Conformations and threshold rotational mechanisms of the (Z)-1,2- diarylethene moiety: A structural correlation study

Journal of Organic Chemistry

Volumn 64, Issue 22, 1999, Pages 8144-8148

  Gur, Erez ^a   Kaftory, Menahem ^b   Biali, Silvio E ^a   Rappoport, Zvi ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONFORMATION; CRYSTAL STRUCTURE; ORGANIC CHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033615587     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9907540     Document Type: Article

References (35)

1. For reviews on molecular propellers, see: Mislow, K.; Gust, D.; Finocchiaro, P.; Boettcher, R. J. Fortschr. Chem. Forschr. 1974, 47, 1. Mislow, K. Acc. Chem. Res. 1976, 9, 26. Meurer, K. P.; Vögtle, F. Top. Curr. Chem. 1985, 127, 1. Willem, R.; Gielen, M.; Hoogzand, C.; Pepermans, H. Adv. Dyn. Stereochem; Gielen, M., Ed.; Academic Press: New York, 1985; Vol. 1, p 207.
2. For reviews on molecular propellers, see: Mislow, K.; Gust, D.; Finocchiaro, P.; Boettcher, R. J. Fortschr. Chem. Forschr. 1974, 47, 1. Mislow, K. Acc. Chem. Res. 1976, 9, 26. Meurer, K. P.; Vögtle, F. Top. Curr. Chem. 1985, 127, 1. Willem, R.; Gielen, M.; Hoogzand, C.; Pepermans, H. Adv. Dyn. Stereochem; Gielen, M., Ed.; Academic Press: New York, 1985; Vol. 1, p 207.
3. For reviews on molecular propellers, see: Mislow, K.; Gust, D.; Finocchiaro, P.; Boettcher, R. J. Fortschr. Chem. Forschr. 1974, 47, 1. Mislow, K. Acc. Chem. Res. 1976, 9, 26. Meurer, K. P.; Vögtle, F. Top. Curr. Chem. 1985, 127, 1. Willem, R.; Gielen, M.; Hoogzand, C.; Pepermans, H. Adv. Dyn. Stereochem; Gielen, M., Ed.; Academic Press: New York, 1985; Vol. 1, p 207.
4. For reviews on molecular propellers, see: Mislow, K.; Gust, D.; Finocchiaro, P.; Boettcher, R. J. Fortschr. Chem. Forschr. 1974, 47, 1. Mislow, K. Acc. Chem. Res. 1976, 9, 26. Meurer, K. P.; Vögtle, F. Top. Curr. Chem. 1985, 127, 1. Willem, R.; Gielen, M.; Hoogzand, C.; Pepermans, H. Adv. Dyn. Stereochem; Gielen, M., Ed.; Academic Press: New York, 1985; Vol. 1, p 207.
5. Biali, S. E.; Rappoport, Z. J. Am. Chem. Soc. 1984, 106, 477. For a review on vinyl propellers, see: Rappoport, Z.; Biali, S. E. Acc. Chem. Res. 1997, 30, 307.
6. Biali, S. E.; Rappoport, Z. J. Am. Chem. Soc. 1984, 106, 477. For a review on vinyl propellers, see: Rappoport, Z.; Biali, S. E. Acc. Chem. Res. 1997, 30, 307.
7. Gust, D.; Mislow, K. J. Am. Chem. Soc. 1973, 95, 1535.
8. Biali, S. E.; Nugiel, D. A.; Rappoport, Z. J. Am. Chem. Soc. 1989, 111, 846. Frey, J.; Schottland, E.; Rappoport, Z.; Bravo-Zhivotovskii, D.; Nakash, M.; Botoshansky, M.; Kaftory, M.; Apeloig, Y. J. Chem. Soc., Perkin Trans. 2 1994, 2555. Correction: J. Chem. Soc., Perkin Trans. 2 1995, 2377.
9. Biali, S. E.; Nugiel, D. A.; Rappoport, Z. J. Am. Chem. Soc. 1989, 111, 846. Frey, J.; Schottland, E.; Rappoport, Z.; Bravo-Zhivotovskii, D.; Nakash, M.; Botoshansky, M.; Kaftory, M.; Apeloig, Y. J. Chem. Soc., Perkin Trans. 2 1994, 2555. Correction: J. Chem. Soc., Perkin Trans. 2 1995, 2377.
10. Biali, S. E.; Nugiel, D. A.; Rappoport, Z. J. Am. Chem. Soc. 1989, 111, 846. Frey, J.; Schottland, E.; Rappoport, Z.; Bravo-Zhivotovskii, D.; Nakash, M.; Botoshansky, M.; Kaftory, M.; Apeloig, Y. J. Chem. Soc., Perkin Trans. 2 1994, 2555. Correction: J. Chem. Soc., Perkin Trans. 2 1995, 2377.
11. For reviews on polyarylethenols, see: (a) Rappoport, Z.; Biali, S. E. Acc. Chem. Res. 1988, 21, 175.
12. (b) Hart, H.; Rappoport, Z.; Biali, S. E. In The Chemistry of Enols; Rappoport, Z., Ed.; Wiley: Chichester, 1990; Chapter 8, p 481.
13. Bürgi, H.-B.; Dunitz, J. D. Acc. Chem. Res. 1983, 16, 153.
14. Schweizer, W. B. In Structure Correlation; Burgi, H.-B., Dunitz, J. D., Eds.; VCH: Weinheim, 1994; Vol. 1, pp 369-404.
15. For early calculations on 1,1-diphenylethene, see: (a) Stegemeyer, H.; Rapp, W. Ber. Bunsen-Ges. Phys. Chem. 1971, 76, 1665.
16. (b) Baraldi, I.; Gallinella, E.; Momicchioli, F. J. Chim. Phys. 1986, 83, 653.
17. (a) Kaftory, M.; Nugiel, D. A.; Biali, S. E.; Rappoport, Z. J. Am. Chem. Soc. 1989, 111, 8181.
18. (b) Rappoport, Z.; Biali, S. E.; Kaftory, M. J. Am. Chem. Soc. 1990, 112, 7742.
19. Presented in part: Gur, E.; Biali, S. E.; Rappoport, Z.; Kaftory, M. 56th Annual Meeting of the Israel Chemical Society, Jerusalem, Feb 11-12, 1991; Abstract 98.
20. Hohlneicher, G.; Müller, M.; Demmer, M.; Lex, J.; Penn, J. H.; Gan, L.; Loesel, P. D. J. Am. Chem. Soc. 1988, 110, 4483.
21. For a discussion on conformational maps, see: Dunitz, J. D. X-ray Analysis and the Structure of Organic Molecules; Cornell University Press: Ithaca, NY, 1979; Chapter 10.
22. Allinger, N. L. Molecular Mechanics. Operating Instructions for the MM3 Program. 1989 Force Field (updated 5/6/92); Technical Utilization Corp.
23. (a) Traetteberg, M.; Frantsen, W. B. J. Mol. Struct. 1975, 26, 69.
24. (b) Fronczek, F. R.; Swan, A. M.; Corkern, J. A.; Gandour, R. D. Acta Crystallogr., Sect. C 1984, 40, 1875.
25. Andersonn, P. G. Tetrahedron Lett. 1994, 35, 2609.
26. Sprague, J. T.; Tai, J. C.; Yuh, Y.; Allinger, N. L. J. Comput. Chem. 1987, 8, 581. Kao, J.; Allinger, N. L. J. Am. Chem. Soc. 1987, 109, 3817. Warshel, A.; Huler, E.; Rabinovich, B.; Shakked, Z. J. Mol. Struct. 1974, 23, 175. Huler, E.; Warshel, A. Acta Crystallogr. 1974, B30, 1822. Warshel, A. J. Chem. Phys. 1975, 62, 214.
27. Sprague, J. T.; Tai, J. C.; Yuh, Y.; Allinger, N. L. J. Comput. Chem. 1987, 8, 581. Kao, J.; Allinger, N. L. J. Am. Chem. Soc. 1987, 109, 3817. Warshel, A.; Huler, E.; Rabinovich, B.; Shakked, Z. J. Mol. Struct. 1974, 23, 175. Huler, E.; Warshel, A. Acta Crystallogr. 1974, B30, 1822. Warshel, A. J. Chem. Phys. 1975, 62, 214.
28. Sprague, J. T.; Tai, J. C.; Yuh, Y.; Allinger, N. L. J. Comput. Chem. 1987, 8, 581. Kao, J.; Allinger, N. L. J. Am. Chem. Soc. 1987, 109, 3817. Warshel, A.; Huler, E.; Rabinovich, B.; Shakked, Z. J. Mol. Struct. 1974, 23, 175. Huler, E.; Warshel, A. Acta Crystallogr. 1974, B30, 1822. Warshel, A. J. Chem. Phys. 1975, 62, 214.
29. Sprague, J. T.; Tai, J. C.; Yuh, Y.; Allinger, N. L. J. Comput. Chem. 1987, 8, 581. Kao, J.; Allinger, N. L. J. Am. Chem. Soc. 1987, 109, 3817. Warshel, A.; Huler, E.; Rabinovich, B.; Shakked, Z. J. Mol. Struct. 1974, 23, 175. Huler, E.; Warshel, A. Acta Crystallogr. 1974, B30, 1822. Warshel, A. J. Chem. Phys. 1975, 62, 214.
30. Sprague, J. T.; Tai, J. C.; Yuh, Y.; Allinger, N. L. J. Comput. Chem. 1987, 8, 581. Kao, J.; Allinger, N. L. J. Am. Chem. Soc. 1987, 109, 3817. Warshel, A.; Huler, E.; Rabinovich, B.; Shakked, Z. J. Mol. Struct. 1974, 23, 175. Huler, E.; Warshel, A. Acta Crystallogr. 1974, B30, 1822. Warshel, A. J. Chem. Phys. 1975, 62, 214.
31. In (Z)-p-ethinyl-p′-nitrostilbene (Hockless, B. C.; Whittall, I. R.; Humphrey, M. G. Acta Crystallogr. C 1996, 52, 3222) the dihedral angles are 51.5° and 12°. The remarkable small dihedral angle of the p-nitrophenyl ring (12°) is probably due to crystal packing forces, since AM1 calculations predict torsional angles of 44.4° and 40.9° for the p-ethinylphenyl and p-nitrophenyl rings, respectively.
32. The conformation of saturated five-membered rings is usually discussed in terms of the envelope and half-chair conformation (Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley: New York, 1994; p 758).
33. Bernstein, J. Acta Crystallogr., Sect. B 1975, B31, 418.
34. (a) Faraggi, E. Z. MSc. Thesis, The Hebrew University of Jerusalem, 1992.
35. (b) Faraggi, E. Z.; Frey, J.; Rappoport, Z. 11th IUPAC Conference on Physical Organic Chemistry, Ithaca College, Ithaca, Aug 2-7, 1992, Abstr. C-13.