The Hammett equation applied to the nucleophilic displacement of ions and ion pairs on substituted benzenesulphonates

Journal of Physical Organic Chemistry

Volumn 14, Issue 5, 2001, Pages 265-270

  Alunni, Sergio ^a   Pica, Monica ^a   Reichenbach, Gustavo ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

Hammett equation; Ion pairs; Ions; Nucleophilic displacement

Indexed keywords

EID: 0035340086     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.364     Document Type: Article

References (34)

1. See for example (a) Szwarc M. Ions and Ion Pairs in Organic Reactions. Wiley-Interscience: New York, 1974;
2. (b) Reichardt C. Solvents and Solvent Effects in Organic Chemistry. VCH: Weinheim: 1990;
3. (c) Lai ZG, Westaway KC. Can. J. Chem. 1989, 67: 21-26;
4. (d) Baciocchi E, Ruzziconi R, Sebastiani GV. J. Org. Chem. 1979, 44: 3718-3720;
5. (e) Svoboda M, Hapala J, Zavada J. Tetrahedron Lett. 1972, 4: 265-268;
6. (f) Smid J, Varma AJ, Shah SC. J. Am. Chem. Soc. 1979, 101: 5764-5769;
7. (g) Coddington J, Wherland S. Inorg. Chem. 1996, 35: 4023-4028;
8. (h) Romeo R, Arena G, Scolaro LM, Plutino MR. Inorg. Chim. Acta. 1995, 240: 81-92;
9. (i) Harder S, Streitwieser A, Petty JT, von R, Schleyer P. J. Am. Chem. Soc. 1995, 117: 3253-3259:
10. (j) Macchioni A, Bellachioma G, Cardaci G, Travaglia M, Zuccaccia C, Milani B, Corso G, Zangrando E, Mestroni G, Carfagna C, Formica M. Organometallics, 1999, 18: 3061-3069;
11. (k) Jia L, Yang X, Stern CL, Marks TJ. Organometallics, 1997, 16: 842-857;
12. (l) Masnovi JM, Kochi JK. J. Am. Chem. Soc. 1985, 107: 7880-7893.
13. (a) Acree SF. Am. Chem. J. 1912, 48: 352-380;
14. (b) Cayzergues P, Geourgoulis C, Mathieu G. J. Chim. Phys. Phys.-Chim. Biol. 1987, 84: 63-70;
15. (c) Mathieu G. Ph.D. Thesis, University Pierre et Marie Curie, Paris, 1985;
16. (d) Pregel MG, Dunn EJ, Buncel E. Can. J. Chem. 1990, 68: 1846-1858;
17. (e) Msayb KJ, Watt CIF. Chem. Soc. Rev. 1992, 21, 237-243;
18. (f) Poli R, Owens BE, Link RG. Inorg. Chem. 1992, 31: 662-667;
19. (g) Beronius P, Pataki L. J. Am Chem. Soc. 1970, 92: 4518-4521.
20. Alunni S, Pero A, Reichenbach G. J. Chem. Soc., Perkin Trans. 2 1998: 1747-1750.
21. Reichenbach G, Bellachioma G, Cambi R, Cardaci G, Lanfaloni C, Macchioni A, Ricci R, Vetralla G, Inorg. Chim. Acta, 1999, 288: 200-205.
22. Weast RC (ed). CRC Handbook of Chemistry and Physics, (67th edn). CRC Press Inc.: West Palm Beach, FL, 1986.
23. (a) Gutman V, Mayer U. Adv. Inorg. Chem. Radiochem. 1975, 17: 189ff;
24. (b) Gutman V. The Donor-Acceptor Approach to Molecular Interaction. Plenum Press: New York, 1978.
25. Svorstol I, Songstad J. Acta Chem. Scand. Ser. B 1985, 39: 639-655.
26. (a) Hirsch E, Fuoss RM. J. Am. Chem. Soc. 1960, 82: 1018-1022;
27. (b) Boche G. Angew. Chem Int., Ed. Engl. 1992, 31: 731-732;
28. (c) Abbot AP, Schriffin DJ. J. Chem. Soc., Faraday Trans. 1990, 86: 1453-1459.
29. Moras D, Metz B, Weiss K. Acta Crystallogr. Sect. B 1973, 29: 383-388; Boileau S, Hemery P, Justice JC. J. Solution Chem. 1975, 4: 873-891.
30. Moras D, Metz B, Weiss K. Acta Crystallogr. Sect. B 1973, 29: 383-388; Boileau S, Hemery P, Justice JC. J. Solution Chem. 1975, 4: 873-891.
31. Glasstone S. An Introduction to Electrochemistry. Van Nostrand D: New York, 1959.
32. Exner O. In Correlation Analysis in Chemistry, Chapman NB, Shorter J (eds). Plenum Press: New York, 1978; 469-476.
33. Lee I, Choi YH, Rhyu KW, Shim CS. J. Chem. Soc., Perkin Trans. 2 1989: 1881-1889.
34. Streitwieser A, Choy GS, Abu-Hasanayn F. J. Am. Chem. Soc. 1997, 119: 5013-5019.