The electron density vs. NICS scan: A new approach to assess aromaticity in molecules with different ring sizes

Physical Chemistry Chemical Physics

Volumn 12, Issue 39, 2010, Pages 12630-12637

  Foroutan Nejad, Cina ^a   Shahbazian, Shant ^b   Rashidi Ranjbar, Parviz ^a  

^a UNIVERSITY OF TEHRAN   (Iran)

^b SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77957896836     PISSN: 14639076     EISSN: None     Source Type: Journal    
DOI: 10.1039/c004254d     Document Type: Article

References (58)

1. W. G. Proctor, F. C. Yu Phys. Rev., 1950, 77, 717.
2. J. T. Arnold, S. S. Dharmatti, M. E. Packard J. Chem. Phys., 1951, 19, 507.
3. This is due to the well-known fact that the eigenfunctions of excited states enter into the perturbation expression for the response, and shielding is related to the response of the wave function to an external magnetic field’s perturbation. On the other hand, the one-electron charge density is a ground state property. However, following the Hohenberg-Kohn theorems (P. Hohenberg, W. Kohn Phys. Rev., 1964, 136, 864.), one could argue that as the ground state electron density determines the Hamiltonian which yields all eigenfunctions (ground and excited states) there must be a theoretical link, though quite complicated, between the one-electron density and shielding, although not yet worked out
4. Z. Chen, T. Heine, P. v. R. Schleyer, and D. Sundholm, in Calculation of NMR and EPR Parameters, Theory and Applications, ed. M. Kaupp, M. Bühl, V. G. Malkin, Wiley-VCH, Weinheim, Germany, 2004, ch. 24, p. 397
5. P. v. R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N. J. R. v. E. Hommes J. Am. Chem. Soc., 1996, 118, 6317.
6. Z. Chen, C. S. Wannere, C. Corminboeuf, R. Puchta, P. v. R. Schleyer Chem. Rev., 2005, 105, 3842. and references therein
7. P. v. R. Schleyer, H. Jiao, N. J. R. v. E. Hommes, V. G. Malkin, O. Malkina J. Am. Chem. Soc., 1997, 119, 12669.
8. P. W. Fowler, E. Steiner Mol. Phys., 2000, 98, 945.
9. E. Steiner, P. W. Fowler, L. W. Jennesskens Angew. Chem., Int. Ed., 2001, 40, 362.
10. P. Lazzeretti Phys. Chem. Chem. Phys., 2004, 6, 217.
11. P. v. R. Schleyer, M. Manoharan, Z. X. Wang, B. Kiran, H. Jiao, R. Puchta, N. J. R. v. E. Hommes Org. Lett., 2001, 3, 2465.
12. C. Corminboeuf, T. Heine, J. Weber Phys. Chem. Chem. Phys., 2003, 5, 246.
13. T. Heine, P. v. R. Schleyer, C. Corminboeuf, G. Seifert, R. Reviakine, J. Weber J. Phys. Chem. A, 2003, 107, 6470.
14. C. Corminboeuf, T. Heine, G. Seifert, P. v. R. Schleyer, J. Weber Phys. Chem. Chem. Phys., 2004, 6, 273. and references therein
15. H. Fallah-Bagher-Shaidaei, C. S. Wannere, C. Corminboeuf, R. Puchta, P. v. R. Schleyer Org. Lett., 2006, 8, 863.
16. A. Stanger J. Org. Chem., 2006, 71, 883.
17. J. O. C. Jiménez-Halla, E. Matito, J. Robles, M. Sola J. Organomet. Chem., 2006, 691, 4359.
18. A. Stanger Chem.-Eur. J., 2006, 12, 2745.
19. P. Seal, S. Chakrabarti J. Phys. Chem. A, 2007, 111, 9988.
20. P. Seal THEOCHEM, 2009, 893, 31.
21. N. S. Mills, K. B. Llagoster J. Org. Chem., 2007, 72, 9163.
22. F. Feixas, E. Matito, J. Poater, M. Sola J. Comput. Chem., 2008, 29, 1543.
23. M. K. Cyrański Chem. Rev., 2005, 105, 3773.
24. H. J. J. Dauben, D. J. Wilson, J. L. Laity J. Am. Chem. Soc., 1968, 90, 811.
25. W. Haberditzl Angew. Chem., Int. Ed. Engl., 1966, 5, 288.
26. T. G. Schmalz, C. L. Norris, W. H. Flygare J. Am. Chem. Soc., 1973, 95, 7961.
27. J. Poater, X. Fradera, M. Duran, M. Sola Chem.-Eur. J., 2003, 9, 1113.
28. G. Merino, A. Vela, T. Heine Chem. Rev., 2005, 105, 3812.
29. A. R. Katritzky, P. Barczynski, G. Musumarra, D. Pisano, M. Szafran J. Am. Chem. Soc., 1989, 111, 7.
30. M. K. Cyrański, T. M. Krygowski, A. R. Katritzky, P. v. R. Schleyer J. Org. Chem., 2002, 67, 1333.
31. M. Palusiak, T. M. Krygowski Chem.-Eur. J., 2007, 13, 7996.
32. A. Mohajeri, A. Ashrafi Chem. Phys. Lett., 2008, 458, 378.
33. F. Feixas, E. Matito, M. Sola, J. Poater J. Phys. Chem. A, 2008, 112, 13231. and supporting information of the manuscript, MCI for 2π-electron species (cyclobutadiene dication) is more than two times greater than that of 6π-electron species while the inverse trend is expected.
34. A. Stanger Chem. Commun., 2009, 1939.
35. P. Bultinck, R. Ponec, S. Van Damme J. Phys. Org. Chem., 2005, 18, 706.
36. P. Bultinck, M. Rafat, R. Ponec, B. Gheluwe, R. Carbó-Dorca, P. Popelier J. Phys. Chem. A, 2006, 110, 7642.
37. J. Cioslowski, E. Matito, M. Sola J. Phys. Chem. A, 2007, 111, 6521. INB and ING values for planar and twisted cyclooctatetraene, which are antiaromatic and non-aromatic, respectively, are very close
38. M. Giambiagi, M. S. de Giambiagi, C. D. dos Santos, A. P. de Figueiredo Phys. Chem. Chem. Phys., 2000, 2, 3381.
39. E. Matito, M. Duran, M. Solà J. Chem. Phys., 2005, 122, 014109.
40. J. Kruszewski, T. M. Krygowski Tetrahedron Lett., 1972, 13, 3839.
41. A. D. Becke J. Chem. Phys., 1993, 98, 5648.
42. A. D. Becke Phys. Rev. A: At., Mol., Opt. Phys., 1988, 38, 3098.
43. C. Lee, W. Yang, R. G. Parr Phys. Rev. B: Condens. Matter, 1988, 37, 785.
44. R. A. Kendall, T. H. Dunning Jr., R. J. Harrison J. Chem. Phys., 1992, 96, 6796.
45. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, and J. A. Pople, GAUSSIAN 98 (Revision A.9), Gaussian, Inc., Pittsburgh, PA, 1998
46. I. Morao, F. P. Cossio J. Org. Chem., 1999, 64, 1868.
47. R. F. W. Bader, Atoms in Molecules: A Quantum Theory, Oxford University Press, Oxford, 1990
48. F. Biegler-König, J. Schönbohm, D. Bayles J. Comput. Chem., 2001, 22, 545.
49. F. Biegler-König, J. Schönbohm J. Comput. Chem., 2002, 23, 1489.
50. J. Pipek, P. G. Mezey J. Chem. Phys., 1989, 90, 4916.
51. NBO 5.X. E. D. Glendening, J. K. Badenhoop, A. E. Reed, J. E. Carpenter, J. A. Bohmann, C. M. Morales, F. Weinhold, (Theoretical Chemistry Institute, University of Wisconsin, Madison, WI, 2003); http://www.chem.wisc.edu/
52. V. G. Malkin, O. L. Malkina, M. E. Casida, D. R. Salahub J. Am. Chem. Soc., 1994, 116, 5898.
53. S. T. Howard, T. M. Krygowski Can. J. Chem., 1997, 75, 1174.
54. M. Mandado, P. Bultinck, M. Gonzalez-Mao, R. A. Mosquera Chem. Phys. Lett., 2006, 433, 5.
55. R. Salcedo, C. Olvera THEOCHEM, 1999, 460, 221.
56. K. B. Wiberg Chem. Rev., 2001, 101, 1317.
57. P. W. Fowler, E. Steiner J. Phys. Chem. A, 1997, 101, 1409.
58. G. Winkelhofer, R. Janoschek, F. Fratev, G. W. Spitznagel, J. Chandrasekhar, P. v. R. Schleyer J. Am. Chem. Soc., 1985, 107, 332.