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Comparative study of ring-chain isomeric transitions of 2-cyano-substituted benzamides and benzenesulfamides

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The rate constants of cyclization and the constant of ring-chain equilibrium of N-isopropyl-2-cyano-substituted benzamide and benzamide and benzenesulfamide by the methods of PMR and IR spectroscopy, and it was shown that in the transition from 2-cyanobenzamides to 2-cyanobenzenesulfamides a sharp destabilization of the cyclic isomeric form is observed; however, the cyclization of 2-cyanobenzenesulfamides proceeds at a higher rate than the cyclization of 2-cyanobenzamides.

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Literature cited

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    D. É. Balode, R. É. Valter, and S. P. Valter, Khim. Geterotsikl. Soedin., No. 2, 1632 (1978).

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Communication 4 of the series “Ring-Chain Conversions with the Participation of the C≡N Group”; for communication 3, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1635–1637, December, 1983.

Let us express our gratitude to Prof. Yu. N. Sheinker for the critical suggestions that he made during the defense of the candidate's dissertation of D. E. Balode, which promoted us to conduct the present investigation.

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Valter, R.É., Kampare, R.B., Valtere, S.P. et al. Comparative study of ring-chain isomeric transitions of 2-cyano-substituted benzamides and benzenesulfamides. Chem Heterocycl Compd 19, 1290–1292 (1983). https://doi.org/10.1007/BF00842833

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  • Spectroscopy
  • Organic Chemistry
  • Benzamide
  • Isomeric Form
  • Isomeric Transition