Anion nucleophilicity in ionic liquids: A comparison with traditional molecular solvents of different polarity

Tetrahedron Letters

Volumn 46, Issue 23, 2005, Pages 3961-3963

  Landini, Dario ^a   Maia, Angelamaria ^b  

^a UNIVERSITY OF MILAN   (Italy)

^b CNR   (Italy)

Author keywords

Anion reactivity; Hydrogen bonding effect; Ionic liquids; Nucleophilic substitutions; Water effect

Indexed keywords

ANION; CHLOROBENZENE; DIMETHYL SULFOXIDE; HALIDE; HYDROXIDE; ORGANIC COMPOUND; SOLVENT; SULFONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; HYDROPHILICITY; LIQUID; NUCLEAR MAGNETIC RESONANCE; POLARIZATION; SOLVENT EFFECT; TEMPERATURE;

EID: 18844389523     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.04.044     Document Type: Article

References (34)

1. See inter alia: T. Welton Chem. Rev. 99 1999 2071 2083
2. P. Wasserscheid, and W. Keim Angew. Chem., Int. Ed. 39 2000 3772 3789
3. K.R. Seddon, A. Stark, and M. Torres Pure Appl. Chem. 72 2000 2275 2287
4. R. Sheldon Chem. Commun. 2001 2399 2407
5. J. Dupont, R.F. de Souza, and P.A.Z. Suarez Chem. Rev. 102 2002 3667 3692
6. P. Wasserscheid, and T. Welton Ionic Liquids in Synthesis 2003 VCH Weihneim
7. R.D. Rogers K.R. Seddon Green Industrial Applications of Ionic liquids 2003 Kluwer Dordrecht
8. R.D. Rogers K.R. Seddon Ionic liquids as Green Solvents: Progress and Prospects ACS Symposium Series 856 2003 American Chemical Society Washington, DC
9. J.G. Huddleston, A.E. Visser, W.M. Reichert, H.D. Willauer, G.A. Broker, and R.D. Rogers Green Chem. 3 2001 156 164
10. T. Welton Coord. Chem. Rev 248 2004 2459 2477
11. N.L. Lancaster, T. Welton, and G.B. Young J. Chem. Soc. Perkin Trans. 2 2001 2267 2270
12. N.L. Lancaster, T. Welton, and G.B. Young J. Org. Chem. 69 2004 5986 and references cited therein
13. C. Wheeler, K.N. West, C.L. Liotta, and C.A. Eckert Chem. Commun. 2001 887 888
14. C. Chiappe, D. Pieraccini, and P. Saullo J. Org. Chem. 68 2003 6710 6715
15. See inter alia: D.W. Kim, and D.Y. Chi Angew. Chem., Int. Ed. 43 2004 483 484 and references cited therein
16. D.W. Kim, C.E. Song, and D.Y. Chi J. Org. Chem. 68 2003 4281 4285
17. L. Bianchi, R. Germani, and G. Savelli Tetrahedron Lett. 44 2003 2027 2029
18. L. Bianchi, R. Germani, and G. Savelli Tetrahedron Lett. 44 2003 6583 6585
19. N.M.T. Lourenco, and C.A.M. Afonso Tetrahedron 59 2003 789 794
20. Z.M.A. Judh, H. Shen, B.C. Chi, and L. Feng Tetrahedron Lett. 43 2002 9381 9384
21. M. Cavazza, and F. Pietra Tetrahedron Lett. 45 2004 3633 3634
22. C. Reichardt Solvents and Solvent Effects in Organic Chemistry 3rd ed. 2003 Wiley-VCH Weinheim pp 237-273 and references cited therein
23. 8
24. A. Maia Pure Appl. Chem. 67 1995 697 702 and references cited therein
25. D. Albanese, D. Landini, A. Maia, and M. Penso Ind. Eng. Chem. Res. 40 2001 2396 2401 and references cited therein
26. D. Landini, A. Maia, and F. Montanari J. Am. Chem. Soc. 100 1978 2796 2801 and references cited therein
27. A. Mele, C.D. Tran, and S.H. De Paoli Lacerda Angew. Chem., Int. Ed. 42 2003 4364 4366
28. A.G. Avent, P.A. Chaloner, M.P. Day, K.R. Seddon, and T. Welton J. Chem. Soc., Dalton Trans. 1994 3405 3413
29. M.J. Muldoon, C.M. Gordon, and I.R. Dunkin J. Chem. Soc., Perkin Trans. 2 2001 433 435
30. S.N. Baker, G.A. Baker, and F.V. Bright Green Chem. 4 2002 165 169
31. L. Crowhurst, N.L. Lancaster, J.M.P. Arlandis, and T. Welton Phys. Chem. Chem. Phys. 5 2003 2790 2794
32. C.E. Cannizzaro, and K.N. Houk J. Am. Chem. Soc. 124 2002 7163 7169
33. Recent ATR-IR measurements have proven a preferential interaction between anions and water in ILs. See inter alia: L. Cammarata, S.G. Kazaria, P.A. Salter, and T. Welton Phys. Chem. Chem. Phys. 3 2001 5192 5200
34. 2a