Advertisement

Journal of Chemical Crystallography

, Volume 35, Issue 12, pp 949–955 | Cite as

Synthesis and structures of thienyl-substituted 5-dipyrromethane isomers

  • Nilkamal Maiti
  • Junseong Lee
  • Youngkyu Do
  • Hack Soo Shin
  • David G. Churchill
Article

Abstract

The compounds 5(2-thienyl)-and 5(3-thienyl)-dipyrromethane (1 and2, respectively) have been synthesized and isolated from the acid-catalyzed reaction between thiophenes-carboxaldehyde and pyrrole. Characterization by X-ray diffraction confirms molecular structures involving twoortho-substituted pyrrolyl and one thienyl groups. Both the compounds1 and2 were crystallized in the monoclinic space groupP21/n with cell parametersa = 5.7149(16) Å,b = 17.338(6) Å, andc = 11.785(4) Å, β = 98.466(9),V = 1155.0(6) Å3 for compound1; anda = 5.828(4) Å,b = 17.424(10) Å,c = 11.822(8) Å, β = 98.10(2), andV = 1188.4(13) Å3 for compound2.

Keywords

5-Dipyrromethane crystal structure corrole precursor 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Littler, B.J.; Miller, M.A.; Hung, C.H.; Wagner, R.W.; O'Shea, D.F.; Boyle, P.D.; Lindsey, J.S. J. Org. Chem. 1999, 64, 1391–1396.Google Scholar
  2. 2.
    D'Auria, M.; DeLuca, E.; Esposito, V.; Mauriello, G.; Racioppi, R. Tetrahedron 1997, 53, 1157–1166.Google Scholar
  3. 3.
    Gryko, D.T. Eur. J. Org. Chem. 2002, 1735–1743.Google Scholar
  4. 4.
    Brinas, R.P.; Bruckner, C. Synlett 2001, 442–444.Google Scholar
  5. 5.
    Gryko, D.T.; Jadach, K. J. Org. Chem. 2001, 66, 4267–4275.CrossRefGoogle Scholar
  6. 6.
    Gryko, D.T.; Piechota, K.E. J. Porphyrins Phthalocyanines 2002, 6, 81–97.CrossRefGoogle Scholar
  7. 7.
    Gryko, D.T.; Koszarna, B. Org. Biomol. Chem. 2003, 1, 350–357.CrossRefGoogle Scholar
  8. 8.
    Guilard, R.; Gryko, D.T.; Canard, G.; Barbe, J.M.; Koszarna, B.; Brandes, S.; Tasior, M. Org. Lett. 2002, 4, 4491–4494.CrossRefGoogle Scholar
  9. 9.
    Paolesse, R.; Marini, A.; Nardis, S.; Froiio, A.; Mandoj, F.; Nurco, D.J.; Prodi, L.; Montalti, M.; Smith, K.M. J. Porphyrins Phthalocyanines 2003, 7, 25–36.Google Scholar
  10. 10.
    Speckbacher, M.; Yu, L.H.; Lindsey, J.S. Inorg. Chem. 2003, 42, 4322–4337.CrossRefGoogle Scholar
  11. 11.
    Sridevi, B.; Narayanan, S.J.; Chandrashekar, T.K.; Englich, U.; Ruhlandt-Senge, K. Chem.–-a Eur. J. 2000, 6, 2554–2563.Google Scholar
  12. 12.
    Bruckner, C.; Barta, C.A.; Brinas, R.P.; Bauer, J.A.K. Inorg. Chem. 2003, 42, 1673–1680.CrossRefGoogle Scholar
  13. 13.
    Lin, K.-J.; Wu, J.-Y.; Chen, C.-T. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1996, C52, 3114–3116.Google Scholar
  14. 14.
    Bennis, V.; Gallagher, J.F. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1998, C54, 130–132.Google Scholar
  15. 15.
    Foxon, S.P.; Lindsay Smith, J.R.; O'Brien, P.; Reginato, G. J. Chem. Soc., Perkin Trans. 2, 2001, 1145–1153.Google Scholar
  16. 16.
    Patra, G.K.; Diskin-Posner, Y.; Goldberg, I. Acta Crystallogr., Sect. E: Struct. Rep. Online 2002, E58, o530–o531.Google Scholar
  17. 17.
    Cambridge Structural Database, version 5.26 (November 2004).Google Scholar
  18. 18.
    SAINT, version 5.0, Data Integraton Software, Bruker AXS, Inc., Madison, WI, 1998.Google Scholar
  19. 19.
    Sheldrick, G.M. SADABS, Program for absorption correction with the Bruker SMART system, Universitat Göttingen: Germany, 1996.Google Scholar
  20. 20.
    The corresponding 5,10,15-substituted corroles and metal corrolates have been formed and some structural characterization has been obtained. Maiti, N., Lee, J., Do, Y. and Churchill, D.G. Preliminary results, February, 2005.Google Scholar
  21. 21.
    Cornia, M.; Capacchi, S.; Pogetto, M.D.; Pelosi, G.; Fava, G.G. Tetrahedron: Asymmetry 1997, 8, 2905–2912.Google Scholar
  22. 22.
    Gallagher, J.F.; Moriarty, E. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1999, C55, 1079–1082.Google Scholar

Copyright information

© Springer Science + Business Media, Inc. 2005

Authors and Affiliations

  • Nilkamal Maiti
    • 1
  • Junseong Lee
    • 1
  • Youngkyu Do
    • 1
  • Hack Soo Shin
    • 1
  • David G. Churchill
    • 1
  1. 1.Department of Chemistry and School of Molecular Science-BK 21Korea Advanced Institute of Science and TechnologyYuseong-guRepublic of Korea

Personalised recommendations