.38 mmol),
NaAuCl4·3H2O (0.15 g, 0.38 mmol), thiodiglycol
(0.11 cm3), ethanol (3 cm3), H2O (5 cm3), brown solid.