Systematic errors in computed alkane energies using B3LYP and other popular DFT functionals

Organic Letters

Volumn 8, Issue 17, 2006, Pages 3631-3634

  Wodrich, Matthew D ^a   Corminboeuf, Clémence ^a   Schleyer, Paul Von Ragué ^a  

^a UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748591851     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061016i     Document Type: Article

References (65)

1. (a) Lynch, B. J.; Fast, P. L.; Harris, M.; Truhlar, D. G. J. Phys. Chem. A 2000, 104, 4811.
2. (b) Zhao, Y.; Tishchenko, O.; Truhlar, D. G. J. Phys. Chem. B 2005, 109, 19046.
3. (c) Tsuzuki, S.; Luthi, H. P. J. Chem. Phys. 2001, 114, 3949.
4. (d) Duncan, J. A.; Spong, M. C. J. Phys. Org. Chem. 2005, 18, 462.
5. (a) Raghavachari, K.; Stefanov, B. B.; Curtiss, L. A. Mol. Phys. 1997, 91, 555.
6. (b) Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. J. Chem. Phys. 1997, 106, 1063.
7. (c) Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople J. A. J. Chem. Phys. 2000, 112, 7374.
8. (d) Saeys, M.; Reyniers, M-F.; Marin, G. B.; van Speybroeck, V.; Waroquier, J. J. Phys. Chem. A 2003, 107, 9147.
9. (a) Feng, Y.; Liu, L.; Wang, J.-T.; Huang, H.; Guo, Q.-X. J. Chem. Inf. Comput. Sci. 2003, 43, 2005.
10. (b) Fu, Y.; Dong, X. Y.; Wang, Y. M.; Liu, L.; Guo, Q.-X. Chin. J. Chem. 2005, 23, 474.
11. (c) Coote, M. L.; Pross, A.; Radom, L. In Fundamental World of Quantum Chemistry; Brandas, E. J., Kryachko, E. S., Eds.; Kluwer Academic Publishers: The Netherlands, 2004; Vol. III, p 563.
12. (d) Izgorodina, E. I.; Coote, M. L.; Radom, L. J. Phys. Chem. A 2005, 109, 7558.
13. Redfern, P. C.; Zapol, P.; Curtiss, L. A.; Raghavachari, K. J. Phys. Chem. A 2000, 104, 5850.
14. (a) Check, C. E.; Gilbert, T. M. J. Org. Chem. 2005, 70, 9828.
15. (b) Schreiner, P. R.; Fokin, A. A.; Pascal, R. A.; deMeijere, A. Org. Lett. 2006, 8, 3635.
16. (c) Grimme, S. Angew. Chem. Int. Ed. 2006, 45, 625-629 and references cited.
17. (a) Gaussian 98. Revision A.11: Frisch, M. J.; et al. Gaussian, Inc.: Pittsburgh, 1998.
18. (b) Gaussian 03, Revision C.02: Frisch, M. J.; et al. Gaussian, Inc., Wallingford CT, 2004.
19. (c) MOLPRO, a package of ab initio programs designed by Werner, J.-J.; Knowles, P. J. version 2002.1. contributed by Amos. R. D.; Bernhardsson, A.; Berning, A.; et al. Full references for 6 are in the Supporting Information.
20. (a) Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200.
21. (b) Slater, J. C. Quantum Theory of Molecular Solids: The Self-Consistent Field for Molecular and Solids; McGraw-Hill: New York, 1974; Vol. 4.
22. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
23. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
24. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
25. (a) Handy, N. C.; Cohen, A. J. Mol. Phys. 2001, 99, 403.
26. (b) Hoe, W. M.; Cohen, A. J.; Handy, N. C. Chem. Phys. Lett. 2001, 341, 319.
27. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77. 3865.
28. Perdew, J. P. In Electronic Structure in Solids '91; Ziesche, P., Eschig, H., Eds.; Akademie Verlag: Berlin, 1991; p 11.
29. Hamprecht, F. A.; Cohen, A. J.; Tozer, D. J.; Handy, N. C. J. Chem. Phys. 1998, 109, 6264.
30. Adamo, C.; Barone, V. J. Chem. Phys. 1998, 108, 664.
31. (a) Staroverov, V. N.; Scuseria, G. E.; Tao, J.; Perdew, J. P. J. Chem. Phys. 2003, 119, 12129.
32. (b) Tao, J.; Perdew, J. P.; Staroverov, V. N.; Scuseria, G. E. Phys. Rev. Lett. 2003, 91, 146401.
33. (a) Rey, J.; Savin, A. Int. J. Quantum Chem. 1998, 69, 581.
34. (b) Krieger, J. B.; Chen, J.; Iafrate, G. J.; Savin, A. In Electron Correlations and Materials Properties; Gonis, A., Kioussis, N., Eds.; Plenum: New York. 1999; p 463.
35. (c) Toulouse, J.; Savin, A.; Adamo, C. J. Chem. Phys. 2002, 117, 10465.
36. Zhao, Y.; Lynch, B. J.; Truhlar, D. G. Phys. Chem. Chem. Phys. 2005, 7, 43.
37. Zhao, Y.; Truhlar, D. G. J. Chem. Theory Comput. 2005, 1, 415.
38. (a) Becke, A. D. J. Chem. Phys. 1996, 104, 1040.
39. (b) Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A 2004, 108, 6908.
40. Becke, A. D. J. Chem. Phys. 1997, 107, 8554.
41. Curtiss, L. A.; Redfern, P. C.; Raghavachari, K.; Rasslov, V.; Pople, J. A. J. Chem. Phys. 1999, 110, 4703.
42. NIST Computational Chemistry Comparison and Benchmark Database, NIST Standard Reference Database Number 101 Release 12, Aug 2005, Editor: Russell D. Johnson III http://srdata.nist.gov/cccbdb.
43. (a) Wodrich, M. D.; Wannere, C. S.; Mo, Y.; Jarowski, P. D.; Houk, K. N.; Schleyer, P. v. R. To be submitted.
44. (b) Schleyer, Paul v. R. Abstracts of Papers (COMP-301), 229th ACS National Meeting, San Diego, CA, March 13-17, 2005.
45. (a) Hehre, W. J.; Ditchfield, R.; Radom, L.; Pople, J. A. J. Am. Chem. Soc. 1970, 92, 4796.
46. (b) Radom, L.; Hehre, W. J.; Pople, J. A. J. Am. Chem. Soc. 1971, 93, 289.
47. (c) Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory, John Wiley & Sons: New York, 1986; p 300.
48. (a) Pitzer, K. S.; Catalano, E. J. Am. Chem. Soc. 1956, 78, 4844.
49. (b) Pitzer, K. S. Adv. Chem. Phys. 1959, 2, 59.
50. Koch, W.; Holthausen, M. C. A Chemist's Guide to Density Functional Theory, 2nd ed.; Wiley-VCH: Weinheim. 2001; p 236.
51. (a) Wu, X.; Vargas, M. C.; Nayak, S.; Lotrich, V.; Scoles, G. J. Chem. Phys. 2001, 115, 8748.
52. (b) Zimmerli, U.; Parrinello, M.; Koumoutsakos, P. J. Chem. Phys. 2004, 120, 2693.
53. (c) von Lilienfeld, O. A.; Tavernelli, I.; Rothlisberger, U.; Sebastiani, D. Phys. Rev. Lett. 2004, 93, 153004.
54. (d) Sato, T.; Tsuneda, T.; Hirao, K. Mol. Phys. 200S. 103, 1151.
55. Becke, A. D. J. Chem. Phys. 1996, 104, 1040.
56. (a) Zhechkov, L.; Heine, T.; Patchkovskii, S.; Seifen, G.; Duarte, H. A. J. Chem. Theory Comput. 2005, 1, 841.
57. (b) Lein, M.; Dobson, J. F.; Gross, E. K. U. J. Comput. Chem. 1999, 20, 12.
58. (c) Valdes, H.; Sordo, J. A. J. Comput. Chem. 2002, 23, 444.
59. Zhang, Y. K.; Pan, W.; Yang, W. T. J. Chem. Phys. 1997, 107. 7921.
60. The BSE for propane changes by only 0.07 kcal/mol in going from B3LYP/6-311+G(d,p) to B3LYP/cc-pVTZ.
61. (a) Grimme, S. J. Comput. Chem. 2004, 25, 1463.
62. (b) Tsuzuki, S.; Uchimaru, T.; Matsumara, K.; Mikami, M.; Tanabe, K. Chem. Phys. Lett. 2000, 319, 547.
63. (c) Hobza, P.; Selzle, H. L.; Schlag, E. W. J. Phys. Chem. 1996, 100, 18790.
64. 5c which provides further examples and an illuminating analysis of "disasterous" DFT failures.
65. Wannere, C. S.; Sattelmeyer, K. W.; Schaefer, H. F.; Schleyer, P. v. R. Angew. Chem., Int. Ed. 2004, 43, 4296.