Synthesis and Calorimetry of Some Derivatives of Dibenzazepine

  • Edward Gipstein
  • Edward M. BarrallII
  • Karen E. Bredfeldt
Conference paper

Abstract

Dibenzazepine consists of two aromatic rings connected by a single double bond bridge. The aromatic rings are prevented from assuming a planar configuration by an imide nitrogen bridge. This is shown in the drawing of a model of propionyl dibenzazepine in Figure 1. Construction of such models indicates that substitution on the nitrogen may give rise to compounds in which free rotation in the derivative is seriously hindered. Indeed, chemical evidence of hindrance was found in several dibenzazepine derivatives synthesized as monomers for polymerization studies (1). The N.M.R. spectrum for each derivative revealed rapid inversion of the non-planar dibenzazepine ring and restricted rotation about the C-N and C-C bonds.

Keywords

Oblate Spheroid Zinc Chloride Solid Transition Trifluoroacetic Anhydride Transition Entropy 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
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References

  1. 1.
    E. Gipstein, W. A. Hewett and O. U. Need, J. Polymer Sci., in press.Google Scholar
  2. 2.
    P. Craig et al., J. Org. Chem. 26, 135 (1961).CrossRefGoogle Scholar
  3. 3.
    Edward M. Barrali and Richard D. Diller, Precision of Purity Determinations by Differential Scanning Calorimetry, Thermochemica Acta, in press.Google Scholar
  4. 4.
    Perkin-Elmer Corp., Norwalk, Conn., Thermal Analysis Newsletter, Nos. 1–6.Google Scholar
  5. 5.
    G. L. Driscoll, I. N. Dulling and F. Magnotta, Purity Determination Using a Differential Scanning Calorimeter, Analytical Calorimetry, R. S. Porter and J. F. Johnson eds., Plenum Press, N. Y. (1968) pp. 271–278.Google Scholar
  6. 6.
    N. J. DeAngelis and G. J. Papariello, J. Pharm. Sci. 57, 1868 (1968).CrossRefGoogle Scholar
  7. 7.
    C. Plato and A. R. Glasgow Jr., Anal. Chem., 41, 330 (1969).CrossRefGoogle Scholar
  8. 8.
    J. Pirsch, Chem. Ber. 70, 12 (1937).Google Scholar
  9. 9.
    A. Bondi, Chem. Rev. 67, 565 (1967).CrossRefGoogle Scholar
  10. 10.
    R. S. Porter, E. M. Barrali and J. F. Johnson, Accounts of Chem. Res. 2, 53 (1969).CrossRefGoogle Scholar
  11. 11.
    W. Wong and E. F. Westrum Jr., J. Phys. Chem. 74, 1303 (1970).CrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1970

Authors and Affiliations

  • Edward Gipstein
    • 1
  • Edward M. BarrallII
    • 1
  • Karen E. Bredfeldt
    • 1
  1. 1.Research LaboratoryInternational Business Machines CorporationSan JoseUSA

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