MCD of non-aromatic cyclic re-electron systems. Part 1. the perimeter model for antiaromatic 4N-electron [n]annulene biradicals

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 5, 1998, Pages 1101-1117

  Höweler, Udo ^a   Downing, John W ^a   Fleischhauer, Jörg ^a,b   Michl, Josef ^a  

^a UNIVERSITY OF COLORADO   (United States)

^b RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0039549785     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a800088c     Document Type: Article

References (34)

1. The project was initiated at the University of Utah. For a preliminary report, see U. Höweler, P. K. Chatterjee, K. A. Klingensmith, J. Waluk and J. Michl, Pure Appl. Chem., 1989, 61, 2117.
2. J. R. Platt, J. Chem. Phys., 1949, 17, 484.
3. W. Moffitt, J. Chem. Phys., 1954, 22, 320.
4. For a more recent summary and extension to higher excited states, see G. Hohlneicher and B. Börsch-Pulm, Ber. Bunsenges. Phys. Chem., 1987, 91, 929.
5. W. Moffitt, J. Chem. Phys., 1954, 22, 1820.
6. E. Heilbronner and J. N. Murrell, Mol. Phys., 1963, 6, 1.
7. M. Gouterman, J. Mol. Spectrosc., 1961, 6, 138.
8. J. Michl, J. Am. Chem. Soc., 1978, 100, 6801.
9. J. Michl, J. Am. Chem. Soc., 1978, 100, 6812.
10. J. Michl, J. Am. Chem. Soc., 1978, 100, 6819.
11. J. Michl, Tetrahedron, 1984, 40, 3845.
12. V. Bonačić-Koutecky, J. Koutecký and J. Michl, Angew. Chem., Int. Ed. Engl., 1987, 26, 170; J. Michl and V. Bonačić-Koutecký, Tetrahedron, 1988, 44, 7559; J. Michl, J. Am. Chem. Soc., 1996, 118, 3568.
13. V. Bonačić-Koutecky, J. Koutecký and J. Michl, Angew. Chem., Int. Ed. Engl., 1987, 26, 170; J. Michl and V. Bonačić-Koutecký, Tetrahedron, 1988, 44, 7559; J. Michl, J. Am. Chem. Soc., 1996, 118, 3568.
14. V. Bonačić-Koutecky, J. Koutecký and J. Michl, Angew. Chem., Int. Ed. Engl., 1987, 26, 170; J. Michl and V. Bonačić-Koutecký, Tetrahedron, 1988, 44, 7559; J. Michl, J. Am. Chem. Soc., 1996, 118, 3568.
15. P.-O. Löwdin, J. Chem. Phys., 1950, 18, 365.
16. C. H. Martin and K. F. Freed, J. Chem. Phys., 1994, 101, 4011; J. Phys. Chem., 1995, 99, 2701.
17. C. H. Martin and K. F. Freed, J. Chem. Phys., 1994, 101, 4011; J. Phys. Chem., 1995, 99, 2701.
18. L. Salem and C. Rowland, Angew. Chem., Int. Ed. Engl., 1972, 11, 92.
19. J. Michl, Mol. Photochem., 1972, 4, 257.
20. C. Doubleday, Jr., J. W. McIver, Jr. and M. Page, J. Am. Chem. Soc., 1982, 104, 6533.
21. W. T. Borden, in Biradicals, ed. W. T. Borden, Wiley, New York, 1982, p. 1.
22. P. N. Schatz and A. J. McCaffery, Q. Rev. Chem. Soc., 1969, 23, 552.
23. AB = [2N]/2 for charged annulenes (axial biradicals).
24. R. Pariser, J. Chem. Phys., 1956, 24, 250.
25. A. D. McLachlan, Mol. Phys., 1959, 2, 271.
26. J. Koutecký, J. Chem. Phys., 1966, 44, 3702.
27. J. Koutecký, J. Paldus and J. ČíŌek, J. Chem. Phys., 1985, 83, 1722.
28. J. Michl, J. Chem. Phys., 1974, 61, 4270.
29. P. J. Stephens, P. N. Schatz, A. B. Ritchie and A. J. McCaffery, J. Chem. Phys., 1968, 48, 132.
30. These characteristics are typical of the class of pair biradicals, to which the uncharged antiaromatic annulenes belong, and of the class of axial biradicals, to which the charged ones belong, respectively.
31. W. T. Borden, in Biradicals, ed. W. T. Borden, Wiley, New York, 1982, p. 58.
32. A. Castellan and J. Michl, J. Am. Chem. Soc., 1978, 100, 6824.
33. R. Pariser and R. G. Parr, J. Chem. Phys., 1953, 21, 466; J. A. Pople, Trans. Faraday Soc., 1953, 49, 1375.
34. R. Pariser and R. G. Parr, J. Chem. Phys., 1953, 21, 466; J. A. Pople, Trans. Faraday Soc., 1953, 49, 1375.