Skip to main content
SpringerLink
Log in

Synthesis and structure of new systems containing pyramidalized double bonds

  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

Syn- andanti-isomers of substituted tetracyclo[6.2.2.23.6.12.7]tetradeca-2(7)-ene have been synthesized. In thesyn-isomers steric interactions between cyclopropane hydrogen atoms lead to a pyramidalization of the C(sp2) atoms of the central double bond. The parameters from three crystal structures are compared with geometry optimized structures using PCWIN, MM3, and MOPAC. Plots of X-ray distances versus theoretically optimized distances give correlation coefficients between 0.91 and 0.97. Analysis of the discrepancies suggest modifications in some molecular mechanics parameters are needed to model the solid state structures.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Borden, W.T..Chem. Rev. 1989,89, 1095.

    Google Scholar 

  2. Watson, W.H. (Ed.).Stereochemistry and reactivity of systems containing πelectrons. Verlag Chemie International: Deerfield Beach.1983.

    Google Scholar 

  3. Watson, W.H.; Galloy, J.; Bartlett, P.D.; Roof, A.A.M.J. Am. Chem. Soc. 1981,103, 2022.

    Google Scholar 

  4. Menzek, A.; Krawicc, M.; Watson, W.H.; Balci, M.J. Org. Chem. 1991,56, 6755.

    Google Scholar 

  5. Menzek, A.; Saracoglu, N.; Krawiec, M.; Watson, W.H.; Balci, M.J. Org. Chem. 1994,59, in press.

  6. Sheldrick, G.M. (1986)SHELXS86. Program for the solution of crystal structures. Univ. of Göttingen: Germany.

    Google Scholar 

  7. Molecular Structure Corporation.TEXSAN. TEXRAY Structure Analysis Package. 1985. 3200 Research Forest Drive. The Woodlands: TX.

    Google Scholar 

  8. Spek, A.L.;Acta Cryst. 1990,A46, C43.

    Google Scholar 

  9. PCWIN. Molecular Modeling Software for Windows,1994, Serena Software: Bloomington. IN.

  10. Allinger, N.L.; Yuh, Y.H.; Lii, J.-H.J. Am. Chem. Soc. 1989,111, 8551. MM3 program from Technical Utilization Corporation, Powell, OH. Update May 1992.

    Google Scholar 

  11. MOPAC 7.0 QCPE 455.

  12. Volland, W.V.; Davidson, E.R.; Borden, W.T.J. Am. Chem. Soc. 1979,101, 533.

    Google Scholar 

  13. Borden, W.T.Chem. Rev. 1989,89, 1095.

    Google Scholar 

  14. Ermer, O.; Mason, S.A.Acta Cryst. 1982,B38, 2200.

    Google Scholar 

  15. Ermer, O.; Bell, P.; Mason, S.A.Angew. Chem. Int. Ed. 1989,28, 1239.

    Google Scholar 

  16. Systematic Analysis of Structural Data as a Research Technique in Organic Chemistry. Allen, F.H.; Kennard, O.; Taylor, R.Acc. Chem. Res. 1983,16, 146.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Texas Christian University, 76129, Fort Worth, Texas

    Metin Balci, Susan A. Bourne & William H. Watson

  2. Department of Chemistry, Faculty of Art and Sciences, Atatürk University, 25240, Erzurum, Turkey

    Abdullah Menzek & Nurullah Saraçoglu

Authors
  1. Metin Balci
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Susan A. Bourne
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Abdullah Menzek
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Nurullah Saraçoglu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. William H. Watson
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Balci, M., Bourne, S.A., Menzek, A. et al. Synthesis and structure of new systems containing pyramidalized double bonds. J Chem Crystallogr 25, 107–116 (1995). https://doi.org/10.1007/BF01665985

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01665985

Key Words

Search

Navigation