Rapid formation and slow collapse of a carbocation - Anion pair to a neutral molecule

Journal of Organic Chemistry

Volumn 73, Issue 1, 2008, Pages 48-55

  Hao, Weifang ^a   Parker, Vernon D ^a  

^a UTAH STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOCATION; NEUTRAL MOLECULE; SOLVOLYSIS REACTIONS; WINSTEIN SCHEME;

ACETIC ACID; COVALENT BONDS; ESTERS; REACTION KINETICS; SOLVENTS; THERMODYNAMICS;

POSITIVE IONS;

4,4',4'' TRIMETHOXYTRITYL DERIVATIVE; ACETIC ACID; ANION; CATION; ESTER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COVALENT BOND; EQUILIBRIUM CONSTANT; REACTION ANALYSIS; SOLVOLYSIS; THERMODYNAMICS;

EID: 37549060595     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702492r     Document Type: Article

References (39)

1. Turgeon, V. C.; LaMer, V. K. J. Am. Chem. Soc. 1952, 74, 5988.
2. Duynstee, E. F. J.; Grunwald, E. J. Am. Chem. Soc. 1959, 81, 4342.
3. Diffenback, R. A.; Sano, K.; Taft, R. W. J. Am. Chem. Soc. 1966, 88, 4747.
4. Ritchie, C. D.; Skinner, G. A.; Badding, V. G. J. Am. Chem. Soc. 1967, 89, 2063.
5. Hill, E. A.; Mueller, W. J. Tetrahedron Lett. 1968, 2565.
6. Noyce, D. S.; Brauman, S. K. J. Am. Chem. Soc. 1968, 90, 5218.
7. Brauman, J. I.; Archie, W. C., Jr. J. Am. Chem. Soc. 1970, 92, 5981.
8. Ritchie, C. D.; Virtanen, P. O. I. J. Am. Chem. Soc. 1972, 94, 4963, 4966.
9. Bunton, C. A.; Huang, K. J. Am. Chem. Soc. 1972, 94, 3536.
10. Ritchie, C. D. Acc. Chem. Res. 1972, 5, 348.
11. Ritchie, C. D.; Virtanen, P. O. I. J. Am. Chem. Soc. 1973, 95, 1882.
12. Bunton, C. A.; Haung, S. K. J. Am. Chem. Soc. 1974, 96, 515.
13. Ritchie, C. D. J. Am. Chem. Soc. 1975, 97, 1170.
14. Ritchie, C. D.; Sawada, M. J. Am. Chem. Soc. 1977, 99, 3754.
15. Ritchie, C. D.; Van Verth, J. E.; Viranen, P. O. I. J. Am. Chem. Soc. 1982, 104, 3491.
16. Ritchie, C. D. J. Am. Chem. Soc. 1984, 106, 7187.
17. Ritchie, C. D. Can. J. Chem. 1986, 64, 2239.
18. Arnett, E. M.; Flowers, R. A.; Ludwig, R. T.; Meekhof, A.; Walek, S. Pure Appl. Chem. 1995, 67, 729.
19. Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66 and references cited therein.
20. Minegishi, S.; Mayr, H. J. Am. Chem. Soc. 2003, 125, 286.
21. Parker, V. D.; Zhao, Y.; Lu, Y.; Zheng, G. J. Am. Chem. Soc. 1998, 120, 12720.
22. Lu, Y.; Zhao, Y.; Parker, V. D. J. Am. Chem Soc. 2001, 123, 5900.
23. Zhao, Y.; Lu, Y.; Parker V. D. J. Chem. Soc., Perkin Trans. 2001, 2, 1481.
24. Parker, V. D.; Zhao, Y. J. Phys. Org. Chem. 2001, 14, 604.
25. Zhao, Y.; Lu, Y.; Parker, V. D. J. Am. Chem. Soc. 2001, 123, 1579.
26. Lu, Y.; Zhao, Y.; Handoo, K. L.; Parker, V. D. Org. Biomol. Chem. 2003, 1, 173.
27. Handoo, K. L.; Lu, Y.; Zhao, Y.; Parker, V. D. Org. Biomol. Chem. 2003, 1, 24.
28. Lu, Y.; Handoo, K. L.; Parker, V. D. Org. Biomol. Chem. 2003, 1, 36.
29. Parker, V. D.; Lu, Y. Org. Biomol. Chem. 2003, 1, 2621.
30. Handoo, K. L.; Lu, Y.; Zhao, Y.; Parker, V. D. J. Am. Chem. Soc. 2003, 125, 9381.
31. Parker, V. D.; Lu, Y.; Zhao, Y. J. Org. Chem. 2005, 70, 1350.
32. Parker, V. D. Pure Appl. Chem. 2005, 77, 1823.
33. Parker, V. D. J. Phys. Org. Chem. 2006, 19, 714.
34. Ridd, J. H. Adv. Phys. Org. Chem. 1978, 16, 1.
35. Clark, J. H.; Emsley, J. J. Chem. Soc., Dalton Trans. 1973, 2760.
36. Guthrie, J. P. J. Am. Chem. Soc. 1978, 100, 5892;
37. 1974, 96, 3608;
38. 1973, 95, 6999.
39. Winstein, S.; Clippenger, E.; Fainsberg, A. H.; Heck, R.; Robinson, G. C. J. Am. Chem. Soc. 1956, 78, 328 and references cited therein.