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L.-J. ZHANG ET AL.
Spectroscopic Data for Some Typical and Liquid Compounds
1-Benzyl-2-phenyl-1H-benzimidazole (1a).[5] 1H NMR (300 MHz, CDCl3)
d: 7.87 (d, J ¼ 7.8 Hz, 1 H), 7.69 (d, J ¼ 7.7 Hz, 2 H), 7.47–7.45 (m, 3 H), 7.34–7.22
(m, 6 H), 7.11 (d, J ¼ 6.7 Hz, 2 H), 5.46 (s, 2 H); 13C NMR (75.4 MHz, CDCl3)
d: 154.1, 143.2, 136.4, 136.0, 130.1, 129.9, 129.2, 129.0, 128.7, 127.7, 125.9, 123.0,
122.6, 120.0, 110.5, 48.3. HR-EI-MS m=z calcd. for C20H16N2 (Mþ) 284.1313; found
284.1308.
1-Butyl-2-propyl-1H-benzimidazole (1k).[5] 1H NMR (300 MHz, CDCl3) d:
7.71–7.68 (m, 1 H), 7.27–7.17 (m, 3 H), 4.04 (t, J ¼ 7.5 Hz, 2 H), 2.80 (t, J ¼ 7.5 Hz,
2 H), 1.94–1.84 (m, 2 H), 1.78–1.68 (m, 2 H), 1.39–1.25 (m, 2 H), 1.04 (t, J ¼ 7.4 Hz,
3 H), 0.93 (t, J ¼ 7.3 Hz, 3 H); 13C NMR (75.4 MHz, CDCl3) d: 153.2, 135.2, 127.4,
124.6, 122.5, 121.5, 110.6, 68.6, 40.8, 36.2, 23.1, 19.3, 13.8, 13.7.
1-Hexyl-2-pentyl-1H-benzimidazole (1l).[18] 1H NMR (300 MHz, CDCl3)
d: 7.71–7.68 (m, 1 H), 7.26–7.16 (m, 3 H), 4.02 (t, J ¼ 7.5 Hz, 2 H), 2.80 (t, J ¼ 7.8 Hz,
2 H), 1.87–1.82 (m, 2 H), 1.75–1.68 (m, 2 H), 1.38–1.28 (m, 10 H), 0.91–0.83
(m, 6 H);13C NMR (75.4 MHz, CDCl3) d: 155.0, 142.6, 135.0, 121.7, 121.5, 119.1,
43.1, 31.7, 31.4, 29.8, 27.5, 26.6, 22.4, 13.9; HR-EI-MS m=z calcd. for C18H28N2
(Mþ) 272.2252; found 272.2247.
2-tert-butyl-1H-benzimidazole (2a).[19] 1H NMR (300 MHz, CDCl3) d:
7.57 (s, 2 H), 7.25–7.20 (m, 2 H), 1.50 (s, 9 H); 13C NMR (75.4 MHz, DMSO) d:
162.7, 121.6, 119.7, 116.4, 116.2, 115.2, 114.7, 33.6, 29.7. HR-EI-MS m=z calcd.
for C11H14N2 (Mþ) 174.1157; found 174.1152.
2-Phenylbenzothiazole (3a).[9] 1H NMR (300 MHz, CDCl3) d: 8.11–8.06 (m,
3 H), 7.91 (d, J ¼ 8.0 Hz, 1 H), 7.50–7.47 (m, 4 H), 7.41–7.36 (m, 1 H); 13C NMR
(75.4 MHz, CDCl3) d: 168.5, 154.1, 134.9, 133.5, 131.0, 129.0, 127.5, 126.3, 125.2,
123.2, 121.6; HR-EI-MS m=z calcd. for C13H9NS (Mþ) 211.0456; found 211.0448.
2-tert-butyl-2,3-dihydrobenzothiazole (4a).[24] 1H NMR (300 MHz,
CDCl3) d: 7.01 (d, J ¼ 7.5 Hz, 1 H), 6.87–6.82 (m, 1 H), 6.66 (t, J ¼ 7.5 Hz, 1 H),
6.56 (d, J ¼ 7.8 Hz, 1 H), 5.17 (s, 1 H), 1.69 (br, s, 1 H), 0.98 (s, 9 H); 13C NMR
(75.4 MHz, CDCl3) d: 147.4, 127.0, 124.9, 122.5, 121.5, 109.4, 78.5, 36.9, 25.4;
HR-EI-MS m=z calcd. for C11H15NS (Mþ) 193.0925; found 193.0929.
2-Propyl-2,3-dihydrobenzothiazole (4b).[14] 1H NMR (300 MHz, CDCl3)
d: 7.08 (d, J ¼ 7.2 Hz, 1 H), 6.94–6.90 (m, 1 H), 6.77–6.64 (m, 2 H), 5.28
(t, J ¼ 5.9 Hz, 1 H), 3.93 (s, br, 1 H), 1.88–1.83 (m, 2 H), 1.50–1.43 (m, 2 H), 0.98
(t, J ¼ 6.9 Hz, 3 H); 13C NMR (75.4 MHz, CDCl3) d: 125.9, 124.6, 122.5, 121.5,
120.8, 110.8, 68.6, 38.5, 20.4, 13.8; HR-EI-MS m=z calcd. for C10H13NS (Mþ)
179.0769l found 179.0773.
1-Dideuteratedbenzyl-2-phenyl-1H-benzimidazole. 1H NMR (300 MHz,
CDCl3) d: 7.86 (d, J ¼ 7.6 Hz, 2 H), 7.08–7.67 (m, 12 H). HR-EI-MS m=z calcd.
for C20H14D2N2 (Mþ) 286.1439, found; 286.1433.