Reversible, room-temperature ionic liquids. Amidinium carbamates derived from amidines and aliphatic primary amines with carbon dioxide

Chemistry of Materials

Volumn 19, Issue 5, 2007, Pages 967-969

  Yamada, Taisuke ^a   Lukac, Paul Joseph ^a   George, Mathew ^a   Weiss, Richard G ^a  

^a GEORGETOWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CLOSED VESSEL; MOLECULAR NITROGEN; ROOM-TEMPERATURE IONIC LIQUIDS (RTIL);

AMINES; CARBON DIOXIDE; ELECTROSTATICS; ESTERS; MOLECULAR DYNAMICS; ORGANIC SOLVENTS;

IONIC LIQUIDS;

EID: 33947256943     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm062622a     Document Type: Article

References (37)

1. (a) Welton, T. Chem. Rev. 1999, 99, 2071-2083.
2. (a) Short, P. L. Chem. Eng. News 2006 (April 24), 15-21.
3. (b) Weyershausen, B.; Hell, K.; Hesse, U. Green Chem. 2005, 7, 283-287.
4. (c) Seddon, K. R. Nat. Mater. 2003, 2, 363-365.
5. (a) Ionic Liquids: Industrial Applications to Green Chemistry; Rogers, R. D., Seddon, K. R., Eds.; ACS Symposium Series 818; American Chemical Society: Washington, DC, 2002.
6. (b) Ionic Liquids IIIA: Fundamentals, Progress, Challenges, and Opportunities; Rogers, R. D., Seddon, K. R., Eds.; ACS Symposium Series 901; American Chemical Society: Washington, DC, 2005.
7. DeSimone, J. M., Tumas, W., Eds. Green chemistry using liquid and supercritical carbon dioxide; Oxford University Press: New York, 2003.
8. Hori, Y.; Nagano, Y.; Nakao, J.; Fukuhara, T.; Taniguchi, T. Chem. Express 1986, 1, 224-227.
9. Jessop, P. G.; Heldebrant, D. J.; Li, X.; Eckert, C. A.; Liotta, C. L. Nature 2005, 436, 1102.
10. 6 Hori, Y.; Nagano, Y.; Nakao, J.; Taniguchi, H. Chem. Express 1986, 1, 173-176.
11. (a) Hori, Y.; Nagano, Y.; Miyake, S.; Teramoto, S.; Taniguchi, T. Chem. Express 1986, 1, 311-314.
12. (b) Heldebrant, D. J.; Jessop, P. G.; Thomas, C. A.; Eckert, C. A.; Liotta, C. L. J. Org. Chem. 2005, 70, 5335-5338.
13. Liu, Y.; Jessop, P. G.; Cunningham, M.; Eckert, C. A.; Liotta, C. L. Science 2006, 313, 958-960.
14. (a) Terech, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133-3159.
15. (b) Weiss, R. G., Terech, P., Eds. Molecular Gels. Materials with Self-Assembled Fibrillar Networks; Springer: Dordrecht, The Netherlands, 2006.
16. (c) George, M.; Weiss, R. G. Acc. Chem Res. 2006, 39, 489-497.
17. (a) George, M.; Weiss, R. G. J. Am. Chem. Soc. 2001, 123, 12393-10394.
18. (b) George, M.; Weiss, R. G. Langmuir 2002, 18, 7124-7135.
19. (c) George, M.; Weiss, R. G. Langmuir 2003, 19, 1017-1025.
20. Rudkevich, D. M.; Xu, H. Chem. Commun. 2005, 2651-2659.
21. Hampe, E. M.; Rudkevich, D. M. Tetrahedron 2003, 59, 9619-9625.
22. (a) Hoerr, C. W.; Harwood, H. J.; Ralston, A. W. J. Org. Chem. 1944, 9, 201-210.
23. (b) Lallau, J.-P.; Masson, J.; Guerin, H. Bull. Soc. Chim. Fr. 1972, 3111-3112.
24. (c) Nakamura, N.; Okada, M.; Okada, Y.; Sugita, K. Mol. Cryst. Liq. Cryst. 1985, 116, 181-186.
25. We have not tested yet all of the RTILs with acyclic aliphatic amidines for their ability to remain liquids in the presence of water. However, we believe that they will behave like the C1-C system.
26. 2. The temperature ranges and pressures over which they remain stable will be determined in future experiments.
27. House, H. O. Modem Synthetic Reaction, 2nd ed.; W. A. Benjamin: Menlo Park, CA, 1972; p 2.
28. (a) Cadena, C.; Anthony, J. L.; Shah, J. K.; Morrow, T. I.; Brenneck, J. F.; Maginn, E. J. J. Am. Chem. Soc. 2004, 126, 5300-5308.
29. (b) Shiflett, M.; Yokozaki, A. Ind. Eng. Chem. Res. 2005, 44, 4453-4464.
30. -1. Protonation of the amidines has been reported: Corset, C.; Froment, F. J. Phys. Chem. 1990, 94, 6908-6911.
31. George, M.; Weiss, R. G. Langmuir 2003, 19, 8168-8176.
32. (a) Reichardt, C. Chem. Rev. 1994, 94, 2319-2358.
33. (b) Reichardt, C. Chem. Soc. Rev. 1992, 21, 147-153.
34. Richter-Egger, D. L.; Tesfal, A.; Flamm, S. J.; Tucker, S. A. J. Chem. Educ. 2001, 78, 1375-1378.
35. Fletcher, K. A.; Storey, I. A.; Hendricks, A. E.; Pandey, S.; Pandey, S. Green Chem. 2001, 3, 210-215.
36. 2 through the ionic layer.
37. See for example: Mandal, P. K.; Samanta, A. J. Phys. Chem. B 2005, 109, 15172-15177.