484
G. LI ET AL.
1-(4-Pyridyl)-2,4,5-triphenylpyridinium perchlorate (3e). IR (KBr) v:
1
1626 (C N), 1578, 1521, 1483, 1454 (C5H4N), 1096, 621 (ClO4 ) cmꢁ1; H NMR
(400 MHz, CD3CN): d ¼ 8.79 (s, 1H, PyH), 8.71 (d, 2H, J ¼ 6.0 Hz, PyH), 8.22 (s,
1H, PyH), 7.38–7.58 (m, 17H, ArH & PyH); 13C NMR (100 MHz, CD3CN):
d ¼ 159.8, 154.6, 152.7, 149.3, 147.0, 140.2, 136.4, 134.7, 132.3, 132.2, 132.1, 131.6,
131.2, 131.0, 130.7, 130.5, 130.0, 129.9, 122.5; MS (API-ES) m=z: 385.1 (Mþ);
HRMS (ESI) calcd. for C28H21N2 (Mþ) 385.1705; found 385.1722. Anal. calcd.
for C28H21N2O4Cl: C, 69.35; H, 4.36; N, 5.78. Found: C, 69.12; H, 4.48; N, 5.92.
ꢁ
=
1-(4-Aminophenyl)-2,3,4,5-tetraphenylpyridinium perchloꢁra1 te (3f). IR
;
1H NMR
ꢁ
=
(KBr) v: 3463, 3370 (NH2), 1628 (C N), 1089, 622 (ClO4 ) cm
(400 MHz, CD3CN): d ¼ 8.82 (s, 1H, PyH), 6.78–7.45 (m, 22H, ArH), 6.52 (d, 2H,
J ¼ 8.8 Hz, ArH), 4.55 (s, 2H, NH2); 13C NMR (100 MHz, CD3CN): d ¼ 158.6,
155.2, 150.8, 145.9, 143.3, 141.1, 136.3, 135.9, 135.3, 132.8, 131.5, 131.4, 130.9,
130.5, 130.3, 129.9, 129.5, 129.3, 129.1, 128.7, 128.5, 128.4, 117.9, 114.5; MS
(API-ES) m=z: 475.2 (Mþ); HRMS (ESI) calcd. for C35H27N2 (Mþ) 475.2174; found
475.2155. Anal. calcd. for C35H27N2O4Cl: C,73.10; H, 4.73; N, 4.87. Found: C,72.92;
H, 4.86; N, 4.70.
1-(4’-Amino-4-biphenylyl)-2,3,4,5-tetraphenylpyridinium
=
(3g). IR (KBr) v: 3470, 3371(NH2), 1623 (C N), 1093, 621 (ClO4 ) cm
perchlorate
ꢁ1
;
1H
ꢁ
NMR(400 MHz, CD3CN): d ¼ 8.89 (s, 1H, PyH), 6.90–7.66 (m, H, ArH), 6.68 (d,
2H, J ¼ 8.4 Hz, ArH), 4.36 (s, 2H, NH2); 13C NMR (100 MHz, CD3CN):
d ¼ 159.6, 154.8, 149.8, 145.5, 145.3, 144.1, 143.5, 141.3, 141.0, 136.2, 135.7, 135.3,
132.4, 131.7, 131.5, 131.2, 131.0, 130.8, 130.7, 130.6, 130.4, 130.0, 129.8, 129.5,
129.4, 128.8, 128.7, 128.5, 128.0, 127.7, 127.1, 126.2, 115.7, 115.6; MS (API-ES)
m=z: 551.2 (Mþ); HRMS (ESI) calcd. for C41H31N2 (Mþ) 551.2487; found
551.2470. Anal. calcd. for C41H31N2O4Cl: C, 75.63; H, 4.80; N, 4.30. Found: C,
75.89; H, 4.67; N, 4.12.
1-(4-Chlorophenyl)-2,3,4,5-tetraphenylpyridinium perchlorate (3h). IR
1
(KBr) v: 1610 (C N), 1022 (Ar-Cl), 1090, 622 (ClO4 ) cmꢁ1; H NMR (400 MHz,
ꢁ
=
CD3CN): d ¼ 8.85 (s, 1H, PyH), 6.86–7.62 (m, 24H, ArH); 13C NMR(100 MHz,
CD3CN): d ¼ 159.5, 154.5, 145.3, 143.3, 141.7, 141.2, 136.9, 136.2, 135.6, 135.2,
132.1, 131.4, 130.9, 130.5, 130.4, 130.3, 129.8, 129.5, 129.4, 129.3, 128.8, 128.7,
128.6, 128.5; MS (API-ES) m=z: 494.2 (Mþ); HRMS (ESI) calcd. for C35H25NCl
(Mþ) 494.1676; found 494.1659. Anal. calcd. for C35H25NO4Cl: C, 70.71; H, 4.24;
N, 2.36. Found: C, 70.42; H, 4.41; N, 2.24.
1-(4-Bromophenyl)-2,3,4,5-tetraphenylpyridinium perchlorate (3i). IR
1
(KBr) v: 1608 (C N), 1018 (Ar-Br), 1086, 622 (ClO4 ) cmꢁ1; H NMR (400 MHz,
ꢁ
=
CD3CN): d ¼ 8.85 (s, 1H, PyH), 6.80–7.63 (m, 24H, ArH); 13C NMR (100 MHz,
CD3CN): d ¼ 159.7, 154.6, 145.3, 143.5, 142.3, 141.3, 136.2, 135.7, 135.3, 133.5,
132.2, 131.5, 131.0, 130.6, 130.0, 129.8, 129.4, 129.3, 128.9, 128.8, 128.7, 128.5,
125.1,; MS (API-ES) m=z: 538.0 (Mþ); HRMS (ESI) calcd for C35H25NBr (Mþ)
538.1170; found 538.1149. Anal. calcd. for C35H25NO4ClBr: C, 65.79; H, 3.94; N,
2.19. Found: C, 66.01; H, 3.78; N, 2.36.