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Synthesis and vibrational spectra of N-exo-arylcarbamoylsydnoneimines and their salts

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A number of arylcarbamoyl derivatives of sydnoneimines were synthesized, and their IR spectra and Raman spectra in the region of the characteristic vibrations of the exocyclic

bond were studied. The integral intensities (A) of the C=O and C=N bands of those compounds constitute evidence for effective electronic interaction of the atoms in the exocyclic group. The structures of salts of the carbamoylsydnoneimines were investigated by means of their IR spectra, and it was proved that the protonation of these compounds takes place at the exocyclic nitrogen atom. It is shown that carbamoylsydnoneimines do not form dications even in solutions of strong acids.

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Literature cited

  1. Z. A. Olovyanishnikova, B. I. Bryantsev, I. S. Slyusarenko, and V. G. Yashunskii, Khim. Geterotsikl. Soedin., No. 9, 1198 (1975).

    Google Scholar 

  2. H. V. Dainiker and T. Druey, Helv. Chim. Acta,45, 2441 (1962).

    Google Scholar 

  3. L. E. Kholodov, I. F. Tishchenkova, Z. A. Pankina, and V. G. Yashunskii, Zh. Org. Khim.,3, 1513 (1967).

    Google Scholar 

  4. I. Suzuki, Bull. Chem. Soc. Jpn.,35, 1273 (1962).

    Google Scholar 

  5. J. Jakes and B. Schneider, Spectrochim. Acta,24A, 286 (1968).

    Google Scholar 

  6. B. E. Zaitsev and Yu. N. Sheinker, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 4074 (1962).

  7. T. L. Brown, J. F. Reagan, R. D. Schultz, and J. S. Sternberg, J. Phys. Chem.,63, 1324 (1959).

    Google Scholar 

  8. C. D. Smulbach and R. S. Drago, J. Phys. Chem.,64, 1956 (1960).

    Google Scholar 

  9. P. P. Shorygin and Z. A. Alaune, Zh. Fiz. Khim.,34, 2299 (1960).

    Google Scholar 

  10. G. Michel and M. Renson, Spectrochim. Acta,23A, 1435 (1967).

    Google Scholar 

  11. V. G. Yashunskii, O. I. Samoilova, and L. E. Kholodov, Zh. Obshch. Khim.,34, 2050 (1964).

    Google Scholar 

  12. Z. A. Olovyanishnikova, V. V. Ogorodnikova, V. I. Mamonov, V. G. Yashunskii, R. A. Al'tshuler, and M. D. Mashkovskii, Khim.-Farm. Zh.,6, 20 (1972).

    Google Scholar 

  13. J. M. Klotz, S. F. Russo, S. Hanlov, and M. A. Stake, J. Am. Chem Soc.,86, 4774 (1964).

    Google Scholar 

  14. J. W. O. Tam and J. M. Klotz, Spectrochim. Acta,29A, 633 (1973).

    Google Scholar 

  15. B. E. Spinner, Spectrochim. Acta,15, 95 (1959).

    Google Scholar 

  16. R. J. Gillespie and T. Birchall, Can. J. Chem.,41, 148 (1963).

    Google Scholar 

  17. M. J. Janssen, Spectrochim. Acta,17, 475 (1961).

    Google Scholar 

  18. R. L. Vold, E. S. Daniel, and S. O. Chan, J. Am. Chem. Soc.,92, 6771 (1970).

    Google Scholar 

  19. G. Wada and T. Takenaka, Bull. Chem. Soc. Jpn.,44, 2877 (1971).

    Google Scholar 

  20. D. A. Ramsey, J. Am. Chem. Soc.,74, 72 (1952).

    Google Scholar 

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 170–175, February, 1978.

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Olovyanishnikova, Z.A., Ivanova, T.M., Sviridova, V.E. et al. Synthesis and vibrational spectra of N-exo-arylcarbamoylsydnoneimines and their salts. Chem Heterocycl Compd 14, 130–135 (1978). https://doi.org/10.1007/BF00945323

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  • DOI: https://doi.org/10.1007/BF00945323

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