A comprehensive theoretical study on the coupling reaction mechanism of propylene oxide with carbon dioxide catalyzed by copper(I) cyanomethyl

Journal of Physical Chemistry A

Volumn 113, Issue 24, 2009, Pages 6710-6723

  Guo, Cai Hong ^a,b   Wu, Hai Shun ^b   Zhang, Xian Ming ^b   Song, Jiang Yu ^b   Zhang, Xiang ^b  

^a TAIYUAN UNIVERSITY OF TECHNOLOGY   (China)

^b SHANXI NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER CENTERS; COUPLING REACTION; CYCLIC CARBONATES; DENSITY FUNCTIONAL THEORY CALCULATIONS; EXPERIMENTAL OBSERVATION; IN-PROCESS; NATURAL BOND ORBITAL ANALYSIS; OVERALL REACTIONS; PROPYLENE OXIDE; REACTION FREE ENERGY; REACTION MECHANISM; THEORETICAL STUDY;

CARBON DIOXIDE; CARBON DIOXIDE PROCESS; CHARGE TRANSFER; CHEMICAL BONDS; COORDINATION REACTIONS; COPPER; COPPER OXIDES; DENSITY FUNCTIONAL THEORY; ION EXCHANGE; PROPYLENE;

ACTIVATED CARBON;

CARBON DIOXIDE; COPPER; EPOXIDE; NITRILE; ORGANOMETALLIC COMPOUND; PROPYLENE OXIDE;

ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMISTRY; COMPUTER SIMULATION;

CARBON DIOXIDE; CATALYSIS; COMPUTER SIMULATION; COPPER; EPOXY COMPOUNDS; MODELS, CHEMICAL; NITRILES; ORGANOMETALLIC COMPOUNDS;

EID: 67149143406     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp809471s     Document Type: Article

References (69)

1. Leitner, W. Coord. Chem. Rev. 1996, 155, 257.
2. Marks, T. J.; et al. Chem. Rev. 2001, 101, 953.
3. Shaikh, A. A. G.; Sivaram, S. Chem. Rev. 1996, 96, 951.
4. See, for example: (a) Paddock, R. L.; Ngugen, S. T. J. Am. Chem. Soc. 2001, 123, 11498.
5. (b) Yamaguchi, K.; Ebitani, K.; Yoshida, T.; Yoshida, H.; Kaneda, K. J. Am. Chem. Soc. 1999, 121, 4526.
6. (c) Yano, T.; Matsui, H.; Koiki, T.; Ishiguro, H.; Fujihara, H.; Yoshihara, M.; Maeshima, T. Chem. Commun. 1997, 1129.
7. (d) Darensbourg, D. J.; Holtcamp, M. W. Coord. Chem. Rev. 1996, 153, 155.
8. (e) Fujinami, T.; Suzuki, T.; Kamiya, M.; Fukuzawa, S.; Sakai, S. Chem. Lett. 1985, 14, 199.
9. (f) Kim, H. S.; Kim, J. J.; Lee, B. G.; Jung, O. S.; Jang, H. G.; Kang, S. O. Angew. Chem., Int. Ed. 2000, 39, 4096.
10. (g) Kmper, W. J.; Deller, D. V. J. Org. Chem. 1995, 60, 725.
11. (h) Kawanami, H.; Ikushima, Y. Chem. Commun. 2000, 2089.
12. (i) Caló, V.; Nacci, A.; Monopoli, A.; Fanizzi, A. Org. Lett. 2002, 4, 256.1.
13. (J) Kihara, N.; Hara, N.; Endo, T. J. Org. Chem. 1993, 58, 6.198.
14. (k) Li, F.; Xia, C.; Xu, L.; Sun, W.; Chen, G. Chem. Commun. 2003, 2042.
15. Lu, X.-B.; Liang, B.; Zhang, Y.-J.; Tian, Y.-Z.; Wang, Y.-M.; Bai, C.-X.; Wang, H.; Zhang, R. J. Am. Chem. Soc. 2004, 126, 3732.
16. (m) Shen, Y.M.; Duan, W.-L.; Shi, M. J. Org. Chem. 2003, 68, 1559.
17. (n) Li, F.; Xiao, L.; Xia, C.; Hu, B. Tetrahedron Lett. 2004, 8307.
18. (o) Jiang, J.-L.; Gao, F.; Hua, R.; Qiu, X. J. Org. Chem. 2005, 70, 381.
19. (p) Shen, Y.-M.; Duan, W.-L.; Shi, M. Eur. J. Org. Chem. 2004, 3080.
20. (q) Huang, J.-W.; Shi, M., J. Org. Chem. 2003, 68, 6705.
21. (r) Jing, H.; Edulji, S. K.; Gibbs, J. M.; Stern, C. L.; Zhou, H.; Nguyen, S. T. Inorg. Chem. 2004, 43, 4315.
22. (s) Sit, W. N.; Ng, S. M.; Kwong, K. Y.; Lau, C P. J. Org. Chem. 2005, 70, 8583.
23. (t) Man, M, L.; Lam, K. C.; Sit, W. N.; Ng, S. M.; Zhou, Z.; Lin, Z.; Lau, C P. Chem.-Eur. J. 2006, 12, 1004.
24. (a) Aida, T.; Inoue, S. J. Am. Chem. Soc. 1983, 105, 1304.
25. (b) Kojima, F.; Aida, T.; Inoue, S. J. Am. Chem. Soc. 1986, 108, 39.1.
26. (c) Hirai, Y.; Aida, T.; Inoue, S. J. Am. Chem. Soc. 1989, 111, 3062.
27. (d) Komatsu, M.; Aida, T.; Inoue, S. J. Am. Chem. Soc. 1991, 113, 8492.
28. (a) Carmona, E.; Palma, P.; Paneque, M.; Poveta, M. L. J. Am. Chem. Soc. 1986, 108, 6424.
29. (b) Carmona, E.; Gutihez-Puebla, E.; Marin, J. M.; Monge, A.; Paneque, M.; Poveta, M. L.; Ruiz, C. Am. Chem. Soc. 1989, 111, 2883.
30. Braunstein, P.; Matt, D.; Nobel, D. J. Am. Chem. Soc. 1988, 110, 3207.
31. (a) Darensbourg, D. J.; Grotsch, G. J. Am. Chem. Soc. 1985, 107, 7473.
32. (b) Darensbourg, D. J.; Ovalles, C. J. Am. Chem. Soc. 1987, 109, 3330.
33. Aye, K. T.; Gelmini, L.; Payne, N. C.; Vittal, J. J.; Puddephatt, R. J. J. Am. Chem. Soc. 1990, 112, 2464.
34. (a) Amatore, C.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 2819.
35. (b) Amatore, C.; Jutand, A. J. Electroanal. Chem. 1991, 306, 141.
36. Tsai, J. C.; Nicholas, K. M. J. Jim. Chem. Soc. 1992, 114, 5117.
37. (a) Sakaki, S.; Ohkubo, K. Inorg. Chem. 1988,27, 2020.
38. (b) Sakaki, S.; Ohkubo, K. Inorg. Chem. 1989, 28, 2583.
39. (c) Sakaki, S.; Ohkubo, K. Organometallics 1989, 8, 2970.
40. Sakaki, S.; Musashi, Y. Inorg. Chem. 1995, 34, 1914.
41. Braustein, P.; Matt, D.; Nobel, D. Chem. Rev. 1988, 88, 747.
42. Tsuda, T.; Chujo, Y.; Saegusa, T. J. Chem. Soc, Chem. Commun. 1976, 415.
43. Chisholm, M. H.; Cotton, F. A.; Extine, M. W.; Reichert, W. W. J. Am. Chem. Soc. 1978, 100, 1727.
44. Tsuda, T.; Chujo, Y.; Saegusa, T. J. Am. Chem. Soc. 1978, 100, 630.
45. Gambarotta, S.; Floriani, C.; Chiesi-Villa, A.; Guastini, C. J. Am. Chem. Soc. 1985, 107, 2985.
46. Aye, K.-T.; Ferguson, G.; Lough, A. J.; Puddephatt, R. J. Angew. Chem, Int. Ed. 1989, 28,161.
47. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
48. (b) Miehlich, B.; Savin, A.; Stall, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200.
49. (c) Lee, C.; Yang, W.; Parr, G. Phys. Rev. B 1988, 37, 785.
50. (d) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F. J. Phys. Chem. 1994, 98, 11623.
51. (a) Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154.
52. (b) Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523.
53. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
54. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650.
55. Reed, E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
56. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Gaussian 03, revision C.01; Gaussian, Inc.: Wallingford, CT, 2004.
57. Himo, F.; Lovell, T.; Hilgraf, R.; Rostovtsev, V. V.; Noodleman, L.; Sharpless, K. B.; Fokin, V. V. J. Am. Chem. Soc. 2005, 127, 210.
58. (a) Zhao, H.; Lin, Z.; Marder, T. B. J. Am. Chem. Soc. 2006, 128, 15637.
59. (b) Dang, L.; Zhao, H.; Lin, Z.; Marder, T. B. Oreanometallics 2007, 26, 2824.
60. Versluis, L.; Ziegler, T.; Fan, L. Inorg. Chem. 1990, 29, 4530.
61. Cordaro, J. G.; Bergman, R. G. J. Am. Chem. Soc. 2004, 126, 16912.
62. (a) Fukui, K. ; Fujimoto, H. In Mechanisms of Molecular Migrations; Thyagarajan, B. S., Ed.;'Interscience: New York, 1968; Vol. 2.
63. (b) Fukui, K. Agg. Chem. Res. 1971, 4, 57.
64. (c) Fukui, K. Angew. Chem., Int. Ed. Engl, 1982, 21, 801.
65. Liu, Z.; Torrent, M.; Morokuma, K. Qiganometallics 2002, 21, 1056-1071.
66. Sun, H.; Zhang, D. J. Phys. Chem. A 2007, 111, 8036.
67. Fraile, J. M.; García, J. L; Martínez-Merino, V.; Mayoral, J. A.; Salvatella, L. J. Am. Chem. Soc. 2001, 123, 7616.
68. Zhou, M.; Zhang, L.; Chen, M.; Zheng, Q.; Qin, Q. J. Phys. Chem. A 2000, 104, 10159.
69. Rauhut, G.; Pulay, P. J. Phys. Chem. 1995, 99, 3093.