Intrinsic structure-reactivity relationships in gas-phase transacylation reactions: Identity exchange of substituted benzoyl chlorides with chloride ion

Journal of the American Chemical Society

Volumn 121, Issue 11, 1999, Pages 2508-2515

  Zhong, Meili ^a   Brauman, John I ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORIDE;

ACYLATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 0033599565     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja973151j     Document Type: Article

References (58)

1. Bender, M. L. Chem. Rev. 1960, 60, 53.
2. Jencks, W. P. Catalysis in Chemistry and Enzymology, Dover: Mineola, 1987.
3. March, J. Advanced Organic Chemistry, 3rd ed.; John Wiley and Sons: New York, 1985.
4. Bender, M. L. J. Am. Chem. Soc. 1951, 73, 1626.
5. Fedor, L. R.; Bruice, T. C. J. Am. Chem. Soc. 1965, 87, 4138.
6. Johnson, S. L. J. Am. Chem. Soc. 1964, 86, 3819.
7. Fraenkel, G.; Watson, D. J. Am. Chem. Soc. 1975, 97, 231.
8. Hand, E. S.; Jencks, W. P. J. Am. Chem. Soc. 1962, 84, 3505.
9. Baer, S.; Brinkman, E. A.; Brauman, J. I. J. Am. Chem. Soc. 1991, 113, 805.
10. Wilbur, J. L.; Brauman, J. I. J. Am. Chem. Soc. 1994, 116, 5839-5846.
11. Wilbur, J. L.; Brauman, J. I. J. Am. Chem. Soc. 1994, 116, 9216-9221.
12. Dodd, J. Ph.D. Dissertation, Stanford University, 1985.
13. Wilbur, J. L. Ph.D. Dissertation, Stanford University, 1993.
14. Zhong, M.; Brauman, J. I. J. Am. Chem. Soc. 1996, 118, 636.
15. Han, C. C.; Brauman, J. I. J. Am. Chem. Soc. 1989, 111, 6491.
16. Larson, J. W.; McMahon, T. B. Can. J. Chem. 1984, 62, 675.
17. Eyler, J. R.; Richardson, D. E. J. Am. Chem. Soc. 1985, 107, 6130.
18. Wladkowski, B. D.; Wilbur, J. L.; Brauman, J. I. J. Am. Chem. Soc. 1994, 116, 2471.
19. Su, T.; Chesnavich, W. J. J. Chem. Phys. 1982, 76, 5183.
20. Frisch, M. J.; et al. Gaussian 94, Revision C.3; Gaussian, Inc: Pittsburgh, PA, 1995.
21. Stewart, J. J. P. MOPAC 6.00, No. 455, 1990.
22. - by only 5 kcal/mol.
23. Wladkowski, B. D.; Lim, K. F.; Allen, W. D.; Brauman, J. I. J. Am. Chem. Soc. 1992, 114, 9136.
24. Viggiano, A. A.; Morris, R. A.; Su, T.; Wladowski, B. D.; Craig, S. L.; Zhong, M.; Brauman, J. I. J. Am. Chem. Soc. 1994, 116, 2213.
25. Craig, S L.; Brauman, J. I. Science 1997, 276, 1536-1538.
26. Craig, S. L.; Zhong, M.; Brauman, J. I. J. Phys. Chem. 1996, 101, 19.
27. Craig, S. L.; Zhong, M.; Brauman, J. I. Manuscript in preparation.
28. Smith, S. C. J. Chem. Phys. 1992, 97, 2406.
29. Robinson, P. J.; Holbrook, K. A. Unimolecular Reactions; Interscience: London, 1972.
30. Forst, W. Theory of Unimolecular Reactions; Academic Press: New York, 1973.
31. Gilbert, R. G.; Smith, S. C. Theory of Unimolecular and Recombination Reactions; Blackwells Scientific: Oxford, 1990.
32. Trular, D. G.; Hase, W. L.; Hynes, J. T. J. Phys. Chem. 1983, 87, 2664.
33. Steinfeld, J. I.; Francisco, J. S.; Hase, W. L. Chemical Kinetics and Dynamics; Prentice Hall, Englewood Cliffs, NJ, 1989.
34. Garrett, B. C.; Truhlar, D. G. J. Chem. Phys. 1979, 70, 1593.
35. Zerner, B.; Bender, M. L. J. Am. Chem. Soc. 1961, 83, 2267.
36. Mader, P. M. J. Am. Chem. Soc. 1965, 73, 3191.
37. Schowen, R. L.; Jayaraman, H.; Kershner, L. J. Am. Chem. Soc. 1966, 88, 3373.
38. Eriksson, S. O.; Holst, C. Acta Chem. Scand. 1966, 20, 1892.
39. Bender, M. L. J. Am. Chem. Soc. 1953, 75, 5986.
40. Asubiojo, O. I.; Brauman, J. I. J. Am. Chem. Soc. 1979, 101, 3175.
41. Bohme, D. K.; Mackay, G. I.; Tanner, S. D. J. Am. Chem. Soc. 1980, 102, 407.
42. McDonald, R. N.; Chowdhury, A. K. J. Am. Chem. Soc. 1983, 105, 7267.
43. Bowie, J. H.; Williams, B. D. J. Am. Chem. Soc. 1974, 27, 1923.
44. Nibbering, N. M. M.; van der wel, H. Recl. Trav. Chim. Pays-Bas. 1988, 107, 479.
45. Larson, J. W.; McMahon, T. B. J. Am. Chem. Soc. 1983, 105, 2944.
46. Larson, J. W.; McMahon, T. B. J. Am. Chem. Soc. 1985, 107, 766-773.
47. Larson, J. W.; McMahon, T. B. J. Am. Chem. Soc. 1987, 109, 6230.
48. Yamabe, S.; Minato, T. J. Org. Chem. 1983, 48, 2972.
49. Blake, J. F.; Jorgensen, W. L. J. Am. Chem. Soc. 1987, 109, 3856.
50. Hammett, L. P. J. Chem. Educ. 1966, 43, 464.
51. Hammett, L. P. Physical Organic Chemistry, 2nd ed.; McGraw-Hill: New York, 1970.
52. Jaffe, H. H. Chem. Rev. 1953, 53, 191.
53. Riveros, J. M.; Ingemann, S.; Nibbering, N. M. M. J. Chem. Soc., Perkin Trans. 2 1991, 1985.
54. DePuy, C. H.; Grabowski, J. J.; Bierbaum, V. M.; Ingemann, S.; Nibbering, N. M. M. J. Am. Chem. Soc. 1985, 107, 1093.
55. Meot-Ner, M.; Kafafi, S. A. J. Am. Chem. Soc. 1988, 110, 6297.
56. This value was obtained from the AMI MOPAC calculation.
57. McMahon, T. B.; Kebarle, P. J. Am. Chem. Soc. 1977, 99, 2222-2230.
58. Jackson, R. L.; Zimmerman, A. H.; Brauman, J. I. J. Chem. Phys. 1979, 71, 2088-2094.