Kinetics and mechanism for the reaction of 1-chloro-2,4-dinitrobenzenewithn-butylamine and piperidine in AOT/n-hexane/water reverse micelles

Arkivoc

Volumn 2003, Issue 10, 2003, Pages 189-200

  Zingaretti, Lilian ^a   Boscatto, Liliana ^a   Chiacchiera, Stella M ^a   Silber, Juana J ^a  

^a DEPARTAMENTO DE QUÍMICA   (Argentina)

Author keywords

AOT; Kinetics; Nucleophilic aromatic substitution; Reverse Micelles

Indexed keywords

1 CHLORO 2,4 DINITROBENZENE; AMINE; BUTYLAMINE; DOCUSATE SODIUM; HEXANE; PIPERIDINE; SURFACTANT; WATER;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; REVERSE MICELLE; SUBSTITUTION REACTION;

EID: 3242687885     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (38)

1. Fendler, J.; Fendler, J. H. Catalysis in Micellar and Macromolecular Systems; Acad. Press, New. York., 1975.
2. Pileni, M. P. Structure and Reactivity of Reverse Micelles; Elsevier: New York, 1989.
3. De, T. K.; Maitra, A. Adv. Colloid Interface Sci., 1995, 59, 95-193.
4. Pileni, M. P. J. Phys. Chem. 1993, 97, 6961-.6973.
5. García-Río, L. Leis, J. R. Iglesias, E. J. Phys. Chem., 1995, 99, 12318-.12326.
6. Blagoeva, I. B.; Gray, P.; Ruasse, M-F. J. Phys. Chem., 1996, 100, 12638-12643.
7. Chiacchiera, S. M.; Singh, J. O.; Anunziata, J. D.; Silber, J. J., J. Chem. Soc. Perkin 2, 1987, 987-.993.
8. Cattana, R. S.; Singh, J. O.; Anunziata, J. D.; Silber, J. J. J. Chem. Soc. Perkin 2, 1987, 79-83.
9. Chiacchiera, S. M.; Singh, J. O.; Anunziata, J. D.; Silber, J. J., J. Chem. Soc. Perkin 2, 1988, 1585-.1589.
10. Chiacchiera, S. M.; Cattana, R. I.; Singh, J. O.; Anunziata, J. D.; Silber, J. J. J. Phys. Org. Chem. 1989, 2, 631-648.
11. Durantini, E. N.; Zingaretti, L.; Anunziata, J. D.; Silber, J. J., J. Phys. Org. Chem. 1992, 2, 557-566.
12. Terrier, F. Nucleophilic Aromatic Displacement, VCH Publishers, Inc., New York, 1991.
13. Nudelman, N. S. The Chemistry of amino, nitroso, nitro and related groups, S. Patai Ed., Wiley, New York, 1996, Chapter 26.
14. Iglesias, E.; Leis, J. R.; Peña, M. E.; Langmuir, 1994, 10, 662-.669.
15. Tang, S.-S.; Chang, G.-G.; J. Org. Chem., 1995, 60, 6183-.6185.
16. Liou, J.-Y.; Huang, T.-M.; Chang, G.-G.; J. Chem. Soc. Perkin Trans 2, 1999, 2171-.2176.
17. Fendler, J. H. Acc. Chem. Res. 1976, 9, 153-161.
18. Durantini, E. N.; Borsarelli; C. D.; J. Chem. Soc. Perkin 2, 1996, 719-.723.
19. Correa, M. N.; Durantini, E. N.; Silber, J. J. J. Org. Chem., 1999, 64, 5757-.5763.
20. Correa, M. N.; Durantini, E. N.; J. J. Silber, J. Org. Chem., 2000, 65, 6427-.6433.
21. Hasegawa, M.; Langmuir 2001, 17, 1426-1431.
22. Forlani, L.; Bosi, M. J. Phys. Org. Chem., 1992, 5, 429-.434.
23. Forlani, L. J. Chem. Soc. Perkin 2, 1993, 1525-.1530.
24. O'Connor, C. J.; Lomax, T. D.; Ramage, R. E. In Solution behavior of surfactants: theoretical and applied aspects, Vol 2, p. 803-831, Eds. Mittal, K. L.; Fendler, E. J. Plenun Press, New York, 1982.
25. Correa, N. M.; Biasutti, M. A.; Silber, J. J. J. Colloid and Interface Sci. 1995, 172, 71-76.
26. Bernasconi, C. F. M. T. P. Int. Rev. Sci. Org. Chem. Ser. One, 1973, 3, 33-63.
27. García-Río, L. Ramón Leis, J. M. Peña, E. Iglesias, E. J. Phys. Chem., 1993, 97, 3437-.3442.
28. a) Encinas M. V. and Lissi, E. A. Chem. Phys. Lett., 1982, 91, 55-57,
29. b) Encinas M. V. and Lissi, E. A. Chem. Phys. Lett., 1986 132, 545-548,
30. c) Lissi, E. A.; Encinas, M. V.; Alvarez, J.; Borsarelli, C. D., J. Colloid Interface Sci., 1993, 160, 472-.474.
31. Bock, C. R.; Connor, J. A.; Gutierrez, A. R.; Meyer, T. J.; Whitten, D. G.; Sullivan, V. P.; Nagle, J. K. J. Am. Chem. Soc., 1979, 101, 4815-.4824
32. Biasutti, M. A.; Correa, N. M.; Silber, J. J. Molecular interactions in Reverse Micelles. Current Topics in colloid & interface Science. Research Trends, Eds. Goñi, F. M.; Hoffmann, H., India 3, 35-51, 1999.
33. Estimated by log P calculated by Chem Plus™ Version 1.6 on geometry optimized structures by means of AM1, performed with Hyperchem™ Pro release 5.1, from Hypercube INC. Estimated Log P
34. Gas Phase dipole moments estimated for geometry optimized structures by means of AM1, performed with Hyperchem™ Pro release 5.1, from Hypercube INC.
35. Correa, N. M.; Silber, J. J. J. Mol. Liq., 1997, 72, 163-.176
36. Miller, J. Aromatic Nucleophilic Substitution, Elsevier, Amsterdam, 1968.
37. Bunnet, J. F.; Sekiguchi, S. L.; A. Smith J. Am. Chem. Soc. 1981, 103, 4865-4871.
38. Bunnet, J. F.; Morath, R. J. J. Am. Chem. Soc. 1955, 77, 5051-5055.