Mechanisms for the formation of epoxide and chlorine- containing products in the oxidation of ethylene by chromyl chloride: A density functional study

Canadian Journal of Chemistry

Volumn 77, Issue 9, 1999, Pages 1476-1491

  Torrent, Maricel ^a   Deng, Liqun ^b   Duran, Miquel ^a   Solà, Miquel ^a   Ziegler, Tom ^b  

^a UNIVERSITY OF GIRONA   (Spain)

^b UNIVERSITY OF CALGARY   (Canada)

Author keywords

Chromyl chloride; DFT; Epoxide; Oxidation of ethylene; Reaction mechanisms

Indexed keywords

1,2 DICHLOROETHANE; ALKENE; ALPHA CHLOROHYDRIN; CHLORIDE; CHLORINE; EPOXIDE; ETHYLENE; OXYGEN; WATER;

ARTICLE; CHEMICAL REACTION; DENSITY; OXIDATION; SYNTHESIS;

EID: 0033324783     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v99-148     Document Type: Article

References (95)

1. (a) S.J. Cristol and K.R. Eilar. J. Am. Chem. Soc 72, 4353 (1950)
2. (b) R.A. Stairs, D.G.M. Diaper, and A.L. Gatzke. Can. J. Chem 41, 1059 (1963)
3. (c) F. Freeman. Rev. React. Species Chem. React 1, 37 (1973)
4. (d) A. Wahhab. Ph.D. thesis. University of Calgary, Calgary. 1987.
5. (d) F.W. Bachelor and U.O. Cheriyan. Can. J. Chem. 50, 4022 (1972).
6. (a) F.A. Carey and R.J. Sundberg. Advanced organic chemistry. Plenum, New York. 359 1977
7. (b) W.A. Nugent and J.M. Mayer. Metal-ligand multiple bonds. Wiley, New York. 248 1988.
8. (a) K.B. Wiberg (Editor). Oxidation in organic chemistry. Part A. Academic Press, New York. 1965. pp. 1-68
9. (b) M. Schröder. Chem. Rev 80, 187 (1980).
10. (a) R.A. Walton, Prog. Inorg. Chem 16, 1 (1972)
11. (b) J. San Filippo, Jr., and C. Chern. J. Org. Chem 42, 2182 (1977)
12. (c) F. Freeman, C.R. Armstead, M.G. Essjg, E.L. Karchefski, C.J. Kojima, V.C. Manopoli, and A.H. Wickman. J. Chem. Soc. Chem. Commun 65 (1980).
13. K.B. Sharpless, A.Y. Teranishi, and J.-E. Bäckvall. J. Am. Chem. Soc. 99, 3120 (1977).
14. F. Freeman. Chem. Rev. 75, 439 (1975).
15. E.G. Samsel, K. Srinivasan, and J.K. Kochi. J. Am. Chem. Soc. 107, 7606 (1985).
16. (a) A.K. Rappé and W.A. Goddard. J. Am. Chem. Soc 102, 5114 (1980)
17. (b) J. Am. Chem. Soc 104, 3287 (1982)
18. (c) T.H. Upton and A.K. Rappé. J. Am. Chem. Soc. 107, 1206 (1985).
19. A.K. Rappé and W.A. Goddard. Nature (London), 285, 311 (1980).
20. (a) J.-E. Bäckvall, M.W. Young, and K.B. Sharpless. Tetrahedron Lett. 40, 3523 (1977)
21. (b ) M.F. Schlecht and H.-J. Kim. Tetrahedron Lett. 27, 4889 (1986)
22. (c) M.F. Schlecht and H.-J. Kim. J. Org. Chem 54, 583 (1989).
23. (a) D. Mansuy, J. Leclaire, M. Fontecave, and P. Dausette. Tetrahedron, 40, 2847 (1984)
24. (b) J.P. Collman, J.I. Brauman, B. Meunier, S.A. Raybuck, and T. Kodadek. Proc. Natl. Acad. Sci. U.S.A. 81, 3245 (1984)
25. (c) P.R. Ortiz de Montellano and E.A. Komives. J. Biol. Chem. 260, 3330 (1985)
26. (d) J.P. Collman, J.I. Brauman, B. Meunier, T. Hayashi, T. Kodadek, and S.A. Raybuck. J. Am. Chem. Soc. 107, 2000 (1985)
27. (e) J.T. Groves and Y. Watanabe. J. Am. Chem. Soc. 108, 507 (1986)
28. (f) E.A. Komives and Ortiz de P.R. Montellano. J. Biol. Chem. 262, 9793 (1987).
29. A.G.M. Barrett, D.H.R. Barton, and T. Tsushima, J. Chem. Soc. Perkin Trans. 1, 639 (1980).
30. J.T. Groves and T.E. Nemo. J. Am. Chem. Soc. 105, 5786 (1983).
31. K. Yamaguchi, Y. Tekahara, and T. Fueno. In Applied quantum chemistry. Edited by V.H. Smith, H.F. Schaefer, and K. Morokuma. D. Reidel, Dordrecht 155 (1986).
32. (a) D.M. Walba, C.H. DePuy, J.J. Grabowski, and V.M. Bierbaum. Organometallics, 3, 498 (1984)
33. (b) H. Kang and J.L. Beauchamp. J. Am. Chem. Soc. 101, 6449 (1979).
34. K.A. Jørgensen and B. Schiøtt. Chem. Rev 90, 1483 (1990).
35. (a) M.J. Calhorda, A.M. Galvão, C. Ünaleroglu, A.A. Zlota, F. Frolow, and D. Milstein. Organometallics, 12, 3316 (1993)
36. (b) J. Bakos, Á. Orosz, S. Cserépi, I. Tóth, and D. Sinou. J. Mol. Catal.A, 116, 85 (1997)
37. (c) B. Bruin, M.J. Boerakker, J.J.J.M. Donners, B.E.C. Christiaans, P.P.J. Schlebos, R. Gelder, J.M.M. Smits, A.L. Spek, and A.W. Gal. Angew. Chem. Int. Ed. Engl 36, 2064 (1997); Angew. Chem. 109, 2153 (1997).
38. (c) B. Bruin, M.J. Boerakker, J.J.J.M. Donners, B.E.C. Christiaans, P.P.J. Schlebos, R. Gelder, J.M.M. Smits, A.L. Spek, and A.W. Gal. Angew. Chem. Int. Ed. Engl 36, 2064 (1997)
39. V.W. Day, W.G. Klemperer, S.P. Lockledge, and D.J. Main. J. Am. Chem. Soc. 112, 2031 (1990).
40. S. Baba, T. Ogura, and S. Kawaguchi. J. Chem. Soc. Chem. Commun. 910 (1972).
41. M. Lenarda, N.B. Pahor, M. Calligaris, M. Graziani, and L. Randaccio. J. Chem. Soc. Dalton Trans. 279 (1978).
42. (a) B.B. Ebbinghaus. Combust. Flame, 101, 311 (1995)
43. (b) C. Limberg, R. Köppe, and H. Schnöckel. Angew. Chem. 110, 512 (1998).
44. (a) E.J. Baerends, D.E. Ellis, and P. Ros. Chem. Phys. 2, 41 (1973)
45. (b) W. Ravenek. In Algorithms and applications on vector and parallel computers. Edited by H.J.J. te Riele, T.J. Dekker, and H.A. van de Vorst. Elsevier, Amsterdam. 1987.
46. (a) P.M. Borrigter, G. te Velde, and E.J. Baerends. Int. J. Quantum Chem. 33, 87 (1987)
47. (b) G. te Velde and E.J. Baerends. J. Comput. Phys 99, 84 (1992).
48. J. Krijn and E.J. Baerends. Fit functions in the HFS-methods; internal report. Free University of Amsterdam, Amsterdam. 1984.
49. (a) G.J. Snijders, E.J. Baerends, and P. Vernooijs. At. Nucl. Data Tables, 26, 483 (1982)
50. (b) P. Vernoois, G.J. Snijders, and E.J. Baerends. Slater type basis functions for the whole periodic system; internal report. Free University of Amsterdam, The Netherlands. 1981.
51. (a) G.J. Snijders, E.J. Baerends, and P. Ros. Mol. Phys. 36, 1789 (1978)
52. (b) Mol. Phys. 38, 1909 (1979).
53. O. Gunnarson and I. Lundquist. Phys. Rev B10, 1319 (1974).
54. S.H. Vosko, L. Wilk, and M. Nusair. Can. J. Phys 58, 1200 (1980).
55. A.D. Becke. Phys. Rev. A, 38, 2398 (1988).
56. (a) J.P. Perdew. Phys. Rev. Lett 55, 1655 (1985)
57. (b) Phys. Rev. B: Condens. Matter, 33, 8822 (1986)
58. (c) J.P. Perdew and Y. Wang. Phys. Rev. B: Condens. Matter, 33, 8800 (1986).
59. M. Torrent, P. Gili, M. Duran, and M. Solà. J. Chem. Phys. 104, 9499 (1996).
60. (a) L. Deng and T. Ziegler. Organometallics, 15, 3011 (1996)
61. (b) T. Ziegler and J. Li. Organometallics, 14, 214 (1995)
62. (c) L. Deng and T. Ziegler. Organometallics, 16, 716 (1997).
63. (a) L. Versluis and T. Ziegler. J. Chem. Phys 88, 322 (1988)
64. (b) L. Fan and T. Ziegler. J. Chem. Phys 95, 7401 (1991)
65. (c) G. Schreckenbach, J. Li, and T. Ziegler. Int. J. Quantum Chem. 56, 477 (1995).
66. L. Fan, L. Versluis, T. Ziegler, E.J. Baerends, and W. Ravenek. Int. J. Quantum Chem. Symp. 22, 173 (1988).
67. A. Banerjee, N. Adams, J. Simons, and R. Shephard. J. Phys. Chem 89, 52. (1985).
68. J. Baker. J. Comput. Chem 7, 385 (1986).
69. L. Fan and T. Ziegler. J. Chem. Phys. 92, 46 (1990).
70. K. Fukui. Acc. Chem. Res. 14, 363 (1981).
71. C. González and H.B. Schlegel. J. Phys. Chem 94, 5523 (1990).
72. L. Deng and T. Ziegler. Int. J. Quantum Chem. 52, 731 (1994).
73. (a) U. Pidun, C. Boehme, and G. Frenking. Angew. Chem. Int. Ed. Engl. 35, 2817 (1996)
74. (b) O. Gonzalez-Blanco, V. Branchadell, K. Monteyne, and T. Ziegler. Inorg. Chem. 37, 1744 (1998)
75. (c) J. Li, G. Schreckenbach, and T. Ziegler. J. Am. Chem. Soc. 117, 486 (1995)
76. (d) E. Folga and T. Ziegler. J. Am. Chem. Soc. 115, 5150 (1993).
77. R. Poli. Chem. Rev. 96, 2135 (1996).
78. (a) S. Kristyán and P. Pulay. Chem. Phys. Lett. 229, 175 (1994)
79. (b) T.C. Wright. J. Chem. Phys. 105, 7579 (1996)
80. (c) J.M. Pérez-Jordà and A.D. Becke. Chem. Phys. Lett. 233, 134 (1995)
81. (d) E. Ruiz, D.R. Salahub, and A. Vela. J. Phys. Chem. 100, 12 265 (1996)
82. (e) A. García, E.M. Cruz, C. Sarasola, and J.M. Ugalde. J. Phys. Chem. A, 101, 3021 (1997).
83. (a) E. Vedejs and K.A.J. Snoble. J. Am. Chem. Soc 95, 5778 (1973)
84. (b) M. Nagayama, O. Okumura, S. Noda, and A. Mori. J. Chem. Soc. Chem. Commun. 841 (1973).
85. M. Torrent, L. Deng, M. Duran, M. Solà, and T. Ziegler. Organometallics, 16, 13 (1997);
86. M. Torrent, L. Deng, and T. Ziegler. Inorg. Chem. 37, 1307 (1998).
87. S. Dapprich, G. Ujaque, F. Maseras, A. Lledós, D.G. Musaev, and K. Morokuma. J. Am. Chem. Soc. 118, 11 660 (1996).
88. A.J. DelMonte, J. Haller, K.N. Houk, K.B. Sharpless, D.A. Singleton, T. Strassner, and A.A. Thomas. J. Am. Chem. Soc 119, 9907 (1997).
89. A. Rosa, A.W. Ehlers, E.J. Baerends, J.G. Snijders, and G. te Velde. J. Phys. Chem. 100, 5690 (1996).
90. (a) K.P. Gable and T.N. Phan. J. Am. Chem. Soc. 115, 3036 (1993)
91. (b) J. Am. Chem. Soc. 116, 833 (1994).
92. M.A. Pietsch, T.V. Russo, R.B. Murphy, R.L. Martin, and A.K. Rappé. Organometallics, 17, 2716 (1998).
93. (a) T. Ziegler, J.G. Snijders, and E.J. Baerends. J. Chem. Phys. 74, 1271 (1981)
94. (b) G. Schreckenbach, J. Li, and T. Ziegler. Int. J. Quantum Chem. 56, 477 (1995).
95. C. Limberg and R. Köppe. Inorg. Chem. 38, 2106 (1999).