Conformational Studies by Dynamic NMR. 99. Experimental and Computed Determination of Rotation Barriers in the Crystalline State: The Case of Naphthylphenylsulfoxide

Journal of Organic Chemistry

Volumn 69, Issue 10, 2004, Pages 3574-3577

  Casarini, Daniele ^a   Lunazzi, Lodovico ^b   Mazzanti, Andrea ^b   Mercandelli, Pierluigi ^c   Sironi, Angelo ^c  

^a UNIVERSITY OF BASILICATA   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

^c UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CHEMICAL BONDS; COMPUTATIONAL METHODS; COMPUTER SIMULATION; NAPHTHALENE; SINGLE CRYSTALS; SULFUR COMPOUNDS; X RAY DIFFRACTION;

CONFORMATIONAL STUDIES; PHENYLS; ROTATION BARRIERS; SOLID-STATE DISPLAYS;

NUCLEAR MAGNETIC RESONANCE;

2 NAPHTHYLPHENYLSULFOXIDE; CARBON; NAPHTHYL GROUP; SULFOXIDE; SULFUR; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTALLIZATION; ENERGY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ROTATION; SOLID STATE; X RAY DIFFRACTION;

EID: 2442620207     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049843p     Document Type: Article

References (56)

1. Part 98: Bartoli, G.; Lunazzi, L.; Massaccesi, M.; Mazzanti, A. J. Org. Chem. 2004, 69, 821.
2. (a) Dynamic Nuclear Magnetic Resonance Spectroscopy; Jackman, L. M., Cotton, F. A., Eds; Academic Press: New York, 1975.
3. (b) Mann, B. E. Prog. NMR Spectroc. 1977, 11, 95.
4. (c) Kaplan, J. I.; Fraenkel, G. NMR of Chemically Exchanging Systems; Academic Press: New York, 1980.
5. (d) Sandström, J. Dynamic NMR Spectroscopy; Academic Press: London, 1982.
6. (e) Oki, M. Applications of Dynamic NMR Spectroscopy to Organic Chemistry; VCH: Deerfield Beach, 1985.
7. (a) Berg, U.; Sandström, J. Adv. Phys. Org. Chem. 1989, 25, 1.
8. (b) Anderson, J. E. In The Chemistry of Alkanes and Cycloalkanes; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1992; Chapter 3.II.D.
9. (c) Bushweller, C. H. In Acyclic Organonitrogen Stereodynamics; Lambert, J. B., Takeuchi, Y., Eds.; VCH: New York, 1992; Chapter 1.
10. (d) Jennings, W. B.; Wilson, V. E. In Acyclic Organonitrogen Stereodynamics; Lambert, J. B., Takeuchi, Y., Eds.; VCH: New York, 1992; Chapter 6.
11. (a) Gavezzotti, A.; Simonetta, M. Chem Rev. 1982, 82, 1.
12. (b) Braga, D. Chem Rev. 1992, 92, 633.
13. (a) Möller, M.; Gronski, W.; Cantow, H.-J.; Höcker, H. J. Am. Chem. Soc. 1984, 106, 5093.
14. (b) Emeis, D.; Cantow, H.-J.; Möller, M. Polym. Bull. (Berlin) 1984, 12, 557.
15. Twyman, J. M.; Dobson, C. M. J. Chem. Soc., Chem. Commun. 1988, 786.
16. (a) Riddell, F. G.; Arumugam, S.; Anderson, J. E. J. Chem. Soc., Chem. Commun. 1991, 1525.
17. (b) Barrie, P. J.; Anderson, J. E. J. Chem. Soc., Perkin Trans. 2 1992, 2031.
18. (c) Anderson, J. E.; Casarini, D.; Lunazzi, L.; Mazzanti, A. J. Org. Chem. 2000, 65, 1729.
19. (d) Anderson, J. E.; Casarini, D.; Lunazzi, L.; Mazzanti, A. Eur. J. Org. Chem. 2000, 479.
20. (e) Aliev, A. E.; Anderson, J. E.; Butler, D.; Gonzalez-Outeriño, J.; Lunazzi, L.; Mazzanti, A.; Steed, J. Wilhelm, R. Eur. J. Inorg. Chem. 2002, 133.
21. (a) Riddell, F. G.; Arumugam, S.; Harris, K. D. M.; Rogerson, M.; Strange. J. H. J. Am. Chem. Soc. 1995, 115, 1881.
22. (b) Riddell, F.G.; Bremner, M.; Strange, J. H. Magn. Reson. Chem. 1994, 32, 118.
23. (c) Riddell, F. G.; Bernath, G.; Fülöp, F. J. Am. Chem. Soc. 1995, 117, 2327.
24. (d) Riddell, F. G.; Rogerson, M. J. Chem. Soc., Perkin Trans. 2 1996, 493.
25. (e) Riddell, F. G.; Cameron, S.; Holmes, S. A.; Strange, J. H. J. Am. Chem. Soc. 1997, 119, 7555.
26. Barnes, J. C.; Chudek, J. A.; Hunter, G.; Blake, A. J.; Dyson, P. J.; Johnson, B. F. G.; Weissensteiner, W. J. Chem. Soc., Faraday Trans. 1995, 91, 2149.
27. (a) Casarini, D.; Lunazzi, L.; Mazzanti, A. J. Org. Chem. 1998, 63, 9125.
28. (b) Casarini, D.; Foresti, E.; Lunazzi, L., Mazzanti, A. Chem. Eur. J. 1999, 5, 3501.
29. (c) Lunazzi, L.; Mazzanti, A.; Casarini, D.; De Lucchi, O.; Fabris, F. J. Org. Chem. 2000, 65, 883.
30. (d) Casarini, D.; Lunazzi, L.; Mazzanti, A.; Simon, G. J. Org. Chem. 2000, 65, 3207.
31. (e) Casarini, D.; Lunazzi, L.; Mazzanti, A. Angew. Chem., Int. Ed. 2001, 40, 2536.
32. Kümmerlen, J.; Sebald, A. Organometallics 1997, 16, 2971.
33. Mercandelli, P.; Moret, M.; Sironi, A. Inorg. Chem. 1998, 37, 2563.
34. Neuman, M. A.; Johnson, M. R.; Radaelli, P. G.; Trommsdorff, H. P.; Parker, S. F. J. Chem. Phys. 1999, 110, 516.
35. Miyoshi, T.; Hayashi, S.; Imashiro, F.; Kaito, A. Macromolecules 2002, 35, 2624.
36. Galli, S.; Mercandelli, P.; Sironi, A. J. Am. Chem. Soc. 1999, 121, 3767.
37. MMX force field as implemented in the computer package PC Model, v 7.5; Serena Software: Bloomington, IN.
38. Jog, P. V.; Brown, R. E.; Bates, D K. J. Org. Chem. 2003, 68, 8240.
39. (a) Casarini, D.; Grilli, S.; Lunazzi, L.; Mazzanti, A. J. Org. Chem. 2001, 66, 2757.
40. (b) Grilli, S.; Lunazzi, L.; Mazzanti, A. J. Org. Chem. 2001, 66, 4444.
41. (c) Grilli, S.; Lunazzi, L.; Mazzanti, A. J. Org. Chem. 2001, 66, 5853.
42. The ortho and meta carbon signals of the solid-state spectrum at +63 °C (125.0 and 128.5 ppm, respectively) were assigned by analogy with the shifts (125.0 and 129.3 ppm, respectively) of the solution spectrum (see Experimental Section). Such an assignment was further supported by the observation that these two signals grow much more than those of all other carbons when a standard single pulse experiment (without cross polarization) is applied with a 16 s delay time. This is due to the faster relaxation rate that is a consequence of the rapid rotation of the phenyl ring at high temperature (all other carbon signals would require a delay at least 10 times longer to display a significant growth in this single pulse experiment).
43. 13C signals, computed for the isolated molecule, is the same as that occurring in the crystal. It has to be stressed, however, that such an assignment is immaterial for the experimental determination of the rotation barrier, since the opposite assignment would obviously yield the same ΔG‡ value.
44. Limbach, H. H.; Henning, J.; Kendrick, R.; Yannoni, C. S. J. Am. Chem. Soc. 1984, 106, 4059.
45. 24 could not be applied anymore.
46. 24 could not be applied anymore.
47. 24 could not be applied anymore.
48. QCPE program 633; Indiana University: Bloomington, IN.
49. Within the experimental uncertainty the ΔG‡ value was found to be independent of temperature, indicating that the ΔS‡ term must be quite small.
50. 3 as solvent) in the presence of a nearly equimolecular amount of the enantiopure (R)-l-1-(9-anthryl)-2,2,2-trifluoroethanol (Pirkle, W. H. J. Am. Chem. Soc. 1966, 88, 1837).
51. (a) Allinger, N. L.; Yuh, Y. H.; Lii, J.-H. J. Am. Chem. Soc. 1989, 111, 8551.
52. (b) Lii, J.-H.; Allinger, N. L. J. Am. Chem. Soc. 1989, 111, 8566.
53. (c) Lii, J.-H.; Allinger, N. L. J. Am. Chem. Soc. 1989, 111, 8576.
54. Karaulova, E. N.; Bardina, T. A.; Gal'pern, G. D.; Bobruiskaya, T. S Neftekhimiya 1966, 6, 480; Chem. Abstr. 1966, 65, 10452g.
55. Karaulova, E. N.; Bardina, T. A.; Gal'pern, G. D.; Bobruiskaya, T. S Neftekhimiya 1966, 6, 480; Chem. Abstr. 1966, 65, 10452g.
56. Rebiere, F.; Samuel, O.; Ricard, L.; Kagan, H. B. J. Org. Chem. 1991, 56, 5991.