SHARGHI ET AL.
17 of 19
7.22(m, 6 H). 13C NMR (CDCl3, 62.9 MHz): δ = 43.8,
127.2, 127.4, 128.3, 128.9, 129.7, 133.5, 134.3, 137.6.
δ = 1.18–1.34 (m, 6 H),3.75–3.95 (m, 4 H), 7.35–7.43 (m,
5 H); 13CNMR (CDCl3, 62.9 MHz): δ = 11.6, 12.8, 47.3,
49.9, 129.1, 130.0, 131.6, 137.2, 195.9. Mass m/z (%): 227
(M++2, 1.2), 226 (M++1, 5.2), 225 (M+, 11.7), 153 (5.6),
116 (64.0), 88 (100.0), 60 (86.7).
5.24 | Morpholine‐4‐carbodithioic acid phenyl
ester (5a):[31]
Light brown solid; mp 130–134 °C; IR (KBr): ν = 540.0 (s),
694.3 (s), 748.3 (s), 856.3 (s), 987.5 (s), 1026.1 (s), 1110.9
(s), 1180.4 (m), 1265.2 (s), 1234.4 (s), 1427.2 (s), 1465.8
(s), 1581.5 (w), 1658.7 (w), 1890.1 (w), 2846.7 (s), 2985.6
5.28 | Benzyl‐phenethyl‐dithiocarbamic acid
phenyl ester (5e):
Brown solid; mp 81–83 °C; IR (KBr): ν = 555.5 (w), 694.3
(s), 740.6 (s), 817.8 (w), 979.8 (s), 1026.1 (s), 1080.1 (m),
1141.8 (s), 1203.5 (s), 1357.8 (s), 1404.1 (s), 1473.5 (s),
1596.9 (m), 1674.1 (w), 1805.2 (w), 1874.7 (w), 2923.9
(m), 3055.0 (w) cm−1 1H NMR (CDCl3, 250 MHz):
.
δ = 3.74 (t, 4 H, J = 4.75 Hz), 4.13 (broad, 4 H), 7.34–
7.43 (m, 5 H), 13CNMR (CDCl3, 62.9 MHz): δ = 51.3,
66.3, 129.2, 130.2, 137.1, 198.0. Mass m/z (%): 240 (M+
+1, 2.8), 239 (M+, 3.5), 149 (13.9), 69 (100.0).
(m), 3024.2 (s), 3026.7 (s) cm−1 1H NMR (CDCl3,
.
250 MHz): δ = 3.16 (t, 2 H, J = 7 Hz), 4.05 (broad, 1 H),
4.21 (broad, 1 H), 5.00 (broad, 1 H), 5.40 (broad, 1 H),
7.25–7.63 (m, 15 H); 13CNMR (CDCl3, 62.9 MHz):
δ = 32.41, 33.87, 53.57, 56.8, 56.90, 58.04, 126.70,
127.04, 127.33, 127.99, 128.15, 128.61, 128.77, 128.97,
129.10, 129.29, 130.25, 131.70, 135.03, 135.85, 137.27,
137.80, 138.71, 197.98, 198.94. Mass m/z (%): 365 (M+
+2, 0.2), 364 (M++1, 0.6), 363 (M+, 2.3), 254 (9.7), 222
(1.6), 167 (2.0), 148 (8.5), 110 (4.0), 91 (100.0), 69 (24.5).
5.25 | Piperidine‐1‐carbodithioic acid phenyl
ester (5b):[31]
Yellow solid; mp 111–112 °C; IR (KBr): ν = 686.6 (s), 748.3
(s), 856.3 (s), 894.9 (s), 972.1 (s), 1010.6 (s), 1126.4 (m),
1234.4 (s), 1357.8 (w), 1427.2 (s), 1473.5 (s), 1581.5 (w),
1658.7 (w), 2669.3 (w), 2854.5 (m), 2939.3 (s), 2993.3 (w),
1
3053.0 (w) cm−1. H NMR (CDCl3, 250 MHz): δ = 1.67
(broad, 6 H), 3.93 (broad, 2 H), 4.21 (broad, 2 H), 7.18–
7.43 (broad, 5 H); 13CNMR (CDCl3, 62.9 MHz): δ = 24.2,
25.4, 26.6, 52.0, 53.0, 129.0, 129.9, 131.6, 137.1, 196.0.
Mass m/z (%): 239 (M++2, 0.5), 238 (M++1, 5.3), 237 (M
+, 10.8), 128 (64.9), 69 (100.0).
5.29 | 4‐phenyl‐piperazine‐1‐carbodithioic
acid phenyl ester (5f):
Yellow solid; mp 148–150 °C; IR (KBr): ν = 686.6 (s), 748.3
(s), 910.3 (w), 941.2 (w), 987.5 (s), 1026.1 (s), 1149.5 (s),
1226.6 (s), 1272.9 (m), 1342.4 (w), 1380.9 (w), 1427.2
(m), 1473.5 (s), 1596.9 (s), 2823.6 (w), 2916.2 (w), 3047.3
5.26 | Pyrrolidine‐1‐carbodithioic acid phenyl
ester (5c):[31]
1
(w) cm−1. H NMR (CDCl3, 250 MHz): δ = 3.29 (t, 4 H,
J = 5.0 Hz), 4.30 (br, 4 H), 6.83–7.43 (m, 10 H); 13CNMR
(CDCl3, 62.9 MHz): δ = 48.9, 116.37, 120.61, 129.2,
129.3, 130.2, 137.1. Mass m/z (%): 316 (M++2, 0.3), 315
(M++1, 13.7), 314 (M+, 29.3), 281 (14.8), 205 (59.5), 160
(11.2), 132 (100.0), 91 (80.5), 57 (46.7).
Yellow solid; mp 102–104 °C; IR (KBr): ν = 509.2 (s), 686.6
(s), 748.3 (s), 864.1 (m), 956.6 (s), 1002.9 (s), 1164.9 (s),
1249.8 (m), 1334.6 (m), 1434.9 (s), 1581.5 (w), 1658.7
(w), 1874.7 (w), 1951.8 (w), 2869.9 (w), 2962.5 (s), 3070.5
1
(w) cm−1. H NMR (CDCl3, 250 MHz): δ = 1.97 (dt, 4 H,
J1 = 32.2, J2 = 6.5 Hz), 3.78 (dt, 4 H, J1 = 34.2,
J2 = 7.0 Hz), 7.32–7.46 (m, 5 H); 13CNMR (CDCl3,
62.9 MHz): δ = 24.4, 26.35, 51.1, 55.3, 129.1, 130.0,
131.1, 136.9, 193.0. Mass m/z (%): 225 (M++2, 1.8), 224
(M++1, 1.5), 223 (M+, 14.9), 114 (79.0), 72(100.0),
55(92.4).
5.30 | Benzyl‐phenethyl‐dithiocarbamic acid
p‐tolyl ester (5 g):
Yellow solid; mp 85–87 °C; IR (KBr): ν = 640.3 (w), 702.0
(s), 740.6 (s), 802.3 (s), 979.8 (s), 1026.1 (s), 1141.8 (s),
1203.5 (s), 1357.8 (s), 1404.1 (s), 1473.5 (s), 1596.9 (m),
1808.2 (w), 1897.8 (w), 1951.8 (w), 2862.2 (W), 2923.9
5.27 | Diethyl‐dithiocarbamic acid phenyl
.
(s), 3024.2 (s) cm−1 1H NMR (CDCl3, 250 MHz):
ester (5d):[31]
δ = 2.32 (s, 3 H), 2.97 (t, 2 H, J = 8.25 Hz), 3.56 (t, 1 H,
J = 7.50 Hz), 4.05 (t, 1 H, J = 7.75 Hz), 4.81 (broad, 1 H),
5.21 (broad, 1 H), 7.10–7.35 (m, 14 H); 13CNMR (CDCl3,
62.9 MHz): δ = 21.6, 32.3, 33.8, 53.4, 56.7, 58.0, 58.2,
126.6, 126.9, 127.3, 127.9, 128.1, 128.2, 128.7, 128.9,
130.1, 135.0, 135.8, 137.0, 137.7, 138.7, 140.5. Mass m/z
Yellow oil; IR (KBr): ν = 509.2 (s), 686.6 (s), 748.3 (s),
825.5 (s), 918.1 (s), 979.8 (s), 1072.3 (s), 1141.8 (s),
1203.5 (s), 1272.9 (s), 1350.1 (s), 1450.4 (s), 1481.2 (s),
1581.5 (w), 1874.7 (w), 1951.8 (w), 2869.9 (w), 2931.6 (s),
1
2977.9 (s), 3055.0 (s) cm−1. H NMR (CDCl3, 250 MHz):