Skip to main content
SpringerLink
Log in

Molecular Structure of 1-Substituted Bicyclo[2.2.0]hexanes: A Combined X-Ray Structural and Ab Initio Study

  • Published:
Structural Chemistry Aims and scope Submit manuscript

Abstract

The synthesis and X-ray crystal structure of the p-bromoanilide derivative of bicyclo[2.2.0]hexane-l-carboxylic acid (1), N-(4-bromophenyl)-bicyclo[2.2.0]hexane-l-carboxamide (2), is reported. N-(4-Bromophenyl)-bicyclo[2.2.0]hexane-l-carboxamide is synthesized in good yield via the DCC coupling of bicyclo[2.2.0]hexane-l-carboxylic acid (1) with p-bromoaniline. Low-temperature X-ray analysis of 2 reveals that the \(C{\kern 1pt} ---{\kern 1pt} C\) bonds of the bicyclo[2.2.0]hexane skeleton vicinal to the amide group show a slight lengthening due to conjugative interaction with the π-accepting amide group. Ab initio calculations at the 6-31G* level of theory on bicyclo[2.2.0]hexane-l-carboxamide, a model for 2, and for other 1-substituted bicyclo[2.2.0]hexanes are also reported.

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. Cremer, S.; Srinivasan, R. Tetrahedron Lett. 1960, 24.

  2. Srinivasan, R. J. Am. Chem. soc. 1961, 83, 4923. (b) Griffin, C. E.; Hepfinger, N. F.; Shapiro, B. L. J. Am. Chem. Soc. 1963, 85, 2683. (c) Steel, C.; Zand, R.; Hurwitz, P.; Cohen, S. G. J. Am. Chem. Soc. 1964, 86, 679. (d) Wiberg, K. B.; Matturo, M. G.; Okarma, P. J.; Jason, M. E.; Dailey, W. P.; Burgmaier, G. J.; Bailey, W. F.; Warner, P. Tetrahedron 1986, 42, 1895.

    Google Scholar 

  3. Forman, M.; Cucinotta, L.; Chopko, E. Unpublished results.

  4. Wiberg, K. B. In Advances in Alicyclic Chemistry, Vol. 2. Harat, H.; Karabatsos, G. J., eds.; Academic Press: New York, 1968, pp. 230–241.

    Google Scholar 

  5. Ingold, K. U.; Walton, J. C. Acc. Chem. Res. 1986, 19, 73. (b) Walton, J. C. J. Chem. Soc., Perkin Trans. 2 1988, 1371.

    Google Scholar 

  6. Wiberg, K. B.; Wendoloski, J. J. Am. Chem. Soc. 1982, 104, 5679. (b) Wiberg, K. B.; Bader, R. F. W.; Lau, C. D. H. J. Am. Chem. Soc. 1987, 109, 985.

    Google Scholar 

  7. Andersen, B.; Srinivasan, R. Acta Chem. Scand. 1972, 26, 3468.

    Google Scholar 

  8. Some selected polysubstituted bicyclo[2.2.0]hexanes include: (a) Golic, L.; Leban, I. Cryst. Struct. Commun. 1980, 9, 739. (b) Craig, D. C.; Paddon-Row, M. Aust. J. Chem. 1987, 40, 1951. (c) de Meijrere, A.; Wenck, H.; Kopf, J. Tetrahedron 1988, 44, 2427. (d) Warrener, R. N.; Abbenante, G.; Kennard, C. H. L. J. Am. Chem. Soc. 1994, 116, 3645. (e) Williams, J. R.; Callhan, J. F.; Blount, J. F. J. Cryst. Mol. Struct. 1979, 9, 245. (f) Della, E. W.; Head, N. J.; Mallon, P.; Walton, J. C. J. Am. Chem. Soc. 1992, 114, 10730. (g) Eaton, P. E.; Millikan, R.; Engel, P. J. Org. Chem. 1990, 55, 2823. (h) Dunand, A.; Gerdil, R. Acta Cryst. B 1980, 36, 472. (i) Wilson, S. R.; Phillips, L. R.; Pelister, Y.; Huffman, J. C. J. Am. Chem. Soc. 1979, 101, 7373. (j) Silverton, J. V.; Milne, G. W. A.; Eaton, P. E.; Nyi, K.; Temme III, G. H. J. Am. Chem. Soc. 1974, 96, 7429. (k) Bellus, D.; Mez, H.-C.; Rihs, G.; Sauter, H. J. Am. Chem. Soc. 1974, 96, 5007.

    Google Scholar 

  9. Giordano, F.; Graziano, M. L.; Iesce, M. R. Gazz. Chim. Ital. 1994, 124, 209.

    Google Scholar 

  10. Allen, F. H. Acta Cryst. 1984, B40, 64.

    Google Scholar 

  11. Allen, F. H. Acta Cryst. 1980, B36, 81.

    Google Scholar 

  12. Irngartiner, H.; Strack, S.; Gredel, F. Liebigs Ann. 1996, 311.

  13. O'Bannon, P. E.; Dailey, W. P.; Carroll, P. J. Struct. Chem. 1990, 1, 491.

    Google Scholar 

  14. bioteX: A suite of programs for the collection, reduction and interpretation of imaging plate data, Molecular Structure Corporation (1995).

  15. teXsan: crystal structure analysis package, Molecular Structure Corporation (1985, 1992).

  16. ABSCOR: A program to correct absorption effects by Fourier series: T. Higashi, Rigaku Corp. (1995).

  17. SIR92: Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, M.; Giacovazzo, C.; Guagliardi, A.; Polidoro, G. J. Appl. Cryst. 1994, 27, 435.

    Google Scholar 

  18. SHELXL-93: Program for the refinement of crystal structures, G. M. Sheldrick, University of Göttingen, Germany, 1993.

    Google Scholar 

  19. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A. J. Comput. Chem. 1993, 14, 1347.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Saint Joseph's University, Philadelphia, Pennsylvania, 19131

    Mark A. Forman, Brian C. Zanoni & Emily C. Chopko

  2. Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania, 19104

    Patrick J. Carroll

Authors
  1. Mark A. Forman
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Brian C. Zanoni
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Emily C. Chopko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Patrick J. Carroll
    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

Forman, M.A., Zanoni, B.C., Chopko, E.C. et al. Molecular Structure of 1-Substituted Bicyclo[2.2.0]hexanes: A Combined X-Ray Structural and Ab Initio Study. Structural Chemistry 9, 27–32 (1998). https://doi.org/10.1023/A:1022431514386

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1022431514386

Search

Navigation