Computational studies of pericyclic reactions between aminoalanes and ethyne, ethene, and dienes. A reactive aminoalane that should prefer [2 + 2] and [4 + 2] cyclizations to dimerization

Organometallics

Volumn 28, Issue 3, 2009, Pages 787-794

  Bailey, John M ^a   Check, Catherine E ^a   Gilbert, Thomas M ^a  

^a NORTHERN ILLINOIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

[2 + 2] CYCLOADDITION; [4 + 2] CYCLOADDITION; ALN; CHEMICAL BEHAVIORS; COMPUTATIONAL STUDIES; CYCLIZATIONS; PERICYCLIC REACTIONS; REACTION ENERGIES;

BUTADIENE; CHEMICAL REACTIVITY; CYCLIZATION; DIMERIZATION; ETHYLENE;

ISOMERS;

EID: 61849137314     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800515e     Document Type: Article

References (36)

1. McGee, A.; Dale, F. S.; Yoon, S. S.; Hamilton, T. P. In Computational Organometallic Chemistry; Cundari, T. R., Ed.; Marcel Dekker: New York, 2001; pp 381-396.
2. 2 with increasing levels of sophistication. For a recent, very high-level approach, see: Grant, D. J.; Dixon, D. A. J. Phys. Chem. A 2006, 110, 12955-12962.
3. (a) Power, P. P. Chem. Rev. 1999, 99, 3463-3503.
4. (b) Brothers, P. J.; Power, P. P. Adv. Organomet. Chem. 1996, 39, 1-69.
5. (a) Bissett, K. M.; Gilbert, T. M. Organometallics 2004, 23, 850-854.
6. (b) Gilbert, T. M. Organometallics 1998, 17, 5513-5520.
7. Gilbert, T. M.; Bachrach, S. M. Organometallics 2007, 26, 2672-2678.
8. Waggoner, K. M.; Ruhlandt-Senge, K.; Wehmschulte, R. J.; He, X.; Olmstead, M. M.; Power, P. P. Inorg. Chem. 1993, 32, 2557-2561.
9. 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.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, A. D.; Rabuck, K. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; 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.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A. 11.4; Gaussian, Inc., Pittsburgh, PA, 1998.
10. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502-16513.
11. 2 core. Similar reasoning applies to formation of 7 prox and 7 dist. If the reactions are endothermic, then regardless of the barrier height, separation of the tricyclic product into 1 and cyclopentadiene will be preferred.
12. Check, C. E.; Gilbert, T. M. J. Org. Chem. 2005, 70, 9828-9834.
13. The M06 suite of DFT models has been so calibrated for several databases of small molecules, showing considerable promise in its energetic predictions. However, the suite still needs to be tested with molecules of the size in this work. We plan to calibrate the M06 suite against the OG2Rx methods in the future using large molecules. See: Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241.
14. A key problem with the B3LYP model, for example, is that its thermochemistry predictions decrease substantially and systematically in accuracy as the number of carbon atoms increases. See ref 10 and: Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. J. Chem. Phys. 2000, 112, 7374-7383.
15. Gille, A. L.; Gilbert, T. M. J. Chem. Theory Comput. 2008, 4, 1681-1689.
16. (a) Vreven, T.; Morokuma, K. J. Phys. Chem. A 2002, 106, 6167-6170.
17. (b) Vreven, T.; Morokuma, K. J. Chem. Phys. 1999, 111, 8799-8803.
18. Curtiss, L. A.; Raghavachari, K. Theor. Chem. Acc. 2002, 108, 61-70.
19. Lynch, B. J.; Truhlar, D. G. J. Phys. Chem. A 2001, 105, 2936-2941.
20. Gilbert, T. M. J. Phys. Chem. A 2004, 108, 2550-2554.
21. Himmel, H.-J. Eur, J. Inorg. Chem. 2003, 2153-2163.
22. Müller, J. J. Am. Chem. Soc. 1996, 118, 6370-6376.
23. Nakamura, K.; Makino, O.; Tachibana, A.; Matsumoto, K. J. Organomet. Chem. 2000, 611, 514-524.
24. Timoshkin, A. Y.; Bettinger, H. F.; Schaefer, H. F., III J. Am. Chem. Soc. 1997, 119, 5668-5678.
25. Hamilton, T. P.; Shaikh, A. W. Inorg. Chem. 1997, 36, 754-755.
26. Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Bohmann, J. A.; Morales, C. M.; Weinhold, F. NBO 5.0; Theoretical Chemistry Institute, University of Wisconsin, Madison, WI, 2001.
27. (a) Glendening, E. D.; Weinhold, F. J. Comput. Chem. 1998, 19, 593-609.
28. (b) Glendening, E. D.; Weinhold, F. J. Comput. Chem. 1998, 19, 610-627.
29. (c) Glendening, E. D.; Weinhold, F. J. Comput. Chem. 1998, 19, 628-646.
30. Wiberg, K. B. Tetrahedron 1968, 24, 1083-1096.
31. For two examples among many, see: (a) Bachrach, S. M.; Gilbert, J. C. J. Org. Chem. 2004, 69, 6357-6364.
32. (b) Leach, A. G.; Goldstein, E.; Houk, K. N. J. Am. Chem. Soc. 2003, 125, 8330-8339.
33. Isomers are designated on the basis of three options: Al means the vinyl substituent lies on the aluminum side of the Al - N bond, and N means it lies on the nitrogen side; prox means the vinyl substituent lies on the six-membered-ring side of the Al - N bond, and dist means it lies on the opposite side; cis means the butadiene adopts a cis geometry, and trans means it adopts a trans geometry.
34. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper & Row: New York, NY, 1987; Chapter 2.3.
35. (a) Gilbert, T. M. Organometallics 2005, 24, 6445-6449.
36. (b) Gilbert, T. M. Organometallics 2003, 22, 3748-3752.