PAPER
Crown-Ester Viologens
913
Table 6 Characterization of the 4,4¢-Bipyridinium-Crown-Ester Relays (16–20)
Producta
FT-IR (KBr, cm–1)
1H NMR (400 MHz, D2O)
d, J (Hz)
MS (FAB)
m/z (%)
Mp
(°C)
16
3080, 2995, 2945, 1715
(C=O), 1680, 1610, 1590,
1505, 1465, 1445, 1425,
8.04 (s, 4 H, ArH), 7.75 (dd, 2 H, ArH), 4.40 (t, 691 (0.011) [M + 1], 271 202 (dec.)
2 H), 4.26 (t, 2 H), 3.50 (mc, 10 H), 3.27 (t, 4
(0.5), 200 (0.03), 156
(3.2), 78 (100), 64 (16)
H), 2.86 (td, 4 H, N+CH2), 2.47 (t, 4 H,
CH2OSO2 ), 1.77 (td, 3J1 = 6.75 Hz, 3J2 = 7.53
¢
–
1390, 1060 (OSO2 )
Hz, 3J3 = 7.11 Hz, 3J4 = 7.02 Hz, 4J = 1.16 Hz,
4 H)
17
18
19
20
3080, 2995, 2950, 1715
(C=O), 1680, 1610, 1585,
1510, 1465, 1450, 1425,
8.04 (s, 4 H, ArH), 7.76 (dd, 2 H, ArH), 4.42 (t, 647 (0.02) [M + 1], 392
2 H), 4.28 (t, 2 H), 3.52 (mc, 6 H), 3.25 (t, 4 H), (1.4), 157 (0.9), 78 (100),
200 (dec.)
248 (dec.)
217 (dec.)
2.86 (td, 4 H, N+CH2), 2.47 (t, 4 H,
64 (42)
–
–
1390, 1060 (OSO2 )
CH2OSO2 ), 1.77 (td, 3J1 = 6.77 Hz, 3J2 = 7.51
Hz, 3J3 = 7.08 Hz, 3J4 = 7.05 Hz, 4J = 1.13 Hz,
4 H)
3080, 2940, 2860, 1730
(C=O), 1670, 1640, 1600,
1510, 1470, 1445, 1430,
8.04 (s, 4 H, ArH),b 7.76 (s, 2 H, ArH), 4.40 (t, 690 (0.004), 390 (1.6),
4 H), 4.26 (t, 2 H), 3.50 (m, 4 H), 3.54 (m, 6 H), 158 (1.3), 78 (100), 64
3.27 (t, 4 H), 2.76 (td, 4 H, N+CH2), 2.47 (t, 4 H, (28)
1385, 1060 (OSO2 ), 728
CH2OSO2 ), 1.77 (td, 3J1 = 6.86 Hz, 3J2 = 4.77
–
–
Hz, 3J3 = 4.12 Hz, 3J4 = 4.08 Hz, 4J = 1.27 Hz,
4 H)
3080, 2985, 2935, 1725
(C=O), 1645, 1580, 1505,
8.04 (s, 4 H, ArH),b 7.75 (s, 2 H, ArH), 4.40 (t, 646 (0.0015), 391 (1.5),
4 H), 4.26 (t, 2 H), 3.65 (m, 2 H), 3.50 (m, 6 H), 157 (1.6), 78 (100), 64
1465, 1445, 1430, 1380, 1060 3.26 (t, 2 H), 2.78 (td, 4 H, N+CH2), 2.47 (t, 4 H, (54)
(OSO2 ), 740
CH2OSO2 ), 177 (td, 3J1 = 6.84 Hz, 3J2 = 4.81
–
–
Hz, 3J3 = 4.12 Hz, 3J4 = 4.02 Hz, 4J = 1.22 Hz,
4 H)
3080, 2990, 2950, 2935, 1715 8.07 (s, 4 H, ArH), 7.77 (s, 2 H, ArH), 4.53 (t, 1 603 (0.013) [M + 1], 391 253 (dec.)
(C=O), 1680, 1650, 1585,
1510, 1470, 1445, 1430,
H), 4.29 (t, 1 H), 3.55 (t, 10 H), 2.85 (s, 2 H,
(3.3), 156 (2.0), 78 (100),
CH2OSO2 ), 2.79 (td, 4 H, N+CH2), 2.69 (s, 2 H, 64 (26)
¢
–
–
1285, 1060 (OSO2 )
CH2OSO2 ), 1.80 (td, 3J1 = 6.78 Hz, 3J2 = 6.46
Hz, 3J3 = 4.12 Hz, 4J = 1.26 Hz, 4 H)
a Satisfactory microanalyses were obtained: C, 0.06; H, 0.04; N, 0.05.
b Broad singlets were obtained due to inferior resolution of the 1H NMR spectra.
(7) (a) Simpson, N. R. M.; Ward, M. D.; Morales, A. F.;
Ventura, B.; Barigelletti, F. J. Chem. Soc., Dalton Trans.
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