Solvent effects on carbocation - Nucleophile combination reactions: A comparison of π-nucleophilicity in aqueous and organic solvents

Journal of the American Chemical Society

Volumn 120, Issue 40, 1998, Pages 10372-10378

  Richard, John P ^a   Szymanski, Paul ^a   Williams, Kathleen B ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ORGANIC SOLVENT; WATER;

AQUEOUS SOLUTION; ARTICLE; HYDROGEN BOND; MOLECULAR INTERACTION; SOLVATION;

EID: 0032517377     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja981842p     Document Type: Article

References (23)

1. Mayr, H.; Patz, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 938-957.
2. Mayr, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1371-1384. Burfeindt, J.; Patz, M.; Müller, M.; Mayr, H. J. Am. Chem. Soc. 1998, 720, 3629-3634.
3. Mayr, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1371-1384. Burfeindt, J.; Patz, M.; Müller, M.; Mayr, H. J. Am. Chem. Soc. 1998, 720, 3629-3634.
4. Pienta, N. J.; Kessler, R. J. J. Am. Chem. Soc. 1992, 114, 2419-2428.
5. McClelland, R. A.; Mathivanan, N.; Steenken, S. J. Am. Chem. Soc. 1990, 112, 4857-4861.
6. McClelland, R. A.; Cozens, F. L.; Li, J.; Steenken, S. J. Chem. Soc., Perkin Trans. 2 1996, 1531-1543.
7. Richard, J. P. Tetrahedron 1995, 51, 1535-1573.
8. McClelland, R. A. Tetrahedron 1996, 52, 6823-6858.
9. Pienta, N. J.; Kessler, R. J. J. Am. Chem. Soc. 1993, 115, 8330-8339.
10. McClelland, R. A.; Kanagasabapathy, V. M.; Banait, N. S.; Steenken, S. J. Am. Chem. Soc. 1992, 114, 1816-1823.
11. Bartl, J.; Steenken, S.; Mayr, H. J. Am. Chem. Soc. 1991, 113, 7710-7716.
12. Richard, J. P.; Lin, S.-S.; Williams, K. B. J. Org. Chem. 1996, 61, 9033-9034.
13. Richard, J. P.; Lin, S.-S.; Buccigross, J. M.; Amyes, T. L. J. Am. Chem. Soc. 1996, 118, 12603-12613.
14. Richard, J. P.; Rothenberg, M. E.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 1361-1372.
15. Richard, J. P. J. Am. Chem. Soc. 1989, 111, 1455-1465.
16. Richard, J. P.; Amyes, T. L.; Vontor, T. J. Am. Chem. Soc. 1992, 114, 5626-5634.
17. calc (±0.4 unit) does not affect any of our interpretations.
18. Mayr, H. Personal communication.
19. Kane-Maguire, L. A. P.; Honig, E. D.; Sweigart, D. A. Chem. Rev. 1984, 84, 525-543.
20. Breslow, R. Acc. Chem. Res. 1991, 24, 159-164.
21. Poulter, C. D.; King, C.-H. J. Am. Chem. Soc. 1982, 104, 1422-1424.
22. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183-278.
23. 32