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RSC Advances
Page 8 of 11
DOI: 10.1039/C6RA23696K
Journal Name
ARTICLE
The spectral (FT-IR, 1H NMR, 13C NMR) and analytical data for
selected β-nitroalcohols are presented below:
65.19, 35.14, 18.89, 15.95; Elemental analysis for C5H11NO3:
Calculated; C 45.10; H 8.33; Found C 45.11; H 8.32
2-Nitro-1-(p-tolyl)ethan-1-ol (Table 3, Entry 2):
1-Nitrotridecan-2-ol (Table 3, Entry 16):
Light yellow oil, IR (KBr, cm-1): ν 3429, 3018, 2408, 1553,
1433, 1221, 1035, 963, 777, 677; 1H-NMR (400 MHz, CDCl3,
TMS): δ 7.27-7.26 (dd, J= 7.6 Hz, 1H), 7.20-7.18 (dd, J= 8 Hz,
1H), 7.10 (d, J= 8 Hz, 2H), 5.41-5.38 (m, 1H), 4.74-4.71 (m,
1H), 4.61-4.55 (m, 1H), 2.34 (s, 3H), 1.52 (s, 1H); 13C-NMR
(100 MHz, CDCl3, TMS): δ 139.04, 138.89, 129.93, 129.67,
125.89, 70.90, 21.16; Elemental analysis for C9H11NO3:
Calculated; C 59.66; H 6.12; Found C 59.67; H 6.11.
Solid, semi-solid, IR (KBr, cm-1): ν 3402, 3018, 2932, 2866,
1527, 1438, 1222; 1H-NMR (400 MHz, CDCl3, TMS): δ 4.46-
4.31 (m, 3H), 2.58 (s, 1H), 1.64-1.04 (m, 20H), 0.88 (t, J= 6 Hz,
3H); 13C-NMR (100 MHz, CDCl3, TMS): δ 80.63, 68.66, 33.70,
31.90, 29.60, 29.51, 29.43, 29.33, 29.31, 25.17, 22.68, 14.12;
Elemental analysis for C13H27NO3: Calculated; C 63.64; H
11.09; Found C 63.66; H 11.07.
4,8-Dimethyl-1-nitronon-7-en-2-ol (Table 3, Entry 17):
Colorless liquid, IR (KBr, cm-1): ν 3588, 3025, 2925, 1620,
1553, 1433, 1387, 1221; 1H-NMR (400 MHz, CDCl3, TMS): δ
5.08 (t, J= 7.2 Hz, 2H), 4.45-4.31 (m, 6H), 2.71 (d, J= 4.8 Hz,
1H), 2.68 (d, J= 4.4 Hz, 1H), 2.06-1.91 (m, 4H), 1.73-1.55 (m,
2H), 1.68 (s, 6H), 1.60 (s, 6H), 1.47-1.37 (m, 4H), 1.20-1.12
(m, 4H), 0.96 (d, J= 6.8 Hz, 3H), 0.92 (d, J= 8 Hz, 3H); 13C-NMR
(100 MHz, CDCl3, TMS): δ 131.71, 131.61, 124.27, 124.22,
81.14, 80.80, 66.98, 66.60, 40.89, 40.57, 37.53, 36.27, 28.87,
28.43, 25.73, 25.31, 25.19, 19.97, 18.81, 17.68; Elemental
analysis for C11H21NO3: Calculated; C 61.37; H 9.83; Found C
61.36; H 9.84.
2-Nitro-1-(4-nitrophenyl)ethan-1-ol (Table 3, Entry 3):
Yellowish liquid, IR (KBr, cm-1): ν 3529, 3451, 3019, 1527,
1434, 1222, 1029, 937, 758, 768; 1H-NMR (400 MHz, CDCl3,
TMS): δ 8.27 (d, J= 8.8 Hz, 2H), 7.64 (d, J= 8.8 Hz, 2H), 5.63-
5.60 (m, 1H), 4.87 (t, J= 6.8 Hz, 1H), 4.64-4.58 (m, 1H), 2.01
(s, 1H); 13C-NMR (100 MHz, CDCl3, TMS): δ 148.09, 145.02,
128.71, 126.96, 124.20, 69.95; Elemental analysis for
C8H8N2O5: Calculated; C 45.29; H 3.80; Found C 45.28; H 3.81.
1-(4-Chlorophenyl)-2-nitroethan-1-ol (Table 3, Entry 4):
Colorless liquid, IR (KBr, cm-1): ν 3408, 3035, 2979, 2989,
2756, 1536, 1428, 1389, 1326, 1275, 1185, 1115, 840, 756;
1H-NMR (400 MHz, CDCl3, TMS): δ 7.35 (d, J= 8.4 Hz, 2H),
7.18 (d, J= 8.4 Hz, 2H), 5.44-5.41 (m, 1H), 4.80 (t, J= 7.2 Hz,
1H), 4.56 (d, J= 3.6 Hz, 1H), 2.57 (s, 1H); 13C-NMR (100 MHz,
CDCl3, TMS): δ 138.37, 132.67, 129.80, 129.18, 127.37, 70.29;
Elemental analysis for C8H8ClNO3: Calculated; C 47.66; H
4.00; Found C 47.68; H 3.98.
6-((tert-Butyldimethylsilyl)oxy)-1-nitrohexan-2-ol (Table 3,
Entry 18):
Colorless oil, IR (KBr, cm-1): ν 1753, 1628, 1528, 1201, 1119,
865, 769, 678; 1H-NMR (400 MHz, CDCl3, TMS): δ 5.25 (s, 1H),
4.51-4.41 (m, 1H), 4.14-4.11 (m, 1H), 3.89 (t, J= 7.2 Hz, 2H),
3.64-3.57 (m, 1H), 1.49-1.39 (m, 6H), 0.83 (s, 9H), 0.26 (s,
6H); 13C-NMR (100 MHz, CDCl3, TMS): δ 80.60, 68.58, 62.83,
36.01, 33.35, 32.13, 25.95, 21.66, -5.31; Elemental analysis
for C12H27NO4Si: Calculated; C 51.95; H 9.81; Found C 51.97;
H 9.79.
1-(4-Bromophenyl)-2-nitroethan-1-ol (Table 3, Entry 5):
Pale yellow oil, IR (KBr, cm-1): ν 3415, 3025, 2939, 2889,
2787, 1550, 1440, 1381, 1331, 1280, 1184, 1120, 840; 1H-
NMR (400 MHz, CDCl3, TMS): δ 7.54 (d, J= 8.4 Hz, 2H), 7.29
(d, J= 8.4 Hz, 2H), 5.44-5.41 (m, 1H), 4.79 (t, J= 7.2 Hz, 1H),
4.57-4.50 (m, 1H), 2.03 (s, 1H); 13C-NMR (100 MHz, CDCl3,
TMS): δ 138.05, 132.14, 129.12, 127.68, 122.89, 70.33;
Elemental analysis for C8H8BrNO3: Calculated; C 39.05; H
3.28; Found C 39.06; H 3.27.
2-Nitro-1-(4-nitrophenyl)propan-1-ol (Table 4, Entry 1):
Reddish liquid, IR (KBr, cm-1): ν 3435, 3330, 3025, 2889, 2789,
1547, 1440, 1320, 1284, 1223, 1185;1H-NMR (400 MHz,
CDCl3, TMS): δ 8.24-8.23 (dd, J= 4.4 Hz, 1H), 8.22-8.21 (dd, J=
4 Hz, 1H), 7.62 (d, J= 4.8 Hz, 2H), 5.21 (d, J= 8.4 Hz, 1H), 4.82-
4.71 (m,1H), 3.26 (s, 1H), 1.48-1.46 (dd, J= 6.8 Hz, 1.5 H),
1.38-1.36 (dd, J= 6.8 Hz, 1.5H); 13C-NMR (100 MHz, CDCl3,
TMS): δ 148.11, 147.71, 128.01, 124.36, 87.88, 75.03, 16.16;
Elemental analysis for C9H10N2O5: Calculated; C 47.79; H 4.46;
Found C 47.77; H 4.48.
2-Nitro-1-(2-nitrophenyl)ethan-1-ol (Table 3, Entry 8):
Oily liquid, IR (KBr, cm-1): ν 3305, 3025, 2939, 2889, 2787,
1553, 1432, 1379, 1323, 1281, 1178, 1121, 845;1H-NMR (400
MHz, CDCl3, TMS): δ 8.13 (d, J= 7.6 Hz, 1H), 8.07 (d, J= 8 Hz,
1H), 7.97 (d, J= 7.6 Hz, 1H), 7.56 (t, J= 8 Hz, 1H), 6.05 (d, J=
9.2 Hz, 1H), 4.87 (d, J= 13.6 Hz, 1H), 4.58-4.52 (m, 1H), 2.60
(s, 1H); 13C-NMR (100 MHz, CDCl3, TMS): δ 134.37, 134.16,
133.81, 131.31, 129.64, 128.77, 124.95, 66.79; Elemental
analysis for C8H8N2O5: Calculated; C 45.29; H 3.80; Found C
45.27; H 3.82.
1-(4-Chlorophenyl)-2-nitropropan-1-ol (Table 4, Entry 2):
Colorless oil, IR (KBr, cm-1): ν 3401, 3025, 2949, 2889, 2786,
1546, 1438, 1381, 1323, 1281, 1179, 1121, 845, 786; 1H-NMR
(400 MHz, CDCl3, TMS): δ 7.81 (d, J= 7.6 Hz, 2H), 7.52 (d, J=
7.6 Hz, 2H), 5.01 (d, J= 8.8 Hz, 1H), 4.75-4.69 (m, 1H), 2.64 (s,
1H), 1.47 (d, J= 6.8 Hz, 3H); 13C-NMR (100 MHz, CDCl3, TMS):
1-(4-Fluorophenyl)-2-nitroethan-1-ol (Table 3, Entry 11):
δ 136.87, 131.47, 128.32, 127.40, 88.25, 31.77, 16.33;
Elemental analysis for C9H10ClNO3: Calculated; C 50.13; H
4.67; Found C 50.14; H 4.66.
Light yellow liquid, IR (KBr, cm-1): ν 3425, 3012, 2909, 2100,
1704, 1526, 1132, 879, 745; H-NMR (400 MHz, CDCl3, TMS):
1
δ 7.41-7.39 (dd, J= 8 Hz, 1H), 7.39-7.37 (dd, J= 8 Hz, 1H), 7.12
(d, J= 8.4 Hz, 2H), 5.47-5.44 (m, 1H), 4.78 (t, J= 6.8 Hz, 1H),
4.59-4.50 (m, 1H), 2.92 (s, 1H); 13C-NMR (100 MHz, CDCl3,
TMS): δ 161.66, 133.86, 127.74, 116.14, 115.93, 70.32;
Elemental analysis for C8H8FNO3: Calculated; C 51.90; H 4.36;
Found C 51.92; H 4.35.
2-Nitro-1-(p-tolyl)propan-1-ol (Table 4, Entry 3):
Colorless liquid, IR (KBr, cm-1):ν3354, 3015, 2929, 2898, 2780,
1550, 1441, 1377, 1345, 1284, 1179, 1110;1H-NMR (400
MHz, CDCl3, TMS): δ 7.24 (d, J= 8 Hz, 2H), 7.20 (d, J= 7.2 Hz,
2H), 5.30 (s, 1H), 4.96 (d, J= 8.8 Hz, 1H), 4.77-4.70 (m, 1H),
2.35 (s, 1H), 1.48-1.47 (dd, J= 6.8 Hz, 1.5H), 1.29-1.27 (dd, J=
6.8 Hz, 1.5H); 13C-NMR (100 MHz, CDCl3, TMS): δ 129.16,
128.89, 126.35, 125.40, 87.98, 75.62, 20.69, 15.95; Elemental
analysis for C10H13NO3: Calculated; C 61.53; H 6.71; Found C
61.55; H 6.69.
1-Nitropentan-2-ol (Table 3, Entry 14):
Yellow liquid, IR (KBr, cm-1): ν 3361, 2846, 1614, 1520, 1206,
1171, 853, 736; H-NMR (400 MHz, CDCl3, TMS): δ 4.57-4.48
(m, 2H), 3.91 (s, 1H), 3.19 (s, 1H), 1.53-1.40 (m, 6H), 0.96 (t,
1
J= 6.4 Hz, 3H); 13C-NMR (100 MHz, CDCl3, TMS): δ 86.47,
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