Theoretical study of the michael addition of acetylacetone to methyl vinyl ketone catalyzed by the ionic liquid 1-butyl-3-methylimidazolium hydroxide

International Journal of Quantum Chemistry

Volumn 110, Issue 5, 2010, Pages 1056-1062

  Wei, Xiaofeng ^a   Zhang, Dongju ^a   Zhang, Changqiao ^a   Liu, Chengbu ^a  

^a SHANDONG UNIVERSITY   (China)

Author keywords

Catalysis; DFT; Ionic liquids; Michael addition

Indexed keywords

ACETYLACETONE; BASIC IONIC LIQUID; CATALYTIC ROLE; DENSITY FUNCTIONAL THEORY CALCULATIONS; INTERMOLECULAR HYDROGEN; ION PAIRS; METHYL VINYL KETONES; MICHAEL ADDITION REACTIONS; MICHAEL ADDITIONS; REACTION MECHANISM; REACTION SYSTEM; THEORETICAL STUDY; UNCATALYZED REACTIONS;

ACETONE; ADDITION REACTIONS; CATALYSIS; DENSITY FUNCTIONAL THEORY; HYDROGEN BONDS; IONIZATION OF LIQUIDS; ORGANIC COMPOUNDS; POSITIVE IONS; PROBABILITY DENSITY FUNCTION;

IONIC LIQUIDS;

EID: 76649108544     PISSN: 00207608     EISSN: 1097461X     Source Type: Journal    
DOI: 10.1002/qua.22028     Document Type: Article

References (49)

1. Seddon, K. R. J Chem Technol Biotechnol 1997, 68, 351.
2. Wassercheid, P.; Keim, W. Angew Chem Int Ed Engl 2000, 39, 3772.
3. Huddleston, J. G.; Visser, A. E.; Reichert, W. M.; Willauer, H. D.; Broker, G. A.; Rogers, R. D. Green Chem 2001, 3, 156.
4. Rogers, R. D.; Seddon, K. R., Eds. Ionic Liquids: Industrial Applications to Green Chemistry; ACS Symposium Series 818; American Chemical Society: Washington, DC, 2002.
5. Welton, T. Chem Rev 1999, 99, 2071.
6. Chiappe, C.; Capraro. D.; Conte, V.; Pieraccini, D. Org Lett 2001, 3, 1061.
7. Stark, A.; MacLean, B.; Singer, R. D. J Chem Soc Dalton Trans 1999, 63.
8. Larson, A. S.; Holbrey, J. D.; Tham, F. S.; Reed, C. A. J Am Chem Soc 2002, 122, 7256.
9. Sheldon, R. Chem Commun 2001, 2399.
10. Yadav, J. S.; Reddy, B. V. S.; Basak, A. K.; Narsaiah, A. V. Chem Lett 2003, 32, 988.
11. Zhao, D. B.; Wu, M.; Kou, Y.; Min, E. Catal Today 2002, 74, 157.
12. Ranu, B. C.; Dey, S. S.; Hajra, A. Tetrahedron 2003, 59, 2417.
13. Welton, T. Coord Chem Rev 2004, 248, 2459.
14. Boon, J. A.; Levinsky, J. A.; Pflug, J. I.; Wilkes, J. S. J Org Chem 1986, 51, 480.
15. Del Popolo, M. G.; Voth, G. A. J Phys Chem B 2004, 108, 1744.
16. Hunt, P. A.; Gould, I. R. J Phys Chem A 2006, 110, 2269.
17. Hunt, P. A.; Kirchner, B.; Welton T. Chem Eur J 2006, 12, 6762.
18. Shah, J.; Brennecke, J.; Maginn, E. Green Chem 2002, 4, 112.
19. Lynden-Bell, R. M.; Atames, N. A.; Vasilyuk, A.; Hanke, C. G. Mol Phys 2002, 100, 3225.
20. Youngs, T. G. A.; Del Popolo, M. G.; Kohanoff, R. M. J Phys Chem B 2006, 110, 5697.
21. Del Popolo, M. G.; Lynden-Bell, R. M.; Kohanoff, J. J Phys Chem B 2005, 109, 5895.
22. Morrow, T. I.; Maginn, E. J. J Phys Chem B 2002, 106, 12807.
23. Barghava, B. L.; Balasubramanian, S. Chem Phys Lett 2006, 417, 486.
24. Rey-Castro, C.; Vega, L. F. J Phys Chem B 2006, 110, 14426.
25. Sun, H.; Zhang, D. J.; Wang, F.; Liu, C. B. J Phys Chem A 2007, 111, 4535.
26. Sun, H.; Zhang, D. J. J Phys Chem A 2007, 111, 8036.
27. Bessac, F.; Maseras, F. J Comput Chem 2008, 29, 892.
28. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992.
29. Leonard, J.; Diez-Barra, E.; Merino, S. Eur J Org Chem 1998, 63, 2051.
30. Fan, Q. H.; Li, A. S.; Chun, A. S. C. Chem Rev 2002, 102, 3385.
31. Yamaguchi, M.; Iagarashi, Y.; Reddy, R. S.; Shirashi, T.; Hirama, M. Tetrahedron 1997, 53, 11223.
32. Yamaguchi, M.; Shirashi, T.; Iagarashi, Y.; Hirama, M. Tetrahedron Lett 1994, 35, 8233.
33. Srivastava, N.; Banik, B. K. J Org Chem 2003, 68, 2109.
34. Shimizu, K. I.; Mivagi, M.; Kan-No, T.; Kodama, T.; Kitayama, Y. Tetrahedron Lett 2003, 44, 7421.
35. Zhang, Z.; Dong, Y. W.; Wang, G. W.; Komatsu, K. Synlett 2004, 61.
36. Ranu, B. C.; Bhar, S.; Sarkar, D. C. Tetrahedron Lett 1991, 32, 2811.
37. Ranu, B. C.; Bhar, S. Tetrahedron 1992, 48, 1327.
38. Horvath, A. Tetrahedron Lett 1996, 37, 4423.
39. Ranu, B. C.; Banerjee, S. Org Lett 2005, 7, 3049.
40. Ranu, B. C.; Banerjee, S.; Jana, R. Tetrahedron 2007, 63, 776.
41. Becke, A. D. Phys Rev A 1988, 38, 3098.
42. Lee, C.; Yang, W. T.; Parr, R. G. Phys Rev B 1988, 37, 785.
43. Fukui, K. J Phys Chem 1970, 74, 4161.
44. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J Chem Phys 1985, 83, 735.
45. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem Rev 1988, 88, 899.
46. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al- Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision D. 01; Gaussian, Inc.: Wallingford CT, 2004.
47. Yamabe, S.; Tsuchida, N.; Miyajima, K. J Phys Chem A 2004, 108, 2750.
48. Fukui, K.; Fujimoto, H. Frontier Orbitals and Reaction Paths: Selected Papers of Kenichi Fukui; World Scientific: Singapore, 1997.
49. Hoffmann, R. Rev Mod Phys 1988, 60, 601.