Theoretical insight into the mechanism of [3 + 2] cycloaddition reactions of 1,3-disila-2-group-13 atomic anions [>Si=M=Si<]- (M = B, Al, Ga, In, and Tl)

Organometallics

Volumn 26, Issue 18, 2007, Pages 4432-4438

  Hsiao, Jun ^a   Su, Ming Der ^a  

^a NATIONAL CHIAYI UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIVITY; DENSITY FUNCTIONAL THEORY; ELECTRONEGATIVITY; NEGATIVE IONS; OLEFINS; POTENTIAL ENERGY SURFACES;

1,3-DISILA-2-GROUP-13 ATOMIC ANIONS; ALLENIC ANION SPECIES; MODEL REACTANTS; SINGLET-TRIPLET ENERGY SPLITTING;

CYCLOADDITION;

EID: 34548550496     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om7002943     Document Type: Article

References (67)

1. For recent reviews, see: (a) Cowley, A. H. Polyhedron 1984, 3, 389.
2. (b) Cowley, A. H. Acc. Chem. Res. 1984, 17. 386.
3. (c) Cowley, A. H.; Norman, N. C. Prog. Inorg. Chem. 1986, 34, 1.
4. (d) Scherer, O. J. Angew. Chem., Int. Ed. Engl. 1990, 29, 1104.
5. (e) Weber, L. Chem. Rev. 1992, 92, 1839.
6. (f) Esoudie, J.; Couret, C.; Ranaivonjatovo, H.; Satge, J. Coord. Chem. Rev. 1994, 130, 421.
7. (g) Driess, M. Coord. Chem. Rev. 1995, 145, 1.
8. (h) Okazaki, R.; West, R. Adv. Organomet. Chem. 1996, 39, 31.
9. (i) Klinkhammer, K. W. Angew. Chem., Int. Ed. Engl. 1997, 36, 2320.
10. (j) Barrau, J.; Rina, G. Coord. Chem. Rev. 1998, 178, 593.
11. (k) Power, P. P. J. Chem. Soc., Dalton Trans. 1998, 2939.
12. (1) Tokitoh, N.; Matsumoto, T.; Okazaki, R. Bull. Chem. Soc. Jpn. 1999, 72, 1665.
13. (m) Robinson, G. H. Acc. Chem. Res. 1999, 32, 773.
14. (n) Leigh, W. J. Pure Appl. Chem. 1999, 71, 453.
15. (o) Tokitoh, N. Pure Appl. Chem. 1999, 71, 495.
16. (p) Power, P. P. Chem. Rev. 1999, 99, 3463.
17. (q) Jones, C. Coord. Chem. Rev. 2001, 215, 151.
18. (r) Grutzmacher, H.; Fassler, T. F. Chem. - Eur. J. 2000, 6, 2317.
19. (s) Clyburne, J. A. C.; McMullen, N. Coord. Chem. Rev. 2000, 210, 73.
20. (t) Sasamori, T.; Arai, Y.; Takeda, N.; Okazki, R.; Furukawa, Y.; Kimura, M.; Nagase, S.; Tokitoh, N. Bull. Chem. Soc. Jpn. 2002, 75, 661.
21. (a) Brook, A. G.; Abdesaken, F.; Gutekunst, B.; Gutekunst, G.; Kallury, R. K. J. Chem. Soc., Chem. Commun. 1981, 191.
22. (b) West, R.; Fink, M. J.; Michl, J. Science 1981, 214, 1343.
23. (c) Smit, C. N.; Lock, F. M.; Bickelhaupt, F. Tetrahedron Lett. 1984, 25, 3011.
24. (d) Wiberg, N.; Schurz, K.; Fisher, G. Angew. Chem., Int. Ed. Engl. 1985, 24, 1053.
25. (e) Wiberg, N.; Schurz, K.; Reber, G.; Müller. G. J. Chem. Soc., Chem. Commun. 1986, 591.
26. (f) Smit, C. N.; Bickelhaupt, F. Organometallics 1987, 6, 1156.
27. (g) Niesmann, J.; Klingebiel, U.; Schäfer, M.; Boese, R. Organometallics 1998, 17, 947.
28. (h) Driess. M.; Rell, S.; Pritzkow, H. J. Chem. Soc., Chem. Commun. 1995, 253.
29. (i) Suzuki, H.; Tokitoh, N.; Nagase, S.; Okazaki, R. J. Am. Chem. Soc. 1994, 116. 11578.
30. (j) Suzuki, H.; Tokitoh, N.; Okazaki, R.; Nagase, S.; Goto, M. J. Am. Chem. Soc. 1998, 120, 11096.
31. (a) Weidenbruch, M. Eur. J. Inorg. Chem. 1999, 373.
32. (b) Power, P. P. Chem. Rev. 1999, 99, 3463.
33. (c) Escudiė, J.; Ranaivonjatovo, H. Adv. Organomet. Chem. 1999, 44, 113.
34. (d) Weidenbruch, M. Organometallics 2003, 22, 4348.
35. (e) Escudiė, J.; Ranaivonjatovo, H.; Rigon, L. Chem. Rev. 2000, 100, 3639.
36. (f) Eichler, B.; West, R. Adv. Organomet. Chem. 2000, 46, 1.
37. (g) Ishida, S.; Iwamoto, T.; Kabuto, C.; Kira, M. Nature 2003, 421, 725.
38. Nakata, N.; Sekiguchi, A. J. Am. Chem. Soc. 2006, 128, 422.
39. Nakata, N.; Izumi, R.; Lee, V. Y.; Ichinohe, M.; Sekiguchi, A. J. Am. Chem. Soc. 2004, 126, 5058.
40. According to a reviewer's comment, multiply bonded compounds of heavier main group elements often undergo [2 + 2] reactions with alkenes and alkynes. In fact, we have checked the [2 + 2] reactions using the RHF/ 3-21G(d), B3LYP/3-21G(d), RHF/LANL2DZ, and B3LYP/6-31G(d) levels of theory. However, they all failed. Only the [3 + 2] reactions can work based on the present theoretical calculations.
41. (a) Becke. A. D. Phys. Rev. A 1988, 38, 3098.
42. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
43. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
44. (a) Su, M.-D. J. Phys. Chem. A 2004, 108, 823.
45. (b) Su, M.-D. Inorg. Chem. 2004, 43, 4846.
46. (c) Su, M.-D. Eur. J. Chem. 2004, 10, 5877, and related references therein.
47. (a) Dunning, T. H., Jr.: Hay. P. J. In Modern Theoretical Chemistry; Schaefer, H. F., III, Ed.; Plenum: New York, 1976; pp 1-28.
48. (b) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270.
49. (c) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 284.
50. (d) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
51. (e) Check, C. E.; Faust, T. O.; Bailey, J. M.; Wright, B. J.; Gilbert, T. M.; Sunderlin, L. S. J. Phys. Chem. A 2001, 105, 8111.
52. It was reported that the shape and symmetry properties of the Kohn-Sham orbitais are very similar to those calculated by the Hartree-Fock method. The energy order of the occupied orbitais is in most cases in agreement among the various methods. We are thus confident that the present calculation results should be reliable. See: Stowasser, R.; Hoffmann, R. J. Am. Chem. Soc. 1999, 121, 3414.
53. Pople, J. A.; Head-Gordon, M.; Raghavachari, K. J. Chem. Phys. 1987, 87, 5968.
54. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; 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.; 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; Gaussian, Inc., Wallingford, CT, 2003.
55. Jorgenson, W. L.; Salem, L. In The Organic Chemist's Book of Orbitals; Academic Press: New York, 1973; pp 122-125.
56. (a) Woodward, R. B.; Hoffmann, R. Angew. Chem., Int. Ed. Engl. 1969, 8, 781.
57. (b) Woodward, R. B.; Hoffmann, R. Angew. Chem., Int. Ed. Engl. 1969, 8, 817.
58. (a) Su, M.-D. J. Phys. Chem. A 2002, 106, 9563.
59. (b) Su, M.-D. Eur. J. Chem. 2004, 10, 5877.
60. Su, M. D. Int. J. Quantum Chem. 1993, 48, 249.
61. Hammond, G. S. J. Am. Chem. Soc. 1954, 77, 334.
62. Allred, A. L. J. Inorg. Nucl. Chem. 1961, 17, 215, and references therein.
63. For details, see: (a) Shaik, S.; Schlegel, H. B.; Wolfe, S. In Theoretical Aspects of Physical Organic Chemistry; John Wiley & Sons Inc.: New York, 1992.
64. (b) Pross, A. In Theoretical and Physical Principles of Organic Reactivity; John Wiley & Sons Inc.: New York, 1995.
65. (c) Shaik, S. Prog. Phys. Org. Chem. 1985, 15, 197.
66. (a) The first paper that originated the CM model: Shaik, S. J. Am. Chem. Soc. 1981, 103, 3692.
67. (b) About the most updated review of the CM model: Shaik, S.; Shurki, A. Angew. Chem., Int. Ed. 1999, 38, 586.