Reformulating the woodward-hoffmann rules in a conceptual density functional theory context: The case of sigmatropic reactions

Croatica Chemica Acta

Volumn 82, Issue 1, 2009, Pages 157-164

  Sablon, Nick ^a   De Proft, Frank ^a   Geerlings, Paul ^a  

^a VRIJE UNIVERSITEIT BRUSSEL   (Belgium)

Author keywords

Conceptual DFT; Hardness; Sigmatropic reactions; Woodward Hoffmann rules

Indexed keywords

EID: 68049134441     PISSN: 00111643     EISSN: 1334417X     Source Type: Journal    
DOI: None     Document Type: Article

References (48)

1. P. Hohenberg and W. Kohn, Phys. Rev. B 136 (1964) 864-871.
2. W. Kohn and L. J. Sham, Phys. Rev. A 140 (1965) 1133-1138.
3. R. G. Parr and W. Yang, Density Functional Theory of Atoms and Molecules, Oxford University Press, New York, 1989.
4. R. M. Dreizler and E. K. U. Gross, Density Functional Theory, Springer-Verlag, Berlin, Heidelberg and New York, 1990.
5. R. G. Parr and W. Yang, Annu. Rev. Phys. Chem. 46 (1995) 701-728.
6. W. Kohn, A. D. Becke, and R. G. Parr, J. Phys. Chem. 100 (1996) 12974-12980.
7. W. Koch and M. Holthausen, A Chemist's Guide to Density Functional Theory, Wiley-VCH, Weinheim, 2001.
8. P. Geerlings, F. De Proft, and W. Langenaeker, Chem. Rev. 103 (2003) 1793-1873.
9. R. B. Woodward and R. Hoffmann, J. Am. Chem. Soc. 87 (1965) 395-397.
10. R. Hoffmann and R. B. Woodward, Acc. Chem. Res. 1 (1968) 17-22.
11. R. B. Woodward and R. Hoffmann, Angew. Chem. 81 (1969) 797-870; Angew. Chem., Int. Ed. Engl. 8 (1969) 781-853.
12. R. B. Woodward and R. Hoffmann, The Conservation of Orbital Symmetry, Academic, New York, 1970.
13. nd ed., Cambridge University Press, Cambridge, 1978.
14. W. A. Goddard, J. Am. Chem. Soc. 92 (1970) 7520-7521.
15. W. A. Goddard and R. C. Ladner, J. Am. Chem. Soc. 93 (1971) 6750-6756.
16. W. A. Goddard, J. Am. Chem. Soc. 94 (1972) 793-807.
17. H. Zimmerman, Acc. Chem. Res. 33 (1971) 272-280.
18. E. Hückel, Z. Phys. 70 (1931) 204-296; Z. Phys. 76 (1932) 628-648; Z. Phys. 83 (1933) 632-635.
19. E. Heilbronner and E. Hückel, Tetrahedron Lett. 5 (1964) 1923-1928.
20. F. De Proft, P. W. Ayers, S. Fias, and P. Geerlings, J. Chem. Phys. 125 (2006) 214101-214109.
21. F. De Proft, P. K. Chattaraj, P. W. Ayers, M. Torrent-Sucarrat, M. Elango, V. Subramanian, S. Giri, and P. Geerlings, J. Chem. Theory Comput. 4 (2008) 595-602.
22. P. K. Chattaraj, P. Fuentealba, B. Gómez, and R. Contreras, J. Am. Chem. Soc. 122 (2000) 348-351.
23. C. Morell, A. Grand, and A. Toro-Labbé, J. Phys. Chem. A 109 (2005) 205-212.
24. C. Morell, A. Grand, and A. Toro-Labbé, Chem. Phys. Lett. 425 (2006) 342-346.
25. J. Padmanabhan, R. Parthasarathi, M. Elango, V. Subramanian, B. S. Krishnamoorthy, S. Gutierrez-Oliva, A. Toro-Labbé, D. R. Roy, and P. K. Chattaraj, J. Phys. Chem. A 111 (2007) 9130-9138.
26. P. W. Ayers, C. Morell, F. De Proft, and P. Geerlings, Chem. Eur. J. 13 (2007) 8240-8247.
27. P. Geerlings, F. De Proft, and W. Langenaeker, Adv. Quantum Chem. 33 (1999) 303.
28. H. Chermette, J. Comput. Chem. 20 (1999) 129-154.
29. P. W. Ayers, J. S. M. Anderson, and L. J. Bartolotti, Int. J. Quantum Chem. 101 (2005) 520-534.
30. P. Geerlings and F. De Proft, Phys. Chem. Chem. Phys. 10 (2008) 3028-3042.
31. R. G. Pearson, J. Am.Chem. Soc. 85 (1963) 3533-3543.
32. R. G. Pearson, Hard and Soft Acids and Bases, Dowen, Hutchinson and Ross, Stroudsberg, 1973.
33. R. G. Pearson, Chemical Hardness, Wiley-VCH, New York, 1997.
34. R. G. Parr and R. G. Pearson, J. Am. Chem. Soc. 105 (1983) 7512-7516.
35. D. J. Tozer and F. De Proft, J. Phys. Chem. A 109 (2005) 8923-8929.
36. F. De Proft, N. Sablon, D. J. Tozer, and P. Geerlings, Faraday Discuss. 135 (2007) 151-159.
37. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, Gaussian 03, revision B03, Gaussian, Inc.: Wallingford, CT, 2004.
38. (a) A. D. Becke, J. Chem. Phys. 98 (1993) 5648-5652,
39. (b) C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B 37 (1988) 785-789,
40. (c) P. J. Stephens, F. J. Devlin, C. F. Chabalowski, and M. J. Frisch, J. Phys. Chem. 98 (1994) 11623-11627.
41. W. J. Hehre, L. Radom, P. v. R. Schleyer, and J. A. Pople, Ab Initio Molecular Orbital Theory, Wiley, New York, 1986.
42. J. P. Perdew, K. Burke, and M. Ernzerhof, Phys. Rev. Lett. 77 (1996) 3865-3868.
43. Z. Zhou, R. G. Parr, J. Am. Chem. Soc. 112 (1990) 5720-5724.
44. W. J. Bouma, M. A. Vincent, and L. Radom, J. Quant. Chem. 14 (1978) 767-777.
45. C. Gonzalez and H. B. Schlegel, J. Chem. Phys. 90 (1989) 2154-2161.
46. C. Gonzalez and H. B. Schlegel, J. Phys. Chem. 94 (1990) 5523-5527.
47. M. Torrent-Sucarrat, J. M. Luis, M. Duran, and M. Sola, J. Chem. Phys. 120 (2004) 10914-10924.
48. M. Torrent-Sucarrat, P. Geerlings, and J. M. Luis, Chem. Phys. Chem. 8 (2007) 1065-1070.