Micellar induced regioselectivity in the two-step consecutive reaction of SO2-3 with Br{single bond}(CH2CH2)n{single bond}Br (n = 2 - 5)

Journal of Colloid and Interface Science

Volumn 312, Issue 2, 2007, Pages 453-459

  Currie, Fredrik ^a   Jarvoll, Patrik ^a   Holmberg, Krister ^a   Romsted, Laurence S ^b   Gunaseelan, Krishnan ^b  

^a CHALMERS UNIVERSITY OF TECHNOLOGY   (Sweden)

^b RUTGERS UNIVERSITY   (United States)

Author keywords

Cationic surfactant; CTAB; Micelle; Nucleophilic substitution; Regioselectivity

Indexed keywords

BROMINE COMPOUNDS; CATIONIC SURFACTANTS; CHEMICAL BONDS; MICELLES; NUCLEAR MAGNETIC RESONANCE; RATE CONSTANTS;

ALKANEDISULFONATE; BROMOALKANESULFONATE; DIBROMOALKANES; NUCLEOPHILIC SUBSTITUTION;

REGIOSELECTIVITY;

ALKANE DERIVATIVE; ALKANESULFONIC ACID; BROMIDE; BUTANE; DECANE; HEXANE; OCTANE; SULFONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; CONCENTRATION (PARAMETERS); HYDROPHILICITY; LIPOPHILICITY; MICELLE; MICELLIZATION; NANOANALYSIS; PRIORITY JOURNAL; REACTION TIME; SUBSTITUTION REACTION; TEMPERATURE;

EID: 34250633619     PISSN: 00219797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jcis.2007.03.056     Document Type: Article

References (41)

1. Holmberg K. Curr. Opin. Colloid Interface Sci. 8 (2003) 187
2. Häger M., Olsson U., and Holmberg K. Langmuir 20 (2004) 6107
3. Häger M., Currie F., and Holmberg K. Top. Curr. Chem. 227 (2003) 53
4. Schwuger M.-J., Stickdorn K., and Schomäker R. Chem. Rev. 95 (1995) 849
5. Sjöblom J., Lindberg R., and Friberg S.E. Adv. Colloid Interface Sci. 65 (1996) 125
6. Jaeger D.A., and Wang J. Tetrahedron Lett. 33 (1992) 6415
7. Garti N. Curr. Opin. Colloid Interface Sci. 8 (2003) 197
8. Engberts J.B.F.N. Pure Appl. Chem. 64 (1992) 1653
9. Rathman J.F. Curr. Opin. Colloid Interface Sci. 1 (1996) 514
10. Ruasse M.-F., Blagoeva I.B., Ciri R., Garcia-Rio L., Leis J.R., Marques A., Mejuto J., and Monnier E. Pure Appl. Chem. 69 (1997) 1923
11. Jaeger D.A., Clennan M.W., and Jamrozik J. J. Am. Chem. Soc. 1990 (1990) 1171
12. Jaeger D.A., and Bolikal D. J. Org. Chem. 51 (1985) 1350
13. Motsage V.A., and Kostenbauder H.B. J. Colloid Sci. 18 (1963) 603
14. Kurz J. J. Phys. Chem. 66 (1962) 2239
15. Duynstee E.F.J., and Grunwald E. J. Am. Chem. Soc. 81 (1959) 4540
16. Currie F. J. Colloid Interface Sci. 277 (2004) 230
17. Jusein M.M., Vera J.H., and Weber M.E. Colloids Surf. A 191 (2001) 241
18. de Rocha Pereira R., Zanette D., and Nome F. J. Phys. Chem. 94 (1990) 356
19. Bunton C.A., and Romsted L.S. In: Kumar P., and Mittal K.L. (Eds). Handbook of Microemulsion Science and Technology: Organic Reactivity in Microemulsions (1999), Dekker, New York 457
20. Romsted L.S. In: Mittal K.L. (Ed). Micellization, Solubilization and Microemulsions: A General Kinetic Theory of Rate Enhancements for Reactions between Organic Substrates and Hydrophilic Ions in Micellar Solutions vol. 2 (1977), Plenum, New York 489
21. Bunton C.A., Nome F., Quina F.H., and Romsted L.S. Acc. Chem. Res. 24 (1991) 357
22. Bunton C.A., Yao J., and Romsted L.S. Curr. Opin. Colloid Interface Sci. 2 (1997) 622
23. Savelli G., Germani R., and Brinchi L. In: Texter J. (Ed). Reactions and Synthesis in Surfactant Systems: Reactivity Control by Aqueous Amphiphilic Self-Assembling Systems vol. 100 (2001), Dekker, New York 175
24. Quina F.H., Politi M.J., Cuccovia I.M., Martins-Franchetti S.M., and Chaimovich H. In: Mittal K.L., and Fendler E.J. (Eds). Solution Behavior of Surfactants: Theoretical and Applied Aspects: Alkaline Hydrolysis in Micellar Sodium Dodecyl Sulfate: The "Binding" of {single bond}OH to Anionic Micelles vol. 2 (1982), Plenum, New York 1125
25. He Z.-M., Loughlin J.A., and Romsted L.S. Bol. Soc. Chil. Quim. 35 (1990) 43
26. Currie F., Holmberg K., and Westman G. Colloids Surf. A 182 (2001) 321
27. Currie F., Holmberg K., and Westman G. Colloids Surf. A 215 (2003) 51
28. Yao J., and Romsted L.S. Colloids Surf. A 123-124 (1997) 89
29. Jencks W.P., and Regenstein J. In: Sober H.A. (Ed). Handbook of Biochemistry: Ionization Constants of Acids and Bases (1970), The Chemical Rubber Co., Cleveland J187
30. Koivurinta J., Kyllonen A., Leinonen L., Valaste K., and Koskikallio J. Finn. Chem. Lett. (1974) 239
31. Romsted L.S. In: Mittal K.L., and Lindman B. (Eds). Surfactants in Solution: Micellar Effects on Reaction Rates and Equilibria vol. 2 (1984), Plenum, New York 1015
32. Lowry T.H., and Richardson K.S. Mechanism and Theory in Organic Chemistry. third ed. (1987), Harper & Row, New York
33. Fife T.H., and Bruice T.C. J. Phys. Chem. 65 (1961) 1079
34. Barsukov I.L., Pervushin K.V., Orekhov V., Barsukov T.L., and Arseniev A.S. Appl. Mag. Res. 3 (1992) 965
35. Frost A.A., and Pearson R.G. Kinetics and Mechanism: A Study of Homogeneous Chemical Reactions. second ed. (1963), Wiley & Sons, New York
36. Gamboa C., Sepulveda L., and Soto R. J. Phys. Chem. 85 (1981) 1429
37. Bartet D., Gamboa C., and Sepulveda L. J. Phys. Chem. 84 (1980) 272
38. J.D. Morgan, Determination of Ion Selectivity Constants by Ion Flotation, Ph.D. thesis, University of Sydney, 1994
39. Morgan J.D., Napper D.H., and Warr G.G. J. Phys. Chem. 99 (1995) 9458
40. Lissi E.A., Abyin E.B., Speulveda L., and Quina F.H. J. Phys. Chem. 88 (1984) 81.0
41. V. Soldi, J. Keiper, L.S. Romsted, I.M. Cuccovia, H. Chaimovich, Langmuir 16