Advertisement

Research on Chemical Intermediates

, Volume 21, Issue 8–9, pp 877–883 | Cite as

Photoacoustic determination of heats of formation and reaction of 5-chloro-1,2-didehydro-1H-azepine, a seven-membered cyclic ketenimine

  • Paul Senn
  • Jakob Wirz
Article

Abstract

The heats of formation and trapping by diethylamine of 5-chloro-1,2-didehydro-1H-azepine have been determined by time-resolved photoacoustic calorimetry (PAC). The results are compared with predictions from semiempirical calculations.

Keywords

Cyclohexane Diethylamine Molecular Nitrogen Kcal Tool Heat Deposition 
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.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    a) H.F. Schuster and G.M. Coppola, Allenes in Organic Synthesis, Wiley, New York, chapter 2.3 (1984); b) R.P. Johnson, Chem. Rev., 89, 1111 (1989).Google Scholar
  2. 2.
    J. Firl, K. Schink and W. Kosbahn, Chem. Lett., 527 (1981).Google Scholar
  3. 3.
    R. Huisgen, E. Langhals and H. Nöth, J. Org. Chem., 55, 1412 (1990).CrossRefGoogle Scholar
  4. 4.
    O.L. Chapman and J.-P. LeRoux, J. Am. Chem. Soc., 100, 282 (1978); O.L. Chapman and R.S. Sheridan, J. Am. Chem. Soc., 101, 3690 (1979); I. Dunkin and P.C.P. Thompson, J. Chem. Soc. Chem. Commun., 499 (1980); C. Wentrup and H.W. Winter, J. Am. Chem. Soc., 102, 6159 (1980); C. Wentrup, C. Thètaz, E. Tagliaferri, H.J. Linder, B. Kitschke, H.W. Winter and H.P. Reisenauer, Angew. Chem. Int. Ed. Engl., 19, 566 (1980); I.R. Dunkin, T. Donelly and T.S. Lockhart, Tetrahedron Lett., 359 (1985); T. Donelly, I.R. Dunkin, D.S.D. Norwood, A. Prentice, C.J. Shields and P.C.P. Thompson, J. Chem. Soc. Perkin Trans. 2, 26, 2147 (1985); J.C. Hayes and R.S. Sheridan, J. Am. Chem. Soc., 112, 5879 (1990); H. Tomioka, N. Ichikawa and K. Komatsu, J. Am. Chem. Soc., 115, 8621 (1993).CrossRefGoogle Scholar
  5. 5.
    a) M. Kuzaj, H. Lüerssen and C. Wentrup, Angew. Chem., 98, 476 (1986); Angew. Chem. Int. Edn. Engl., 25, 480 (1986); b) P.R. West, O.L. Chapman and J.-P. LeRoux, J. Am. Chem. Soc., 106, 7973 (1984); R.J. McMahon, C.J. Abelt, O.L. Chapman, J.W. Johnson, C.L. Kreil, J.-P. LeRoux, A.M. Mooring and P.R. West, J. Am. Chem. Soc. 109, 2456 (1987).CrossRefGoogle Scholar
  6. 6.
    G.B. Schuster and M.S. Platz, Adv. Photochem., in press.Google Scholar
  7. 7.
    Y. Li, J.P. Kirby, M.W. George, M. Poliakoff and G.B. Schuster, J. Am. Chem. Soc., 110 8092 (1988).CrossRefGoogle Scholar
  8. 8.
    C.A. Parker, Photoluminescence of Solutions, Elsevier, Amsterdam, (1968).Google Scholar
  9. 9.
    a) R.R. Hung and J.J. Grabowski, J. Am. Chem. Soc., 114, 351 (1992); b) G.S. Wayne, G.J. Snyder and D.W. Rogers, ibid. J. Am. Chem. Soc., 115, 9860 (1993).CrossRefGoogle Scholar
  10. 10.
    S.E. Braslavsky and K. Heihoff. In: CRC Handbook of Organic Photochemistry, J.C. Scaiano (Ed.), CRC Press, Boca Raton, Vol. I, chapter 14 (1989).Google Scholar
  11. 11.
    D.W. Rogers, G.S. Wayne, W.C. Duty and G.J. Snyder, to be published; personal communication by G. J. Snyder, University of Chicago.Google Scholar
  12. 12.
    S.W. Benson, Thermochemical Kinetics, 2nd ed, Wiley, New York, (1976).Google Scholar
  13. 13.
    R. Fuchs, E.J. Chambers and K. Stepherson, Can. J. Chem., 65, 2624 (1987); R. Fuchs, T.M. Young and R.F. Rodewald, J. Am. Chem. Soc., 96, 4705 (1974).CrossRefGoogle Scholar
  14. 14.
    W. Emmerich and B. Rubin, Chem. Rev., 73, 1 (1973).CrossRefGoogle Scholar
  15. 15.
    M.J.S. Dewar and W. Thiel, J. Am. Chem. Soc., 99, 4899 (1977).CrossRefGoogle Scholar
  16. 16.
    M.J.S. Dewar, E.G. Zoebisch, E.F. Healy and J.J.P. Stewart, J. Am. Chem. Soc. 107, 3902 (1985).CrossRefGoogle Scholar
  17. 17.
    J.J.P. Stewart, J. Comput. Chem., 10, 209 (1989).CrossRefGoogle Scholar
  18. 18.
    B.J. Smith and L. Radom, J. Am. Chem. Soc., 114, 36 (1992).CrossRefGoogle Scholar
  19. 19.
    T. Ni, R.A. Caldwell and L.A. Melton, J. Am. Chem. Soc., 111, 4573 (1989); L.A. Melton T. Ni and Q. Lu, Rev. Sci. Instrum., 60, 3217 (1989).CrossRefGoogle Scholar
  20. 20.
    P.A.S. Smith and J.H. Boyer, Org. Syn., Coll. Vol. IV, 75 (1963).Google Scholar

Copyright information

© Springer 1995

Authors and Affiliations

  • Paul Senn
    • 1
  • Jakob Wirz
    • 1
  1. 1.Institut für Physikalische Chemie der Universität BaselBaselSwitzerland

Personalised recommendations