The Grunwald-Winstein relationship in the solvolysis of crowded tertiary alkyl chlorides. Hindered hydration and hydrophobic effect

Journal of Physical Organic Chemistry

Volumn 14, Issue 4, 2001, Pages 229-238

  Takeuchi, Ken'ichi ^a   Takasuka, Masaaki ^a   Shiba, Eiji ^a   Tokunaga, Hironobu ^a   Endo, Tadasuke ^a   Ushino, Takuhiro ^a   Tokunaga, Kazuhiko ^a   Okazaki, Takao ^a   Kinoshita, Tomomi ^a   Ohga, Yasushi ^a,b  

^a KYOTO UNIVERSITY   (Japan)

^b OITA UNIVERSITY   (Japan)

Author keywords

Grunwald Winstein relationship; Hydrophobic effect; Solvation; Solvent effect; Solvolysis rate; Steric congestion; Tertiary alkyl chloride

Indexed keywords

EID: 18844475376     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.358     Document Type: Article

References (30)

1. Sfreitwieser A Jr. Solvolytic Displacement Reactions. McGraw-Hill: New York, 1962.
2. (a) Liu KT, Sheu HC, Chen HI, Chiu PF, Hu CR. Tetrahedron Lett. 1990; 31: 3611;
3. (b) Liu KT, Hou SJ, Tsao ML. J. Org. Chem. 1998; 63: 1360;
4. (c) Liu KT, Tsao ML. J. Org. Chem. 1998; 63: 9552.
5. (a) Takeuchi K, Ohga Y, Ushino T, Takasuka M. J. Phys. Org. Chem. 1996; 9: 777;
6. (b) Takeuchi K, Ohga Y, Ushino T, Takasuka M. J. Org. Chem. 1997; 62: 4904;
7. (c) Takeuchi K, Ohga Y, Ushino T. Takusuka M. J. Phys. Org. Chem. 1997; 10: 717;
8. (d) Takeuchi K. Pure Appl. Chem. 1998; 70: 2025.
9. Grunwald E, Winstein S. J. Am. Chem. Soc. 1948; 70: 846.
10. (a) Raber DJ, Bingham RC, Harris JM, Fry JL, Schleyer PvR. J. Am. Chem. Soc. 1970; 92: 5977;
11. (b) Bentley TW, Carter GE. J. Am. Chem. Soc. 1982; 104: 5741;
12. (c) Bentley TW, Llewellyn G. Prog. Phys. Org. Chem. 1990; 17: 121.
13. Takeuchi K, Takasuka M, Shiba E, Kinoshita T, Okazaki T, Abboud JLM, Notario R, Castaño O. J. Am. Chem. Soc. 2000; 122: 7351.
14. Brown HC, Berneis HL. J. Am. Chem. Soc. 1953; 75: 10.
15. (a) Bentley TW, Schleyer PvR. J. Am. Chem. Soc. 1976; 98: 7658;
16. (b) Bentley TW, Bowen CT. J. Chem. Soc., Perkin Trans. 2 1978; 557;
17. (c) Bentley TW, Bowen CT, Parker W, Watt CIF. J. Chem. Soc., Perkin Trans. 2 1980; 1244.
18. Richard JP, Jagannadham V, Amyes TL, Mishima M, Tsuno Y. J. Am. Chem. Soc. 1994; 116: 6706.
19. Jorgensen WL, Buckner JK, Huston SE, Rossky PJ. J. Am. Chem. Soc. 1987; 109: 1891.
20. Hoefnagel AJ, Wepster BM. J. Chem. Soc., Perkin Trans. 2 1989; 977.
21. Hansch C, Leo A, Unger SH, Kim KH, Nikaitani D, Lien EJ. J. Med. Chem. 1973; 16: 1207.
22. (a) Kevill DN, D'Souza MJ. J. Chem. Res. (S) 1993; 174;
23. (b) Kevill DN, D'Souza MJ. Tetrahedron Lett. 1998; 39: 3973.
24. Tada EB, Novaki LP, El-Seoud OA. J. Phys. Org. Chem. 2000; 13: 679.
25. Kevill DN, Anderson SW. J Org. Chem. 1991; 56: 1845.
26. Kevill DN, Ismail NHJ, D'Souza MJ. J. Org. Chem. 1994; 59: 6303.
27. Bentley TW, Llewellyn G, Ryu ZH. J. Org. Chem. 1998; 63: 4654.
28. Takeuchi K, Ikai K, Shibata T, Tsugeno A. J. Org. Chem. 1988; 53: 2852.
29. Riddick JA, Bunger WB, Sakano TK. Organic Solvents (4th edn). Wiley: New York, 1986.
30. Reetz MT, Maier WF. Chem. Ber. 1980; 113: 3741.