Topological rotational strengths as chirality descriptors for fullerenes

Chemistry - A European Journal

Volumn 9, Issue 3, 2003, Pages 644-651

  Rassat, André ^a   Làszló, Istvàn ^b   Fowler, Patrick W ^c  

^a ECOLE NORMALE SUPÉRIEURE   (France)

^b BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^c UNIVERSITY OF EXETER   (United Kingdom)

Author keywords

Chirality; Fullerenes; Graph theory; Polyhedra rotational strength

Indexed keywords

MOLECULAR STRUCTURE; TOPOLOGY;

CHIRALITY;

FULLERENES;

FULLERENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; MOLECULAR MODEL; ROTATION; STRENGTH;

EID: 0037415921     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200390072     Document Type: Article

References (63)

1. a) F. Wudl, R. E. Smalley, A. B. Smith, R. Taylor, E. Wasserman, E. W. Godly, Pure Appl. Chem. 1997. 69, 1412-1434;
2. b) E. W. Godly, R. Taylor, Fullerene Sci. Techn. 1997, 5, 1667-1708;
3. c) A. L. Goodson, C. L. Gladys, D. E. Worst, J. Chem. Inf. Comput. Sci. 1995, 35, 969-978;
4. d) A. Herrmann, M. Rüttimann, C. Thilgen, F. Diederich, Helv. Chim. Acta 1995, 78, 1673-1704.
5. a) R. S. Cahn, C. K. Ingold, V. Prelog, Experientia 1956, 12, 81-124;
6. b) R. S. Cahn, C. K. Ingold, V. Prelog, Angew. Chem. 1966, 78, 413-447; Angew. Chem. Int. Ed. Engl. 1966, 5, 385-415;
7. b) R. S. Cahn, C. K. Ingold, V. Prelog, Angew. Chem. 1966, 78, 413-447; Angew. Chem. Int. Ed. Engl. 1966, 5, 385-415;
8. c) V. Prelog, G. Helmchen, Angew. Chem. 1982, 94, 614-631; Angew. Chem. Int. Ed. Engl. 1982, 21, 567-583.
9. c) V. Prelog, G. Helmchen, Angew. Chem. 1982, 94, 614-631; Angew. Chem. Int. Ed. Engl. 1982, 21, 567-583.
10. A. Rassat, P. W. Fowler, B. de La Vaissière, Chem. Eur. J. 2001, 7, 3985-3991.
11. a) W. J. A. Goossens, Mol. Cryst. Liq. Cryst. 1971, 12, 237-244;
12. b) P. G. de Gennes, J. Prost, The Physics of Liquid Crystals, 2nd ed., Oxford University Press, Oxford, 1993.
13. For a general discussion on pseudoscalars and chirality, see also: A. B. Harris, R. D. Kamien, T. C. Lubensky, Rev. Mod. Phys. 1999, 71, 1745-1757.
14. N. Weinberg, K. Mislow, Can. J. Chem. 2000, 78, 41-45.
15. See for instance A. L. Lehninger, Biochemistry, 2nd ed., Worth Publisher, New York, 1975, p. 81-82.
16. See for instance C. S. Hudson, Adv. Carbohydr. Chem. 1948, 3, 1-22; M. A. Rosanoff, J. Am. Chem. Soc. 1906, 28, 114-121.
17. See for instance C. S. Hudson, Adv. Carbohydr. Chem. 1948, 3, 1-22; M. A. Rosanoff, J. Am. Chem. Soc. 1906, 28, 114-121.
18. For another use of the optical rotatory power, see M. A. Osipov, B. T. Pickup, D. A. Dunmur, Mol. Phys. 1995, 84, 1193-1206.
19. D. E. Manolopoulos, P. W. Fowler, J. Chem. Phys. 1992, 96, 7603-7614.
20. a) E. U. Condon, W. Altar, H. Eyring, J. Chem. Phys. 1937, 5, 753-775;
21. b) E. U. Condon, Rev. Mod. Phys. 1937. 9, 432-457;
22. c) W. J. Kauzman, J. E. Walter. H. Eyring, Chem. Rev. 1940, 26, 339-407.
23. The first attempt to calculate the rotational strength of a molecule by Hückel theory was reported in a) A. Moscowitz, Tetrahedron 1961, 13, 48-61; see, however, b) D. A. Lightner, T. W. Powers, K. N. True-blood, G. W. Frank, D. T. Hefelfinger, J. Am. Chem. Soc. 1972, 94, 3492-3497 and c) A. A. Hansen, K. L. Bak, Enantiomer 1999, 4, 455-476.
24. The first attempt to calculate the rotational strength of a molecule by Hückel theory was reported in a) A. Moscowitz, Tetrahedron 1961, 13, 48-61; see, however, b) D. A. Lightner, T. W. Powers, K. N. True-blood, G. W. Frank, D. T. Hefelfinger, J. Am. Chem. Soc. 1972, 94, 3492-3497 and c) A. A. Hansen, K. L. Bak, Enantiomer 1999, 4, 455-476.
25. The first attempt to calculate the rotational strength of a molecule by Hückel theory was reported in a) A. Moscowitz, Tetrahedron 1961, 13, 48-61; see, however, b) D. A. Lightner, T. W. Powers, K. N. True-blood, G. W. Frank, D. T. Hefelfinger, J. Am. Chem. Soc. 1972, 94, 3492-3497 and c) A. A. Hansen, K. L. Bak, Enantiomer 1999, 4, 455-476.
26. a) A. Rassat, D. Seroussi, C. Coulombeau, J. Chim. Physique 1994, 91, 1683-1710;
27. b) A. Rassat, G. Scalmani, D. Seroussi, G. Berthier, THEOCHEM J. Mol. Struct. 1995, 338, 31-41;
28. c) A. Rassat, Chirality 2001, 395-402.
29. H. W. Kroto, Nature 1987, 329, 529-531.
30. P. W. Fowler, D. E. Manolopoulos, An Atlas of Fullerenes, Oxford University Press, Oxford, 1995.
31. D. Cvetkovic, M. Doob, H. Sachs, Spectra of Graphs, 3rd ed., Johann Ambrosius Barth, Basel, 1995.
32. D. Bakowies, W. Thiel, J. Am. Chem. Soc. 1991, 113, 3704-3714.
33. A. Graovac, D. Plavšić, M. Kaufman, T. Pisanski, E. C. Kirby, J. Chem. Phys. 2000, 113, 1925-1931.
34. C. Thilgen, A. Herman, F. Diederich, Helv. Chem. Acta 1997, 80, 183-199.
35. a) V. Schlegel, Verhandlungen (Nova Acta) der Kaiserlichen Leopoldinisch-Carolinischen Deutschen Akademie der Naturforscher 1883, 44, 343-359;
36. b) H. S. M. Coxeter, Regular Polytopes, 3rd ed., Dover Publications, New York, 1973;
37. c) A. J. Wells, The Third Dimension in Chemistry, Oxford University Press, Oxford, 1956.
38. C. Thilgen, F. Diederich, Top. Curr. Chem. 1999, 199, 135-171.
39. L. Rosenfeld, Z. Physik 1928, 52, 161-174.
40. H. F. Hameka, Advanced Quantum Chemistry, Addison-Wesley, Reading, 1965, p. 241.
41. For different forms of this tensor, see T. B. Pedersen, A. E. Hansen, Chem. Phys. Lett. 1995, 246, 1-8 and references therein.
42. W. Moffitt, R. B. Woodward, A. Moscowitz, W. Klyne, C. Djerassi, J. Am. Chem. Soc. 1961, 83, 4013-4018.
43. J. K. O'Loane, Chem. Rev. 1980, 80, 41-61.
44. K. Mislow, P. Bickart, Isr. J. Chem. 1977, 15, 1-6.
45. A. de Meijere, A. E. Khlebnikov, R. R. Kostikov, S. I. Kozhuskov, P. R. Schreiner, A. Wittkopp, D. S. Yufit, Angew. Chem. 1999, 111, 3682-3685; Angew. Chem. Int. Ed. 1999, 38, 3474-3477.
46. A. de Meijere, A. E. Khlebnikov, R. R. Kostikov, S. I. Kozhuskov, P. R. Schreiner, A. Wittkopp, D. S. Yufit, Angew. Chem. 1999, 111, 3682-3685; Angew. Chem. Int. Ed. 1999, 38, 3474-3477.
47. a) For examples, see a) H. O. L. Fischer, E. Baer, Chem. Rev. 1941, 29, 287-316;
48. b) H. Wynberg, G. L. Hekkert, J. P. Houbiers, H. W. Bosch, J. Am. Chem. Soc. 1965, 87, 2635-2639;
49. c) H. W. I. Peerlings, D. C. Trimbach, E. W. Meijer, Chem. Commun. 1998, 497-498;
50. d) H. W. I. Peerlings, M. P. Struijk, E. W. Meijer, Chirality 1998, 10, 46-52.
51. Y. Pinto, D. Avnir, Enantiomer 2001, 6, 211-217.
52. a) D. Bosse, A. de Meijere, Tetrahedron Lett. 1977, 1155-1158;
53. b) D. Bosse, A. de Meijere, Chem. Ber. 1978, 111, 2223-2242.
54. a) R. Ertl, I. Chao, F. Diederich, R. L. Whetten, Nature 1991, 353, 149-153;
55. b) D. E. Manolopoulos, J. Chem. Soc. Faraday Trans. 1991, 87, 2861-2862.
56. F. Diederich, R. L. Whetten, C. Thilgen, R. Ettl, I. Chao, M. N. Alvarez, Science 1991, 254, 1768-1770.
57. F. H. Hennrich, R. H. Michel, A. Fischer, S. Richard-Schneider, S. Gilb, M. M. Kappes, D. Fuchs, M. Burk, K. Kobayashi, S. Nagase, Angew. Chem. 1996, 108, 1839-1841, Angew. Chem. Int. Ed. Engl. 1996, 35, 1732-1734.
58. F. H. Hennrich, R. H. Michel, A. Fischer, S. Richard-Schneider, S. Gilb, M. M. Kappes, D. Fuchs, M. Burk, K. Kobayashi, S. Nagase, Angew. Chem. 1996, 108, 1839-1841, Angew. Chem. Int. Ed. Engl. 1996, 35, 1732-1734.
59. D. E. Manolopoulos, P. W. Fowler, R. Taylor, H. W. Kroto, D. R. M. Walton, J. Chem. Soc. Faraday Trans. 1992, 88, 3117-3118.
60. P. W. Fowler, J. E. Cremona, J. I. Steer, Theor. Chim. Acta 1988, 73, 1-26.
61. a) References to numerous variations of this concept are given for example in a) P. G. Mezey, THEOCHEM J. Mol. Struc. 1998, 455, 183-190;
62. b) M. Petitjean, C. R. Acad. Sci. Paris II C 1999, 2, 25-28;
63. c) N. Weinberg, K. Mislow, Can. J. Chem. 2001, 78, 41-45.