The agreement between clar structures and nucleus-independent chemical shift values in pericondensed benzenoid polycyclic aromatic hydrocarbons: An application of the Y-rule

Journal of Physical Chemistry A

Volumn 108, Issue 49, 2004, Pages 10873-10896

  Ruiz Morales, Yosadara ^a  

^a INSTITUTO MEXICANO DEL PETRÓLEO   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; MAGNETISM; MOLECULAR DYNAMICS; ORBITS; QUANTUM THEORY; REACTION KINETICS;

CHEMICAL SHIFTS; MOLECULAR ORBITALS; QUANTUM CHEMISTRY;

POLYCYCLIC AROMATIC HYDROCARBONS;

EID: 10844283604     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp040179q     Document Type: Article

References (77)

1. (a) Zajac, G. W.; Sethi, N. K.; Joseph, J. T. Scanning Microsc. 1994, 8, 463.
2. (b) Bitumens, Asphalts, and Tar Sands; Chilingarian, G. V., Yen, T. F., Eds.; Elsevier: New York, 1978.
3. Speight, J. G. The Chemistry and Technology of Petroleum; Marcel Dekker: New York, 1980; pp 189-252.
4. Tissot, B. P.; Welte, D. H. Petroleum Formation and Occurrence, 2nd ed.; Springer-Verlag: Berlin, 1984.
5. Chemistry of Asphaltenes; Bunger, J. W., Li, N. C., Eds.; American Chemical Society: Washington, DC, 1984.
6. Asphaltenes: Fundamentals and Applications; Sheu, E. Y., Mullins, O. C., Eds.; Plenum Press: New York, 1995.
7. Structures and Dynamics of Asphallenes; Mullins, O. C., Sheu, E. Y., Eds.; Plenum Press: New York, 1998.
8. Ruiz-Morales, Y. J. Phys. Chem. A 2002, 106, 11283.
9. Clar, E. Polycyclic Hydrocarbons; Academic: London, 1964.
10. Clar, E. The Aromatic Sextet; Wiley: London, 1972.
11. Randic, M. Chem. Rev. 2003, 103, 3449.
12. (a) Havenith, R. W. A.; van Lenthe, J. H.; Dijkstra, F.; Jenneskens, L. W. J. Phys. Chem. A 2001, 105, 3838.
13. (b) Havenith, R. W. A.; Jiao, H.; Jenneskens, L. W.; van Lenthe, J. H.; Sarobe, M.; Schleyer, P. v. R.; Kataoka, M.; Necula, A.; Scott, L. T. J. Am. Chem. Soc. 2002, 124, 2363.
14. Krygowki, T. M.; Cyranski, M. K. Chem. Rev. 2001, 101, 1385.
15. Gomes, J. A. N. F.; Mallion, R. B. Chem. Rev. 2001, 101, 1349.
16. De Proft, F.; Geerlings, P. Chem. Rev. 2001, 101, 1451.
17. Mitchell, R. H. Chem. Rev. 2001, 101, 1301.
18. Garrat, P. J. Aromaticity; John Wiley and Sons: New York, 1986: Chapter 9.
19. Havenith, R. W. A.; van Lcnthe, J. H.; Dijkstra, F.; Jenneskens, L. W. J. Phys. Chem. A 2001, 105, 3838.
20. Moran, D.; Stahl, F.; Bettinger, H. F.; Schaefer, H. F.; Schleyer, P. v. R. J. Am. Chem. Soc. 2003, 125, 6746.
21. Fries, K. Justus Liebigs Ann. Chem. 1927, 454, 121.
22. Randic, M.; Hosoya, H.; Nakada, K. Polycyclic Aromat. Compd. 1995, 4, 249.
23. Hosoya, H.; Yamaguchi, T. Tetrahedron Lett. 1975, 4659.
24. Herndon, W. C.; Hosoya, H. Tetrahedron 1984, 40, 3987.
25. Randic, M. Clar's π-Aromatic Sextet Revisited. In Valence Bond Theory; Cooper, D. L., Ed.; Elsevier: Amsterdam, 2002; Chapter 16, pp 503-533.
26. Hosoya, H.; Hosi, K.; Gutman, I. Theor. Chim. Acta 1975, 38, 37.
27. (a) Aihara, J. J. Org. Chem. 1976, 41, 2488.
28. (b) Aihara, J. J. Chem. Soc., Perkin Trans. 1996, 2, 2185.
29. (c) Aihara, J. J. Phys. Chem. A 1999, 103, 7487.
30. (d) Aihara, J. J. Org. Chem. 1976, 41, 2488.
31. (e) Aihara, J. J. Am. Chem. Soc. 1977, 99, 2048.
32. Herndon, W. C. J. Am. Chem. Soc. 1973, 95, 2404.
33. Herndon, W. C.; Ellzey, M. L. J. Am. Chem. Soc. 1974, 96, 6631.
34. Randić, M. Tetrahedron 1975, 31, 1477.
35. Randić, M. Chem. Phys. Lett. 1976, 38, 68.
36. Randić. M. J. Am. Chem. Soc. 1977, 99, 444.
37. Randić, M. Tetrahedron 1977, 38, 68.
38. Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes N. J. R. v. E. J. Am. Chem. Soc. 1996, 118, 6317.
39. Fleischer, U.; Kutzelnigg, W.; Lazzareii, P.; Mühlenkamp, V. J. Am. Chem. Soc. 1994, 116, 5298.
40. Schleyer, P. v. R. Chem. Rev. 2001, 101, 1115.
41. Patchkovskii, S.; Thiel, W. J. Mol. Model. 2000, 6, 67 and references therein.
42. Watson, M. D.; Fechtenkötter, A.; Müllen, K. Chem. Rev. 2001, 101, 1267.
43. Hajgató, B.; Ohno, K. Chem. Phys. Lett. 2004, 385, 512.
44. Samori, P.; Severin, N.; Simpson, C. D.; Müllen, K.; Rabe, J. J. Am. Chem. Soc. 2002, 124, 9454.
45. Bergmann, U.; Groenzin, H.; Mullins, O. C.; Glatzel, P.; Fetzer, J., Cramer S. P. Chem. Phys. Lett. 2003, 369, 184.
46. Schleyer, P. v. R.; Jiao, H.; Hommes, N. J. R. v. E.; Malkin, V. G.; Malkina, O. L J. Am. Chem. Soc. 1997, 119, 12669.
47. Schleyer, P. v. R.; Manoharan, M.; Wang, Z.-X.; Kiran, B.; Jiao, H.; Puchta, R.; Hommes, N. J. R. v. E Org. Lett. 2001, 3, 2465.
48. Molecular Simulation Incorporated. Cerius2 Modeling Environment, release 4.0; Molecular Simulations Incorporated: San Diego, CA, 1999.
49. (a) Ditchficld, R. Mol. Phys. 1974, 27, 789.
50. (b) Wolinski, K.; Hinton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251.
51. 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, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; 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.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gauisian 98, revision A.7; Gaussian, Inc.: Pittsburgh. PA, 1998.
52. Becke A., Phys. Rev. A: At., Mol., Opt. Phys. 1988, 38, 3098.
53. Lee, C.; Yang, W.; Parr, R. G., Phys. Rev. B: Candens. Matter Mater. Phys. 1988, 37, 785.
54. Chesnut, D. B. In Annual Reports on NMR Spectroscope, Webb, G. A., Ed.; Academic Press: New York, 1994; Vol. 29.
55. Kutzelnigg, W.; Fleischer, U.; Schindler, M. In NMR, Basic Principles and Progress: Springer-Verlag: Berlin, 1990; Vol. 23, p 165.
56. (a) Dias, J. R. Polycyclic Aromat. Compd. 1994, 4, 87.
57. (b) Dias, J. R. HEOCHEM 1991, 230, 155.
58. (c) Dias, J. R. Polycyclic Aromat. Compd. 1994, 4, 87.
59. (d) Dias, J. R. THEOCHEM1993, 284, 11.
60. (e) Dias, J. R. THEOCHEM 1991, 230, 155.
61. (f) Dias, J. R. Theor. Chim. Acta 1990, 77, 143.
62. (g) Dias, J. R. Polycyclic Aromat. Compd. 1999, 14-15, 63.
63. (h) Dias, J. R. Acc. Chem. Res. 1985, 18, 241.
64. Iuliucci, R. J.; Phung, C. G.; Facelli, J. C.; Grant, D. M. J. Am. Chem. Soc. 1996, 118, 4880.
65. (a) Aihara, J. Chem. Phys. Lett. 2002, 365, 34.
66. (b) Aihara, J., Horikawa, T. Bull. Chem. Soc. Jpn. 1983, 56, 1853.
67. (c) Aihara, J. J. Am. Chem. Soc. 1985, 107, 298.
68. (d) Aihara, J. Bull. Chem. Soc. Jpn. 1985, 58, 1045.
69. Steiner, E.; Fowler, P. W. Int. J. Quantum Chem. 1996, 60, 609.
70. Steiner, E.; Fowler, P. W.; Jenneskens, L. W. Angew. Chem., Int. Ed. 2001, 40, 362.
71. Lazzeretti, P. Prog. Nucl. Magn. Reson. Spectrosc. 2000, 36, 1.
72. Gutman, I.; Brunvoll, J.; Cyvin, B. N.; Brendsdal, E.; Cyvin, S. J. Chem. Phys. Lett. 1994, 219, 355.
73. Ligabue, A.; Pincelli, U.; Lazzereti, P.; Zanasi, R. J. Am. Chem. Soc. 1999, 121, 5513.
74. (a) Suresh, C. H.; Gadre, S. R. J. Org. Chem. 1999, 64, 2505.
75. (b) Negri, F.; Castiglione, C.; Tommasini, M.; Zerbi, G. J. Phys. Chem. A 2002, 106, 3306.
76. Bühl, M. Chem.-Eur. J. 37 1998 734.
77. Foster, N. R.; Grieves, G. A.; Buchanan, J. W.; Flynn, N. D. Duncan, M. A. J. Phys. Chem. A 2000, 104, 11055.