Correct values of the rotation barriers of 1,8-ditolylanthracenes

Journal of Organic Chemistry

Volumn 72, Issue 14, 2007, Pages 5391-5394

  Lunazzi, Lodovico ^a   Mancinelli, Michele ^a   Mazzanti, Andrea ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

LINE-SHAPE SIMULATION; ROTATION BARRIERS; VARIABLE-TEMPERATURES;

COMPUTER SIMULATION; DERIVATIVES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THERMAL EFFECTS;

ANTHRACENE;

1,8 DITOLYLANTHRACENE DERIVATIVE; ANTHRACENE DERIVATIVE; UNCLASSIFIED DRUG;

ACCURACY; ARTICLE; MATHEMATICAL ANALYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SIMULATION; STRUCTURE ACTIVITY RELATION; SURFACE CHARGE; TEMPERATURE MEASUREMENT;

EID: 34447319097     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070679q     Document Type: Article

References (46)

1. In partial fulfillment for receiving a Ph.D. degree in Chemical Sciences, University of Bologna
2. House, H. O.; Hrabie, J. A.; VanDerveer, D. J. Org. Chem. 1986, 51, 921.
3. House, H. O.; Holt, J. T.; VanDerveer, D. J. Org. Chem. 1993, 58, 7516.
4. Molecular Mechanics approach using the MMFF force field as in PC Model v 7.5, Serena Software, Bloomington, IN.
5. (a) Casarini, D.; Grilli, S.; Lunazzi, L.; Mazzanti, A. J. Org. Chem. 2001, 66, 2757.
6. (b) Grilli, S.; Lunazzi, L.; Mazzanti, A. J. Org. Chem. 2001, 66, 4444.
7. (c) Grilli, S.; Lunazzi, L.; Mazzanti, A. J. Org. Chem. 2001, 66, 5853.
8. (d) Jog, P. V.; Brown, R. E.; Bates, D. K. J. Org. Chem. 2003, 68, 8240.
9. (e) Casarini, D.; Lunazzi, L.; Mazzanti, A.; Mercandelli, P.; Sironi, A. J. Org. Chem. 2004, 69, 821.
10. Frisch, M. J., et al. Gaussian 03, Revision D.01; Gaussian, Inc.: Wallingford, CT, 2004 (See Supporting Information).
11. Pérez-Trujillo, M.; Maestre, I.; Jaime, C.; Alvarez-Larena, A.; Pinella, J. F.; Virgili, A. Tetrahedron: Asymmetry 2005, 16, 3084.
12. PC version of the DNMR program no. 633, QCPE, Indiana University, Bloomington, IN.
13. Dondoni, A.; Lunazzi, L.; Giorgianni, P.; Macciantelli, D. J. Org. Chem. 1975, 20, 2979.
14. Hoogosian, D. S.; Bushweller, C. H.; Anderson, W. G.; Kigsley, G. J. Phys. Chem. 1976, 80, 643.
15. Lunazzi, L.; Cerioni, G.; Ingold, K. U. J. Am. Chem. Soc. 1976, 98, 7484.
16. Lunazzi, L.; Dondoni, A.; Barbaro, G.; Macciantelli, D. Tetrahedron Lett. 1977, 18, 1079.
17. Forlani L.; Lunazzi L.; Medici, A. Tetrahedron Lett. 1977, 18, 4525.
18. Bernardi, F.; Lunazzi, L.; Zanirato, P.; Cerioni, G. Tetrahedron, 1977, 33, 1337.
19. Lunazzi, L.; Magagnoli, C.; Guerra, M.; Macciantelli, D. Tetrahedron Lett. 1979, 3031.
20. Cremonini, M. A.; Lunazzi, L.; Placucci, G.; Okazaki, R.; Yamamoto, G. J. Am. Chem. Soc. 1990, 112, 2915.
21. Anderson, J. E.; Tocher, D. A.; Casarini, D.; Lunazzi, L. J. Org. Chem. 1991, 56, 1731.
22. Borghi, R.; Lunazzi, L.; Placucci, G.; Cerioni, G.; Foresti, E.; Plumitallo, A. J. Org. Chem. 1997, 62, 4924.
23. Garcia, M. B.; Grilli, S.; Lunazzi, L.; Mazzanti, A.; Orelli, L. R. J. Org. Chem. 2001, 66, 6679.
24. Garcia, M. B.; Grilli, S.; Lunazzi, L.; Mazzanti, A.; Orelli, L. R. Eur. J. Org. Chem. 2002, 4018.
25. Casarini, D.; Rosini, C.; Grilli, S; Lunazzi, L.; Mazzanti, A. J. Org. Chem. 2003, 68, 1815.
26. Casarini, D.; Grilli, S.; Lunazzi, L.; Mazzanti, A. J. Org. Chem. 2004, 69, 345.
27. Bartoli, G.; Lunazzi, L.; Massacesi, M.; Mazzanti, A. J. Org. Chem. 2004, 69, 821.
28. Casarini, D.; Coluccini, C.; Lunazzi, L.; Mazzanti, A.; Rompietti, R. J. Org. Chem. 2004, 69, 5746.
29. -1 (see Lunazzi, L.; Mazzanti, A.; Minzoni, M. J. Org. Chem. 2007, 72, 2501).
30. Lunazzi, L.; Mazzanti, A. J. Am. Chem. Soc. 2004, 126, 12157.
31. (a) Stonehouse, J.; Adell, P.; Keeler, J.; Shaka, A. J. J. Am. Chem. Soc. 1994, 116, 6037.
32. (b) Stott, K.; Stonehouse, J.; Keeler, J.; Hwang, T. L.; Shaka, A. J. J. Am. Chem. Soc. 1995, 117, 4199.
33. (c) Stott, K.; Keeler, J.; Van, Q. N.; Shaka, A. J. J. Magn. Reson. 1997, 125, 302.
34. (d) Van, Q. N.; Smith, E. M.; Shaka, A. J. J. Magn. Reson. 1999, 141, 191.
35. The NOE experiment was carried out at 0°C to avoid the possibility of a saturation transfer process between the two conformers.
36. -1 higher.
37. Lunazzi, L.; Mazzanti, A.; Minzoni, M.; Anderson, J. E. Org. Letters 2005, 7, 1291.
38. Mazzanti, A.; Lunazzi, L.; Minzoni, M.; Anderson, J. E. J. Org. Chem. 2006, 71, 5474.
39. Lunazzi, L.; Mazzanti, A.; Minzoni, M. J. Org. Chem. 2006, 71, 9297.
40. Bott, G.; Field, L. D.; Sternhell, S. J. Am. Chem. Soc. 1980, 102, 5618.
41. Bradley, S. A.; Krishnamurthy, K. Magn. Reson. Chem. 2005, 43, 117.
42. Willker, W.; Leibfritz, D.; Kerssebaum, R.; Bermel, W. Magn. Reson. Chem. 1993, 31, 287.
43. Hurd, R. E.; John, B. K. J. Magn. Reson. 1991, 91, 648.
44. Smallcombe, S. H. J. Am. Chem. Soc. 1993, 115, 4776;
45. Patt, S. J. Magn. Reson. 1992, 96, 94.
46. Kupče, E.; Boyd, J.; Campbell, I. D. J. Magn. Reson., Ser. B 1995, 106, 300.