Empirical corrections to density functional theory highlight the importance of nonbonded intramolecular interactions in alkanes

Journal of Physical Chemistry A

Volumn 112, Issue 45, 2008, Pages 11495-11500

  Wodrich, Matthew D ^a   Jana, Daniel F ^a   Von Ragué Schleyer, Paul ^b   Corminboeuf, Clémence ^a  

^a EPFL   (Switzerland)

^b UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE ISOMERS; BRANCHED ALKANES; DENSITY FUNCTIONALS; DFT METHODS; FUNCTIONAL PROBLEMS; INTERACTION ENERGIES; INTERMOLECULAR COMPLEXES; INTERMOLECULAR INTERACTIONS; INTRAMOLECULAR INTERACTIONS; SHORT-COMINGS; TO MANY; TRAINING SETS; VAN DER WAALS COMPLEXES; VAN DER WAALS ENERGIES;

FLOW INTERACTIONS; HYDROCARBONS; PARAFFINS; PROBABILITY DENSITY FUNCTION; SYSTEMATIC ERRORS; VAN DER WAALS FORCES;

DENSITY FUNCTIONAL THEORY;

EID: 57049167560     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp806619z     Document Type: Article

References (72)

1. Schwabe, T.; Grimme, S. Phys. Chem. Chem. Phys. 2007, 9, 3397.
2. Zhao, Y.; Schultz, N. E.; Truhlar, D. G. J. Chem. Theory Comput. 2006, 2, 364.
3. Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A 2005, 109, 5656.
4. Grimme, S. J. Chem. Phys. 2006, 124, 034108.
5. Grimme, S. J. Comput. Chem. 2006, 27, 1787.
6. Zhao, Y.; Truhlar, D. G. Acc. Chem Res. 2008, 41, 157.
7. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215.
8. Becke, A. D.; Johnson, E. R. J. Chem. Phys. 2005, 123, 154101.
9. Hobza, P.; Sponer, J.; Reschel, T. J. Comput. Chem. 1995, 16, 1315.
10. Cerny, J.; Hobza, P. Phys. Chem. Chem. Phys. 2005, 7, 1624.
11. Tsuzuki, S.; Luthi, H. P. J. Chem. Phys. 2001, 114, 3949.
12. van Mourik, T.; Gdanitz, R. J. J. Chem. Phys. 2002, 116, 9620.
13. Schreiner, P. R. Angew. Chem., Int. Ed. 2007, 46, 4217.
14. Wodrich, M. D.; Corminboeuf, C.; Schleyer, P. v. R. Org. Lett. 2006, 8, 3631.
15. Schreiner, P. R.; Fokin, A. A.; Pascal, R. A., Jr.; de Meijere, A. Org. Lett. 2006, 8, 3635.
16. Wodrich, M. D.; Corminboeuf, C.; Schreiner, P. R.; Fokin, A. A.; Schleyer, P. v. R. Org. Lett. 2007, 9, 1851.
17. Chekc, C. E.; Gilbert, T. M. J. Org. Chem. 2005, 70, 9828.
18. Izgorodina, E. I.; Coote, M. L.; Radom, L. J. Phys. Chem. A 2005, 109, 7558.
19. Zhao, Y.; Truhlar, D. G. Org. Lett. 2006, 8, 5753.
20. Grimme, S.; Steinmetz, M.; Korth, M. J. Chem. Theory Comput. 2007, 3, 42.
21. Wodrich, M. D.; Wannere, C. S.; Mo, Y.; Jarowski. P. D.; Houk, K. N.; Schleyer, P. v. R. Chem. Eur. J. 2007, 13, 7731.
22. Grimme, S. Angew. Chem., Int. Ed. 2006, 45, 4460.
23. Pitzer, K. S.; Catalano, E. J. Am. Chem. Soc. 1956, 78, 4844.
24. Mori-Sanchez, P.; Cohen, A. J.; Yang, W. J. Chem. Phys. 2006, 125, 201102.
25. Cohen, A. J.; Mori-Sanchez, P.; Yang, W. Phys. Rev. B 2008, 77, 115123.
26. Mori-Sanchez, P.; Cohen, A. J.; Yang, W. Phys. Rev. Lett. 2008, 100, 146401.
27. Johnson, E. R.; Mori-Sanchez, P.; Cohen, A. J.; Yang, W. Submitted for publication.
28. Cohen, A. J.; Mori-Sanchez, P.; Yang, W. T. Science 2008, 321, 792.
29. Ruzsinsky, A.; Perdew, J. P.; Csonka, G. I.; Vydrov, O. A.; Scuseria, G. E. J. Chem. Phys. 2007, 126, 104102.
30. von Lilienfeld, O. A.; Tavernelli, I.; Rothlisberger, U.; Sebastiani, D. Phys. Rev. Lett. 2004, 93, 153004.
31. Becke, A. D.; Johnson, E. R. J. Chem. Phys. 2007, 127, 154108.
32. Becke, A. D.; Johnson, E. R. J. Chem. Phys. 2006, 124, 014104.
33. Johnson, E. R.; Becke, A. D. Chem. Phys. Lett. 2006, 432, 600.
34. Johnson, E. R.; Becke, A. D. J. Chem. Phys. 2006, 124, 174104.
35. Becke, A. D.; Johnson, E. R. J. Chem. Phys. 2005, 123, 154101.
36. Becke, A. D.; Johnson, E. R. J. Chem. Phys. 2005, 122, 154104.
37. Johnson, E. R.; Becke, A. D. J. Chem. Phys. 2005, 123, 024101.
38. Grimme, S. J. Comput. Chem. 2004, 25, 1463.
39. Jurecka, P.; Cerny, J.; Hobza, P.; Salahub, D. R. J. Comput. Chem. 2006, 28, 555.
40. Ducere, J.-M.; Cavallo, L. J. Phys. Chem. B 2007, 111, 13124.
41. Zimmerli, U.; Parrinello, M.; Koumoutsakos, P. J. Chem. Phys. 2004, 120, 2693.
42. Elstner, M.; Hobza, P.; Frauenheim, T.; Suhai, S.; Kaxiras, E. J. Chem. Phys. 2001, 114, 5149.
43. Wu, Q.; Yang, W. J. Chem. Phys. 2002, 116, 515.
44. Antony, J.; Grimme, S. Phys. Chem. Chem. Phys. 2006, 8, 5287.
45. Fonseca Guerra, C.; Snijders, J. G.; te Velde, G.; Baerends, E. J. Theor. Chem. Acc. 1998, 99, 391.
46. te Velde, G.; Bickelhaupt, F. M.; van Gisbergen, S. J. A.; Fonseca Guerra, C.; Baerends, E. J.; Snijders, J. G.; Ziegler, T. J. Comput. Chem. 2001, 22, 931.
47. ADF 2005.01, SCM, Theoretical Chemistry; Vrije Universiteit: Amsterdam, The Netherlands; http://www.scm.com.
48. Koster, A. M.; Calaminici, P.; Casida, M. E.; Flores-Moreno, R.; Geudtner, G.; Goursot, A.; Heine, T.; Ipatov, A.; Janetzko, F.; del Campo, J. M.; Patchkovskii, S.; Reveles, J. U.; Salahub, D. R.; Vela, A. deMon2k; The International DeMon Developers Community: Mexico, 2006.
49. Bondi, A. J. Phys. Chem. 1964, 68, 441.
50. Slater, J. C.; Kirkwood, J. G. Phys. Rev. 1931, 37, 682.
51. Buckingham, A. D.; Fowler, P. W.; Hutson, J. M. Chem. Rev. 1988, 88, 963.
52. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865.
53. Schafer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571.
54. Afeefy, H. Y. Liebman, J. F. Stein, S. E. Neutral Thermochemical Data. In NIST Chemistry Webbook, NIST Standard Reference Database Number 69; National Institute of Standards and Technology: Gaithersburg, MD (http://webbook.nist.gov).
55. Hehre, W. J.; Ditchfield, R.; Radom, L.; Pople, J. A. J. Am. Chem. Soc. 1970, 92, 4796.
56. Radom, L.; Hehre, W. J.; Pople, J. A. J. Am. Chem. Soc. 1971, 93, 289.
57. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; John Wiley & Sons: New York, 1986.
58. Computations employed Gaussian 03 using the cc-pVTZ basis set with the Opt=Tight and Int=Ultrafine keywords. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; 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.; Bakken, V.; 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, Revision E.01; Gaussian, Inc.: Wallingford, CT, 2004.
59. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
60. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
61. See, for example, refs 29 and 62.
62. Mori-Sanchez, P.; Cohen, A. J.; Yang, W. J. Chem. Phys. 2006, 124, 091192.
63. Sinnokrot, M. O.; Sherrill, C. D. J. Phys. Chem. A 2004, 108, 10200.
64. Sato, T.; Tsuneda, T.; Hirao, K. J. Chem. Phys. 2005, 123, 104307.
65. Waller, M. P.; Robertazzi, A.; Platts, J. A.; Hibbs, D. E.; Williams, P. A. J. Comput. Chem. 2006, 27, 491.
66. Hill, J. G.; Platts, J. A.; Werner, H. J. Phys. Chem. Chem. Phys. 2006, 8, 4072.
67. Janowski, T.; Pulay, P. Chem. Phys. Lett. 2007, 447, 27.
68. Grimme, S. Angew. Chem., Int. Ed. 2008, 47, 3430.
69. See also: Phys. Chem. Chem. Phys. 2008, 10, 2581-2868.
70. Riley, K. E.; Hobza, P. J. Phys. Chem. A 2007, 111, 8257.
71. Riley, K. E.; Vondrasek, J.; Hobza, P. Phys. Chem. Chem. Phys. 2007, 9, 5555.
72. Zhao, Y.; Truhlar, D. G. Phys. Chem. Chem. Phys. 2005, 7, 2701.