Using Kamlet-Taft solvent descriptors to explain the reactivity of anionic nucleophiles in ionic liquids

Journal of Organic Chemistry

Volumn 71, Issue 23, 2006, Pages 8847-8853

  Crowhurst, Lorna ^a   Falcone, Ruben ^a   Lancaster, N Llewellyn ^a   Llopis Mestre, Veronica ^a   Welton, Tom ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

HALOGEN COMPOUNDS; HYDROGEN BONDS; IONIZATION OF LIQUIDS; RATE CONSTANTS; SOLVENTS; SUBSTITUTION REACTIONS;

ANIONIC NUCLEOPHILES; DICHLOROMETHANE; KAMLET TAFT SOLVENT DESCRIPTORS; NUCLEOPHILES;

REACTION KINETICS;

ACETIC ACID; ANION; CYANIDE; DICHLOROMETHANE; DIMETHYL SULFOXIDE; HALIDE; IMIDAZOLE DERIVATIVE; IONIC LIQUID; METHANOL; PYRROLIDINE DERIVATIVE; SOLVENT; THIOCYANATE; TRIFLUOROACETIC ACID;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CORRELATION ANALYSIS; HYDROGEN BOND; ORGANIC CHEMISTRY;

EID: 33750857135     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0615302     Document Type: Article

References (52)

1. (a) Zhao, H.; Malhotra, S. V. Aldrichimica Acta 2002, 35, 75.
2. (b) Olivier-Bourbigou, H.; Magna, L. J. Mol. Catal. A 2002, 182, 419.
3. (c) Zhao, D.; Wu, M.; Kou, Y.; Min, E. Catal. Today 2002, 74, 157.
4. (d) Sheldon, R. Chem. Commun. 2001, 2399.
5. (e) Gordon, C. M. Appl. Catal., A 2001, 222, 101.
6. (f) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772.
7. (g) Welton, T. Chem. Rev. 1999, 99, 2071.
8. Ionic Liquids in Synthesis; Welton, T., Wasserscheid, P., Eds.; VCH-Wiley: Weinheim, 2002.
9. Scammells, P. J.; Scott, J. L.; Singer, R. D. Aust. J. Chem. 2005, 58, 155.
10. Freemantle, M. Chem. Eng. News 1998, 76, 32.
11. Chiappe, C.; Pieraccini, D. J. Phys. Org. Chem. 2005, 18, 275 and references therein.
12. (a) Ingold, C. K. Structure and Mechanism in Organic Chemistry, 2nd ed.; Bell: London, 1969.
13. (b) Hughes, E. D.; Ingold, C. K. J. Chem. Soc. 1935, 244.
14. (c) Hughes, E. D. Trans. Faraday Soc. 1941, 37, 603.
15. (d) Hughes, E. D.; Ingold, C. K. Trans. Faraday Soc. 1941, 37, 657.
16. (e) Cooper, K. A.; Dhar, M. L.; Hughes, E. D.; Ingold, C. K.; MacNulty, B. J.; Woolf, L. I. J. Chem. Soc. 1948, 2043.
17. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 2nd ed.; VCH (UK) Ltd.: Cambridge, 1998.
18. (a) Lancaster, N. L.; Welton, T. J. Org. Chem. 2004, 69, 5986.
19. (b) Lancaster, N. L.; Salter, P. A.; Welton, T.; Young, G. B. J. Org. Chem. 2002, 67, 8855.
20. Crowhurst, L.; Lancaster, N. L.; Pérez Arlandis, J. M.; Welton, T. J. Am. Chem. Soc. 2004, 126, 11549.
21. Chiappe, C.; Pieraccini, D.; Saullo, P. J. Org. Chem. 2003, 68, 6710.
22. (a) Chiappe, C.; Leandri, E.; Pieraccini, D. Chem. Commun. 2004, 2536.
23. (b) Chiappe, C.; Pieraccini, D. J. Org. Chem. 2004, 69, 6059.
24. (c) Chiappe, C.; Conte, V.; Pieraccini, D. Eur. J. Org. Chem. 2002, 2831.
25. (d) Chiappe, C.; Capraro, D.; Conte, V.; Pieraccini, D. Org. Lett. 2001, 3, 1061.
26. (a) Skrzypczak, A.; Neta, P. Int. J. Chem. Kinet. 2004, 36, 253-258.
27. (b) Swiderski, K.; McLean, A.; Gordon, C. M.; Vaughan, D. H. Chem. Commun. 2004, 590.
28. (c) McLean, A. J.; Muldoon, M. J.; Gordon, C. M.; Dunkin, I. R. Chem. Commun. 2002, 1880.
29. (d) Grodkowski, J.; Neta, P.; Wishart, J. F. J. Phys. Chem. A 2003, 107, 9794.
30. (e) Skrzypczak, A.; Neta, P. J. Phys. Chem. A 2003, 107, 7800.
31. (a) Alluni, S.; Pica, M.; Reichenbach, G. J. Phys. Org. Chem. 2001, 14, 265.
32. (b) Alluni, S.; Pero, A.; Reichenbach, G. J. Chem. Soc., Perkin Trans. 2 1998, 1747.
33. (c) Bunting, J. W.; Mason, J. M.; Heo, C. K. M. J. Chem. Soc., Perkin Trans. 2 1994, 2291.
34. (d) Dietze, P. E.; Hariri, R.; Khattak, J. J. Org. Chem. 1989, 54, 3317.
35. (e) Kurz, J. L.; Lu, Y.-W. J. Phys. Chem. 1983, 87, 1444.
36. (a) Wakai, C.; Oleinikova, A.; Ott, M.; Weingärtner, H. J. Phys. Chem. B 2005, 109, 17028.
37. (b) Bonhôte, P.; Dias, A.-P.; Papageorgiou, N.; Kalyanasundaram, K.; Grätzel, M. Inorg. Chem. 1996, 35, 1168.
38. (c) Baker, S. N.; Baker, G. A.; Kane, M. A.; Bright, F. V. J. Phys. Chem. B 2001,105, 9663.
39. (d) Angelini, G.; Chiappe, C.; De Maria, P.; Fontana, A.; Gasparrini, F.; Pieraccini, D.; Pierini, M.; Siani, G. J. Org. Chem. 2005, 70, 8193.
40. Marcus, Y. J. Phys. Chem. 1991, 95, 8886.
41. (a) Crowhurst, L.; Mawdsley, P. R.; Perez-Arlandis, J. M.; Salter, P. A.; Welton, T. Phys. Chem. Chem. Phys. 2003,5, 2790.
42. (b) Huddleston, J. G.; Broker, G. A.; Willauer, H. D.; Rodgers, R. D. ACS Symp. Ser. 2002, 818, 270.
43. (c) Muldoon, M. J.; Gordon, C. M.; Dunkin, I. R. J. Chem. Soc., Perkin Trans. 2 2001, 433.
44. Kamlet, M. J.; Abboud, J. L. M.; Abraham, M. H.; Taft, R. W. J. Org. Chem. 1983, 48, 2877.
45. For information, see www.minitab.com.
46. McManus, S. P.; Somani, S.; Harris, J. M.; McGill, R. A. J. Org. Chem. 2004, 69, 8865.
47. Catalan, J.; Diaz, C.; Garcai-Blanco, F. J. Org. Chem. 1999, 64, 6512.
48. Kamlet, M. J.; Taft, R. W. J. Chem. Soc., Perkin Trans. 2 1979, 350.
49. Shimizu, N.; Tsutsumi, T.; Tsuno, Y. Chem. Lett. 1991, 2065.
50. Hunt, P.; Kirchner, B.; Welton, T. Chem.-Eur. J. 2006, 12, 600.
51. Hardacre, C.; Holbrey, J. D.; McMath, S. E. J.; Bowron, D. T.; Soper, A. K. J. Chem. Phys. 2003, 118, 273.
52. Cammarata, L.; Kazarian, S. G.; Salter, P. A.; Welton, T. Phys. Chem. Chem. Phys. 2001, 3, 5192.