B. Wang et al.: Syntheses of guanidine hydrochlorides as sensor for fluorideꢂꢁꢀꢀꢀꢂ603
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429, 1391, 1361, 1251, 1235, 1201, 1172, 1079, 1046, 959, 875, 9.85 (s, 2H, –OH), 8.90 (s, 2H, –NH–N), 8.23 (s, 2H,
803, 768, 725, 644.
–CH=N), 7.54 (s, 2H, –C H ), 7.22 (t, Jꢀ=ꢀ2.4 Hz, 2H, –C H ),
6
3
6
3
6
.85 (d, Jꢀ=ꢀ14.7 Hz, 2H, –C H ), 3.62 (s, 6H, –OCH ) ppm.
6
3
3
1
3
–
C NMR (100 MHz, DMSO-d ): δꢀ=ꢀ152.91, 150.08, 148.58,
6
2
.2.7 1,3-Bis(4-iso-propylphenyl-methylideneamino)
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25.46, 123.36, 115.85, 112.23, 110.68, 65.32 ppm. – IR (KBr
guanidine hydrochloride (DG7)
−1
disc, cm ): 3376, 2963, 1656, 1603, 1517, 1450, 1430, 1383,
283, 1217, 1200, 1170, 1123, 1059, 1034, 948, 858, 784, 761,
68, 613.
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6
White needle solid, yield: 1.569 g (81%), m.p.: 209–
2
1
11°C. – H NMR (400 MHz, DMSO-d ): δꢀ=ꢀ12.21 (br, 2H,
6
–
NHꢀ·ꢀHCl), 8.96 (s, 2H, –NH–N), 8.40 (s, 2H, –CH=N), 7.85
(
d, Jꢀ=ꢀ8.3 Hz, 4H, –C H ), 7.35 (d, Jꢀ=ꢀ8.3 Hz, 4H, –C H ),
6
4
6
4
2
.2.11 1,3-Bis(4-methylsulfonyl-phenyl-
2
.98–2.90 (m, 2H, –CH–), 1.22 (d, Jꢀ=ꢀ6.9 Hz, 12H, –CH )
3
methylideneamino)guanidine hydrochloride
13
ppm. – C NMR (100 MHz, DMSO-d ): δꢀ=ꢀ153.79, 151.68,
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(DG11)
144.74, 129.22, 127.10, 126.83, 33.90, 24.08 ppm. – IR (KBr
−1
disc, cm ): 3364, 3232, 3133, 2958, 1645, 1511, 1460, 1405,
345, 1302, 1229, 1182, 1052, 1015, 962, 828, 669, 555.
Light yellow solid, yield: 1.422 g (62%), m.p.: 273–
1
1
2
–
75°C. – H NMR (400 MHz, DMSO-d ): δꢀ=ꢀ12.63 (br, 2H,
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NHꢀ·ꢀHCl), 8.90 (s, 2H, –NH–N), 8.55 (s, 2H, –CH=N), 8.23
2
.2.8 1,3-Bis(2-nitrophenyl-methylideneamino)
(d, Jꢀ=ꢀ8.5 Hz, 4H, –C H ), 8.02 (d, Jꢀ=ꢀ8.4 Hz, 4H, –C H ),
6
4
6
4
1
3
guanidine hydrochloride (DG8)
3.28 (s, 6H, –CH ) ppm. – C NMR (100 MHz, DMSO-d ):
3
6
δꢀ=ꢀ150.48, 145.12, 144.74, 140.15, 129.04, 127.38, 43.87 ppm.
−1
Orange red solid, yield: 1.532 g (78%), m.p.: 240–244°C. – – IR (KBr disc, cm ): 3345, 3226, 3013, 2926, 1641, 1595,
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H NMR (400 MHz, DMSO-d ): δꢀ=ꢀ12.72 (br, 2H, –NHꢀ·ꢀHCl), 1525, 1420, 1398, 1306, 1292, 1176, 1141, 1087, 1053, 969, 937,
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8
.97 (s, 2H, –NH–N), 8.77 (s, 2H, –CH=N), 8.49 (d, Jꢀ=ꢀ7.4 Hz, 830, 772, 713, 622, 555, 535, 469.
2
H, –C H ), 8.12 (dd, Jꢀ=ꢀ8.2 and 1.0 Hz, 2H, –C H ), 7.86
6
4
6
4
(
t, Jꢀ=ꢀ7.3 Hz, 2H, –C H ), 7.79–7.70 (m, 2H, –C H ) ppm. –
6 4 6 4
13
C NMR (100 MHz, DMSO-d ): δꢀ=ꢀ153.91, 148.20, 145.01, 2.2.12 1,3-Bis(4-dimethylamino-phenylethylideneamino)
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1
34.80, 131.97, 129.61, 128.43, 125.56 ppm. – IR (KBr disc,
guanidine hydrochloride (DG12)
−1
cm ): 3327, 3029, 1671, 1645, 1598, 1518, 1470, 1440, 1359,
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312, 1218, 1172, 1090, 965, 924, 867, 785, 646, 518, 454.
Light yellow solid, yield: 1.169 g (60%), m.p.: 183–
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1
85°C. – H NMR (400 MHz, DMSO-d ): δꢀ=ꢀ11.14 (br, 2H,
6
–
NHꢀ·ꢀHCl), 8.96 (s, 2H, –NH–N), 8.13 (s, 2H, –CH=N),
2
.2.9 1,3-Bis(3-hydroxy-phenyl-methylideneamino)
7.44 (d, Jꢀ=ꢀ6.9 Hz, 4H, –C H ), 6.74 (d, Jꢀ=ꢀ7.4 Hz, 4H,
6
4
1
3
guanidine hydrochloride (DG9)
–C H ), 2.96 (s, 12H, –N(CH ) ) ppm. – C NMR (100 MHz,
DMSO-d ): δꢀ=ꢀ153.78, 152.05, 147.54, 129.86, 121.81, 111.69,
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4
3 2
6
1
−1
White solid, yield: 1.113 g (67%), m.p.: 165–168°C. – H NMR 51.82 ppm. – IR (KBr disc, cm ): 3434, 3309, 3252, 1681,
(
400 MHz, DMSO-d ): δꢀ=ꢀ11.52 (br, 2H, –NHꢀ·ꢀHCl), 9.83 (s, 1609, 1525, 1432, 1360, 1229, 1183, 1167, 1122, 995, 945, 816,
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2
H, –OH), 8.96 (s, 2H, –NH–N), 8.25 (s, 2H, –CH=N), 7.30 (dt, 668, 568, 527.
Jꢀ=ꢀ7.6 and 1.5 Hz, 2H, –C H ), 7.21 (t, Jꢀ=ꢀ1.5 Hz, 2H, –C H ),
6
4
6
4
7
.14 (t, Jꢀ=ꢀ7.5 Hz, 2H, –C H ), 6.87 (dt, Jꢀ=ꢀ7.5 and 1.4 Hz, 2H,
6
4
13
–
C H ) ppm. – C NMR (100 MHz, DMSO-d ): δꢀ=ꢀ156.29, 2.2.13 1,3-Bis(4-methoxy-phenylethylideneamino)
6
4
6
1
54.44, 145.51, 133.48, 131.37, 128.46, 120.53, 116.84 ppm. –
guanidine hydrochloride (DG13)
−1
IR (KBr disc, cm ): 3313, 1643, 1589, 1540, 1454, 1351, 1313,
269, 1180, 1159, 1048, 970, 948, 872, 686, 552, 458.
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1
White solid, yield: 1.511 g (84%), m.p.: 215–218°C. – H NMR
400 MHz, DMSO-d ): δꢀ=ꢀ12.04 (br, 2H, –NHꢀ·ꢀHCl), 8.98 (s,
(
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2
H, –NH–N), 8.34 (s, 2H, –CH=N), 7.88 (d, Jꢀ=ꢀ8.8 Hz, 4H,
2
.2.10 1,3-Bis(3-hydroxy-4-methoxyphenyl-
–C H ), 7.03 (d, Jꢀ=ꢀ8.8 Hz, 4H, –C H ), 3.82 (s, 6H, –OCH )
6 4 6 4 3
1
3
methylideneamino)guanidine hydrochloride
ppm. – C NMR (100 MHz, DMSO-d ): δꢀ=ꢀ161.28, 150.79,
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(DG10)
147.94, 131.04, 127. 38, 114.86, 55.94 ppm. – IR (KBr disc,
−1
cm ): 3342, 3165, 2936, 2838, 1650, 1606, 1575, 1514, 1463,
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White solid, yield: 1.534 g (78%), m.p.: 174–176°C. – H 1424, 1346, 1307, 1255, 1178, 1112, 1052, 1027, 954, 831, 779,
NMR (400 MHz, DMSO-d ): δꢀ=ꢀ11.74 (br, 2H, –NHꢀ·ꢀHCl), 635, 582, 530.
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