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Can. J. Chem. Vol. 81, 2003
–
CH2-C-SO3 )), 2.91–3.25 (m, 12H, N+(CH3)2, N+CH2, CH2-
(C-CH3), 20.63–34.40 ((CH2)10), 49.90 (CH2-C-SO3), 53.52
and 54.36 (NCH3), 64.21 and 66.06 (NCH2), 66.34
(CH2SO3 ). Anal. calcd. (%) for C31H67N2SO3Br (627.87): C
59.20, H 10.74, N 4.45, S 5.09; found: C 59.79, H 10.35, N
4.42, S 5.55.
–
CH2SO3 ). 13C NMR (200 MHz, D2O) δ: 20.75–31.65
–
((CH2)10), 46.52 (NCH3), 49.84 (CH2-C-SO3), 53.16
–
(N+CH3), 61.4 4 (NCH2), 64.52 (N+CH2), 66.72 (CH2SO3 ).
Anal. calcd. (%) for C19H42N2SO3 (378.6): C 60.27, H 11.18,
N 7.40, S 8.47; found: C 59.93, H 11.02, N 7.07, S 8.54.
1-(N,N-Dimethylammonio,N-propyl-1-sulfonate)-16-(N′,N′-
dimethyl,N′-dodecylammonium bromide) hexadecane, 1e
Yield: 85%.White powder, mp = 135°C. IR (KBr) ν: 1485
1-(N,N-Dimethylammonio,N-propyl-1-sulfonate)-12-(N′,N′-
dimethylamino) hexadecane, 3e
1
(C-N+), 1040 (S = 0). H NMR (80 MHz, D2O) δ: 0.87 (t,
Yield: 75%. White powder, mp = 238°C. IR (KBr) ν:
1480 (C-N+), 1040 (S = 0). H NMR (80 MHz, D2O) δ: 1.22
1
J = 7.3, 3H, CH3), 1.24–1.35 (m, 48H, (CH2)14, (CH2)10),
2.13 (m, 2H, CH2C-S), 2.91–3.13 (m, 14H, 2 × N(CH3)2,
CH2SO3), 3.35 (m, 8H, 4 × N+CH2). 13C NMR (200 MHz,
D2O) δ: 18.13 (CH3), 21.10–35.12 ((CH2)14, (CH2)10), 48.98
(CH2-C-S), 50.40 and 52.2 (NCH3), 60.62, 64.75, and 65.81
(N+CH2), 66.75 (CH2S). Anal. calcd. (%) for
C35H75N2SO3Br (683.98): C 61.36, H 11.03, N 4.09, S 4.68;
found: C 61.82, H 10.35, N 4.98, S 4.35.
(m, 28H, (CH2)14), 1.72 (m, 2H, NCCH2), 2.13–2.55 (m, 8H,
–
N(CH3)2, NCH2), 2.84 (m, 2H, CH2-CSO3 ), 3.18 (m, 8H,
N+(CH3)2, N+CH2), 3.45 (t, J = 7.9, 2H, SO3CH2). 13C NMR
(200 MHz, D2O) δ: 19.51–29.6 ((CH2)14), 45.54 (NCH3),
47.6 3 (CH2-C-SO3), 50.61 (N+CH3), 60.40 (N+CH2), 63.52
(N+CH2), 63.4 2 (N+CH2), 64.54 (CH2SO3). Anal. calcd. (%)
for C23H50N2SO3 (434.4): C 63.59, H 11.52, N 6.44, S 7.37;
found: C 62.93, H 11.22, N 7.01, S 7.54.
1-(N,N-Dimethylammonio,N-propyl-1-sulfonate)-12-(N′,N′-
dimethyl,N′-ethylammonium bromide) dodecane, 1f
Yield: 90%.White powder, mp = 125°C. 1H NMR
(80 MHz, D2O) δ: 1.13 (t, J = 7.2, 3H, CH3), 1.34 (m, 16H,
(CH2)8), 2.25 (m, 2H, CH2-C-SO3), 2.94–3.25 (m, 14H, 2 ×
N(CH3)2, CH2SO3), 3.31 (m, 8H, 4 × NCH2), 3.52 (t, J =
7.2, 2H, NCH2-C-C-S). 13C NMR (200 MHz, D2O) δ: 10.03
(CH3), 20.73–31.12 ((CH2)8), 49.81 (CH2-C-S), 52.43
(NCH3), 53.21 (CH3N-S), 62.0, 64.48, and 65.75 (NCH2),
66.6 (CH2S). Anal. calcd. (%) for C21H47N2SO3Br (487.62):
C 49.88, H 9.77, N 5.54, S 4.08; found: C 50.12, H 10.02, N
5.38, S 4.32.
Typical procedure for the synthesis of compounds 1
A mixture of sulfobetaine 3 (10–2 mol) and of haloalkane
(1.2 × 10–2 mol) in 50 mL of absolute MeOH was heated at
reflux for 4 h. After removing the solvent in vacuo, the re-
sidual oil was precipitated by trituration with anhydrous ether.
After filtration, the solid was washed by 3 × 20 mL of anhy-
drous ether and dried in vacuo over phophorus pentoxide.
1-(N,N-Dimethylammonio,N-propyl-1-sulfonate)-8-(N′,N′-
dimethyl,N′-dodecylammonium bromide) octane, 1b
Yield: 87%. White powder, mp = 120°C. IR (KBr) ν:
1
1480 (C-N+), 1040 (S = 0). H NMR (80 MHz, D2O) δ: 0.85
References
(t, J = 7.3, 3H, CH3-C11), 1.26 (m, 32H, (CH2)10, (CH2)6),
–
2.09 (m, 2H, CH2-C-SO3 )), 2.64–3.33 (m, 22H, 2 ×
1. P.K. Eggers, T.M. Fyles, K.D.D. Mitchell, and T. Sutherland.
J. Org. Chem. 68, 1050 (2003).
–
N(CH3)2, 4 × NCH2, CH2SO3 ). 13C NMR (200 MHz, D2O)
δ: 16.61 (C-CH3), 20.75–34.61 ((CH2)6, (CH2)10), 49.90
(CH2-C-SO3), 53.51 and 54.45 (NCH3), 64.46 and 66.32
2. L.M. Cameron, T.M. Fyles, and C. Hu. J. Org. Chem. 67, 1548
(2002).
3. J.H. Fuhrhop and D. Fritsch. Acc. Chem. Res. 19, 130 (1986).
4. Y. Yan, J. Huang, Z. Li, F. Han, and J. Ma. Langmuir, 19, 972
(2003).
5. N. Aydogan and N.L. Abbott. J. Colloid Interface Sci. 242,
411 (2001).
6. Y. Chevalier. Curr. Opin. Colloid Interface Sci. 7, 3 (2002).
7. R.C. Advincula, C. Xia, J. Locklin, and X. Fan. Polymer
Preprints (Am. Chem. Soc.), 43, 345 (2002).
8. S. Souirti and M. Baboulène. Synth. Commun. 31, 9 (2001).
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10. S. Souirti. Ph.D thesis, Toulouse University, France, 2002.
11. J.W. Gibbs. The collected works of J.W. Gibbs. Longmans and
Green, London. 1928. Vol. 1. p. 119.
12. S. Franceschi, N. De Viguerie, E. Perez, M. Rivière, and A.
Lattes. J. Dispersion Sci. Technol. 20, 1523 (1999).
13. F. Brisset, R. Garelli-Calvet, J. Azema, C. Chebli, A.
Moissant, and I. Rico-Lattes. New. J. Chem. 20, 95 (1996).
14. J.H. Fuhrhop, H.H. David, J. Mathieu, U. Liman, H.J. Winter,
and E. Boekema. J. Am. Chem. Soc. 108, 1785 (1986).
15. J.H. Fuhrhop and R. Bach. Supramol. Chem. 2, 25 (1992).
16. Y. Okahata and T. Kunitake. J. Am. Chem. Soc. 101, 5231
(1979).
–
(NCH2), 66.69 (CH2SO3 ), 69.35 (N+CH2). Anal. calcd. (%)
for C27H59N2SO3Br (574.77): C 56.61, H 10.38, N 4.89, S
5.59; found: C 56.95, H 10.95, N 4.80, S 6.00.
1-(N,N-Dimethylammonio,N-propyl-1-sulfonate)-10-(N′,N′-
dimethyl,N′-dodecylammonium bromide) decane, 1c
Yield: 92%. White powder, mp = 115°C. IR (KBr) ν:
1
1480 (C-N+), 1040 (S = 0). H NMR (80 MHz, D2O) δ: 0.85
(t, J = 7.1, 3H, CH3-C), 1.23 (m, 36H, (CH2)10, (CH2)8),
–
1.72–2.15 (m, 10H, CH2CN, CH2-C-SO3 ), 2.84–3.05 (m,
12H, 2 × N(CH3)2), 3.35 (m, 2H, CH2SO3). 13C NMR
(200 MHz, D2O) δ: 16.63 (C-CH3), 20.75–34.59 (CH2)8,
(CH2)10), 49.96 (CH2-C-SO3), 53.25 and 53.63 (NCH3), 64.33
–
and 66.96 (NCH2), 66.48 (CH2SO3 ), 69.76 (N+CH2). Anal.
calcd. (%) for C29H63N2SO3Br (599.86): C 57.96, H 10.57, N
4.66, S 5.33; found: C 58.79, H 10.05, N 4.42, S 5.55.
1-(N,N-Dimethylammonio,N-propyl-1-sulfonate)-12-(N′,N′-
dimethyl,N′-dodecylammonium bromide) dodecane, 1d
Yield: 85%. White powder, mp = 105°C. IR (KBr) ν:
1
1480 (C-N+), 1040 (S = 0). H NMR (80 MHz, D2O) δ: 0.85
17. S. Bhattacharya and S. De. Langmuir, 15, 3400 (1999).
18. S. Bhattacharya, S. De, and S.K. George. Chem. Commun. 23,
2287 (1997).
(t, J = 7.2, 3H, CH3-C11), 1.27 (m, 40H, 2 × (CH2)10,), 2.09
–
(m, 2H, CH2-C-SO3 )), 3.07–3.33 (m, 22H, 2 × N(CH3)2,
–
4 × NCH2, CH2SO3 ). 13C NMR (200 MHz, D2O) δ: 16.61
© 2003 NRC Canada