Two faces of the structural aspects of aromaticity

Physical Chemistry Chemical Physics

Volumn 6, Issue 2, 2004, Pages 249-255

  Krygowski, Tadeusz Marek ^a   Cyrański, Michał Ksawery ^a  

^a UNIVERSITY OF WARSAW   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ANALYTIC METHOD; AROMATIZATION; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFERENCE PAPER; GEOMETRY; MOLECULAR MODEL; QUANTITATIVE ANALYSIS;

EID: 0942301226     PISSN: 14639076     EISSN: None     Source Type: Journal    
DOI: 10.1039/b310874k     Document Type: Conference Paper

References (91)

1. A. Kekulé, Bull. Soc. Chim. Fr. (Paris), 1865, 3, 98.
2. T. M. Krygowski, M. K. Cyrański, Z. Czarnocki, G. Häfelinger and A. R. Katritzky, Tetrahedron, 2000, 56, 1783-1896.
3. Institute for Scientic Information, Philadelphia (1981-2003). The data from ref. 2 updated in July 2003.
4. R. McWeeny, Coulson's Valence, Oxford University Press, Oxford, 1979.
5. Aromaticity, Pseudoaromaticity and Antiaromaticity, Proc. of an International Symposium held in Jerusalem 1970, Israel Academy of Sciences and Humanities, Jerusalem, ed. E. D. Bergmann and B. Pullman, 1971.
6. V. I. Minkin, M. N. Glukhovtsev and B. Ya. Simkin, Aromaticity and Antiaromaticity. Electronic Structural Aspects, J. Wiley, New York, 1994.
7. (a) F. Sondheimer, Pure Appl. Chem., 1963, 363-388;
8. (b) M. J. S. Dewar, Tetrahedron Suppl., 1966, 8, 75-102; J. A. Elvidge and L. M. Jackman, J. Chem. Soc., 1961, 859-866.
9. (b) M. J. S. Dewar, Tetrahedron Suppl., 1966, 8, 75-102; J. A. Elvidge and L. M. Jackman, J. Chem. Soc., 1961, 859-866.
10. M. K. Cyrański, T. M. Krygowski, A. R. Katritzky and P. v. R. Schleyer, J. Org. Chem., 2002, 67, 1333-1338.
11. P. v. R. Schleyer and H. Jiao, Pure Appl. Chem., 1996, 68, 209-218.
12. (a) L. Pauling and J. Sherman, J. Chem. Phys., 1933, 1, 606-611;
13. (b) B. Kistiakowski, J. R. Ruhoffm, H. A. Smith and W. E. Vaughan, J. Am. Chem. Soc., 1936, 58, 146-153.
14. J. W. Armit and R. Robinson, J. Chem. Soc., 1925, 127, 1604-1618.
15. M. K. Cyrański, P. v. R. Schleyer, T. M. Krygowski, H. Jiao and G. Hohlneicher, Tetrahedron, 2003, 59, 1657-1665.
16. (a) L. Pauling, The Nature of the Chemical Bond, University Press. Ithaca, New York, 1960;
17. (b) R. Daudel, R. Lefebre and C. Moser, Quantum Chemistry, Interscience, New York, 1959;
18. (c) C. A. Coulson, Valence, Oxford University Press, New York, London, 1961.
19. M. J. S. Dewar and C. de Llano, J. Am. Chem. Soc., 1969, 91, 789-795.
20. B. A. Hess Jr. and L. J. Schaad, J. Am. Chem. Soc., 1971, 93, 305-310.
21. L. J. Schaad and B. A. Hess, Jr., Chem. Rev., 2001, 101, 1465-1476.
22. (a) W. J. Hehre, R. Ditchfield, L. Radom and J. A. Pople, J. Am. Chem. Soc., 1970, 92, 4796-4801;
23. (b) P. George, M. Trachtman, C. W. Bock and A. M. Brett, J. Chem. Soc., Perkin Trans. 2, 1976, 1222;
24. (c) W. J. Hehre, L. Radom, P. v. R. Schleyer and J. A. Pople, Ab Initio Molecular Orbital Theory, John Wiley & Sons, New York, 1986.
25. (a) W. J. Hehre, R. T. McIver, J. A. Pople and P. v. R. Schleyer, J. Am. Chem. Soc., 1974, 96, 7162-7163;
26. (b) L. Radom, J. Chem. Soc., Chem. Commun., 1974, 403-404;
27. (c) P. George, M. Trachtman, C. W. Boch and A. M. Brett, Theor. Chim. Acta, 1975, 38, 121;
28. (d) P. George, M. Trachtman, A. M. Brett and C. W. Bock, J. Chem. Soc., Perkin Trans. 2, 1977, 1036-1047.
29. (a) J. D. Cox and G. Pilcher, Thermochemistry of Organic and Organometallic Compounds, Academic, London, 1970;
30. (b) J. B. Pedley, R. D. Naylor and S. P. Kirby, Thermodynamical Data of Organic Compounds, Chapman & Hall, London, 1986;
31. (c) S. W. Slayden and J. F. Liebmann, Chem. Rev., 2001, 101, 1541-1566.
32. T. M. Krygowski and M. K. Cyrański, Chem. Rev., 2001, 101, 1385-1420.
33. P. v. R. Schleyer and M. N. Glukhovtsev, Chem. Phys. Lett., 1992, 198, 547-554.
34. P. v. R. Schleyer and F. Pülhoher, Org. Lett., 2002, 4, 2873-2876.
35. A. Julg and P. Françoise, Theor. Chim. Acta, 1967, 7, 249.
36. C. Castro, C. M. Isborn, W. L. Karney, M. Mauksch and P. v. R. Schleyer, Org. Lett., 2002, 4, 3431-3434.
37. (a) D. Delaere, M. T. Nguyen and L. G. Vanquickenborne, J. Phys. Chem. A, 2003, 107, 838-846;
38. (b) D. Delaere, M. T. Nguyen and L. G. Vanquickenborne, J. Organomet. Chem., 2002, 643, 194-201;
39. (c) E. Mattmann, F. Mathey, A. Sevin and G. Frison, J. Org. Chem., 2002, 67, 1208-1213;
40. (d) D. Delaere, A. Dransfeld, M. T. Nguyen and L. G. Vanquickenborne, J. Org. Chem., 2000, 65, 2631-2636.
41. (a) D. Quinonero, C. Garau, A. Frontera, P. Ballester, A. Costa and P. M. Deya, Chem. Eur. J., 2002, 8, 433-438;
42. (b) P. v. R. Schleyer, K. Najafian, B. Kiran and H. J. Jiao, J. Org. Chem., 2000, 65, 426-431.
43. M. S. de Giambiagi, M. Giambiagi and A. P. de Figueiredo, Z. Naturforsch., Teil A, 2001, 56, 413-415.
44. J. Kruszewski and T. M. Krygowski, Tetrahedron Lett., 1972, 3839-3842.
45. T. M. Krygowski, J. Chem. Inf. Comput. Sci., 1993, 33, 70-78.
46. K. Kveseth, R. Seip and D. A. Kohl, Acta Chem. Scand., Ser. A, 1980, A34, 31-42.
47. G. A. Jeffrey, J. R. Ruble, R. K. McMullan and J. A. Pople, Proc. R. Soc. London, Ser. A, 1987, 414, 47-57.
48. P. v. R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao and N. J. R. v. E. Hommes, J. Am. Chem. Soc., 1996, 118, 6317-6318.
49. J. Kruszewski and T. M. Krygowski, Symposium on "Synthesis, Structure and Properties of Heterocyclic Compounds", Poznań, 1972.
50. (a) C. W. Bird, Tetrahedron, 1985, 41, 1409-1414;
51. (b) C. W. Bird, Tetrahedron, 1986, 42, 89-92;
52. (c) C. W. Bird, Tetrahedron, 1987, 43, 4725-4730;
53. (d) C. W. Bird, Tetrahedron, 1990, 46, 5697-5702;
54. (e) C. W. Bird, Tetrahedron, 1992, 48, 1675-1682;
55. (f) C. W. Bird, Tetrahedron, 1992, 48, 7857-7862;
56. (g) C. W. Bird, Tetrahedron, 1993, 49, 8441-8448;
57. (h) C. W. Bird, Heterocycles, 1994, 37, 249-255;
58. (i) C. W. Bird, Tetrahedron, 1997, 53, 13111-13118.
59. W. Gordy, J. Chem. Phys., 1947, 15, 305-310.
60. V. Schomaker and D. P. Stevenson, J. Am. Chem. Soc., 1941, 63, 37-40.
61. C. W. Bird, Tetrahedron, 1992, 48, 335-340.
62. (a) T. M. Krygowski and A. Ciesielski, J. Chem. Inf. Comput. Sci., 1995, 35, 1001-1003;
63. (b) M. Prato, T. Suzuki, F. Wudl, V. Lucchini and M. Maggini, J. Am. Chem. Soc., 1993, 115, 7876-7877;
64. (c) A. Pasquarello, M. Schulter and R. C. Haddon, Science, 1992, 257, 1660-1661.
65. T. M. Krygowski and M. K. Cyrański, Tetrahedron, 1996, 52, 1713-1722.
66. T. M. Krygowski and M. K. Cyrański, Tetrahedron, 1996, 52, 10255-10264.
67. L. Pauling, J. Am. Chem. Soc., 1947, 69, 542-553.
68. T. M. Krygowski, M. Cyrański, A. Ciesielski, B. Świrska and P. Leszczyński, J. Chem. Inf. Comput. Sci., 1996, 36, 1135-1142.
69. E. Clar, The Aromatic Sextet, J. Wiley & Sons, Chichester, 1972.
70. (a) S. S. Shaik, P. C. Hiberty, J. M. Lefour and G. Ohanessian, J. Am. Chem. Soc., 1987, 109, 363-374;
71. (b) S. S. Shaik and P. C. Hiberty, J. Am. Chem. Soc., 1985, 107, 3089-3095;
72. (c) P. C. Hiberty, S. S. Shaik, G. Ohanessian and J. M. Lefour, J. Org. Chem., 1986, 51, 3908-3909;
73. (d) P. C. Hiberty, Top. Curr. Chem., 1990, 153, 27;
74. (e) K. Jug, P. C. Hiberty and S. Shaik, Chem. Rev., 2001, 101, 1477-1500;
75. (f) S. Shaik, A. Shurki, D. Danovich and P. C. Hiberty, Chem. Rev., 2001, 101, 1500-1540.
76. G. Subramanian, P. v. R. Schleyer and H. Jiao, Angew. Chem., Int. Ed., 1996, 35, 2638-2641.
77. M. K. Cyrański, T. Krygowski, A. Krutosikova and R. Sleziak, Tetrahedron, 2001, 57, 8867-8873.
78. I. Novak, J. Mol. Struct. (THEOCHEM), 1997, 398, 315-323.
79. B. T. Stȩpień, T. M. Krygowski and M. K. Cyrański, J. Org. Chem., 2002, 67, 5987-5992.
80. B. T. Stȩpień, T. M. Krygowski and M. K. Cyrański, J. Phys. Org. Chem., 2003, 16, 426-430.
81. B. T. Stȩpień, M. K. Cyrański and T. M. Krygowski, Chem. Phys. Lett., 2001, 350, 537-542.
82. (a) A. Stanger, J. Am. Chem. Soc., 1991, 113, 8277;
83. (b) Z. B. Maksić, M. Ekert-Maksić, M. Hodoscek, W. Koch and D. Kovacek, in Molecules in Natural Science and Medicine, ed. Z. B. Maksic and M. Eckert-Maksic, Ellis Horwood, Chichester, 1991, p. 334.
84. T. M. Krygowski, E. Pindelska, M. K. Cyrański and G. Haefelinger, Chem. Phys. Lett., 2002, 359, 158-162.
85. P. W. Fowler, R. W. A. Havenith, L. W. Jenneskens, A. Soncini and E. Steiner, Angew. Chem., 2002, 114, 1628-1630.
86. R. W. A. Havenith, L. W. Jenneskens and P. W. Fowler, Chem. Phys. Lett., 2003, 367, 468-474.
87. P. W. Fowler, R. W. A. Hevenith, L. W. Jenneskens, A. Soncini and E. Steiner, Chem. Commun., 2001, 22, 2386-2387.
88. F. H. Allen, J. E. Davies, J. J. Galloy, O. Johnson, O. Kennard, M. McRae, E. M. Mitchell, G. F. Mitchell, J. M. Smith and D. G. Watson, J. Chem. Inf. Comput. Sci., 1991, 31, 187-204.
89. P. v. R. Schleyer, P. K. Freeman, H. Jiao and B. Goldfuss, Angew. Chem., Int. Ed. Engl., 1995, 34, 337-340.
90. I. Oonishi, S. Ohshima, S. Fujisawa, J. Aoki, Y. Ohashi and T. M. Krygowski, J. Mol. Struct., 1992, 265, 283.
91. T. M. Krygowski, A. Ciesielski and M. Cyrański, Chem. Pap. (Bratislava), 1995, 49, 128-132.