Quantification of the (anti)aromaticity of fulvenes subject to ring size

Tetrahedron Letters

Volumn 49, Issue 17, 2008, Pages 2776-2781

  Kleinpeter, Erich ^a   Fettke, Anja ^a  

^a UNIVERSITY OF POTSDAM   (Germany)

Author keywords

Antiaromaticity; Aromaticity; Fulvenes; GIAO, NICS; MP2 ab initio calculations; Through space NMR shieldings

Indexed keywords

EXOCYCLIC DOUBLE BOND; FULVENE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; AROMA; ARTICLE; CHEMICAL STRUCTURE; CONJUGATION; ELECTRON; NUCLEAR MAGNETIC RESONANCE;

EID: 40949152348     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.02.137     Document Type: Article

References (56)

1. Staley S.W., and Norden T.D. J. Am. Chem. Soc. 106 (1984) 3699
2. Billups W.E., Lin L.-J., and Casserley E.W. J. Am. Chem. Soc. 106 (1984) 3698
3. Maier G., Hoppe M., Lanz K., and Reisenauer P. Tetrahedron Lett. 25 (1984) 5645
4. Thiele J. Chem. Ber. 33 (1900) 666
5. Thiele J., and Balhorn H. Ann. Chem. 348 (1906) 1
6. Neuenschwander M., and Iseli R. Helv. Chim. Acta 60 (1977) 1061
7. Doering W.v.E., and Wiley D.H. Tetrahedron (1960) 184
8. Doering W.v.E., and Wiley D.H. Angew. Chem. 67 (1955) 429
9. Neuenschwander M., and Frey A. Chimia 28 (1974) 119
10. Neuenschwander M., and Frey A. Chimia 29 (1975) 212
11. Norden T.D., Staley S.W., Taylor W.H., and Harmony M.D. J. Am. Chem. Soc. 108 (1986) 7918
12. Baron P.A., Brown R.D., Burden F.R., Domaille P.J., and Kent J.E. J. Mol. Spectrosc. 43 (1972) 401
13. Kamatsu K., Fujimori M., and Okamoto K. Tetrahedron 33 (1977) 2791
14. Hollenstein R., Philipsborn W.v., Vögeli R., and Neuenschwander N. Helv. Chim. Acta 56 (1973) 847
15. Hollenstein R., Mooser A., Neuenschwander M., and Philipsborn W.v. Angew. Chem., Int. Ed. Engl. 13 (1974) 551
16. Schenk W.K., Kyrburz R., and Neuenschwander M. Helv. Chim. Acta 58 (1975) 1099
17. Neuenschwander M. Pure Appl. Chem. 58 (1986) 55
18. Chai S., and Neuenschwander M. Helv. Chim. Acta 77 (1994) 1377
19. Furrer J., Bönzli P., Frey A., and Neuenschwander M. Helv. Chim. Acta 70 (1987) 862
20. Chai S., Bönzli P., and Neuenschwander M. Helv. Chim. Acta 78 (1995) 215
21. Scott A.P., Agranat I., Biedermann P.U., Riggs N.V., and Radom L. J. Org. Chem. 62 (1997) 2026 and references cited therein
22. Möllerstedt H., Piqueras M.C., Crespo R., and Ottoson H. J. Am. Chem. Soc. 126 (2004) 13938 and references cited therein
23. Collier W., Saebø A., and Pittman Jr. C.U. J. Mol. Struct. (Theochem) 549 (2001) 1
24. Halton B., Boese R., and Dixon G.M. Tetrahedron Lett. 45 (2004) 2167
25. Najafian K., Schleyer P.v.R., and Tidwell T.T. Org. Biomol. Chem. 1 (2003) 3410
26. Ste{ogonek}pień B.T., Cyrański M.K., and Krygowski T.M. Chem. Phys. Lett. 350 (2001) 537
27. Ste{ogonek}pień B.T., Cyrański M.K., and Krygowski T.M. J. Org. Chem. 67 (2002) 5987
28. Bachrach S.M., and Lui M. J. Phys. Org. Chem. 4 (1991) 242
29. Höltzl T., Nguyed M.T., and Veszprémi T. J. Mol. Struct. (Theochem) 811 (2007) 27 and references cited therein
30. Burk P., Abboud J.-L.-M., and Koppel I.K. J. Phys. Chem. 100 (1996) 6992
31. Hinchliffe A., and Machado H.J.S. Int. J. Mol. Sci. 1 (2000) 39
32. Kleinpeter E., Klod S., and Rudorf W.D. J. Org. Chem. 69 (2004) 4317
33. Kleinpeter E., and Schulenburg A. Tetrahedron Lett. 46 (2005) 5995
34. Chen Z., Wannere C.S., Corminboeuf C., Puchta R., and Schleyer P.v.R. Chem. Rev. 105 (2005) 3842
35. Klod S., and Kleinpeter K. J. Chem. Soc., Perkin Trans. 2 (2001) 1893
36. Kleinpeter E., Klod S., and Koch A. J. Mol. Struct. (Theochem) 811 (2007) 45
37. Schleyer P.v.R., Manoharan M., Wang Z.X., Kiran B., Jiao Y., Puchta R., and Hommes N.J.R.v.E. Org. Lett. 3 (2001) 2465
38. Sebastiani D. ChemPhysChem 7 (2006) 164
39. Montero-Campillo M.M., Rodríguez-Otero J., and Cabaleiro-Lago E.M. J. Mol. Mod. 13 (2007) 919
40. Kleinpeter E., Holzberger A., and Wacker Ph. J. Org. Chem. 73 (2008) 1323
41. Kleinpeter E., Klod S., and Koch A. J. Org. Chem. 21 (2008) 173
42. Fallah-Bagher-Shaidaei H., Wannere C.S., Corimboeuf C., and Schleyer P.v.R. Org. Lett. 5 (2006) 683
43. Stanger A. Chem. Eur. J. 12 (2006) 2745
44. Lazzeretti P. PhysChemChemPhys 6 (2004) 217
45. Wannere C.S., and Schleyer P.v.R. Org. Lett. 5 (2003) 605
46. Viglione R.G., Zanasi R., and Lazzeretti P. Org. Lett. 6 (2004) 2265
47. Wannere C.S., Corimboeuf C., Allen W.A., Schaefer III H.F., and Schleyer P.v.R. Org. Lett. 7 (2005) 1457
48. Faglioni F., Ligabue A., Pelloni S., Soncini A., Viglione R.G., Ferraro M.B., Zanasi R., and Lazzeretti P. Org. Lett. 7 (2004) 3457
49. Martin N.H., Loveless D.M., Main K.L., and Wade D.C. J. Mol. Graph. Model. 25 (2006) 389
50. Frisch M. J., et al., gaussian 03, Revision C.02; Gaussian: Wallingford, CT, 2004.
51. Ditchfield J.R. Mol. Phys. 27 (1974) 789
52. Cheeseman J.R., Trucks G.W., Keith T.A., and Frisch M.J. J. Chem. Phys. 104 (1996) 5497
53. The lattice points ('ghost atoms') should be sensor points only without energy contribution in the present calculations. Only if HF calculations are applied will this prove to be true; in case of electron correlation calculations, the 'ghost atoms' get their own electron density and are of some influence on the energy of the studied molecule hereby. In these cases, the TSNMRS surfaces proved to get heavily distorted.
54. sybyl 7.1, Tripos, 1699 South Hanley Road, St. Louis MO, 2005.
55. Reed A.E., Weinstock R.B., and Weinhold F.J. J. Chem. Phys. 83 (1985) 735
56. Klod S., Koch A., and Kleinpeter E. J. Chem. Soc., Perkin Trans. 2 (2002) 1506