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Basicities and tautomerism of 4,4,6-trimethyl-2-aryl-amino-4H-1, 3-thiazines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The relative basicities of 4,4,6-trimethyl-2-arylamino-4H-1,3-thiazines, which are capable of amine-imine tautomerism, and of model compounds with fixed amino and imino structures were determined by potentiometric titration in methanol. Good correlation was observed between the pKa values and the Hammett σ constants in the investigated reaction series. The anomalous pKa values of the model amines and imines are explained by the different character of the electronic interactions in them, which is due to the change in the three-dimensional orientation of the aromatic ring and the amidine fragment.

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Authors and Affiliations

  1. M. V. Lomonosov Moscow Institute of Fine Chemical Technology, USSR

    L. A. Ignatova, P. L. Ovechkin, A. E. Gekhman & B. V. Unkovskii

Authors
  1. L. A. Ignatova
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  2. P. L. Ovechkin
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  3. A. E. Gekhman
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  4. B. V. Unkovskii
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 777–780, June, 1975.

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Ignatova, L.A., Ovechkin, P.L., Gekhman, A.E. et al. Basicities and tautomerism of 4,4,6-trimethyl-2-aryl-amino-4H-1, 3-thiazines. Chem Heterocycl Compd 11, 675–678 (1975). https://doi.org/10.1007/BF00959959

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  • DOI: https://doi.org/10.1007/BF00959959

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