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K. Gholivand, F. Ghaziani/Chemical Papers 65 (5) 691–699 (2011)
Table 2. Spectral data of newly prepared compoundsa
Compound
Spectral data
IR, ν˜/cm−1: 3160 (s, NH), 3035 (s, NH), 2640 (m), 1588 (m), 1488 (m), 1399 (w), 1299 (m), 1242 (w), 1179 (s,
I
—
P
O), 1147 (s, SO2), 1092 (m), 950 (s, PN), 898 (w), 828 (m), 739 (m, PN), 584 (m), 537 (m)
—
1H NMR (DMSO-d6), δ: 6.61 (d, 2H, 3J = 8.4 Hz, ArH), 6.74 (s, 4H, ArH), 7.04 (s, 2H, NH2), 7.88 (d, 2H, 3J =
2
2
7.85 Hz, ArH), 8.40 (d, 1H, J(P,NH) = 8.1 Hz, NH), 8.59 (d, 2H, J(P,NH) = 17.2 Hz, NHP(O)NH)
13C NMR (DMSO-d6), δ: 109.59 (d, J(P,C) = 12.5 Hz), 116.39 (d, J(P,C) = 7.78 Hz), 119.13, 126.60, 131.75 (d,
3
3
2J(P,C) = 13.49 Hz), 135.35, 145.46
2
2
31P NMR (DMSO-d6), δ: 11.63 (dt, J(P,NH) = 16.9 Hz, J(P,NH )
ꢀ
= 8 Hz)
II
IR, ν˜/cm−1: 3385 (s, NH), 3215 (s, CH), 3070 (s, CH), 2940 (m), 1596 (m), 1499 (m), 1459 (m), 1301 (s), 1196 (m,
—
—
—
P
O), 1173 (s, P O), 1150 (s, SO2), 1079 (m), 948 (m), 833 (m), 710 (m), 540 (m), 425 (w)
—
1H NMR (DMSO-d6), δ: 1.20 (m, 2H, CH2), 1.29 (m, 2H, CH2), 1.50 (m, 2H, CH2), 1.61 (m, 2H, CH2), 1.66 (m,
2
4H, CH2), 1.80 (m, 2H, CH2), 2.89 (m, 2H, CH), 3.40 (m, 2H, CH), 4.64 (d, 1H, J(P,NH) = 10.7 Hz, NH), 4.71 (d,
2
2
2
1H, J(P,NH) = 9.9 Hz, NH), 4.82 (d, 1H, J(P,NH) = 10.0 Hz, NH), 4.83 (d, 1H, J(P,NH) = 10.2 Hz, NH), 6.62
(s, 2H, NH2), 6.64 (s, 2H, NH2), 7.22 (d, 2H, 3J = 8.8 Hz, ArH), 7.25 (d, 2H, 3J = 8.8 Hz, ArH), 7.35 (d, 2H, 3J
= 8.9 Hz, ArH), 7.52 (d, 1H, J(P,NH) = 7.1 Hz, NH), 7.55 (d, 1H, J(P,NH) = 7.2 Hz, NH), 7.57 (d, 2H, 3J = 8.8
2
2
Hz, ArH)
3
3
13C NMR (DMSO-d6), δ: 20.91, 20.94, 23.89, 23.97, 29.64 (d, J(P,C) = 6.6 Hz, CH2), 30.10 (d, J(P,C) = 5.0 Hz,
3
3
2
CH2), 30.49 (d, J(P,C) = 12.2 Hz, CH2), 30.72 (d, J(P,C) = 13.6 Hz, CH2), 52.34 (d, J(P,C) = 8.3 Hz), 52.42 (d,
2J(P,C) = 8.4 Hz), 59.97 (d, J(P,C) = 7.8 Hz), 60.12 (d, J(P,C) = 6.7 Hz), 116.65 (d, J(P,C) = 6.7 Hz, Cortho),
116.68 (d, J(P,C) = 6.6 Hz, Cortho), 116.97 (d, J(P,C) = 6.6 Hz, Cortho), 126.30, 126.33, 126.49, 134.36, 134.39,
134.45, 146.73, 146.88, 147.00
31P NMR (DMSO-d6), δ: 21.74 (m), 21.87 (m), 23.30 (m)
2
2
3
3
3
III
IV
IR, ν˜/cm−1: 3390 (s, NH), 3385 (s, NH), 3210 (m, CH), 3040 (w, CH), 2880 (w), 1595 (m), 1500 (m), 1418 (m),
—
1318 (m), 1283 (s), 1203 (m), 1178 (s, P O), 1148 (s, SO2), 1100 (s), 946 (m), 910 (m), 835 (m), 710 (m), 646 (m),
—
538 (m), 409 (w)
3
2
1H NMR (DMSO-d6), δ: 3.23 (d, 4H, J(P,H) = 9.8 Hz, CH2), 4.60 (d, 2H, J(P,NH) = 11.7 Hz, NH), 7.01 (bs, 2H,
NH2), 7.12 (d, 2H, 3J = 8.2 Hz, ArH), 7.54 (d, 1H, J(P,NH) = 9.8 Hz, NH), 7.57 (d, 2H, 3J = 8.3 Hz, ArH)
13C NMR (DMSO-d6), δ: 41.00 (d, J(P,C) = 9.9 Hz, CH2), 116.45 (d, 2C, J(P,C) = 6.9 Hz), 126.59, 134.40, 146.76
2
2
3
31P NMR (DMSO-d6), δ: 23.28 (m)
IR, ν˜/cm−1: 3320 (s, NH), 3195 (s, NH), 2930 (m), 1588 (m), 1490 (m), 1468 (w), 1332 (w), 1305 (w), 1178 (s,
—
P
O), 1143 (s, SO2), 1086 (m), 918 (m, PN), 825 (m, PN), 536 (m)
—
3
1H NMR (DMSO-d6), δ: 1.54 (s, 2H, CH2), 3.04 (d, 2H, J(P,H) = 24.9 Hz, CH), 3.15 (s, 2H, CH), 4.46 (s, 2H,
NH), 6.80 (bs, 2H, NH2), 7.19 (d, 2H, 3J = 8.45 Hz, ArH), 7.58 (d, 3J = 8.35 Hz, ArH), 7.66 (d, 1H, J(P,H) = 9.85
2
Hz, NH)
3
3
13C NMR (DMSO-d6), δ: 26.78 (d, J(P,C) = 7.57 Hz, CH2), 41.71, 116.45 (d, 2C, J(P,C) = 6.71 Hz), 126.49,
134.21, 146.63
31P NMR (DMSO-d6), δ: 5.13 (m)
V
IR, ν˜/cm−1: 3390 (s, NH), 3325 (s, NH), 3207 (m, NH), 3052 (m, NH), 2975 (m, NH), 2973 (m, CH), 2874 (m, CH),
—
1499 (m, CH), 1473 (m, SO2), 1299 (m, SO2), 1179 (s, P O), 1153 (s, SO2), 1098 (m, CH), 900 (m, SN), 540 (m,
—
SO2)
1H NMR (DMSO-d6), δ: 1.12 (d, 3H, 3J = 6.4 Hz, CH3), 1.14 (d, 3H, 3J = 6.4 Hz, CH3), 2.50 (m, CH2), 2.79 (m,
2
2
CH2), 3.35 (m, CH), 3.64 (m, CH), 4.55 (d, 1H, J(P,NH) = 10.3 Hz, NH), 4.61 (d, 1H, J(P,NH) = 10.9 Hz, NH),
4.73 (d, 1H, J(P,NH) = 10.6 Hz, NH), 4.76 (d, 1H, J(P,NH) = 10.3 Hz, NH), 7.04 (s, 2H, NH2), 7.14 (d, 2H, 3J =
2
2
8.8 Hz, ArH), 7.18 (d, 2H, 3J = 8.8 Hz, ArH), 7.48 (d, 1H, J(P,NH) = 6.9 Hz, NH), 7.53 (d, 1H, J(P,NH) = 7.4
2
2
Hz, NH), 7.56 (d, 2H, 3J = 8.5 Hz, ArH), 7.59 (d, 2H, 3J = 8.5 Hz, ArH)
13C NMR (DMSO-d6), δ: 21.31 (d, J(P,C) = 10.4 Hz, CH3), 22.14 (d, J(P,C) = 5.6 Hz, CH3), 48.23 (d, J(P,C)
=
3
3
2
2
2
2
10.0 Hz), 48.61 (d, J(P,C) = 6.0 Hz), 48.73 (d, J(P,C) = 5.8 Hz, CH2), 48.83 (d, J(P,C) = 10.6 Hz, CH2), 116.45
(d, J(P,C) = 7.0 Hz), 116.56 (d, J(P,C) = 7.0 Hz), 126.51, 126.58, 134.31, 134.37, 146.76, 146.82
31P NMR (D2O), δ: 21.76 (m), 22.52 (m)
3
3
31P NMR (DMSO-d6), δ: 2.17 (m), 3.72 (m)
31P NMR (D2O with β-cyclodextrin), δ: 1.76 (m), 1.80 (m), 3.25 (m)
IR, ν˜/cm−1: 3260 (m, NH), 2930 (w, CH), 1595 (s), 1516 (s, NO2), 1340 (s, NO2), 1295 (s, P O), 1173 (s, P O),
—
—
—
—
VI
1110 (m, SO2), 953 (m, PN), 835 (m, PN), 746 (m), 630 (m), 551 (w), 412 (w)
2
1H NMR (DMSO-d6), δ: 1.14 (m, CH3), 2.81 (m, CH2), 3.34 (m, CH), 3.67 (m, CH), 4.74 (d, 1H, J(P,NH) = 11.1
2
2
2
Hz, NH), 4.80 (d, 1H, J(P,NH) = 11.8 Hz, NH), 4.91 (d, 1H, J(P,NH) = 10.6 Hz, NH), 4.94 (d, 1H, J(P,NH)
=
11.1 Hz, NH), 7.2 (d, 2H, 3J = 9.1 Hz, ArH), 7.25 (d, 2H, 3J = 9.3 Hz, ArH), 8.05 (m, 2H, ArH), 8.11 (d, 1H,
2J(P,NH) = 7.3 Hz, NH)
13C NMR (DMSO-d6), δ: 21.20 (d, J(P,C) = 9.8 Hz, CH3), 22.02 (d, J(P,C) = 5.7 Hz, CH3), 48.08 (d, J(P,C)
3
3
2
=
2
2
2
9.7 Hz), 48.43 (d, J(P,C) = 8.8 Hz), 48.60 (d, J(P,C) = 9.0 Hz, CH2), 48.70 (d, J(P,C) = 9.2 Hz, CH2), 116.44
3
3
(d, J(P,C) = 7.0 Hz, ArC), 116.56 (d, J(P,C) = 6.9 Hz, ArC), 124.96, 125.02, 139.13, 139.19, 150.71, 150.75
31P NMR (DMSO-d6), δ: 21.33 (m), 22.11 (m)