Solvent and substituent effects in solvolyses of benzoyl chlorides. Variation of mechanisms from Grunwald-Winstein correlation analyses with YBnCl scales

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 4, 2000, Pages 893-898

  Liu, Kwang Ting ^a   Chen, Hung I ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL ANALYSIS; COMPOSITION EFFECTS; CORRELATION METHODS; IONIZATION; ORGANIC ACIDS; ORGANIC SOLVENTS; RATE CONSTANTS; REGRESSION ANALYSIS; SUBSTITUTION REACTIONS;

AROMATIC ACID CHLORIDES; BENZOYL CHLORIDES; GRUNWALD-WINSTEIN CORRELATION; HAMMETT-TYPE PLOTS; IONIZING POWER; SOLVOLYSIS; TRIFLUOROETHANOL;

AROMATIC HYDROCARBONS;

EID: 0034175157     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a905125b     Document Type: Article

References (56)

1. For comprehensive treatises, see, for example: (a) S. Patai (editor), The Chemistry of Acyl Halides, Interscience, New York, 1972
2. (b) S. Patai (editor), The Chemistry of Acid Derivatives, Supplements B, Interscience, New York, 1992, vol. 2, related chapters
3. (c) A. R. Katrizky, O. Meth-Cohn and C. W. Rees (editors), Comprehensive Organic Functional Groups Transformations, Elsevier Science Ltd., Oxford, 1995, vol. 5, Section 5.01 and related pages.
4. (a) For a review of early mechanistic work on substitution at carbonyl carbon, see, for example, A. Kivinen, (a) S. Patai (editor), The Chemistry of Acyl Halides, Interscience, New York, 1972; pp. 177-230
5. (b) for a recent report see, for example: T. W. Bentley, G. Llewellyn and J. A. McAlister, J. Org. Chem., 1996, 61, 7927.
6. G. Berger and S. C. J. Olivier, Recl. Trav. Chim., 1927, 46, 521
7. S. C. J. Olivier, Recl. Trav. Chim., 1929, 48, 227.
8. R. F. Hudson and J. E. Wardill, J. Chem. Soc., 1950, 1729
9. R. F. Hudson and B. L. Archer, J. Chem. Soc., 1950, 3259.
10. E. Grunwald and S. Winstein, J. Am. Chem. Soc., 1948, 70, 846.
11. C. G. Swain and R. B. Mosely, J. Am. Chem. Soc., 1955, 77, 3727.
12. R. F. Hudson and D. A. Brown, J. Chem. Soc., 1953, 883.
13. R. F. Hudson and C. E. Moss, J. Chem. Soc., 1962, 5157.
14. Ref. 2(a) and literature cited therein.
15. (a) Leading early papers are (a) I. Lee, C. S. Koo, C. S. Shon and H. H. Lee, Bull. Korean Chem. Soc., 1982, 3, 92
16. (b) I. Lee, D. D. Sung, T. S. Uhm and Z. H. Ryu, J. Chem. Soc., Perkin Trans. 2, 1989, 1697
17. (c) T. W. Bentley, G. E. Carter and H. C. Harris, J. Chem. Soc., Perkin Trans. 2, 1985, 983.
18. For a more recent paper; (d) T. W. Bentley and C. S. Shim, J. Chem. Soc., Perkin Trans. 2, 1993, 2351.
19. T. W. Bentley, I. S. Koo and S. J. Norman, J. Org. Chem., 1991, 56, 1604.
20. T. W. Bentley, and H. C. Harris, J. Chem. Soc., Perkin Trans. 2, 1986, 619.
21. T. W. Bentley and I. S. Koo, J. Chem. Soc., Perkin Trans. 2, 1989, 1385.
22. T. W. Bentley, and C. S. Shim, J. Chem. Soc., Perkin Trans. 2, 1993, 1659.
23. T. W. Bentley, H. C. Harris and I. S. Koo, J. Chem. Soc., Perkin Trans. 2, 1988, 783.
24. K.-T. Liu, Y.-F. Duann and S.-J. Hou, J. Chem. Soc., Perkin Trans. 2, 1998, 2181.
25. (a) K.-T Liu, and H.-C. Sheu, J. Org. Chem., 1991, 56, 3021
26. (b) K.-T. Liu, L.-W. Chang, D.-G. Yu, P.-S. Chen and J.-D. Fan, J. Phys. Org. Chem., 1997, 10, 879.
27. M. Fujio, T. Susuki, M. Goto, Y. Tsuji, K. Yatsugi, Y. Saeki, S. H. Kim and Y. Tsuno, Bull. Chem. Soc. Jpn., 1994, 67, 2233.
28. D. N. Kevill and S. W. Anderson, J. Chem. Res. (S), 1991, 356
29. D. N. Kevill and M. J. D'Souza, J. Chem. Res. (S), 1993, 174.
30. S. Winstein, E. Grunwald and H. W. Jones, J. Am. Chem. Soc., 1951, 73, 2700.
31. T. W. Bentley and G. Llewellyn, Prog. Phys. Org. Chem., 1990, 17, 121.
32. H. C. Brown and Y. Okamoto, J. Am. Chem. Soc., 1951, 80, 1913.
33. R. S. Mulliken, J. Chem. Phys., 1955, 23, 1833.
34. W. J. Hehre, L. Radom, P. v. R. Schleyer and J. A. Pople, Ab Initio Molecular Orbital Theory, J. Wiley and Sons, New York, 1986.
35. D. N. Kevill, N. H. J. Ismail and M. J. D'Souza, J. Org. Chem., 1994, 59, 6303
36. D. N. Kevill and M. J. D'Souza, J. Chem. Soc., Perkin Trans. 2, 1995, 973.
37. BnCl, see ref. 17(b).
38. L. Kaspi and Z. Rappoport, J. Am. Chem. Soc., 1980, 102, 3829.
39. For an early example, see: K.-T. Liu, L.-W. Chang and P.-S. Chen, J. Org. Chem., 1992, 57, 4791.
40. K.-T. Liu, S.-J. Hou and M.-L. Tsao, J. Org. Chem., 1998, 63, 1360.
41. M. L. Bender, H. Ladenheim and M. C. Chen, J. Am. Chem. Soc., 1961, 83, 123.
42. H. H. Jaffe, Chem. Rev., 1953, 53, 191.
43. K.-T. Liu, P.-S. Chen, P.-F. Chiu, and M.-L. Tsao, Tetrahedron Lett., 1992, 33, 6499
44. K.-T. Liu, P.-S. Chen, C.-R. Hu and H.-C. Sheu, J. Phys. Org. Chem., 1993, 6, 122, 433
45. K.-T. Liu and P.-S. Chen, J. Chem. Res. (S), 1994, 310
46. K.-T. Liu, C.-P. Chin, Y.-S. Lin and M.-L. Tsao, Tetrahedron Lett., 1995, 36, 6919
47. K.-T. Liu and Y.-S. Lin, Tetrahedron Lett., 1997, 38, 1419.
48. B. D. Song, and W. P. Jencks, J. Am. Chem. Soc., 1989, 111, 8470.
49. (a) L. E. Chirlian and M. M. Francl, J. Comput. Chem., 1987, 8, 894
50. (b) C. M. Breneman and K. B. Wiberg, J. Comput. Chem., 1990, 11, 361.
51. (a) A. E. Reed and F. Weinhold, J. Chem. Phys., 1983, 78, 4066
52. (b) J. E. Carpenter and F. Weinhold, J. Mol. Struct. (Theochem), 1988, 169, 41.
53. Acetyl chloride was used to make the initial reactants and final products in the isodesmic reactions as similar as possible, W. J. Hehre, L. Radom, P. v. R. Schleyer and J. A. Pople, Ab Initio Molecular Orbital Theory, J. Wiley and Sons, New York, 1986, p. 298.
54. K.-T. Liu, J. Chem. Soc., Perkin Trans. 2, 1996, 327.
55. K.-T. Liu, Y.-S. Lin and M.-L. Tsao, J. Phys. Org. Chem., 1998, 11, 223.
56. D. Perrin and W. L. F. Armarego, Purification of Laboratory Chemicals, 3rd edn, Pergamon Press, New York, 1988.