Aromaticity of giant polycyclic aromatic hydrocarbons with hollow sites: Super ring currents in super-rings

Chemistry - A European Journal

Volumn 12, Issue 22, 2006, Pages 5757-5769

  Hajgató, Balázs ^a   Deleuze, Michael S ^b   Ohno, Koichi ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b HASSELT UNIVERSITY   (Belgium)

Author keywords

Ab initio calculations; Aromaticity; Polarizabilities; Polycyclic aromatic hydrocarbons; Ring currents

Indexed keywords

ELECTRIC CURRENTS; ELECTRONIC PROPERTIES; MAGNETIC FIELD EFFECTS; MAGNETIC PROPERTIES; METALLIC COMPOUNDS; PROBABILITY DENSITY FUNCTION;

AB INITIO CALCULATIONS; AROMATICITY; POLARIZABILITIES; RING CURRENTS;

POLYCYCLIC AROMATIC HYDROCARBONS;

EID: 33746904777     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200501321     Document Type: Article

References (112)

1. G. C. Smith, J. F. Sinski, Appl. Spectrosc. 1999, 53, 1459.
2. P. M. V. B. Barone, R. S. Braga, A. Camilo, Jr., D. S. Galvão, THEOCHEM 2000, 505, 55.
3. J. L. Weisman, T. J. Lee, F. Salama, M. Head-Gordon, Astrophys. J. 2003, 587, 256.
4. X. Chillier, P. Boulet, H. Chermette, F. Salama, J. Weber, J. Phys. Chem. 2001, 115, 1769.
5. F. Salama, J. Mol. Struct. 2001, 563, 19.
6. P. Bréchignac, T. Pino, Astron. Astrophys. 1999, 343, L49.
7. A. Shimizu, H. Tachikawa, Electrochim. Acta 2003, 48, 1727.
8. C. D. Dimitrakopoulos, S. Purishotoman, J. Kymissis, A. Callegari, M. J. Shaw, Science 1999, 283, 822.
9. F. Dötz, J. D. Brand, S. Ito, L. Gherghel, K. Müllen, J. Am. Chem. Soc. 2000, 122, 7707.
10. C. D. Simpson, J. D. Brand, A. J. Berresheim, L. Przybilla, H. J. Räder, K. Müllen, Chem. Eur. J. 2002, 8, 1424.
11. J. Wu, L. Gherghel, M. D. Watson, J. Li, Z. Wang, C. D. Simpson, U. Kolb, K. Müllen, Macromolecules 2003, 36, 7082.
12. S. E. Stein, R. L. Brown, J. Am. Chem. Soc. 1987, 109, 3721.
13. P. Du, F. Salama, G. H. Loew, Chem. Phys. 1993, 173, 421.
14. K. Hiruta, S. Tokita, K. Nishimoto, J. Chem. Soc., Perkin Trans. 2 1985, 1443.
15. B. Hajgató, K. Ohno, Chem. Phys. Lett. 2004, 385, 512.
16. C. Niederalt, S. Grimme, S. D. Peyerimhoff, Chem. Phys. Lett. 1995, 245, 455.
17. J. V. Goodpaster, J. F. Harrison, V. L. McGuffin, J. Phys. Chem. 1988, 92, 3372.
18. Y. Bito, N. Shida, T. Toru, Chem. Phys. Lett. 2000, 328, 310.
19. M. S. Deleuze, J. Chem. Phys. 2002, 116, 7012.
20. M. S. Delȩuze, J. Phys. Chem. A 2004, 108, 9244.
21. S. Hirata, T. J. Lee, M. Head-Gordon, J. Chem. Phys. 1999, 111, 8904.
22. T. M. Halasinski, J. L. Weisman, R. Ruiterkamp, T. J. Lee, F. Salama, M. Head-Gordon, J. Phys. Chem. A 2003, 107, 3660.
23. For some organic chemistry textbooks, see: K. P. C. Vollhart, N. E. Schore, Organic Chemistry, 2nd ed., W. H. Freeman and Company, New York, 1994.
24. M. Bühl, A. Hirsch, Chem. Rev. 2001, 101, 1153.
25. R. V. Williams, Chem. Rev. 2001, 101, 1185.
26. R. H. Mitchell, Chem. Rev. 2001, 101, 1301.
27. J. A. N. F. Gomes, R. B. Mallion, Chem. Rev. 2001, 101, 1349.
28. T. M. Krygowski, M. K. Cyrañski, Chem. Rev. 2001, 101, 1385.
29. F. De Proft, P. Geerlings, Chem. Rev. 2001, 101, 1451.
30. S. W. Slayden, J. F. Liebman, Chem. Rev. 2001, 101, 1541.
31. L. J. Schaad, B. A. Hess, Jr., Chem. Rev. 2001, 101, 1465.
32. S. Shaik, A. Shurki, D. Danovich, P. C. Hiberty, Chem. Rev. 2001, 101, 1501.
33. E. Clar, Polycyclic Hydrocarbons, Vols. I and II Academic Press, London, 1963.
34. E. Clar, The Aromatic Sextet, Wiley, London 1972.
35. a) A. F. Pozharskii, A. T. Soldatenkov, A. R. Katritzky, Heterocycles in Life and Society, Wiley, New York, 1997;
36. b) A. R. Katritzky, K. Jug, D. C. Oniciu, Chem. Rev. 2001, 101, 1421.
37. P. George, M. Trachtman, C. W. Bock, A. M. Brett, J. Chem. Soc., Perkin Trans. 2 1976, 1223.
38. R. C. Haddon, V. R. Haddon, L. J. Jackman, Nuclear Magnetic Resonance of Annulenes. Topics in Current Chemistry, Vol. 16, Springer, Berlin, 1971, p. 2.
39. J. A. Elvidge, L. M. Jackman, J. Chem. Soc. 1961, 859.
40. J. A. Elvidge, J. Chem. Soc. Chem. Commun. 1965, 160.
41. C. A. Coulson, J. A. N. F. Gomes, R. B. Mallion, Mol. Phys. 1975, 30, 713.
42. C. A. Coulson, R. B. Mallion, J. Am. Chem. Soc. 1976, 98, 592.
43. R. B. Mallion, Pure Appl. Chem. 1980, 52, 1541.
44. J. A. N. F. Gomes, R. B. Mallion, J. Org. Chem. 1981, 46, 719.
45. R. B. Mallion, Nature 1987, 325, 760.
46. C. W. Haigh, R. B. Mallion, Progress in Nuclear Magnetic Resonance Spectroscopy, Vol. 13, Pergamon Press, Oxford, 1979/1980, p. 303.
47. J. A. N. F. Gomes, R. B. Mallion, Concepts in Chemistry, Research Studies Press Limited, Taunton (UK) and Wiley, New York, 1997, Chapter 7. p. 205.
48. P. Lazaretti, Progress in Nuclear Magnetic Resonance Spectroscopy, Vol. 36, Elsevier, Amsterdam, 2000, p. 1.
49. C. F. Wilcox, J. P. Uetrecht, G. D. Grantham, K. G. Grohmann, J. Am. Chem. Soc. 1975, 97, 1914.
50. C. F. Wilcox, E. N. Farley, J. Am. Chem. Soc. 1984, 106, 7195.
51. C. F. Wilcox, E. N. Farley, J. Org. Chem. 1985, 50, 351.
52. a) C. W. Bird, Tetrahedron 1985, 41, 1409;
53. b) C. W. Bird, Tetrahedron 1986, 42, 89;
54. c) C. W. Bird, Tetrahedron 1987, 43, 4725.
55. a) P. von R. Schleyer, P. K. Freeman, H. Jiao, B. Goldfuss, Angew. Chem. 1995, 107, 332;
56. Angew. Chem. Int. Ed. Engl. 1995, 34, 337.
57. L. Nyulászi, P. von R. Schleyer, J. Am. Chem. Soc. 1999, 121, 6872.
58. For example, see: M. K. Cyrañski, T. M. Krygowski, A. R. Katritzky, P. von R. Schleyer, J. Org. Chem. 2002, 67, 1333, and references therein.
59. H. Hosoya, K. Hosoi, I. Gutman, Theor. Chim. Acta 1975, 38, 37.
60. R. B. Mallion, Proc. R. Soc. London, Ser. A, 1975, 341, 429.
61. I. Gutman, Bull. Soc. Chim. Beograd 1982, 47, 453.
62. I. Gutman, O. E. Polansky, Mathematical Concepts in Organic Chemistry, Springer, Heidelberg, 1986.
63. S. J. Cyvin, I. Gutman, Kekulé Structures in Benzenoid Hydrocarbons: Lecture Notes in Chemistry, 46, Springer, Heidelberg, 1988.
64. I. Gutman, S. J. Cyvin, Introduction to the Theory of Benzenoid Hydrocarbons, Springer, Heidelberg, 1989, Chapter 7, p. 93.
65. C. W. Haigh, R. B. Mallion, Croat. Chem. Acta 1989, 61, 1.
66. M. Randić, Chem. Rev. 2003, 103, 3449.
67. "Delocalization - Pi and Sigma", Complete 10th issue, Chem. Rev. 2005, 105, 3343-3947.
68. F. Jensen, Introduction to Computational Chemistry, Wiley, Chichester, 1999, Chapter 10.
69. A. D. Buckingham, Adv. Chem. Phys. 1967, 12, 106.
70. P. W. Fowler, Annu. Rep. Prog. Chem., Sect. C 1987, 83, 3.
71. See, for example: J.-M. André, J. Delhalle, J.-L. Brédas, Quantum Chemistry Aided Design of Organic Polymers, World Scientific, Singapore, 1991.
72. Gaussian 03 (Revision C.02), 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, J. A. Pople, Gaussian, Inc., Wallingford CT, 2004.
73. J. Gerratt, I. M. Mills, J. Chem. Phys. 1968, 49, 1719.
74. J. M. L. Martin, J. El-Yazal, J.-P. François, Mol. Phys. 1995, 86, 1437.
75. M. S. Deleuze, M. G. Giuffreda, J.-P. François, J. Phys. Chem. A 2002, 106, 5626.
76. P. von R. Schleyer, C. Maeker, A. Dransfeld, H. Jiao, N. J. R. van Eikema Hommes, J. Am. Chem. Soc. 1996, 118, 6317.
77. P. von R. Schleyer, H. Jiao, N. J. R. van Eikema Hommes, V. G. Malkin, O. Malkina, J. Am. Chem. Soc. 1997, 119, 12669.
78. See also Paragraph VI in ref. 27 (p. 1366).
79. R. Ditchfield, Mol. Phys. 1974, 27, 789.
80. M. J. Lacey, Aust. J. Chem. 1970, 23, 1421.
81. S. P. Kwasniewski, J.-P. François, M. S. Deleuze, Int. J. Quantum Chem. 2000, 80, 672.
82. M. W. Casida, C. Jamorski, K. C. Casida, D. R. Salahub, J. Chem. Phys. 1988, 88-89, 4439.
83. D. J. Tozer, N. C. Handy, J. Chem. Phys. 1998, 109, 10180.
84. S. Grimme, M. Parac, ChemPhysChem 2003, 4, 292.
85. P. Otto, A. Martinez, A. Czaja, J. Ladik, J. Chem. Phys. 2002, 117, 1908.
86. S. Suhai, Chem. Phys. Lett. 1983, 96, 619.
87. S. Suhai, Phys. Rev. B 1983, 27, 3506.
88. M. S. Miao, P. E. Van Camp, V. E. van Doren, J. J. Ladik, J. W. Mintimre, J. Chem. Phys. 1998, 109, 9623.
89. O. Kwon, M. L. McKee, J. Phys. Chem. B 2000, 104, 1686.
90. P. R. Rablen, S. A. Pearlman, J. Finkbiner, J. Phys. Chem. A 1999, 103, 7357.
91. B. Wang, U. Fleischer, J. F. Hinton, P. Pulay, J. Comput. Chem. 2001, 22, 1887.
92. a) F. Diederieh, H. A. Staab, Angew. Chem. 1978, 90, 383;
93. Angew. Chem. Int. Ed. Engl. 1978, 17, 372.
94. J.-M. Gilles, J. F. M. Oth, F. Sondheimer, E. P. Woo, J. Chem. Soc. B 1971, 2177.
95. a) E. Steiner, P. W. Fowler, L. W. Jenneskens, Angew. Chem. 2001, 113, 375;
96. Angew. Chem. Int. Ed. 2001, 40, 362.
97. E. Steiner, P. W. Fowler, L. W. Jenneskens, A. Acocella, Chem. Commun. 2001, 659.
98. J. Aihara, Chem. Phys. Lett. 2002, 365, 34.
99. J. Aihara, Chem. Phys. Lett. 2004, 393, 7.
100. V. Elser, R. C. Haddon, Nature 1987, 325, 792.
101. NBO (Version 3.1), E. D. Glendening, A. E. Reed, J. E. Carpenter, F. Weinhold, Madison, 1988.
102. 1 transitions are the same for the planar and the corresponding bowl-shaped forms and are 0.34, 1.80, and 0.80 eV for 62/62 b, 63/63 b, and 64/64b, respectively.
103. B. R. M. de Castro, J. A. N. F. Gomes, R. B. Mallion, J. Mol. Struct. 1992, 265-275, 123.
104. B. R. M. de Castro, J. A. N. F. Gomes, R. B. Mallion, J. Mol. Struct. 1992, 265-275, 133.
105. B. R. M. de Castro, J. A. N. F. Gomes, R. B. Mallion, Croat. Chem. Acta 1993, 65, 49.
106. X. Yang, B. Hajgató, M. Yamada, K. Ohno, Chem. Lett. 2005, 34, 506.
107. W. Gordy, J. Chem. Phys. 1947, 15, 305.
108. M. Randiæ, Chem. Phys. Lett. 1976, 38, 68.
109. S. Verlaak, S. Steudel, P. Heremans, D. Janssen, M. S. Deleuze, Phys. Rev. B 2003, 68, 195409.
110. R. E. Peierls, Quantum Theory of Solids, Clarendon Press, Oxford, 1955.
111. V. V. Walatka, M. M. Labes, J. H. Perlstein, Phys. Rev. Lett. 1973, 31, 1139.
112. L. Greene, G. B. Street, L. J. Suter, Phys. Rev. Lett. 1977, 38, 1305.