Structural Chemistry

, Volume 5, Issue 4, pp 283–289 | Cite as

Molecular structures and packing arrangements of five 2,5-bis(aryl-2-vinyl)-1,4-dimethoxybenzene derivatives

  • Hermann Irngartinger
  • Jochen Lichtenthäler
  • Rüdiger Herpich
Article

Abstract

The crystal and molecular structures of five 2,5-bis(aryl-2-vinyl)-1,4-dimethoxybenzene derivatives1a-1e were determined by X-ray diffraction with respect to topochemical aspects. We found three types of packing arrangements: (1)α-type packing with 7 Å stacking axes, (2)β-type packing with 4 Å stacking axes and (3) a third intermediate packing type. The intermolecular distances between the vinylic double bonds of all derivatives exceed the limits of 4 Å in the crystals. Therefore photochemical [2+2]cycloadditions were not observed in the crystals of these compounds. A correlation between the inclination angle of the molecular plane to the stacking axis and the separation between potentially reactive double bonds was detected.

Key words

Distyryl-1,4-dimethoxybenzene derivatives molecular structures packing arrangements photochemical behavior 

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References

  1. 1.
    Irngartinger, H.; Lichtenthäler, J.; Fenske, D.; Baum, G. Z.Naturforsch. 1993,48b, 1411–1418.Google Scholar
  2. 2.
    Hasegawa, M.Adv. Polym. Sci. 1982,42, 1–49. Chung, C.-M.; Hasegawa, M.J. Am. Chem. Soc. 1991,113, 7311–7316. Maekawa, Y.; Kato, S.; Hasegawa, M.J. Am. Chem. Soc. 1991,113, 3867–3872. Addadi, L.; Lahav, M.J. Am. Chem. Soc. 1979,101, 2152–2156. Addadi, L.; Lahav, M.Pure Appl. Chem. 1979,51, 1269–1284.Google Scholar
  3. 3.
    Main, P.; Fisher, S. J.; Hull, S. E.; Lessinger, L.; Germain, G.; Leclercq, J. P.; Woolfson, M. M.MULTAN 11/82—A System of Computer Program for the Automatic Solution of Crystal Structures from X-ray diffraction Data; University of York: York, England, 1982.Google Scholar
  4. 4.
    Burla, M. C.; Camalli, M.; Cascarano, G.; Giacovazzo, G.; Polidori, G.; Spagna, R.; Viterbo, D.J. Appl. Crystallogr. 1989,22, 389–393.Google Scholar
  5. 5.
    Sheldrick, G. M. InCrystallographic Computing 3; Sheldrick, G. M.; Krüger, C.; Goddard, R. Eds.; Oxford University Press, 1985, pp 175–189.Google Scholar
  6. 6.
    B. A. Frenz and Assoc, Inc., College Station, Texas, und Enraf-Nonius, Delft, Holland, 1982.Google Scholar
  7. 7.
    Fair, C. K.Structure Determination System; Delft Instruments X-Ray Diffraction B. V., Delft, Niederlande, 1990.Google Scholar
  8. 8.
    Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW England, 1992.Google Scholar
  9. 9. (a)
    Venkatesan, K.; Ramamurthy, V. InPhotochemistry in Organized and Constrained Media; Ramamurthy, V. Ed.; VCH: New York, 1991; Chap. 4;Google Scholar
  10. 9. (b)
    Desiraju, G. R.Crystal Engineering: The Design of Organic Solids; Elsevier: Amsterdam, 1989;Google Scholar
  11. 9. (c)
    Ramamurthy, V.; Venkatesan, K.Chem. Rev. 1987,87, 433–481;Google Scholar
  12. 9. (d)
    Desiraju, G. R.Organic Solid State Chemistry; Elsevier: Amsterdam, 1987.Google Scholar
  13. 10.(a)
    Desiraju, G. R. In Ref. 9(d), Chap. 14;Google Scholar
  14. 10.(b)
    Schmidt, G. M. J.et al. InSolid State Photochemistry; Ginsburg, D.; Ed.; Verlag Chemie: Weinheim, 1976.Google Scholar
  15. 11.
    Meier, H.Angew. Chem. 1992,104, 1425–1446.Google Scholar
  16. 12.
    Nakanishi, H.; Ueno, K.J. Polym. Sci., Polym. Phys. Ed. 1973,16, 767–773.Google Scholar
  17. 13.
    Nakanishi, H.; Ueno, K.Acta Crystallogr., Sect. B 1978,34, 2036–2038.Google Scholar
  18. 14.
    Nakanishi, H.; Ueno, K.; Sasada, Y.Acta Crystallogr., Sect. B 1976,32, 1616–1618.Google Scholar
  19. 15.
    Ueno, K.; Nakanishi, H.; Hasegawa, M.; Sasada, Y.Acta Crystallogr., Sect. B 1978,34, 2034–2035.Google Scholar
  20. 16.
    Sasada, Y.; Shimanouchi, H.; Nakanishi, H.; Hasegawa, M.Bull. Chem. Soc. Jpn. 1971,44, 1262–1270.Google Scholar
  21. 17.
    Nakanishi, H.; Jones, W.; Parkinson, G. M.Acta Crystallogr., Sect. B 1979,35, 3103–3106.Google Scholar
  22. 18.
    Nakanishi, H.; Ueno, K.Acta Crystallogr., Sect. B 1978,34, 2209–2214.Google Scholar
  23. 19.
    Berkovitch-Yellin, Z.Acta Crystallogr., Sect. B 1980,36, 2440–2442.Google Scholar

Copyright information

© Plenum Publishing Corporation 1994

Authors and Affiliations

  • Hermann Irngartinger
    • 1
  • Jochen Lichtenthäler
    • 1
  • Rüdiger Herpich
    • 1
  1. 1.Organisch-Chemisches Institut der Universität HeidelbergHeidelbergGermany

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