Application of AM1 method in studying tautomeric conversions of 1,3-diiminoisoindoline and its nitro and amino derivatives

Authors

  • А. B. Любимцев Ivanovo State Chemical Technology Academy, Ivanovo 15340
  • А. Бараньски Institute of Organic Chemistry and Technology, Krakow Polytechnic, Krakow 31–155
  • М. K. Исляйкин Ivanovo State Chemical Technology Academy, Ivanovo 15340
  • P. П. Смирнов Ivanovo State Chemical Technology Academy, Ivanovo 15340

Abstract

The semiempirical method AM1 was used to calculate transition states corresponding to conformational and tautomeric conversions of 1,3-diiminoisoindoline, and also its nitro and amino derivatives. Tautomeric conversions through an intermolecular mechanism involving a protic solvent have a lower energy barrier than in the case of intramolecular proton transfer. Substitution in the benzene ring of 1,3-diiminoisoindoline does not have any significant effect on the energy barriers of the conformational transitions and tautomeric conversions. Calculated IR and electronic spectra of 1,3-diiminoisoindoline are in satisfactory agreement with the experimental spectra.

How to Cite
Lyubimtsev, A. V.; Baran'ski, A.; Islyaikin, M. K.; Smirnov, R. P. Chem. Heterocycl. Compd. 1997, 33, 937. [Khim. Geterotsikl. Soedin. 1997, 1074.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF02253165

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Published

1997-08-25

Issue

No. 8 (1997)

Section

Original Papers