ꢁꢀꢀꢀ
M. Stapf et al.: Synthesis and UV/Vis analysis of receptors involving anion complexationꢂ
ꢂ417
3
4.11 N,N′-[(3,3′-Dimethylbiphenyl-4,4′-diyl)- 3JHH ꢀ=ꢀ 6.8 Hz), 2.10 (m, 2H, CH(CH3)2, JHH ꢀ=ꢀ 5.2 Hz), 2.27
(s, 6H, CH3-Ar), 4.16 (dd, 2H, CHCOOH, 3JHH ꢀ=ꢀ 4.9 Hz, 3JHH ꢀ=ꢀ
bis(iminocarbonyl)]-di(l-alanine) (9)
3
8.6 Hz), 6.95 (d, 2H, NH, JHH ꢀ=ꢀ 8.7 Hz), 7.36 (d, 2H, H-Ar,
3
l-Alanine and 4,4′-diisocyanato-3,3′-dimethylbiphenyl JHH ꢀ=ꢀ 8.5 Hz), 7.41 (s, 2H, H-Ar), 7.93 (d, 2H, H-Ar, 3JHH ꢀ=ꢀ 8.9
were used; reaction period: 9.5 h; white powder (45 %); Hz), 7.95 (s, 2H, NH), 12.55 (br, COOH). – 13C NMR: δC ꢀ=ꢀ 1 7.7,
m. p. 341–342 °C. – [ α]D20 ꢀ=ꢀ −47.1 (c ꢀ=ꢀ 0.18, CH3OH). – IR 18.2, 19.2, 30.4, 57.4, 120.2, 123.8, 126.5, 127.7, 133.3, 137.1,
+
(KBr): νmax ꢀ=ꢀ 3322, 2984, 2946, 1742, 1635, 1591, 1546, 1454, 155.2, 173.9. – MS (ESI): m/z ꢀ=ꢀ 499.5 [M+H] . – C26H34N4O6
−1
1375, 1302, 1239, 1166, 1128, 1068, 865, 796, 761, 650 cm . – · ½ H2O: calcd. C 61.52, H 6.95, N 11.04; found: C 61.73, H
1H NMR: δH ꢀ=ꢀ 1.31 (d, 6H, CHCH3, 3JHH ꢀ=ꢀ 7.3 Hz), 2.26 (s, 6H, 7.09, N 11.02.
3
CH3-Ar), 4.17 (m, 2H, CHCOOH, JHH ꢀ=ꢀ 7.3 Hz), 7.18 (d, 2H,
NH, 3JHH ꢀ=ꢀ 7.3 Hz), 7.34 (dd, 2H, H-Ar, 3JHH ꢀ=ꢀ 8.5 Hz, 4JHH ꢀ=ꢀ 1.8
Hz), 7.39 (d, 2H, H-Ar, 4JHH ꢀ=ꢀ 1.5 Hz), 7.88 (d, 2H, H-Ar, 3JHH ꢀ=ꢀ
4.14 N,N′-[(3,3′-Dimethylbiphenyl-4,4′-diyl)-
bis(iminocarbonyl)]-di(l-leucine) (12)
8.5 Hz), 8.05 (s, 2H, NH). – 13C NMR: δC ꢀ=ꢀ 18.2, 18.3, 48.1,
120.3, 123.7, 126.8, 127.7, 133.4, 137.1, 154.9, 175.0. – MS (ESI):
+
m/z ꢀ=ꢀ 907.4 [2·M+Na] . – C22H26N4O6 · H2O: calcd. C 57.38, H
l-Leucine and 4,4′-diisocyanato-3,3′-dimethylbiphenyl
were used; reaction period: 20 h; white powder (55 %); m.
p. 259–260 °C (dec.). – [ α]D20 ꢀ=ꢀ −5.5 (c ꢀ=ꢀ 0.53, CH3OH). – IR
(KBr): νmax ꢀ=ꢀ 3338, 3031, 2955, 2870, 1717, 1647, 1591, 1543,
1496, 1445, 1388, 1369, 1299, 1245, 1169, 1125, 1068, 1036,
6.13, N 12.17; found: C 57.57, H 6.13, N 11.83.
4.12 N,N′-[(3,3′-Dimethylbiphenyl-4,4′-diyl)-
bis(iminocarbonyl)]-di(l-phenylalanine)
(10)
−1
1
878, 821, 758, 653, 574 cm . – H NMR: δH ꢀ=ꢀ 0.91 (d, 6H,
3
3
CH(CH3)2, JHH ꢀ=ꢀ 6.6 Hz), 0.94 (d, 6H, CH(CH3)2, JHH ꢀ=ꢀ 6.6
Hz), 1.53 (m, 4H, CH2, 3JHH ꢀ=ꢀ 8.5 Hz), 1.72 (m, 2H, CH(CH3)2,
3JHH ꢀ=ꢀ 6.6 Hz), 2.26 (s, 6H, CH3-Ar), 4.20 (m, 2H, CHCOOH,
l-Phenylalanine
and
4,4′-diisocyanato-3,3′-
dimethylbiphenyl were used; reaction period: 7.5 h; white
powder (70 %); m. p. 322–324 °C (dec.). – [ α]D20 ꢀ=ꢀ +70.9
(c ꢀ=ꢀ 0.59, CH3OH). – IR (KBr): νmax ꢀ=ꢀ 3351, 3088, 3056,
3028, 2927, 1723, 1638, 1591, 1543, 1496, 1454, 1442, 1385,
1302, 1242, 1119, 1081, 1062, 1030, 878, 821, 755, 701, 650
3JHH ꢀ=ꢀ 8.5 Hz), 6.96 (d, 2H, NH, JHH ꢀ=ꢀ 8.0 Hz), 7.35 (d, 2H,
3
H-Ar, 3JHH ꢀ=ꢀ 8.6 Hz), 7.41 (s, 2H, H-Ar), 7.87 (s, 2H, NH), 7.91
(d, 2H, H-Ar, JHH ꢀ=ꢀ 8.4 Hz), 12.52 (br, COOH). – 13C NMR:
3
δC ꢀ=ꢀ 18.1, 21.6, 22.8, 24.4, 41.0, 50.8, 120.2, 123.7, 126.6, 127.7,
+
133.3, 137.0, 155.0, 175.0. – MS (ESI): m/z ꢀ=ꢀ 527.2 [M+H] . –
cm . – 1H NMR: δH ꢀ=ꢀ 2.24 (s, 6H, CH3-Ar), 2.97 (dd, 2H, CH2,
−1
C28H38N4O6 · H2O: calcd. C 61.75, H 7.40, N 10.29; found: C
61.29, H 7.42, N 10.25.
3JHH ꢀ=ꢀ 7.7 Hz), 3.09 (dd, 2H, CH2, 3JHH ꢀ=ꢀ 5.1 Hz), 4.49 (m, 2H,
CHCOOH, 3JHH ꢀ=ꢀ 5.4 Hz), 7.01 (d, 2H, NH, 3JHH ꢀ=ꢀ 7.9 Hz), 7.24
(6H, H-Ar), 7.31 (4H, H-Ar), 7.35 (dd, 2H, H-Ar, 3JHH ꢀ=ꢀ 8.5 Hz,
4
4JHH ꢀ=ꢀ 1.8 Hz), 7.40 (d, 2H, H-Ar, JHH ꢀ=ꢀ 1.7 Hz), 7.85 (d, 2H,
3
H-Ar, JHH ꢀ=ꢀ 8.5 Hz), 8.04 (s, 2H, NH), 12.81 (br, COOH). – 4.15 N,N′-[(3,3′-Dimethylbiphenyl-4,4′-diyl)-
13C NMR: δC ꢀ=ꢀ 18.2, 37.6, 53.9, 120.7, 123.7, 126.5, 127.1, 127.8,
bis(iminocarbonyl)]-di(l-proline) (13)
128.3, 129.4, 133.6, 137.0, 137.4, 154.9, 173.6. – MS (ESI):
+
m/z ꢀ=ꢀ 595.4 [M+H] . – C34H34N4O6 · 2 H2O: calcd. C 64.75, H l-Proline and 4,4′-diisocyanato-3,3′-dimethylbiphenyl
6.07, N 8.88; found: C 64.44, H 5.75, N 8.75.
were used; reaction period: 7.5 h; white powder (73 %);
m. p. 288–290 °C. – [ α]D20 ꢀ=ꢀ −76.4 (c ꢀ=ꢀ 0.20, CH3OH). – IR
(KBr): νmax ꢀ=ꢀ 3345, 2965, 2927, 2889, 2604, 1723, 1622, 1594,
4.13 N,N′-[(3,3′-Dimethylbiphenyl-4,4′-diyl)- 1515, 1451, 1394, 1366, 1242, 1201, 1131, 1084, 1021, 922, 824,
−1
1
751, 577, 527 cm . – H NMR: δH ꢀ=ꢀ 1.93 (m, 6H), 2.18 (m,
bis(iminocarbonyl)]-di(l-valine) (11)
3
3
2
2H, JHH ꢀ=ꢀ 5.3 Hz, JHH ꢀ=ꢀ 9.1 Hz, JHH ꢀ=ꢀ 12.8 Hz), 2.25 (s, 6H,
3
l-Valine and 4,4′-diisocyanato-3,3′-dimethylbiphenyl CH3-Ar), 3.49 (m, 2H, JHH ꢀ=ꢀ 7.3 Hz), 3.57 (m, 2H), 4.33 (m,
3
were used; reaction period: 6 h; white powder (43 %); 2H, CHCOOH), 7.41–7.36 (4H, H-Ar, JHH ꢀ=ꢀ 8.4 Hz), 7.46 (s,
m. p. 315–316 °C. – [ α]D20 ꢀ=ꢀ +12.3 (c ꢀ=ꢀ 0.20, CH3OH). – IR 2H, H-Ar), 7.77 (s, 2H, NH), 12.46 (br, COOH). – 13C NMR:
(KBr): νmax ꢀ=ꢀ 3300, 3031, 2961, 2936, 2876, 1739, 1714, 1632, δC ꢀ=ꢀ 18.1, 24.0, 29.4, 46.1, 58.8, 123.7, 125.5, 127.9, 132.6,
+
1587, 1543, 1496, 1445, 1394, 1302, 1245, 1188, 1160, 1128, 135.8, 136.9, 154.3, 174.4. – MS (ESI): m/z ꢀ=ꢀ 495.3 [M+H] .
−1
1
1065, 1036, 872, 802, 758, 647 cm . – H NMR: δH ꢀ=ꢀ 0.91 – C26H30N4O6 · H2O: calcd. C 60.92, H 6.29, N 10.93; found: C
3
(d, 6H, CH(CH3)2, JHH ꢀ=ꢀ 6.8 Hz), 0.94 (d, 6H, CH(CH3)2, 60.20, H 6.41, N 10.50.
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