Butanolysis of 2-methylbenzenediazonium ions: Product distribution, rate constants of product formation, and activation parameters

Journal of Physical Organic Chemistry

Volumn 22, Issue 5, 2009, Pages 390-396

  Pastoriza Gallego, M José ^a   Bravo Díaz, Carlos ^a  

^a UNIVERSITY OF VIGO   (Spain)

Author keywords

Kinetics; Reverse micelles; Solvolysis

Indexed keywords

1-BUTANOL; ACTIVATION PARAMETER; ARYL CATIONS; BIMOLECULAR REACTION; COMPOSITION RANGES; CONTROL SOLUTIONS; DEDIAZONIATION; DERIVATIZATION; EFFECT OF TEMPERATURE; ENTHALPY OF ACTIVATION; ENTROPY OF ACTIVATION; EXPERIMENTAL CONDITIONS; INTERFACIAL REGION; PRODUCT DISTRIBUTIONS; PRODUCT FORMATION; PRODUCT YIELDS; RATE-LIMITING FORMATION; REDUCTION PRODUCTS; REVERSE MICELLES; SODIUM DODECYL SULFATE; SOLUTION COMPOSITION; SOLVOLYSIS; SUBSTRATE LOSS; TETRAFLUOROBORATE; UV-VIS SPECTROSCOPY;

ACIDITY; AZO DYES; BELT DRIVES; CHROMATOGRAPHIC ANALYSIS; DIFFUSERS (OPTICAL); ETHERS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH PRESSURE LIQUID CHROMATOGRAPHY; HYDROCHLORIC ACID; MICELLES; OPTICAL SWITCHES; SODIUM SULFATE; SOLVENTS; THERMAL EFFECTS; TOLUENE; ULTRAVIOLET SPECTROSCOPY;

RATE CONSTANTS;

EID: 65949106161     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1457     Document Type: Article

References (59)

1. R. Ta-Shma Z. Rappoport, Adv. Phys. Org. Chem. 1992, 27, 239.
2. T. W. Bentley, D. N. Ebdon, E. Kim, I. Koo, J. Org. Chem. 2005, 70, 1647-1653.
3. D. J. Jobe, H. B. Dunford, M. Pickard, J. F. Holwarth, Reactions in Compartmental Liquids (Ed.: W. Knoche), Springer Verlag, Helldelberg, Germany, 1989.
4. C. A. Bunton, L. S. Romsted, in Handbook of Microemulsion Science and Technology (Eds.: P. Kumar, K. L. Mittal), Marcel Dekker, New York, 1999.
5. L. Garcia-Rio, J. R. Leis, J. C. Mejuto, M. Perez-Lorenzo, Pure Appl. Chem. 2007, 79, 1111-1123.
6. M. A. Lopez-Quintela C. Tojo, M. C. Blanco, L. Garcia Rio, J. R. Leis, Curr. Opinion Colloid Interf. Sci. 2004, 9, 264-278.
7. N. L. Klyachko, A. V. Levashov, Curr. Opinion Colloid Interf. Sci. 2003, 8, 179.
8. C. M. L. Carvalho, J. M. S. Cabral, Biochimie 2000, 82.
9. R. Bagwe, K. C. Kilar, Langmuir 2000, 16, 905.
10. M. P. Pileni, Structure and Reactivity in Reverse Micelles. Elsevier, New York, 1989.
11. K. Sawada M. Ueda J. Chem. Technol. Biotechnol. 2004, 79, 369.
12. V. Uskokovic, M. Drofenik, Adv. Colloid Interf. Sci. 2007, 133, 23-234.
13. P. L. Luisi, B. E. Straub, Reverse Micelles: Biological and Technological Relevance of Amphiphilic Structures in Apolar Media. Plenum Press, New York, 1984.
14. E. Pramauro, E. Pelizzetti, TrAC, Trends Anal. Chem. 1988, 7, 260.
15. E. Pramauro, E. Pelizzetti, Surfactants in Analytical Chemistry: Applications of Organized Media in Comprehensive Analytical Chemistry. Elsevier, New York, 1996.
16. G. Behera B. Mishra P. Behera M. Panda Adv. Colloid Interf. Sci. 1999, 82, 1.
17. L. García-Rio, J. R. Leis, J. C. Mejuto, M. E. Peña Langmuir 1994, 10, 1676-1683.
18. N. W. Fadnavis, A. Deshpande, Curr. Org. Chem. 2002, 6, 393.
19. C. A. Bunton, G. Savelli, Adv. Phys. Org. Chem. 1986, 22, 213.
20. C. A. Bunton, F. Nome, F. H. Quina L. S. Romsted, Acc. Chem. Res. 1991, 24, 357.
21. G. Savelli, R. Germani, L. Brinchi, Reactivity control by aqueous self-assembling systems, in Reactions and Synthesis in Surfactant Systems (Ed.: J. Texter), Marcel-Dekker, New York, 2001, 175.
22. K. Holmberg, Eur. J. Org. Chem. 2007, 15, 731-742.
23. J. Pileni, Self-assemblies of organic and inorganic materials, in Self-Organized Morphology in Nanostructured Materials, vol. 99. Springer Series in Materials Science, 2008.
24. A. Spernath, A. Aserin, Adv. Colloid. Interf. Sci. 2006, 128-130, 47-64.
25. G. Astray, A. Cid, L. Garcia Rio, P. Hervella J. C. Mejuto, M. Pé rez-Lorenzo, Prog. React. Kin. Mechanism 2008, 33, 81-97.
26. R. Pazo-LLorente, M. J. Rodriguez-Sarabia E. Gonzalez-Romero, C. Bravo-Díaz, Int. J. Chem. Kinet. 1999, 31, 73.
27. R. Pazo-Llorente, M. J. Sarabia-Rodriguez, E. Gonzalez-Romero, C. Bravo-Díaz, Int. J. Chem. Kin. 1999, 31, 531.
28. R. Pazo-Llorente, C. Bravo-Díaz, E. González-Romero, Eur. J. Org. Chem. 2003, 17, 3421.
29. R. Pazo-Llorente, C. Bravo-Díaz, E. González-Romero, Eur. J. Org. Chem. 2004, 15, 3221.
30. R. Pazo-Llorente, H. Maskill, C. Bravo-Díaz, E. González-Romero, Eur. J. Org. Chem. 2006, 9, 2201.
31. M. J. Pastoriza-Gallego, C. Bravo-Díaz, E. González-Romero, Langmuir 2005, 21, 2675.
32. E. Rodenas, E. Pé rez-Benito, J. Phys. Chem. 1991, 95, 9496.
33. E. Rodenas, E. Pé rez-Benito, J. Phys. Chem. 1991, 95, 4552.
34. T. Kuokkanen, Finn. Chem. Lett. 1981, 81.
35. T. Kuokkanen, Finn. Chem. Lett. 1980, 192.
36. C. Bravo-Diaz, M. Soengas-Fernandez, M. J. Rodriguez-Sarabia E. Gonzalez-Romero, Langmuir 1998, 14, 5098.
37. M. C. Garcia-Meijide, C. Bravo-Diaz, L. S. Romsted, Int. J. Chem. Kinet. 1998, 30, 31-39.
38. C. Bravo-Díaz, E. González-Romero, J. Chromatog. A 2003, 989, 221-229.
39. A. F. Hegarty, Kinetics and mechanisms of reactions involving diazonium and diazo groups, in The Chemistry of Diazonium and Diazo Compounds (Ed.: S. Patai), John Wiley & Sons, New York, 1978.
40. K. H. Saunders, R. L. M. Allen, Aromatic Diazo Compounds. Edward Arnold, Baltimore, MD, 1985.
41. H. Zollinger, Color Chemistry. VCH, Zurich, Switzerland, 1991.
42. H. Zollinger, Diazo Chemistry I, Aromatic and Heteroaromatic Compounds. VCH, Wheinheim, Germany, 1994.
43. R. Pazo-Llorente, C. Bravo-Díaz, E. González-Romero, Fresenius J. Anal. Chem. 2001, 369, 582-586.
44. P. S. J. Canning, K. McCrudden, H. Maskill, B. Sexton, J. Chem. Soc. Perkin Trans. 2. 1999, 12, 2735.
45. P. S. J. Canning, H. Maskill, K. Mcrudden, B. Sexton, Bull. Chem. Soc. Jpn. 2002, 75, 789.
46. R. Pazo-Llorente, C. Bravo-Díaz, E. González-Romero, Langmuir 2003, 19, 9142.
47. H. Maskill, The Physical Basis of Organic Chemistry. Oxford University Press, Oxford, 1995.
48. A. Pross, Theoretical & Physical Principles of Organic Reactivity. John Wiley & Sons, New York, 1995.
49. J. I. Finnenman, J. C. Fishbein, J. Am. Chem. Soc. 1995, 117, 4228.
50. S. Steenken, M. Ashokkumar, P. Maruthamuthu, R. A. McClelland, J. Am. Chem. Soc. 1998, 120, 11925.
51. I. M. Cuccovia I. N. da Silva H. Chaimovich, L. S. Romsted, Langmuir 1997, 13, 647.
52. C. Bravo-Díaz, M. E. Romero-Nieto, E. Gonzalez-Romero, Langmuir 2000, 16, 42-4248.
53. I. M. Cuccovia M. A. da Silva H. M. C. Ferraz, J. R. Pliego, J. M. Riveros, H. Chaimovich, J. Chem. Soc. Perkin Tans. 2 2000, 9, 1896.
54. C. Bravo-Díaz, E. González-Romero, Reactivity of arenediazonium ions in micellar and macromolecular systems, Curr. Topics Colloid Interf. Sci. 0972-4494, Trivandum, India 2001, 57.
55. L. S. Romsted, Interfacial compositions of surfactant assemblies by chemical trapping with arenediazonium ions: method and applications, in Reactions and Synthethis in Surfactant Systems (Ed.: J. Texter), Marcel Dekker, New York, 2001.
56. L. S. Romsted, Langmuir. 2007, 23, 414-424.
57. E. S. Lewis, W. H. Hinds, J. Am. Chem. Soc. 1952, 74, 304-308.
58. CRC. Handbook of Chemsitry and Physics. CRC Press, Boca Raton, 1997.
59. R. Pazo-Llorente, M. C. Rodríguez-Menacho, E. González- Romero, C. Bravo-Díaz, J. Colloid Interf. Sci. 2002, 248, 169-175.