Spectral Charecterization of Compounds

SPECTRAL CHARECTERIZATION OF COMPOUNDS

1-Ethyl-3-methylimidazolium bromide(1): yield 97%; pale brown liquid; 1H NMR(CD3OD, 400 MHz): δ 0.665-0.671 (t, 3H, CH3, J= 7.43 Hz), 3.670 (s, 3H, N-CH3), 3.203-3.962 (m, 2H, CH2), 7.218-7.222 (d, 1H, Ar-H, J= 1.72 Hz), 7.257-7.259 (d, 1H, Ar-H, J= 3.24), 8.508 (s, 1H, Ar-H, J= 3.24); MS (APCI): 112.1(M+1).

1-Propyl-3-methylimidazolium bromide (2): yield 94%; pale brown liquid; 1H NMR(CD3OD, 400 MHz): δ 0.661-0.698 (t, 3H, CH3, J= 7.44 Hz), 1.629-1.684 (m, 2H, CH2), 3.672 (s, 3H, N-CH3), 3.198-3.953 (t, 2H, CH2, J= 7.04 Hz), 7.212-7.215 (d, 1H, Ar-H, J= 1.72 Hz), 7.254-7.257 (d, 1H, Ar-H, J= 3.24), 8.499 (s, 1H, Ar-H, J= 3.24); MS (APCI): 126.1(M+1).

1-Isopropyl-3-methylimidazolium bromide (3): yield 91%; pale brown liquid; 1H NMR(CD3OD, 400 MHz): δ 1.073-1.089 (d, 6H, 2xCH3, J= 6.72 Hz), 3.586 (s, 3H, N-CH3), 4.300-4.333 (m, 1H, CH), 7.181-7.185 (d, 1H, Ar-H, J= 1.84 Hz), 7.204-7.208 (d, 1H, Ar-H, J= 3.24); MS (APCI): 126.1(M+1).

1-Butyl-3-methylimidazolium bromide (4):yield 92%; pale brown liquid; 1H NMR(CD3OD, 400 MHz): δ 0.935-0.972 (t, 3H, CH3, J= 7.36 Hz), 1.338-1.412 (m, 2H, CH2), 1.878-1.953 (m, 2H, -CH2), 4.131 (s, 3H, N-CH3), 4.353-4.390 (t, 2H, CH2, J= 7.36 Hz), 7.212-7.215 (d, 1H, Ar-H, J= 1.64 Hz), 7.774-7.778 (d, 1H, Ar-H J= 1.60), 9.670 (s, 1H, Ar-H); MS (APCI): 140.1(M+1).

1-Pentyl-3-methylimidazolium bromide (5): yield 88%; pale brown liquid; 1H NMR(CD3OD, 400 MHz): δ 0.939-0.975 (t, 3H, CH3, J= 7.36 Hz), 1.342-1.418 (m, 2H, CH2), 1.886-1.970 (m, 2H, -CH2), 2.156-2.258 (m, 2H, -CH2), 4.157 (s, 3H, N-CH3), 4.362-4.419 (t, 2H, CH2, J= 7.36 Hz), 7.225-7.237 (d, 1H, Ar-H, J= 1.66 Hz), 7.794-7.808 (d, 1H, Ar-H J= 1.62), 10.032 (s, 1H, Ar-H); MS (APCI): 154.1(M+1).

1-Cycopentyl-3-methylimidazolium bromide (6): yield 76%; brown liquid; 1H NMR(CD3OD, 400 MHz): δ 1.879-1.942 (m, 4H, CH2), 2.329-2.399 (m, 4H, CH2), 4.133 (s, 3H, N-CH3), 7.585-7.593 (d, 1H, Ar-H, J= 1.68 Hz), 7.718-7.728 (d, 1H, Ar-H J= 4.00), 10.069 (s, 1H, Ar-H); MS (APCI): 152.1(M+1).

1-Hexyl-3-methylimidazolium bromide (7): yield 85%; pale brown liquid; 1H NMR(CD3OD, 400 MHz): δ 0.944-0.986 (t, 3H, CH3, J= 7.36 Hz), 1.346-1.429 (m, 2H, CH2), 1.892-1.965 (m, 2H, -CH2), 2.162-2.236 (m, 2H, -CH2), 2.284-2.331 (m, 2H, -CH2), 4.205 (s, 3H, N-CH3), 4.366-4.408 (t, 2H, CH2, J= 7.36 Hz), 7.215-7.227 (d, 1H, Ar-H, J= 1.64 Hz), 7.786-7.798 (d, 1H, Ar-H J= 1.62), 9.981 (s, 1H, Ar-H); MS (APCI): 168.1(M+1).

1,3-Diethylimidazolium bromide (8):yield 82%; pale brown semisolid; 1H NMR(CD3OD, 400 MHz): δ 0.928-0.966 (t, 6H, 2x CH3, J= 7.30 Hz), 1.342-1.427 (m, 4H, 2x CH2), 4.151-4.212 (s, 3H, N-CH3), 4.33 (t, 2H, CH2, J= 7.91 Hz), 7.40 (d, 1H, 4-Ar-H, J= 2.02 Hz), 7.50 (d, 1H, 5-Ar-H J= 1.99 Hz); MS (APCI): 126.1(M+1).

1,3-Dipropylimidazolium bromide (9):yield 79%; pale brown liquid; 1H NMR(CD3OD, 400 MHz): δ 0.936-0.978 (t, 6H, 2x CH3, J= 7.60 Hz), 1.312-1.390 (m, 4H, 2x CH2), 4.450-4.521 (m, 4H, 2x N-CH2), 7.578 (s, 2H, 2x Ar-H), 10.212 (s, 1H, Ar-H); MS (APCI): 154.1(M+1).

1,3-Diisopropylimidazolium bromide (10):yield 75%; viscous brown liquid; 1H NMR(CD3OD, 400 MHz): δ 1.616-1.653 (t, 12H, 3x CH3, J= 8.04 Hz), 4.947-5.014 (m, 2H, 2x N-CH), 7.548 (s, 2H, 2x Ar-H), 10.548 (s, 1H, Ar-H); MS (APCI): 154.1(M+1).

1,3-Dibutylimidazolium bromide (11):yield 67%; brown liquid; 1H NMR(CD3OD, 400 MHz): δ 0.945-0.983 (t, 6H, 2x CH3, J= 7.40 Hz), 1.341-1.436 (m, 4H, 2x CH2), 1.885-1.960 (m, 4H, 2x CH2), 4.365-4.402 (m, 4H, 2x N-CH2), 7.660 (s, 2H, 2x Ar-H), 10.168 (s, 1H, Ar-H); MS (APCI): 182.2(M+1).

1,3-Dipentylimidazolium bromide (12):yield 67%; brown liquid; 1H NMR(CD3OD, 400 MHz): δ 0.960-1.013 (t, 6H, 2x CH3, J= 7.48 Hz), 1.352-1.438 (m, 4H, 2x CH2), 1.905-1.992 (m, 4H, 2x CH2), 2.155-2.221 (m, 4H, 2x CH2), 4.371-4.426 (m, 4H, 2x N-CH2), 7.710 (s, 2H, 2x Ar-H), 10.187 (s, 1H, Ar-H); MS (APCI): 210.2(M+1).

1,3-Dicyclopentyl bromide (13):yield 62%; pale solid; 1H NMR(CD3OD, 400 MHz): δ 1.80-1.83 (m, 16H, 8x CH2, J= 7.63 Hz), 4.75 (m, 2H, 2x CH), 7.19 (s, 2H, 4-Ar-H, 5-Ar-H), 1.84 (m, 2H, CH2), 4.05 (s, 3H, N-CH3), 4.33 (t, 2H, CH2, J= 7.91 Hz), 7.93 (s, 2H, 2x Ar-H) 9.501 (s, 1H, Ar-H); MS (APCI): 206.2(M+1).

1,3-Dihexylimidazolium bromide (14): yield 53%; brown liquid; 1H NMR(CD3OD, 400 MHz): δ 0.965-1.022 (t, 6H, 2x CH3, J= 7.40 Hz), 1.362-1.450 (m, 4H, 2x CH2), 1.911-1.982 (m, 4H, 2x CH2), 2.172-2.239 (m, 4H, 2x CH2), 2.392-2.445 (m, 4H, 2x CH2), 4.364-4.471 (m, 4H, 2x N-CH2), 7.726 (s, 2H, 2x Ar-H), 10.119 (s, 1H, Ar-H); MS (APCI): 238.2(M+1).