Quantitative chirality of helicenes

Tetrahedron Asymmetry

Volumn 11, Issue 13, 2000, Pages 2695-2704

  Katzenelson, Omer ^a   Edelstein, Joseph ^a   Avnir, David ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

HELICENE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CHROMATOGRAPHY; CONTROLLED STUDY; CORRELATION FUNCTION; ENANTIOMER; GEOMETRY; OPTICAL ROTATION; PRIORITY JOURNAL; QUANTITATIVE ASSAY; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0034647806     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00235-4     Document Type: Article

References (40)

1. Zabrodsky, H.; Avnir, D. J. Am. Chem. Soc. 1995, 117, 462.
2. (a) Pinto, Y.; Salomon, Y.; Avnir, D. J. Math. Chem. 1998, 13, 13;
3. (b) Salomon, Y.; Avnir, D. J. Comput. Chem. 1999, 20, 772.
4. (a) Pinto, Y.; Fowler, P. W.; Mitchell, D.; Avnir, D. J. Phys. Chem. 1998, 102, 5776;
5. (b) Keinan, S.; David, A. J. Am. Chem. Soc. 1998, 120, 6152;
6. (c) Pinto, Y.; Hel-Ol, H. Z.; Avnir, D. J. Chem. Soc., Faraday Trans. 1996, 92, 2523.
7. (a) Zabrodsky, H.; Peleg, S.; Avnir, D. J. Am. Chem. Soc. 1992, 114, 7843;
8. (b) Salomon, Y.; Avnir, D. J. Comput. Chem. 1999, 20, 772;
9. (c) Katzenelson, O.; Zabrodsky, H.; Avnir, D. Chem. Europ. J. 1996, 2, 174.
10. (a) Avnir, D.; Katzenelson, O.; Keinan, S.; Pinsky, M.; Pinto, Y.; Salomon, Y.; Zabrodsky Hel-Or, H. In Concepts in Chemistry; Research Studies Press, Somerset, 1997; Chapter 9, pp. 283;
11. (b) Avnir, D.; Zabrodsky Hel-Or, H.; Mezey, P. G. In Encyclopedia of Computational Chemistry; Wiley: Chichester, 1981; Vol. 4, p. 2890.
12. (a) Grimme, S. Chem. Phys. Lett. 1998, 297, 15;
13. (b) Gao, D.; Schefzick, S.; Lipkowitz, K. B. J. Am. Chem. Soc. 1999, 121, 9481;
14. (c) Lipkowitz, K. B.; Gao, D.; Katzenelson, O. J. Am. Chem. Soc. 1999, 121, 5559;
15. (d) Alikhanidi, S.; Kuz'min, V. J. Mol. Model. 1999, 5, 116.
16. (a) Gilat, G. Chem. Phys. Lett. 1985, 121, 9;
17. (b) Osipov, M. A.; Pickup, B. T.; Fehervari, M.; Dunmur, D. A. Molec. Phys. 1998, 94, 283;
18. (c) Petitjean, M. J. Math. Chem. 1997, 22, 185;
19. (d) Mezey, P. Z. Chirality 1998, 10, 173;
20. (e) Mezey, P. G. J. Math. Chem. 1998, 23, 65;
21. (f) and other references cited in these papers and in our reviews (Ref. 5).
22. Zabrodsky, H.; Peleg, S.; Avnir, D. J. Am. Chem. Soc. 1993, 115, 8278.
23. Munoz, V.; Serrano, L. Nature: Struct. Biol. 1994, 1, 399.
24. Gil-Av, E.; Mikes, F.; Boshart, G. J. Chromatogr. 1976, 122, 205.
25. The [5]-helicene was resolved as well but on a different coating, and therefore is not included here.
26. Gil-Av, E.; Mikes, F.; Boshart, G. J. C. Chem. Comm. 1976, 99.
27. (a) Petricek, V.; Cisarova, I.; Hummel, L.; Kroupa, J.; Brezina, B. Acta. Crystallogr., Sect. B. (Str. Sci.) 1990, 46, 830;
28. (b) Hirshfeld, F. L.; Sandler, S.; Scmidt, G. M. J. J. Chem. Soc. 1963, 2108;
29. (c) Kuroda, R. J. Chem. Soc., Perkin Trans. 2 1982, 789;
30. (d) Rango; Tsoucaris, G.; Declercq, J. P.; Germain, G.; Putzyes, J. P. Cryst. Struct. Comm. 1973, 2, 189;
31. (e) Joly, M.; Defay, N.; Martin, R. H.; Declarcq, J. P.; Germain, G.; Soubrier-Payen, B.; Meerssche, M. v. Helv. Chim. Acta. 1977, 60, 537;
32. (f) Bas, G. L.; Navaza, A.; Mauguen, d. R. C. Y. Cryst. Struct. Comm. 1976, 5, 357;
33. (g) Bas, G. L.; Navaza, A.; Knossow, d. R. C. M. Cryst. Struct. Comm. 1976, 5, 713.
34. SPARTAN; 4.1 ed.; Wavefunction, Inc. 18401 Von Karman Ave., Ste. 370 Irvine, CA 96216, USA.
35. 2-symmetric counter point, and the other is the permutation of each point with itself. See Ref. 8 for technical details.
36. (a) [5]-Helicene: Martin R. H.; Marchant, M. J. Tetrahedron Lett. 1972, 3707;
37. (b) [6,7,8,9]-helicenes: Martin R. H.; Marchant, M. J. Tetrahedron 1974, 30, 347.
38. Kitaigorodskii, A. I. In Organic Chemical Crystallography; Consultants Bureau: New York, 1961; Chapter 4.
39. The melting points for [4]-[13]-helicenes are from CRC Handbook of Chemistry and Physics, Lide, D. R. Ed.-in-Chief, 72nd Edition, CRC Press: Boca Raton, 1991-1992; and for phenanthrene from the Dictionary of Organic Compounds, Cadogan, J. I. G., Ed.; 6th ed., Vol. 4, Chapman & Hall: London, 1996.
40. The melting points for [4]-[13]-helicenes are from CRC Handbook of Chemistry and Physics, Lide, D. R. Ed.-in- Chief, 72nd Edition, CRC Press: Boca Raton, 1991-1992; and for phenanthrene from the Dictionary of Organic Compounds, Cadogan, J. I. G., Ed.; 6th ed., Vol. 4, Chapman & Hall: London, 1996.