Thermochromism at room temperature in overcrowded bistricyclic aromatic enes: Closely populated twisted and folded conformations

European Journal of Organic Chemistry

Volumn , Issue 31, 2007, Pages 5198-5211

  Levy, Amalia ^a   Pogodin, Sergey ^a   Cohen, Shmuel ^a   Agranat, Israel ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

Conformation analysis; Density functional calculations; Strained molecules; Thermochromism

Indexed keywords

EID: 35848930812     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700414     Document Type: Article

References (63)

1. a) G. Shoham, S. Cohen, R. M. Suissa, I. Agranat, in Molecular Structure: Chemical Reactivity and Biological Activity (Eds.: J. J. Stezowski, J.-L. Huang, M.-C. Shao), IUCr Crystallographic Symposia 2, Oxford University Press, Oxford, 1988, pp. 290-312;
2. b) P. U. Biedermann, J. J. Stezowski, I. Agranat, in Advances in Theoretically Interesting Molecules (Ed.: R. P. Thummel), vol. 4, JAI Press: Stanford, CN, 1988, pp. 245-322;
3. c) P. U. Biedermann, J. J. Stezowski, I. Agranat, Eur. J. Org. Chem. 2001, 15-34.
4. C. de la Harpe, W. A. Van Dorp, Ber. Dtsch. Chem. Ges. 1875, 8, 1048-1050.
5. a) J. H. Day, Chem. Rev. 1963, 63, 65-80;
6. b) E. D. Bergmann, Prog. Org. Chem. 1955, 3, 81-171;
7. c) G. Kortüm, Ber. Bunsen-Ges. Phys. Chem. 1974, 78, 391-403;
8. d) H. Bouas-Laurent, H. Dürr, Pure Appl. Chem. 2001, 73, 639-665.
9. A. Samat, V. Lokshin, in Organic Photochromic and Thermochromic Compounds (Eds.: J. C. Crano, R. J. Guglielmetti), vol. 2, Plenum Press, New York, 1999, p. 415.
10. P. U. Biedermann, J. J. Stezowski, I. Agranat, Chem. Eur. J. 2006, 12, 3345-3354.
11. a) H. Meyer, Ber. Dtsch. Chem. Ges. 1909, 42, 143-145;
12. b) H. Meyer, Monatsh. Chem. 1909, 30, 165-177.
13. D. L. Fanselow, H. G. Drickamer, J. Chem. Phys. 1974, 61, 4567-4574.
14. a) Y. Hirshberg, Compt. Rend. 1950, 231, 903-904;
15. b) G. Kortüm, W. Theilacker, V. Braun, Z. Physik. Chem. 1954, NF 2, 179-196;
16. c) T. Bercovici, R. Korenstein, K. A. Muszkat, E. Fischer, Pure Appl. Chem. 1970, 24, 531-565;
17. d) E. Fischer, Chem. Unserer Zeit 1975, 9, 85-95;
18. e) E. Fischer, Rev. Chem. Intermed. 1984, 5, 393-422;
19. f) K. A. Muszkat in The Chemistry of Quinonoid Compounds (Eds.: S. Patai, Z. Rappoport), vol. 2, Wiley, Chichester, 1988, pp. 203-224;
20. g) W. H. Laarhoven in Photochromism, Molecules and Systems (Eds.: H. Dürr, H. Bouas-Laurent), Elsevier, Amsterdam, 1990, pp. 270-313;
21. h) Organic Photochromic and Thermochromic Compounds (Eds.: J. C. Crano, R. J. Guglielmetti), Topics in Applied Chemistry, vol. 1, Photochromic Families, vol. 2, Physicochemical Studies, Biological Applications, and Thermochromism, Plenum Press, New York, 1999.
22. B. L. Feringa, Acc. Chem. Res. 2001, 34, 504-513.
23. a) K. Linde, G. Ramirez, C. D. Mulrow, A. Pauls, W. Weidenhammer, D. Melchart, Brit. Med. J. 1996, 313, 253-258;
24. b) M. Philipp, R. Kohnen, K.-O. Hiller, K. Linde, M. Berner, Brit. Med. J. 1999, 319, 1534-1539.
25. R. Herges, Chem. Rev. 2006, 106, 4820-4842.
26. a) W. T. Grubb, G. B. Kistiakowsky, J. Am. Chem. Soc. 1950, 72, 419-424;
27. b) W. Theilacker, G. Kortüm, G. Friedheim, Ber. Dtsch. Chem. Ges. 1950, 83, 508-519;
28. c) Y. Hirschberg, E. Fischer, J. Chem. Soc. 1953, 629-636;
29. d) G. Kortüm, Angew. Chem. 1958, 70, 14-20;
30. e) Z. R. Grabowski, M. S. Balasiewicz, Trans. Faraday Soc. 1968, 64, 3346-3353;
31. f) Y. Tapuhi, O. Kalisky, I. Agranat, J. Org. Chem. 1979, 44, 1949-1952;
32. g) T. Natsue, D. H. Evans, J. Electroanal. Chem. 1984, 168, 287-298.
33. a) E. Harnik, J. Chem. Phys. 1956, 24, 297-299;
34. b) E. Wasserman, R. E. Davis, J. Chem. Phys. 1959, 30, 1367;
35. c) G. Kortüm, G. Bayer, Ber. Bunsen-Ges. Phys. Chem. 1963, 67, 24-28;
36. d) R. Korenstein, K. A. Muszkat, E. Fischer, Helv. Chim. Acta 1970, 53, 2102-2109.
37. P. U. Biedermann, J. J. Stezowski, I. Agranat, Chem. Commun. 2001, 954-955.
38. A. Levy, P. U. Biedermann, I. Agranat, Org. Lett. 2000, 2, 1811-1814.
39. Yu. V. Zefirov, Crystallogr. Rep. (Kristallografiya) 1997, 42, 111-116.
40. A. Levy, S. Cohen, I. Agranat, Org. Biomol. Chem. 2003, 1, 2755-2763.
41. R. M. Suissa, Ph. D. Thesis, The Hebrew University of Jerusalem, Jerusalem, 1988 (in Hebrew).
42. E. D. Bergmann, Y. Hirschberg, D. Lavie, Bull. Soc. CMm. Fr. 1952, 19, 268-270.
43. A. F. A. Ismail, Z. M. El-Shafei, J. Chem. Soc. 1957, 3393-3396.
44. a) D. H. R. Barton, B. J. Wills, J. Chem. Soc. Perkin Trans. 1 1972, 305-310;
45. b) D. H. R. Barton, F. S. Guziec, I. Shahak, J. Chem. Soc. Perkin Trans. 1 1974, 1794-1799.
46. A. Schönberg, W. I. Awad, N. Latif, J. Chem. Soc. 1951, 1368-1369.
47. M. S. Raasch, J. Org. Chem. 1979, 44, 632-633.
48. S. Scheibye, R. Shabana, S.-O. Lawesson, C. Roemming, Tetrahedron 1982, 38, 993-1001.
49. M. Regitz, Chem. Ber. 1964, 97, 2742-2754.
50. A. Levy, P. U. Biedermann, S. Cohen, I. Agranat, J. Chem. Soc. Perkin Trans. 2 2001, 2329-2341.
51. A. Schönberg, K. Junghans, Chem. Ber. 1962, 95, 2137-2143.
52. CCDC-645716 to -645718 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
53. P. A. Apgar, E. Wasserman, unpublished results (Allied Chemical), 1978, quoted in ref. 1a.
54. I. Agranat, Y. Tapuhi, J. Org. Chem. 1979, 44, 1941-1948.
55. a) F. DeProft, P. Geerling, Chem. Rev. 2001, 101, 1451-1464;
56. b) W. Koch, M. C. Holthausen, A Chemist Guide to Density Functional Theory, Wiley-VCH, Weinheim, 2000.
57. S. Pogodin, I. D. Rae, I. Agranat, Eur. J. Org. Chem. 2006, 5059-5068.
58. P. George, M. Trachtman, C. W. Bock, A. M. Brett, Theor. Chim. Acta 1975, 38, 121-129.
59. E. D. Bergmann, Isomerism and Isomerization of Organic Compounds, Interscience Publishers, New York, 1948, p. 48.
60. A. Ault, R. Kopet, A. Serianz, J. Chem. Educ. 1971, 48, 410-411.
61. Gaussian 03, Revision C.02, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Wallingford CT, 2004.
62. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
63. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.