Structural Ambiguities Revisited in Two Bridged Ring Systems Exhibiting Enantiotopic Elements, Using Natural Abundance Deuterium NMR in Chiral Liquid Crystals

Journal of Physical Chemistry A

Volumn 107, Issue 50, 2003, Pages 10911-10918

  Aroulanda, Christie ^a   Lesot, Philippe ^a   Merlet, Denis ^a   Courtieu, Jacques ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANISOTROPY; CHEMICAL BONDS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE; ORGANIC SOLVENTS; PROTONS; RESONANCE; SOLUTIONS; STEREOCHEMISTRY;

ENANTIOMERS; SOLUTES;

NEMATIC LIQUID CRYSTALS;

EID: 0346937400     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp030137m     Document Type: Article

References (60)

1. Saupe, A.; Englert, G. Phys. Rev. Lett. 1963, 11, 462.
2. Emsley, J. W.; Lindon, J. C. NMR Spectroscopy Using Liquid Crystal Solvents; Pergamon Press: Oxford, 1975.
3. Diehl, P. In Nuclear Magnetic Resonance of Liquid Crystals; Emsley, J. W., Ed.; Reidel: Dordrecht, The Netherlands, 1985.
4. (a) Fung, B. M. Prog. Nucl. Magn. Reson. Spectrosc. 2002, 41, 171.
5. (b) Sandström, D.; Summamen, K. T.; Levitt, M. H J. Am. Chem. Soc. 1994, 126, 9357.
6. (c) Madiot, V.; Lesot, P.; Grée, D.; Courtieu, J.; Grée, R. Chem. Commun. 2000, 169.
7. (a) Gochin, M.; Pines, A.; Rosen, M. E.; Rucker, S. P.; Schmidt, C. Mol. Phys. Lett. 1990, 69, 671.
8. (b) Emsley, J. W.; Foord, E. K.; Gandy, P. J.; Turner, D. L.; Zimmermann, H. Liq. Cryst. 1994, 17, 303.
9. (a) Tabayashi, K.; Akasaka, K. J. Phys. Chem. B1997, 101, 5108.
10. (b) Ramanthan, K. V.; Suryaprakash, N.; Vivekanandan, S. J. Magn. Reson. 1998, 135, 265.
11. Lesot, P.; Merlet, D.; Loewenstein, D.; Courtieu, J. Tetrahedron: Asymmetry 1998, 9, 1871.
12. (a) Tjandra, N.; Bax, A. Science 1997, 278, 1111.
13. (b) Ottiger, M.; Bax, A. J. J. Biomol. NMR 1998, 12, 361.
14. (c) Tian, F.; Valafar, H.; Prestegard, J. H. J. Am. Chem. Soc, 2001, 123, 447.
15. (d) De Alba, E.; Tjandra, N. Prog. Nucl. Magn. Reson. 2002, 40, 175.
16. (a) Bhagavantam, B.; Suryanarayana, D. Acta Crystallogr. 1949, 2, 21.
17. (b) Zannoni, C. In Nuclear Magnetic Resonance of Liquid Crystal; Emsley, J. W., Ed.; Reidel: Dordrecht, The Netherlands, 1985.
18. Zannoni, C. In The Molecular Physics of Liquid Crystals; Luckhurst, G. R., Gray, G. W., Eds.; Academic Press: 1979.
19. Merlet, D.; Emsley, J. W.; Lesot, P.; Courtieu, J. J. Chem. Phys. 1999, 111, 6890.
20. Merlet, D.; Loewenstein, A.; Smadja, W.; Courtieu, J.; Lesot, P. J. Am. Chem. Soc. 1998, 720, 963.
21. Aroulanda, C.; Merlet, D.; Courtieu, J.; Lesot, P. J. Am. Chem. Soc. 2001, 123, 12059.
22. Eliel, A. L.; Wilen, A. H. Stereochemistry of Organic Compounds; Wiley and Sons, Inc.: New York, 1994.
23. Aroulanda, C.; Sarfati, M.; Courtieu, J.; Lesot, P. Enantiomer 2001, 6, 281.
24. Tori, K.; Hata, Y.; Muneyuki, R.; Takano, Y.; Tsuji, T.; Tanida, H. Can. J. Chem. 1964, 42, 926.
25. (a) Khetrapal, C. L.; Ramanathan, K. V. Nucl. Magn. Reson. 1998, 27, 458.
26. (b) Khetrapal, C. L Concepts Magn. Reson. 1998, 10, 16.
27. (c) Khetrapal, C. L. Curr. Org. Chem. 2000, 4, 85.
28. (a) Jonströmer, M.; Strey, R. J. Chem. Phys. 1992, 96, 5993.
29. (b) Rückert, M.; Otting, G. J. Am. Chem. Soc. 2000, 722, 7793.
30. Sarfati, M.; Lesot, P.; Merlet, D.; Courtieu, J. Chem. Commun. 2000, 2069 references therein.
31. (a) Emsley, J. W.; Merlet, D.; Smith, K. J.; Suryaprakash, N. J. Magn. Reson, 2002, 154, 303.
32. (b) Farjon, J.; Merlet, D.; Lesot, P.; Courtieu, J. J. Magn. Reson. 2002, 158, 169.
33. (a) Merlet, D.; Ancian, B.; Courtieu, J.; Lesot, P. J. Am. Chem. Soc. 1999, 121, 5249.
34. (b) Lesot, P.; Sarfati, M.; Merlet, D.; Courtieu, J.; Ancian, B.; Brevard, C. Bruker Rep. 2001, 149, 29.
35. Lesot, P.; Sarfati, M.; Courtieu, J. Eur. J. Chem. 2003, 9, 1724.
36. (a) Lesot, P.; Merlet, D.; Meddour, A.; Loewenstein, A.; Courtieu, J. J. Chem. Soc., Faraday Trans. 1995, 91, 1371.
37. (b) Meddour, A.; Berdagué, P.; Hedli, A.; Courtieu, J.; Lesot, P. J. Am. Chem. Soc. 1997, 119, 4502.
38. Kalinowski, H. A.; Berger, S.; Braun, S. Carbon-13 NMR Spectroscopy; Wiley and Sons: New York, 1988.
39. Diehl, P.; Henrichs, P. M.; Niederberger, W. Mol. Phys. 1971, 1, 139.
40. Lesot, P.; Merlet, D.; Rantala, T. T.; Jokisaari, J.; Emsley, J. W.; Courtieu, J. J. Phys. Chem. 1997, 101, 5719.
41. Paasivirta, J. Suom. Kemistil. 1963, B36, 77.
42. Marchand, A. P.; Marchand, N. W. Tetrahedron Lett. 1971, 78, 1365.
43. Tori, K.; Aono, K.; Hata, Y.; Muneyuki, R.; Tsuji, T.; Tanida, H. Tetrahedron Lett. 1966, 1, 9.
44. Franzus, B.; Baird, W. C.; Chamberlain, N. F.; Hines, T.; Snyder, E. I. J. Am. Chem. Soc. 1968, 90, 3721.
45. (a) Garbisch, E. W. Chem. Commun. 1968, 332.
46. (b) Abraham, R. J.; Fisher, J. Magn. Reson. Chem. 1985, 23, 866.
47. (c) Parella, T.; Sanchez-Fernando, E.; Virgili, A. Magn. Reson. Chem. 1995, 33, 196.
48. (a) Aroulanda, C.; Boucard, V.; Guibé, E.; Courtieu, J.; Merlet, D. Chem. Eur. J. 2003, 9, 4536-4539.
49. (b) Thiele, C.; Berger, S. Org. Lett. 2003, 5, 705.
50. (c) Verdier, L.; Sakhaii, P.; Zwecktetter, M.; Griesinger, C. J. Magn. Reson. 2003, 163, 353-359.
51. (a) Alvira, E.; Breton, J.; Plata, J. Chem. Phys. 1991, 155, 7.
52. (b) Helfrich, J.; Hentschke, R.; Apel, U. M. Macromolecules 1994, 27, 472.
53. (c) Celebre, G. J. Chem. Phys. 2001, 775, 9552.
54. Canlet, C.; Merlet, D.; Lesot, P.; Meddour, A.; Loewenstein, A.; Courtieu, J. Tetrahedron: Asymmetry 2000, 77, 1911.
55. (a) Franceschi, F.; Guardigli, M.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Inorg. Chem. 1997, 36, 4099.
56. (b) Rosi, M.; Sgamellotti, A.; Franceschi, F.; Floriani, C. Inorg. Chem. 1999, 38, 1520.
57. (c) Hammond, G. S.; Turro, N. J.; Fischer, A. J. Am. Chem. Soc. 1961, 83, 4674.
58. (d) Card, R. J.; Neckers, D. C. J. Org. Chem. 1978, 43, 2958.
59. (a) Bach, R. D.; Schilke, I. L.; Schlegel, H. B. J. Org. Chem. 1996, 67, 4845.
60. (b) Mizuno, K.; Fukuyama, T.; Kutchitsu, K. Chem. Lett. 1972, 249.