Chemistry of Heterocyclic Compounds

, Volume 20, Issue 8, pp 865–869 | Cite as

Structure of 2-amino-4-thiazolinone

  • S. M. Ramsh
  • N. A. Smorygo
  • A. I. Ginak
Article

Abstract

It was shown by the methods of IR and NMR spectroscopy that 2-amino-4-thiazolinone (“pseudothiohydantoin”) exists in an amino form in the crystalline state and in solutions in dimethyl sulfoxide, water, and trifluoroacetic acid, and in this amino form all the nitrogen-carbon bonds are partially double. In dimethyl sulfoxide and trifluoroacetic acid there is an autoassociation with the formation of dimers. Inhibited rotation of the amino group around the exocyclic nitrogen-carbon bond was detected. The results of a calculation of the IR spectrum of 2-amino-4-thiazolinone according to the force-field method agrees with the experimental data.

Keywords

Spectroscopy Experimental Data Organic Chemistry Dimethyl Sulfoxide 

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Literature cited

  1. 1.
    S. M. Ramsh, A. I. Ginak, N. A. Smorygo, Yu. G. Basova, and E. G. Sochilin, Zh. Org. Khim., 14, 1327 (1978).Google Scholar
  2. 2.
    J. P. Mornon and B. Raveau, Acta Crystallogr., 27B, 95 (1971).Google Scholar
  3. 3.
    J. P. Mornon and R. Bally, Acta Crystallogr., 28B, 2074 (1972).Google Scholar
  4. 4.
    D. Petrovic, B. Ribar, G. Argay, A. Kalman, and W. Nowacki, Acta Crystallogr., 33B, 106 (1977).Google Scholar
  5. 5.
    N. G. Furmanova, Usp. Khim., 50, 1491 (1981).Google Scholar
  6. 6.
    N. N. Khovratovich and I. I. Chizhevskaya, Khim. Geterotsikl. Soedin., No. 4, 637 (1967).Google Scholar
  7. 7.
    R. V. Ananthamurthy, M. R. Udupa, and B. V. R. Murthy, Z. Kristallogr., 137, 316 (1973).Google Scholar
  8. 8.
    V. Amirthalingam and K. V. Muralidharan, Acta Crystallogr., 28B, 2421 (1972).Google Scholar
  9. 9.
    L. A. Plastas and J. M. Stewart, Chem. Commun., 811 (1969).Google Scholar
  10. 10.
    L. M. Jackman and T. Jen, J. Am. Chem. Soc., 97, 2811 (1975).Google Scholar
  11. 11.
    H. Kessler, Angew. Chem., 72, 237 (1970).Google Scholar
  12. 12.
    R. S. Lebedev, V. I. Yakimenko, A. V. Korshunov, N. I. Afanas'eva, and V. E. Volkov, Izv. Vyssh. Uchebn. Zaved., Fizika, 14, No. 9, 76 (1971).Google Scholar
  13. 13.
    Yu. G. Basova, Dissertation for the Degree of Candidate of Chemical Sciences [in Russian], Leningrad (1980).Google Scholar
  14. 14.
    V. Amirthalingam and K. V. Muralidharan, Acta Crystallogr., 28B, 2417 (1972).Google Scholar
  15. 15.
    N. G. Dolinnaya and E. S. Gromova, Usp. Khim., 52, 138 (1983).Google Scholar
  16. 16.
    Ch. F. Howell, W. Fulmor, N. Q. Quinones, and R. A. Hardy, J. Org. Chem., 29, 370 (1964).Google Scholar
  17. 17.
    R. Silverstein, G. Bassler, and T. Morrill, Spectrometric Identification of Organic Compounds, Wiley (1974).Google Scholar
  18. 18.
    N. M. Turkevich, V. M. Vvedenskii, and L. M. Petlichnaya, Ukr. Khim. Zh., 27, 680 (1961).Google Scholar
  19. 19.
    M. V. Vol'kenshtein, L. A. Gribov, M. A. El'yashevich, and V. I. Stepanov, Molecular Vibrations [in Russian], Nauka, Moscow (1972).Google Scholar

Copyright information

© Plenum Publishing Corporation 1985

Authors and Affiliations

  • S. M. Ramsh
    • 1
  • N. A. Smorygo
    • 1
  • A. I. Ginak
    • 1
  1. 1.Lensovet Leningrad Technological InstituteLeningrad

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