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R. Engel et al. / Chemistry and Physics of Lipids 160 (2009) 105–108
Table 1
Analytical and yield data for newly synthesized dicationic strings.
.
Cpd. no.
1
RX
n
Yield
1H NMR (solvent) (ı)
13 C NMR (ı)
Analyses
2
82.5%
(D2O) 1.88–1.91 (4H) br, 3.12 (12H)
s, 3.30–3.50 (8H) br, 3.65 (4H) t
26.1, 53.3, 60.4, 62.6, 64.8
Calcd: C12 H30N2O2Br2(H2O); C:
34.96%; H: 7.82%; found: C: 34.71%;
H: 7.87%
2
3
3
3
61.5%
64.0%
(D2O) 0.88 (6H) t, 1.70 (4H) br, 2.20
(2H) br, 3.03 (12H) s, 3.21–3.32
(8H) br
9.7, 15.7, 16.7, 50.6, 60.1, 66.2
19.1, 27.4, 53.2, 60.4, 62.6, 64.8
Calcd: C13 H32N2Br2; C: 41.50%; H:
8.57%; found: C: 41.31%; H: 8.66%
(D2O) 1.90–2.01 (4H) br, 2.22–3.20
(2H) br, 3.10 (12H) s, 3.33–3.55
(8H) br, 3.69 (4H) t
Calcd: C13 H32N2O2Cl2; C: 48.90%;
H: 10.10%; found: C: 48.99%; H:
10.39%
4
5
3
3
88.0%
74.2%
(D2O) 2.33 (2H) br, 3.17 (6H) s, 3.19
(6H) s, 3.44–3.54 (12H) br, 4.23
(2H) m
16.9, 51.9, 52.1, 61.2, 61.4, 63.6, 66.0,
66.2
Calcd: C13 H32N2O2Cl2(H2O); C:
48.59%; H: 10.66%; found: C:
48.31%; H: 10.84%
Cl(CH2)6OH
(D2O) 1.30–1.37 (8H) br, 1.45–1.62
(4H) br, 1.68–1.78 (4H) br,
14.8, 20.0, 22.8, 23.3, 29.1, 48.8,
58.1, 59.7, 62.9,
Calcd: C19 H44N2O2Cl2; C: 56.56%;
H: 10.99%; found: C: 56.81%; H:
10.70%
2.20–2.28 (2H) br, 3.07 (12H) s,
3.25–3.34 (8H) m, 3.51 (4H) t
(CDCl3) 0.82 (6H) t, 1.12–1.35 (34H)
br, 1.66 (4H) br, 1.87 (4H) br, 3.30
(12H) s, 3.46–3.52 (8H) br
6
CH3(CH2)11 Br
3
74.3%
14.1, 20.9, 22.6, 22.8, 26.2, 29.2,
29.26, 29.34, 29.4, 29.5, 31.8, 45.2,
51.4, 55.6, 64.1
Calcd: C31 H68N2Br2; C: 59.22%; H:
10.90%; found: C: 59.13%; H: 10.98%
7
4
4
4
4
54.3%
73.0%
68.5%
88.5%
(D2O) 1.23–1.38 (4H) m, 1.40–1.55
(4H) br, 2.98 (12H) s, 3.17–3.32
(8H) br, 3.50 (4H) t
20.0, 22.6, 51.3, 62.3, 63.7, 65.0
Calcd: C14 H34N2O2Cl2; C: 50.44%;
H: 10.28%; found: C: 50.80%; H:
10.21%
8
Cl(CH2)6OH
Cl(CH2)10 OH
CH3(CH2)16 Br
(D2O) 1.33–1.47 (8H) br, 1.48–1.49
(4H) br, 1.61–1.64 (8H) br, 3.16
(12H) s, 3.33 (8H) m, 3.69 (4H) t
18.8, 21.5, 24.2, 24.9, 30.6, 50.2,
61.2, 62.5, 63.9
Calcd: C20H46N2O2Cl2; C: 57.54%;
H: 11.11%; found: C: 57.27%; H:
11.40%
9
(D2O) 1.35–1.49 (20H) br, 1.51–1.52
(8H) br, 1.63–1.66 (8H) br, 3.19
(12H) s, 3.35 (8H) m, 3.71 (4H) t
18.2, 18.5, 18.8, 19.2, 19.7, 21.5, 24.3,
24.9, 30.7, 50.2, 61.2, 62.6, 63.9
Calcd: C28H62N2O2Cl2; C: 63.49%;
H: 11.80%; found: C: 63.41%; H:
11.91%
10
(CDCl3) 0.81 (6H) t, 1.11–1.31 (52H)
br, 1.68 (4H) br, 2.09 (4H) br, 3.21
(12H) s, 3.35 (4H) br, 3.86 (4H) br
14.2, 19.9, 22.7, 22.9, 26.3, 27.3,
29.2, 29.3, 29.4, 29.49, 29.51, 29.63,
29.66, 29.68, 29.72, 31.9, 42.7, 50.9,
63.7
Calcd: C40H86N2Br2; C: 63.64%; H:
11.48%; found: C: 63.62%; H: 11.57%
11
12
CH3I
6
6
91.5%
87.0%
(D2O) 1.34 (4H) br, 1.71 (4H) br,
3.01 (18H) s, 3.23 (4H) br
22.2, 25.0, 52.8, 66.4
Calcd: C12 H30N2I2; C: 31.59%; H:
6.63%; found: C: 31.48%; H: 6.72%
(D2O) 0.86 (6H) t, 1.29 (4H) br, 1.78
(8H) br, 2.94 (12H) s, 3.16 (8H) br
14.7, 18.2, 20.9, 24.2, 49.6, 62.9,
64.5
Calcd: C16 H38N2I2; C: 37.51%; H:
7.48%; found: C: 37.44%; H: 7.62%
13
14
6
6
77.6%
47.0%
(D2O) 1.23–1.38 (8H) m, 1.38–1.51
(4H) m, 2.90 (12H) s, 3.12–3.25 (8H)
m, 3.45–3.58 (4H) t
24.1, 26.8, 27.5, 52.8, 63.4, 66.0, 66.2
Calcd: C16 H38N2O2Cl2(H2O); C:
50.65%; H: 10.63%; found: C:
50.88%; H: 10.59%
(D2O) 1.32 (4H) br, 1.69 (4H) br,
3.05 (6H) s, 3.06 (6H) s, 3.28–3.34
(8H) m, 3.46–3.48 (4H) m, 4.15 (2H)
m
21.8, 25.0, 51.5, 51.7, 63.6, 65.3,
65.6, 66.1
Calcd: C16 H38N2O4Cl2; C: 48.85%;
H: 9.74%; found: C: 48.48%; H:
9.54%
15
16
CH3(CH2)3Br
Cl(CH2)6OH
6
6
72.0%
60.1%
(D2O) 0.83 (6H) t, 1.29 (8H) br, 1.61
(8H) br, 2.92 (12H) s, 3.17 (8H) br
12.8, 19.0, 21.8, 23.8, 25.1, 42.5,
50.4, 63.6
Calcd: C18 H42N2Br2; C: 48.44%; H:
9.48%; found: C: 48.21%; H: 9.59%
(D2O) 1.28–1.32 (12H) br, 1.43–1.49
(4H) br, 1.66–1.67 (8H) br, 2.94
(12H) s, 3.16–3.20 (8H) m, 3.49 (4H)
t
22.2, 24.7, 24.9, 25.5, 25.6, 31.3,
46.1, 62.1, 64.1, 64.3
Calcd: C22H50N2O2Cl2; C: 59.31%;
H: 11.31%; found: C: 59.38%; H:
11.41%
17
C6H5CH2Cl
6
37.0%
(D2O) 1.33 (4H) br, 1.80 (4H) br,
2.91 (12H) s, 3.19 (4H) br, 4.28 (4H)
br, 7.57 (10H) br
22.0, 25.2, 42.9, 49.6, 67.8, 127.2,
129.1, 130.8, 132.8
Calcd: C24H38N2Cl2; C: 71.47%; H:
7.89%; found: C: 71.48%; H: 8.13%