Halogenation of Acetone. A Method for Determining pKas of Ketones in Aqueous Solution, with an Examination of the Thermodynamics and Kinetics of Alkaline Halogenation and a Discussion of the Best Value for the Rate Constant for a “Diffusion-Controlled Reaction”. Energetic Requirements for a Diffusion-Controlled Reaction Involving Heavy-Atom Bond Formation

Journal of the American Chemical Society

Volumn 106, Issue 5, 1984, Pages 1351-1360

  Guthrie, J Peter ^a   Cossar, John ^a   Klym, Alex ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL OPERATIONS; CHEMICAL REACTIONS; DIFFUSION;

HALOGENATION;

ACETONE;

EID: 0021756737     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00317a030     Document Type: Article

References (72)

1. Guthrie, J. P. Can. J. Chem. 1978, 56, 962.
2. Guthrie, J. P. Can. J. Chem. 1974, 52, 2037.
3. Guthrie, J. P. Can. J. Chem. 1981, 59, 45.
4. Bell, R. P. Trans. Faraday Soc. 1943, 39, 253.
5. Pearson, R. G.; Dillon, R. L. J. Am. Chem. Soc. 1953, 75, 2439.
6. Bell, R. P.; Smith, P. W. J. Chem. Soc. B 1966, 241.
7. Hine, J. “Structural Effects on Equilibria in Organic Chemistry”; Wiley: New York, 1975; p 185.
8. House, H. O. “Modern Synthetic Reactions”, 2nd ed.; Benjamin: Menlo Park, CA, 1972; p 494.
9. Matthews, W. S.; Bares, J. E.; Bartmess, J. E.; Bordwell, F. G.; Cornforth, F. J.; Drucker, G. E.; Margolin, Z.; McCallum, R. J.; McCollum, G. J.; Vanier, N. R. J, Am. Chem. 1975, 97, 7006.
10. Ritchie, C. D. In “Solute-Solvent Interactions”; J. F. Coetzee, J. F., Richie, C. D., Eds.; Dekker: New York, 1969; Vol. 1, p 229.
11. Haspra, P.; Sutter, A.; Wirz, J. Angew. Chem., Int. Ed. Engl. 1979, 18, 617.
12. Guthrie, J. P.; Cullimore, P. A. Can. J. Chem. 1979, 57, 240.
13. Guthrie, J. P. Can. J. Chem. 1979, 57, 797.
14. Guthrie, J. P. Can. J. Chem. 1979, 57, 1177.
15. Bartlett, P. D. J. Am. Chem. Soc. 1934, 56, 967.
16. Bartlett, P. D.; Vincent, J. E. J. Am. Chem. Soc. 1935, 57, 1596.
17. Cullis, C. F.; Hashmi, M. H. J. Chem. Soc. 1956, 2512.
18. J. Chem. Soc. 1957, 3080.
19. Tapuhi, E.; Jencks, W. P. J. Am. Chem. Soc. 1982, 104, 5758.
20. Swain, C. G.; Dunlap, R. P. J. Am. Chem. Soc. 1972, 94, 7204.
21. Knipe, A. C.; Cox, B. G. J. Org. Chem. 1973, 38, 3429.
22. Guthrie, J. P.; Klym, A.; Cossar, J. J. Am. Chem. Soc. 1982, 104, 895.
23. Benson, S. W. “Thermochemical Kinetics”, 2nd ed.; Wiley: New York, 1976.
24. Benson, S. W.; Buss, J. H. J. Chem. Phys. 1958, 29, 546.
25. Hine, J.; Mookerjee, P. K. J. Org. Chem. 1975, 40, 292.
26. Wagman, D. D.; Evans, W. H.; Parker, V. B.; Halow, I.; Bailey, S. M.; Schumm, R. H. “Selected Values of Chemical Thermodynamic Properties”. Natl. Bur. Stand. (U.S.) Circ. 1970, Tech. Note 270–3.
27. Morris, J. C. J. Phys. Chem. 1966, 70, 3798.
28. Kelley, C. M.; Tartar, H. V. J. Am. Chem. Soc. 1956, 78, 5752.
29. Schwartzenbach, G. Zeit. Phys. Chem. 1936, 176, 133.
30. Eigen, M. Angew. Chem., Int. Ed. Engl. 1964, 3, 1.
31. Debye, P. Trans. Electrochem. Soc. 1942, 82, 265.
32. Turner, D. H.; Flynn, G. W.; Sutin, N.; Beitz, J. V. J. Am. Chem. Soc. 1972, 94, 1554.
33. Ritchie, C. D.; Virtanen, P. O. I. J. Am. Chem. Soc. 1972, 94, 1589.
34. Ritchie, C. D.; Virtanen, P. O. I. J. Am. Chem. Soc. 1972, 94, 4966.
35. Crampton, M. R.; Thompson, J. T.; Williams, D. L. H. J. Chem. Soc., Perkin Trans. 2 1979, 18.
36. Ridd, J. H. Adv. Phys. Org. Chem. 1978, 16, 1.
37. Bell, R. P.; Rawlinson, D. J. J. Chem. Soc. 1961, 63.
38. Kulic, J.; Vecera, M. Colect. Czech. Chem. Commun. 1974, 39, 171.
39. Bell, R. P.; Cox, B. G. J. Chem. Soc. B 1971, 652.
40. Tee, O. S.; Paventi, M. J. Org. Chem. 1980, 45, 2072.
41. Tee, O. S.; Thackray, D. C.; Berks, C. G. Can. J. Chem. 1978, 56, 2970.
42. Tee, O. S.; Paventi, M. J. Org. Chem. 1981, 46, 4172.
43. Tee, O. S.; Berks, C. G. J. Org. Chem. 1980, 45, 830.
44. Tee, O. S.; Komblatt, M. J.; Berks, C. G. J. Org. Chem. 1982, 47, 1018.
45. Tee, O. S.; Pavanti, M. J. Am. Chem. Soc. 1982, 104, 4142.
46. Robinson, R. A.; Stokes, R. H. “Electrolyte Solutions”, 2nd ed.; Butterworths: London, 1970; p 492.
47. Guthrie, J. P.; Cilllimore, P. A. Can. J. Chem. 1980, 58, 1281.
48. Hine, J. J. Am. Chem. Soc. 1971, 93, 3701.
49. Guthrie, J. P. j. Am. Chem. Soc. 1978, 100, 5892.
50. Biggs, I. D.; Williams, D. L. H. J. Chem. Soc., Perkin Trans. 2 1975, 107.
51. Ritchie, C. D. Acc. Chem. Res. 1972, 5, 348.
52. Sole, K.; Stockmayer, W. H. Int. J. Chem. Kin. 1973, 5, 733.
53. Hermann, R. B. J. Phys. Chem. 1972, 76, 2754.
54. Toullec, J.; Dubois, J. E. Tetrahedron 1973, 29, 2851.
55. Dubois, J. E.; Toullec, J. Tetrahedron 1973, 29, 2859.
56. Young, P. R.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 8238.
57. Dubois, J. E.; El-Alaoui, M.; Toullec, J. J. Am. Chem. Soc. 1981, 103, 5393.
58. Downs, A. J.; Adams, C. J. In “Comprehensive Inorganic Chemistry”; Bailar, J. C., Jr., Emeleus, H. J., Nyholm, Sir R., Trotman-Dickenson, A. F., Eds.; Pergamon: Oxford, 1973; p 1191.
59. Bell, R. P.; Yates, K. J. Chem. Soc. 1962. 2285.
60. Lii, R.-R.; Miller, S. I. J. Chem. Soc. B 1975, 2269.
61. Ayers, E. B.; Hauser, C. R. J. Am. Chem. Soc. 1943, 65, 1095.
62. Ariyama, N. J. Biol. Chem. 1928, 77, 359.
63. Rhys, P. Angew. Chem., Int. Ed. Engl. 1977, 16, 807.
64. Hine, J.; Hampton, K. G.; Menon, B. C. J. Am. Chem. Soc. 1967, 89, 2664.
65. Gutsche, C. D.; Redmore, D.; Buriks, R. S.; Nowotny, K.; Grassner, H.; Armbruster, C. W. J. Am. Chem. Soc. 1967, 89, 1235.
66. Hine, J.; Hampton, K. G.; Menon, B. C. J. Am. Chem. Soc. 1967, 89, 2664.
67. Spoehr, H. A.; Strain, H. H. J. Biol. Chem. 1930, 89, 503.
68. Hine, J.; Koser, G. F. J. Org. Chem. 1971, 36, 3591.
69. Guthrie, J. P. Can. J. Chem. 1981, 59, 45.
70. Guthrie, J. P.; Dawson, B. A. Can. J. Chem. 1983, 61, 171.
71. Bevington, P. R. Data Reduction and Error Analysis for the Physical Sciences McGraw-Hill: New York, 1969.
72. Cotton, F. A.; Wilkinson, G. “Advanced Inorganic Chemistry”; 4th ed.; Wiley: New York, 1980; p 556.