Chemistry of Heterocyclic Compounds

, Volume 20, Issue 4, pp 405–408 | Cite as

Investigation of the barriers to retarded internal rotation in N-acyl-1-methyl-1,2,3,4-tetrahydroisoquinolines

  • S. N. Dvoryantsev
  • V. I. Mstislavskii
  • V. M. Dem'yanovich


The effect of a number of alkyl substituents attached to the carbon atom of the acyl group on the activation parameters of retarded internal rotation about the C-N bond in N-acyl-1-methyl-1,2,3,4-tetrahydroisoquinolines was studied. Correlation of the free energies of activation ΔG 298 with the steric factors (Es) and the σ* substituent constants was examined.


Free Energy Organic Chemistry Carbon Atom Internal Rotation Activation Parameter 
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Literature cited

  1. 1.
    V. M. Potapov, V. M. Dem'yanovich, L. B. Krivdin, T. V. Skvortsova, and Z. I. Bkhatti, Khim. Geterotsikl. Soedin., No. 5, 662 (1981).Google Scholar
  2. 2.
    D. A. Kleier and G. Binsch, J. Magn. Reson., 3, 146 (1970).Google Scholar
  3. 3.
    D. A. Kleier and G. Binsch, DNMR3: A Computer Program for the Calculation of Complex Exchange-Broadened Spectra. Program 165. Quantum Chemistry Program Exchange, Indiana Univ. (1970).Google Scholar
  4. 4.
    V. Dimitrov, J. Magn. Reson., 22, 71 (1976).Google Scholar
  5. 5.
    N. M. Sergeev, J. NMR Spectroscopy, Izd. Mosk. Gos. Univ., Moscow (1981), p. 106.Google Scholar
  6. 6.
    L. B. Krivdin, V. N. Torocheshnikov, N. M. Sergeev, I. G. Il'ina, and N. B. Kazennova, Khim. Geterotsikl. Soedin., No. 8, 1092 (1980).Google Scholar
  7. 7.
    L. M. Jackman, in: Dynamic Nuclear Magnetic Resonance Spectroscopy, L. M. Jackman and F. Cotton, eds., Academic Press, New York (1975), p. 203.Google Scholar
  8. 8.
    V. A. Palm (editor), Progress in Science and Technology, Vol. 5, Tables of Rate and Equilibrium Constants of Heterolytic Organic Reactions [in Russian], Moscow (1979).Google Scholar
  9. 9.
    A. L. van Geet, Anal. Chem., 40, 2227 (1948).Google Scholar

Copyright information

© Plenum Publishing Corporation 1984

Authors and Affiliations

  • S. N. Dvoryantsev
    • 1
  • V. I. Mstislavskii
    • 1
  • V. M. Dem'yanovich
    • 1
  1. 1.M. V. Lomonosov Moscow State UniversityMoscow

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