Revisiting the reactions of nucleophiles with arenediazonium ions: Dediazoniation of arenediazonium salts in aqueous and micellar solutions containing alkyl sulfates and alkanesulfonates and an ab initio analysis of the reaction pathway

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 9, 2000, Pages 1896-1907

  Cuccovia, Iolanda M ^a   Da Silva, Marcia A ^a   Ferraz, Helena M C ^a   Pliego Jr , Josefredo R ^a   Riveros, José M ^a   Chaimovich, Hernan ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

CALCULATIONS; IONS; MICELLES; PHENOLS; POTENTIAL ENERGY; SALTS; SODIUM COMPOUNDS; SOLUTIONS; SULFUR COMPOUNDS; SURFACES; WATER;

AB INITIO CALCULATIONS; ALKANESULFONATES; ALKYL SULFATES; ARENEDIAZONIUM IONS; DEDIAZONIATION; MICELLAR SOLUTIONS; NUCLEOPHILES; SODIUM DODECANESULFONATE; SODIUM METHYL SULFATE; TRIMETHYLBENZENEDIAZONIUM TETRAFLUOROBORATE;

AROMATIC HYDROCARBONS;

EID: 0034286449     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/b003079l     Document Type: Article

References (43)

1. (a) J. A. Loughlin and L. S. Romsted, Colloids and Surfaces, 1990, 48, 123
2. A. Chaudhuri, J. A. Loughlin, L. S. Romsted and J. Yao, J. Am. Chem. Soc., 1993, 115, 8351.
3. A. Chaudhuri, L. S. Romsted and J. Yao, J. Am. Chem. Soc., 1993, 115, 8362.
4. P. K. Das, V. Srilakshmi and A. Chaudhuri, Langmuir, 1999, 15, 981.
5. C. Bravo-Diaz, M. J. Sarabia-Rodriguez, P. Barreiro-Sio and E. Gonzalez-Romero, Langmuir, 1999, 15, 282.
6. I. M. Cuccovia, A. Agostinho-Neto, C. M. A. Wendel, H. Chaimovich and L. R. Romsted, Langmuir, 1997, 13, 5032.
7. E. S. Lewis and J. E. Cooper, J. Am. Chem. Soc., 1962, 84, 3847.
8. C. G. Swain, J. E. Sheats and K. G. Harbison, J. Am. Chem. Soc., 1975, 97, 783.
9. (a) S. L. Lewis, L. D. Hartung and B. M. McKay, J. Am. Chem. Soc., 1969, 91, 419
10. (b) E. S. Lewis, J. Am. Chem. Soc., 1958, 80, 1371.
11. J. O. Edwards and R. G. Pearson, J. Am. Chem. Soc., 1962, 84, 16.
12. (a) K. H. Saunders and R. L. M. Allen, Aromatic Diazo Compounds, 3rd edn, Edward Arnold, Baltimore, 1985
13. A. F. Hegarty, The Chemistry of the Diazonium and Diazo Groups, part 2, ed. S. Patai, Wiley, New York, 1978
14. (a) Zollinger H. Diazo Chemistry I, VCH, Germany, 1994.
15. R. G. Bergstrom, R. G. M. Landells, G. H. Wahls and H. Zollinger, J. Am. Chem. Soc., 1976, 98, 3301.
16. C. G. Swain, J. E. Sheats and K. G. Harbison, J. Am. Chem. Soc., 1975, 97, 796.
17. L. S. Romsted, Zhang J. and L. Zhuang, J. Am. Chem. Soc., 1998, 120, 10046.
18. J. L. Kurtz, J. Phys. Chem., 1962, 66, 2239.
19. O. Schales and S. S. Schales, J. Biol. Chem., 1941, 140, 879.
20. G. R. Chalkley, D. J. Snodin, G. Stevens and M. C. Whiting, J. Chem. Soc. (C), 1970, 682.
21. C. A. Bunton and Y. F. Frei, J. Chem. Soc., 1951, 1872.
22. J. H. Fendler and E. J. Fendler, in Catalysis in Micellar and Macromolecular Systems, Academic Press, New York, 1975.
23. E. Buncel, C. Chuaqui, K. R. Lynn and A. Raoult, Bioorg. Chem., 1978, 7, 1.
24. J. P. Guthrie, Can. J. Chem., 1973, 51, 3494.
25. J. L. Kice and J. M. Anderson, J. Am. Chem. Soc., 1966, 88, 5242.
26. J. B. Foresman, T. A. Keith, K. B. Wiberg, J. Snoonian and M. J. Frisch, J. Phys. Chem., 1996, 100, 16098.
27. J. R. Pliego Jr. and W. B. De Almeida, J. Phys. Chem. A, 1999, 103, 3904.
28. M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez and J. A. Pople, GAUSSIAN 94, Revision D.2, Gaussian Inc., Pittsburgh PA, 1995.
29. This is a simplified version of the canonical flexible transition state theory. See reference 26 and references therein.
30. J. R. Pliego Jr. and W. B. De Almeida, Phys. Chem. Chem. Phys., 1999, 1, 1031.
31. M. L. Crossley, R. H. Kienle and C. K. Benbrook, J. Am. Chem. Soc., 1940, 62, 1400.
32. A. N. Nesmeyanov, I. G. Makarova and T. P. Tolskaya, Tetrahedron, 1957, 1, 145.
33. C. Bravo-Diaz, M. Soengas-Fernandez, M. J. Rodriguez-Sarabia and E. Gonzalez-Romero, Langmuir, 1998, 14, 5098.
34. V. R. Correia, I. M. Cuccovia, M. Stelmo and H. Chaimovich, J. Am. Chem. Soc., 1992, 114, 2144.
35. I. M. Cuccovia, I. N. Silva, H. Chaimovich and L. S. Romsted, Langmuir, 1997, 13, 647.
36. T. H. I. Lowry and K. S. Richardson, Mechanism and Theory in Organic Chemistry, 3rd edn., Harper and Row, New York, 1987, p. 367.
37. M. Garcia-Meijide, C. Bravo-Diaz and L. S. Romsted, Int. J. Chem. Kinet., 1998, 30, 31.
38. R. Pazo-Llorente, M. J. Sarabia-Rodriguez, C. Bravo-Diaz and E. Gonzalez-Romero, Int. J. Chem. Kinet., 1999, 31, 73.
39. P. S. J. Canning, K. McCrudden, H. Maskill and B. Sexton, J. Chem. Soc., Perkin Trans. 2, 1999, 2735.
40. H. B. Ambroz and T. J. Kemp, Chem. Soc. Rev., 1979, 8, 353.
41. R. Glaser and C. J. Horan, J. Org. Chem., 1995, 60, 7518.
42. V. Solidi, J. Keiper, L. R. Romsted, I. M. Cuccovia and H. Chaimovich, Langmuir, 2000, 16, 59.
43. J. C. Scaiano and N. Kim-Thuan, J. Photochem., 1983, 23, 269.