The importance of the ortho effect in the solvolyses of 2,6-difluorobenzoyl chloride

Journal of Physical Organic Chemistry

Volumn 25, Issue 3, 2012, Pages 267-270

  Park, Kyoung Ho ^a   Kevill, Dennis N ^a  

^a NORTHERN ILLINOIS UNIVERSITY   (United States)

Author keywords

fluorine substituents; Grunwald Winstein equation; ortho effect; solvolysis

Indexed keywords

ADDITION-ELIMINATION; BENZOYL CHLORIDES; DESTABILIZING INFLUENCES; DOMINANT PATHWAYS; FLUORINE SUBSTITUENTS; FLUOROALCOHOL; GRUNWALD-WINSTEIN EQUATION; IONIZATION MECHANISMS; ORTHO EFFECT; SOLVOLYSES; SOLVOLYSIS;

FLUORINE; IONIZATION; SOLVENTS;

CHLORINE COMPOUNDS;

EID: 80052185294     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1906     Document Type: Article

References (32)

1. K.-H. Park, D. N. Kevill, Journal of Physical Organic Chemistry 2011, 24, in press (D01 10.1002/poc.1851)
2. M. L. Bender, M. C. Chen, Journal of the American Chemical Society 1963, 85, 30-36.
3. T. W. Bentley, H. C. Harris, I. S. Koo, Journal of Chemical Society Perkin Transaction 2, 1988, 783-789.
4. T. W. Bentley, G. Llewellyn, Progress in Physical Organic Chemistry 1990, 17, 121-158.
5. F. L. Schadt, T. W. Bentley, P. v. R. Schleyer, Journal of the American Chemical Society 1976, 98, 7667-7674.
6. D. N. Kevill, in Advances in Quantative Structure-Property Relationships. Ed.:, M Charton, JAI Press, Greenwich, CT, 1996, pp. 81-115.
7. D. N. Kevill, S. W. Anderson, Journal of Organic Chemistry 1991, 56, 1845-1850.
8. E. Grunwald, S. Winstein, Journal of the American Chemical Society 1948, 70, 846-854.
9. S. Winstein, E. Grunwald, H. W. Jones, Journal of the American Chemical Society 1951, 73, 2700-2707.
10. D. N. Kevill, Z. H. Ryu, Int. Journal of Molecular Science 2006, 7, 451-455.
11. D. N. Kevill, M. J. D'Souza, Journal of Chemical Research (S) 1993, 174-175.
12. D. N. Kevill, M. J. D'Souza, Journal of Chemical Research 2008, 61-66.
13. T. W. Bentley, G. E. Carter, Journal of the American Chemical Society 1982, 104, 5741-5747.
14. O. Exner, in Correlation Analysis in Chemistry, Recent Advances (Eds., N. B. Chapman, J. Shorter,), Plenum Press, New York, NY, 1978, Chap. 10.
15. J. Shorter, Correlation Analysis of Organic Reactivity, Research Studies Press, New York, NY, 1982, Chap. 3.
16. H. C. Brown, Y. Okamoto, Journal of the American Chemical Society 1958, 80, 4979-4987.
17. J. Shorter, in Advances in Linear Free Energy Relationships (Eds., N. B. Chapman, J. Shorter,), Plenum Press, New York, NY, 1972, chap. 2.
18. J. E. Leffler, E. Grunwald, Rates and Equilibria of Organic Reactions, Wiley, New York, NY, 1963, p. 225.
19. M. Charton, Journal of the American Chemical Society 1969, 91, 6649-6654.
20. M. Charton, Progress in Physical Organic Chemistry 1971, 8, 235-317.
21. M. Charton, Progress in Physical Organic Chemistry 1981, 13, 119-252.
22. I. Lee, I. S. Koo, S. C. Sohn, H. H. Lee, Bulletin of the Korean Chemical Society 1982, 3, 92-98.
23. I. Lee, D. D. Sung, T. S. Uhm, Z. H. Ryu, Journal of Chemical Society Perkin Transaction 2 1989, 1697-1701.
24. T. W. Bentley, I. S. Koo, Journal of Chemical Society Perkin Transaction 2 1989, 1385-1392.
25. T. W. Bentley, I. S. Koo, S. J. Norman, Journal of Organic Chemistry 1991, 56, 1604-1609.
26. K.-T. Liu, H.-I. Chen, Journal of Chemical Society Perkin Transaction 2 2000, 893-898.
27. D. N. Kevill, M. J. D'Souza, Journal of Physical Organic Chemistry 2002, 15, 881-888.
28. A. Streitwieser, Solvolytic Displacement Reactions, McGraw-Hill, New York, NY, 1962.
29. P. R. Wells,. Linear Free Energy Relationships, Academic Press, New York, NY, 1968.
30. A. H. Fainberg, S. Winstein, Journal of the American Chemical Society 1956, 78, 2770-2777.
31. P. R. Wells, Chemistry Review 1963, 63, 171-219.
32. H. J. Koh, K. L. Han, H. W. Lee, I. Lee, Journal of Organic Chemistry 1998, 63, 9834-9839.