14
M. MUSTHAFA ET AL.
The reaction mixture was poured into hydrochloric acid cymene phenyl-H), 2.88–2.81 (m, 1H, p-cymene CH(CH3)2),
(0.1 N, 200 mL) and the resulting pale yellow/brown sub-
stance was filtered off. Recrystallisation purified the solid
2.14 (s, 3H, p-cymene CH3), 1.82–1.75 (d, J ¼ 10.0 Hz, 6H, p-
cymene CH(CH3)2). 13C NMR (125 MHz, CDCl3): d, ppm 178.39
product from a chloroform/ethanol mixture (1/2).
(C ¼ Se), 168.67 (C ¼ O), 135.6, 133.5, 133.5, 131.0, 130.9,
129.5, 128.8, 128.4, 128.1, 85.5 (benzene carbon). LC-MS ¼
þ
611.41 [M]
.
4.1.1 N-(phenylcarbamoselenoyl)benzamide (L1)
Yield: 1.25 g, 74%. Yellow solid, m.p.: 154 ꢃC. Anal. Calc. for
C14H12N2OSe (%): C, 55.46; H, 3.99; N, 9.24. Found: C, 55.38;
H, 4.05; N, 9.20. UV–Vis (DMF): kmax, nm 260, 309. FT-IR: V,
cmꢁ1 3344, 3260 (N ꢁ H), 3027 (¼C ꢁ H), 1667 (C ¼ O), 1262
4.2.2 [Ru(II)(g6-p-cymene) L2] (2)
[RuCl2(g6- p-cymene)]2 (0.22 g, 0.44 mmol) and L2 (0.317 g,
0.88 mmol) were used. Yield: 83%. Yellowish orange solid,
m.p.: 210 ꢃC. Anal. Calc. for C27H22Cl2N2O2RuSe: C, 42.93; H,
3.93; N, 4.55; S, 5.21. Found: C, 42.52; H, 3.35; N, 4.44; S, 5.15.
UV-Vis (DMF): kmax, nm 275, 347, 436. FT-IR: V, cmꢁ1 3219,
3155 (N–H), 3155 (¼C–H), 1657 (C ¼ O), 1274 (C ¼ Se). 1H
NMR (500 MHz, CDCl3): d, ppm 12.92 (s, 1H, NH), 11.32 (s, 1H,
NH), 8.64 (s, 1H), 8.60 (d, J ¼ 8.7 Hz, 2H), 8.01 (s, 1H), 7.97 (dd,
J ¼ 14.0, 7.5 Hz, 4H), 7.65 (t, J ¼ 7.4 Hz, 2H), 7.43 (s, 2H), 7.14
(s, 1H), 5.34–5.27 (d, J ¼ 10.0 Hz, 2H, p-cymene phenyl-H),
5.26-5.25 (d, J ¼ 5.0 Hz, 2H, p-cymene phenyl-H), 2.95–2.92
(m, 1H, p-cymene CH(CH3)2), 2.88 (s, 3H, p-cymene CH3),
2.23-1.69 (d, J ¼ 10.0 Hz, 6H, p-cymene CH(CH3)2). 13C NMR
(125 MHz, CDCl3): d, ppm 178.59 (C ¼ Se), 163.52 (C ¼ O),
137.22, 136.42, 135.50, 134.99, 129.37, 128.61, 126.43 (aro-
matic carbons), 102.83, 83.22, 82.39, 81.33, 80.57 (aromatic
1
(C ¼ Se). H NMR (500 MHz, CDCl3): d, ppm 12.98 (s, 1H, NH),
11.80 (s, 1H, NH), 8.00-7.98 (d, J ¼ 4 Hz, 2H), 7.69-7.68 (d,
J ¼ 4 Hz, 3H), 7.58-7.56 (d, J ¼ 8 Hz, 2H), 7.55-7.47 (t, J ¼ 6 Hz,
2H), 7.45–7.34 (m, 1H). 13C NMR (125 MHz, CDCl3): d, ppm
180.96 (C ¼ Se), 168.61 (C ¼ O), 139.47, 133.71, 132.43, 129.26,
129.18, 128.92, 127.39, 125.62. LC-MS ¼ 303.02 [M – H]–.
4.1.2
N-(phenylcarbamoselenoyl)thiophene-2-carboxa-
mide (L2)
Yield: 1.30 g, 72%. Yellow solid, m.p.: 160 ꢃC. Anal. Calc. for
C21H16N2OSeS (%): C, 46.61; H, 3.26; N, 9.06; S, 10.37. Found:
C, 46.51; H, 3.29; N, 9.04; S, 10.12. UV-Vis (DMF): kmax, nm
276, 314. FT-IR: V, cmꢁ1 3389, 3270 (N ꢁ H), 3069 (¼C ꢁ H),
1668 (C ¼ O), 1269 (C ¼ Se). 1H NMR (500 MHz, CDCl3): d,
ppm 11.80 (s, 1H, NH), 9.14 (s, 1H, NH), 7.74–7.72 (d, J ¼ 4 Hz,
1H), 7.62–7.60 (d, J ¼ 4 Hz, 1H), 7.48–7.46 (d, J ¼ 8 Hz, 2H),
7.43–7.42 (t, J ¼ 6 Hz, 2H), 7.39–7.21 (m, 2H). 13C NMR
(125 MHz, CDCl3): d, ppm 179.72 (C ¼ Se), 161.11 (C ¼ O),
138.43, 135.62, 134.73, 131.04, 129.06, 128.67, 127.65, 124.72.
LC-MS ¼ 308.96 [M – H]–.
carbons of p-cymene), 30.55, 22.30, 18.41 (aliphatic carbons).
þ
LC-MS ¼ 616.42 [M]
.
4.2.3 [Ru(II)(g6-p-cymene) L3] (3)
[RuCl2 (g6- p-cymene)]2 (0.22 g, 0.44 mmol) and L3 (0.331 g,
0.88 mmol) were used. Yield: 75%. Orange solid, m.p.: 205 ꢃC.
Anal. Calc. for C27H22Cl2N2ORuSeS: C, 44.09; H, 4.04; N, 4.67.
Found: C, 43.09; H, 4.08; N, 4.39. UV–Vis (DMF): kmax, nm 287,
382, 453. FT-IR: V, cmꢁ1 3225, 3149 (N–H), 3040 (¼C–H), 1675
(C ¼ O), 1268 (C ¼ Se). 1H NMR (500 MHz, CDCl3): d, ppm
12.82 (s, 1H, NH), 11.19 (s, 1H, NH), 5.36–5.23 (d, J ¼ 10.0 Hz,
2H, p-cymene phenyl-H), 5.26–5.25 (d, J ¼ 5.0 Hz, 2H, p-cym-
ene phenyl-H), 2.94-2.23 (m, 1H, p-cymene CH(CH3)2), 2.86 (s,
3H, p-cymene CH3), 1.65–1.29 (d, J ¼ 10.0 Hz, 6H, p-cymene
CH(CH3)2). 13C NMR (125 MHz, CDCl3): d, ppm 178.59 (C ¼ Se),
158.84 (C ¼ O), 137.17, 129.38, 128.66, 126.47, 122.82 (aro-
matic carbons), 112.91, 102.88, 98.90, 83.23, 82.33 (aromatic
4.1.3 N-(phenylcarbamoselenoyl)furan-2-carboxamide (L3)
Yield: 1.06 g, 71%. Pale yellow solid, m.p.: 145 ꢃC. Anal. Calc.
for C21H16N2O2Se (%): C, 49.01; H, 3.47; N, 9.52. Found: C,
49.82; H, 3.53; N, 9.56; UV–Vis (DMF): kmax, nm 283, 336. FT-
IR: V, cmꢁ1 3275, 3118 (N ꢁ H), 3045 (¼C ꢁ H), 1670 (C ¼ O),
1
1279 (C ¼ Se). H NMR (500 MHz, CDCl3): d, ppm 12.66 (s, 1H,
NH), 9.48 (s, 1H, NH), 7.63–7.62 (d, J ¼ 4 Hz, 1H), 7.58–7.38 (d,
J ¼ 4 Hz, 1H), 7.36–7.35 (d, J ¼ 8 Hz, 2H), 7.28–7.27 (t, J ¼ 6 Hz,
2H), 7.25–6.58 (m, 2H). 13C NMR (125 MHz, CDCl3): d, ppm
179.72 (C ¼ Se), 156.61 (C ¼ O), 146.73, 144.70, 138.47, 129.02,
127.58, 124.69, 119.35, 113.54. LC-MS ¼ 293.05 [M – H]–.
carbons of p-cymene), 31.25, 29.70, 18.42 (aliphatic carbons).
þ
LC-MS ¼ 600.42 [M]
.
4.2. Synthesis of complexes
4.2.1 [Ru(II)(g6-p-cymene) L1] (1)
[Ru(II)(g6-p-cymene)]2 (0.22 g, 0.44 mmol) and L1 (0.326 g,
0.88 mmol) were used. Yield: 71%. Orange solid, m.p.: 206 ꢃC.
Anal. Calc. for C29H24Cl2N2ORuSe: C, 47.30; H, 4.30; N, 4.60.
Found: C, 47.15; H, 4.42; N, 4.56. UV–Vis (DMF): kmax, nm 267,
334, 430. FT-IR: V, cmꢁ1 3207, 3120 (N–H), 3022 (¼C–H), 1663
(C ¼ O), 1262 (C ¼ Se). 1H NMR (500 MHz, CDCl3): d, ppm
13.17 (s, 1H, NH), 11.50 (s, 1H, NH), 8.25–8.24 (d, J ¼ 5.0 Hz,
1H), 7.92–7.84 (d, J ¼ 5.0 Hz, 1H), 7.82–7.61 (m, 4H), 7.39–7.60
(m, 1H), 7.43–7.08 (t, J ¼ 5.0 Hz, 1H), 5.39–5.27 (d, J ¼ 10.0 Hz,
Acknowledgments
The author Moideen Musthafa is thankful to MHRD, Govt. of India for
providing senior research fellowship and Ramaiah Konakanchi, thanks
the Malla Reddy Engineering College for Women (Autonomous
Institution), Hyderabad, India, for support and encouragement during
this research work.
Disclosure statement
2H, p-cymene phenyl-H), 5.14–5.20 (d, J ¼ 5.0 Hz, 2H, p- No potential conflict of interest was reported by the authors.