Intermediates in Nucleophilic Aromatic Substitution. IV.1 Kinetic Study of the Interaction of 1,3,5-Trinitrobenzene with the Lyate Ions of Water, Methanol, and Ethanol in the Respective Solvents2

Journal of the American Chemical Society

Volumn 92, Issue 15, 1970, Pages 4682-4688

  Bernasconi, Claude F ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33947294939     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00718a035     Document Type: Article

References (43)

1. Part III: C. F. Bernasconi, J. Org. Chem., 35, 1214 (1970).
2. J. Meisenheimer, Ann., 323, 205 (1902).
3. For recent reviews see: (a) R. Foster and C. A. Fyfe, Rev. Pure Appl. Chem., 16, 61 (1966);
4. E. Buncel, A. R. Norris, and K. E. Russell, Quart. Rev. Chem. Soc., 22, 123 (1968);
5. P. Buck, Angew. Chem. Int. Ed. Engl, 8, 120 (1969);
6. J. Miller, “Aromatic Nucleophilic Substitution,” Elsevier Publishing Co., Amsterdam, 1968;
7. M. R. Crampton, Advan. Phys. Org. Chem., 7, 211 (1969).
8. G. Briegleb, W. Liptay, and M. Cantner, Z. Phys. Chem. (Frankfurt), 26, 55 (1960).
9. R. E. Miller and W. F. K. Wynne-Jones, J. Chem. Soc., 2375 (1959);
10. R. E. Miller and W. F. K. Wynne-Jones, Nature, 186, 149 (1960).
11. V. Gold and C. H. Rochester, J. Chem. Soc., 1692 (1964).
12. R. J. Pollitt and B. C. Saunders, Proc. Chem. Soc., 176 (1962).
13. E. Buncel and E. A. Symons, Can. J. Chem., 44, 771 (1966).
14. M. R. Crampton and V. Gold, J. Chem. Soc., B, 498 (1966).
15. C. F. Bernasconi, J. Amer. Chem. Soc., 92, 129 (1970).
16. T. Abe, Bull. Chem. Soc Jap., 33, 41 (1960);
17. V. Gold and C. H. Rochester, J. Chem. Soc., 1710 (1964).
18. E. F. Caldin and G. Long, Proc Roy. Soc., Ser. A, 226, 263 (1955);
19. G. Lambert and R. Schaal, J. Chim. Phys., 59, 1170 (1962).
20. K. L. Servis, J. Amer. Chem. Soc., 87, 5495 (1965);
21. J. Amer. Chem. Soc., 89, 1508 (1967).
22. J. H. Fendler, E. J. Fendler, and C. E. Griffin, J. Org. Chem., 34, 689 (1969);
23. E. J. Fendler, J. H. Fendler, C. E. Griffin, and J. W. Larsen, J. Org. Chem., 35, 287 (1970).
24. M. Eigen and L. DeMaeyer, Tech. Org. Chem., 8, 895 (1963).
25. H. A. Benesi and J. H. Hildebrand, J. Amer. Chem. Soc., 71, 2703 (1949).
26. J. F. Bunnett and G. T. Davis, J. Amer. Chem. Soc., 76, 3011 (1954);
27. J. Murto, Acta Chem. Scand., 18, 1024 (1964);
28. E. Tommila and J. Murto, Acta Chem. Scand., 16, 53 (1962);
29. J. Murto, Ann. Acad. Sci. Fenn., Ser. A2, No. 117 (1962).
30. M. L. Bender and W. A. Glasson, J. Amer. Chem. Soc., 81, 1590 (1959);
31. W. P. Jencks and M. Gilchrist, J. Amer. Chem. Soc., 84, 2910 (1962).
32. P. Ballinger and F. A. Long, J. Amer. Chem. Soc., 82, 795 (1960).
33. J. Hine and M. Hine, J. Amer. Chem. Soc., 74, 5266 (1952).
34. T. C. Bruice and S. J. Benkovic, “Bioorganic Mechanisms,” Vol. I, W. A. Benjamin Inc., New York, N. Y., 1966, p 102.
35. S. A. Shain and J. F. Kirsch, J. Amer. Chem. Soc., 90, 5848 (1968).
36. C. F. Bernasconi, J. Amer. Chem. Soc., 90, 4982 (1968).
37. M. R. Crampton and V. Gold, J. Chem. Sac, B, 893 (1966).
38. J. Hine, J. Amer. Chem. Soc., 85, 3239 (1963);
39. J. Hine, L. G. Mahone, and C. L. Liotta, J. Amer. Chem. Soc., 89, 5911 (1967).
40. M. L. Crossley, R. H. Kienle, and C. H. Benbrook, J. Amer. Chem. Soc., 62, 1400 (1940).
41. A. R. Norris, Can. J. Chem., 47, 2895 (1969).
42. J. Miller, J. Amer. Chem. Soc., 85, 1628 (1963).
43. D. L. Hill, K. E. Ho, and J. Miller, J. Chem. Soc., B, 299 (1966).