Journal of Chemical Crystallography

, Volume 34, Issue 11, pp 723–726 | Cite as

Molecular structure of 3-mesityl-1,4-benzoquinonemonoxime



The X-ray crystal structure of 3-mesityl-1,4-benzoquinonemonoxime is described. The structure reveals that hydrogen-bonds are formed between the oxime and keto groups to form one-dimensional hydrogen bonded ribbons. The structure (C15H15NO2) is orthorhombic with a = 8.9098(7), b = 10.6399(8), c = 13.7086(10) Å and space group P212121.

3-Mesityl-1,4-benzoquinonemonoxime crystal structure hydrogen bond one-dimesional 


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  1. Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: Amsterdam, 1989;Google Scholar
  2. Crystal Engineering: From Molecules to Crystals to Materials; Braga, D.; Greponi, F.; Orpen, A. G., Eds.; NATO Science Series 538; Kluwer: Dordrecht, The Netherlands, 1999;Google Scholar
  3. Aakeroy, C. B. Acta Crystallogr. B 1997, 53, 569.Google Scholar
  4. For reviews of hydrogen-bonding in crystal engineering see: Subramanian, S.; Zaworotko, M. J. Coord. Chem. Rev. 1994, 137, 357;Google Scholar
  5. Steiner, T. Angew. Chem. Int. Ed. 2002, 41, 48;Google Scholar
  6. Sherrington, D. C.; Taskinen, K. A. Chem. Soc. Rev. 2001, 30, 83.Google Scholar
  7. For reviews of coordination chemistry in crystal engineering see: Transition Metals in Supramolecular Chemistry; Fabrizza, L.; Poggi, A., Eds.; Kluwer Academic Publishers: The Netherlands, 1994;Google Scholar
  8. Biradha, K.; Fujita, M. Adv. Supramol. Chem. 2000, 6, 1.Google Scholar
  9. For examples combining hydrogen-bonding and coordination chemistry in crystal engineering see: Brammer, L.; Rivas, J. C. M.; Atencio, R.; Fang, S.; Pigge, F. C. J. Chem. Soc., Dalton Trans. 2000, 3855;Google Scholar
  10. Aakeröy, C. B.; Beatty, A. C.; Helfrich, B. A. J. Chem. Soc., Dalton Trans. 1998, 1943;Google Scholar
  11. Kuehl, C. J.; Tabellion, F. M.; Arif, A. M.; Stang, P. J. Organometallics 2001, 20, 1956;Google Scholar
  12. Desiraju, G. R. J. Chem. Soc., Dalton Trans. 2000, 3745.Google Scholar
  13. For examples of halogen-amine interactions see: Walsh, R. B.; Padgett, C. W.; Metrangolo, P.; Resnati, G.; Hanks, T. W.; Pennington, W. P. Cryst. Growth Des. 2001, 1, 165;Google Scholar
  14. Crihfield, A.; Hartwell, J.; Phelps, D.; Walsh, R. B.; Harris, J. L.; Payne, J. F.; Pennington, W. T.; Hanks, T. W. Cryst. Growth Des. 2003, ASAP Article;Google Scholar
  15. Blackstock, S. C.; Lorand, J. P.; Kochi, J. K. J. Org. Chem. 1987, 52, 1451.Google Scholar
  16. See for example: Kim, J. H.; Lindeman, S. V.; Kochi, J. K. J. Am. Chem. Soc. 2001, 123, 4951;Google Scholar
  17. Bosch, E.; Radford, R.; Barnes, C. L. Org. Lett. 2001, 3, 881.Google Scholar
  18. Desiraju, G. R. Acc. Chem. Res. 2002, 35, 565.Google Scholar
  19. Bosch, E.; Petty, G. W., Jr.; Barnes, C. L. J. Chem. Cryst. 2001, 31, 105.Google Scholar
  20. See also: Bosch, E.; Kochi, J. K. J. Org. Chem. 1995, 102, 4775.Google Scholar
  21. The mechanism and potential synthetic utility of this demethylation reaction will be studied in detail in future along with the decomposition of the benzoquinonemonoxime.Google Scholar
  22. Sheldrick, G. M. SHELXS-97, Crystal Structure Solution; University of Göttingen: Germany, 1997.Google Scholar
  23. Sheldrick, G. M. SHELXL-7, Crystal Structure Refinement; University of Göttingen: Germany, 1997.Google Scholar
  24. Barbour, L.; Atwood, J. A. Cryst. Growth Des. 2003, 3, 3.Google Scholar
  25. Talberg, H. J. Acta Chem. Scand., Ser. A 1974, 28, 910.Google Scholar
  26. Sardone, N.; Carugo, O.; Charalambous, J.; Ragh, D. V. Acta Crystallogr., C 1996, 52, 3202.Google Scholar
  27. Adatia, T.; Barjesteh, H.; Charalambous, J.; Choi, N.; McPartlin, M. Acta Crystallogr., C 1995, 51, 1187.Google Scholar
  28. Maurin, J. K. Acta Crystallogr. 1998, B54, 866.Google Scholar
  29. Aakeröy, C. B.; Beatty, A. M.; Leinen, D. S. J. Am. Chem. Soc. 1998, 120, 7383;Google Scholar
  30. Aakeröy, C. B.; Beatty, A. M.; Leinen, D. S. Cryst. Eng. Commun. 2000, 27, 1;Google Scholar
  31. Aakeröy, C. B.; Beatty, A. M.; Leinen, D. S. Crystal Growth Des. 2001, 1, 47.Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2004

Authors and Affiliations

  1. 1.Chemistry DepartmentSouthwest Missouri State UniversitySpringfieldUSA
  2. 2.Chemistry DepartmentUniversity of MissouriColumbiaUSA

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