Trisannelated benzenes - Aromatic molecules or 1,3,5-cyclohexatriene derivatives subjected to magnetic properties

Journal of Molecular Structure: THEOCHEM

Volumn 857, Issue 1-3, 2008, Pages 89-94

  Kleinpeter, Erich ^a   Koch, Andreas ^a  

^a UNIVERSITY OF POTSDAM   (Germany)

Author keywords

4n Annuleno 4n + 2 annulene; Ab initio calculation; Aromaticity; GIAO; NICS; Through space NMR shielding values; Tricyclobutabenzene

Indexed keywords

EID: 42649129696     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2008.02.013     Document Type: Article

References (52)

1. Siegel J.S. Angew. Chem. Int. Ed. Engl. 33 (1994) 1721
2. Z.B. Maksic, M. Eckert-Maksic, O. Ms, M. Yaqez. Theoretical and Computational Chemistry, vol. 6, Pauling's Legacy. Modern Modeling of the Chemical Bonding, Elsevier, Amsterdam, 1999.
3. Krygowski T.M., and Cyranski M.K. Chem. Rev. 101 (2001) 1385
4. Havenith R.W.A., Jenneskens L.W., Fowler P.W., and Soncini A. Org. Biomol. Chem. 2 (2004) 1281
5. Heilbronner E., Kovač B., Nutakul W., Taggert A.D., and Thummel R.P. J. Org. Chem. 46 (1981) 5279
6. Boese R., Bläser D., Billups W.E., Haley M.M., Maulitz A.H., Mohler D.L., and Vollhardt K.P.C. Angew. Chem. Int. Ed. Engl. 33 (1994) 313
7. Stanger A., Ashkenazi N., Boese R., Bläser D., and Stellberg P. Chem. Eur. J. 3 (1997) 208
8. Hamura T., Ibusuki Y., Uekusa H., Matsumoto T., Siegel J.S., Baldridge K.K., and Suzuki K. J. Am. Chem. Soc. 128 (2006) 10032
9. Neidlein R., Christen D., Poignée V., Boese R., Bläser D., Gieren A., Ruiz-Pérez C., and Hübner Th. Angew. Chem. Int. Ed. Engl. 27 (1988) 294
10. Boese R., and Bläser D. Angew. Chem. Int. Ed. Engl. 27 (1988) 304
11. Kawase T., Minami Y., Nishigaki N., Okano S., Kuruta H., and Oda M. Angew. Chem. Int. Ed. Engl. 44 (2005) 316
12. Diercks P., and Vollhardt K.P.C. J. Am. Chem. Soc. 108 (1986) 3150
13. Boese R., Matzger A.J., Mohler D.L., and Vollhardt K.P.C. Angew. Chem. Int. Ed. Engl. 34 (1994) 1478
14. Chen Z., Wannere C.S., Corminboeuf C., Puchta R., and Schleyer P.v.R. Chem. Rev. 105 (2005) 3842
15. Schleyer P.v.R., Manoharan M., Wang Z.X., Kiran B., Jiao H., Puchta R., and Hommes N.J.R.v.E. Org. Lett. 3 (2001) 2465
16. Klod S., and Kleinpeter E. J. Chem. Soc. Perkin Trans. 2 (2001) 1893
17. Klod S., Koch A., and Kleinpeter E. J. Chem. Soc. Perkin Trans. 2 (2002) 1506
18. Kleinpeter E., Klod S., and Rudorf W.-D. J. Org. Chem. 69 (2004) 4317
19. Kleinpeter E., and Klod S. J. Am. Chem. Soc. 126 (2004) 2231
20. Kleinpeter E., Schulenburg A., Zug I., and Hartmann H. J. Org. Chem. 70 (2005) 6592
21. Kleinpeter E., and Schulenburg A. J. Org. Chem. 71 (2006) 3869
22. Kleinpeter E., Klod S., and Koch A. J. Mol. Struct. (THEOCHEM) 811 (2007) 45
23. Kleinpeter E., Klod S., and Koch A. J. Org. Chem. 73 (2008) 173
24. Kleinpeter E., Holzberger A., and Wacker Ph. J. Org. Chem. 73 (2008) 56
25. Alkorta I., and Elguero J. New J. Chem. (1998) 381
26. Martin N.H., Allen III N.W., Moore K.D., and Vo L. J. Mol. Struct. (THEOCHEM) 454 (1998) 161
27. Martin N.H., Allen III N.W., and Moore J.C. J. Mol. Graph Model. 18 (2000) 242
28. Martin N.H., Allen III N.W., Minga E.K., Ingrassia S.T., and Brown J.D. Struct. Chem. 9 (1998) 403
29. Martin N.H., Allen III N.W., Minga E.K., Ingrassia S.T., and Brown J.D. Proceedings of ACS Symposium, Modeling NMR Chemical Shifts: Gaining Insight into Structure and Environment (1999), ACS Press
30. Martin N.H., Allen III N.W., Minga E.K., Ingrassia S.T., and Brown J.D. Struct. Chem. 10 (1999) 375
31. Martin N.H., Allen III N.W., Ingrassia S.T., Brown J.D., and Minga E.K. J. Mol. Graph. Model. 18 (2000) 1
32. Martin N.H., and Nance K.H. J. Mol. Graph. Model. 21 (2002) 51
33. Martin N.H., Allen III N.W., Brown J.D., Kniec Jr. D.M., and Vo L. J. Mol. Graph. Model. 22 (2003) 127
34. Martin N.H., Loveless D.M., and Wade D.C. J. Mol. Graph. Model. 23 (2004) 285
35. Waugh J.S., and Fessenden R.W. J. Am. Chem. Soc. 79 (1957) 846
36. Johnson C.E., and Bovey F.A. J. Chem. Phys. 29 (1958) 1012
37. Jonathan N., Gordon S., and Dailey B.P. J. Chem. Phys. 36 (1962) 2443
38. Barfield M., Grant D.M., and Ikenberry D. J. Am. Chem. Soc. 97 (1975) 6956
39. Agarwal A., Barnes J.A., Fletcher J.L., McGlinchey M.J., and Saver B.G. Can. J. Chem. 55 (1977) 2575
40. Haigh C.W., and Mallion R.B. Progress in NMR Spectroscopy vol. 13 (1980), Pergamon Press Ltd., New York pp. 303
41. Haigh C.W., and Mallion R.B. Mol. Phys. 22 (1971) 955
42. Haigh C.W., and Mallion R.B. Org. Magn. Reson. 4 (1972) 203
43. Dailey B.P. J. Chem. Phys. 41 (1964) 2304
44. M.J. Frisch et al., Gaussian 03, Revision C.02, Gaussian, Inc., Wallingford, CT, 2004.
45. Møller C., and Plesset M.S. Phys. Rev. 46 (1934) 618
46. Schleyer P.v.R., Maerker C., Dransfeld A., Jiao H., and Hommes N.J.R.v.E. J. Am. Chem. Soc. 118 (1996) 6317
47. The lattice points ("ghost atoms") should be sensor points only without energy contribution in the present calculations. Only if HF calculations are applied this proved 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.
48. SYBYL 7.2 Tripos Inc. 1699 South Hanley Road, St. Louis, Missouri 63144, USA, 2006.
49. Wannere C.S., and Schleyer P.v.R. Org. Lett. 5 (2003) 605
50. Viglione R.G., Zanasi R., and Lazzeretti P. Org. Lett. 6 (2004) 2265
51. Wannere C.S., Corminboeuf C., Allen W.A., Schaefer III H.F., and Schleyer P.v.R. Org. Lett. 7 (2005) 1457
52. Faglioni F., Ligabue A., Pelloni S., Soncini A., Viglione R.G., Ferraro M.B., Zanasi R., and Lazzeretti P. Org. Lett. 7 (2004) 3457