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2-(1-Isonicotinoylhydrazinoalkylidene)-5,5-dimethyl-1,3-cyclohexanediones and their polychromism. A new type of compound with intramolecular charge transfer through the hydrazonocarbonyl bridge

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Abstract

The product of condensation of 2-formyldimedone with the hydrazide of isonicotinic acid, namely 2-isonicotinoylhydrazinomethylene-5,5-dimethyl-1,3-cyclohexanedione, has been obtained in three forms — red, colorless, and yellow — which with methyl iodide give one and the same iodide 2-[N-(1-methyl-4-pyridiniumcarbonyl)hydrazinomethylene]-5, 5-dimethyl-1, 3-cyclohexanedione. On the basis of UV spectra and x-ray structure analysis of this betaine and also the dark-red iodide of N-(4-diethylaminobenzal)-N′-(1-methyl-4-pyridiniumcarbonyl)hydrazine, it has been shown that intramolecular charge transfer in these linear molecules proceeds along the system of bonds D:-RC=N-NH-CO-A through the hydrazonocarbonyl bridge, which does not interrupt the conjugation chain. The existence of colored forms of the 2-isonicotinoylhydrazinomethylene-5,5-dimethyl-1,3-cyclohexanedione can be explained by an admixture of the betaine form.

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Authors and Affiliations

  1. Riga Technical University, LV-1658 PDP, Riga

    A. Ya. Strakov, O. Ya. Neiland, N. N. Tonkikh, S. V. Belyakov, M. V. Petrova & I. Ya. Gudele

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  1. A. Ya. Strakov
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  2. O. Ya. Neiland
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  3. N. N. Tonkikh
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  4. S. V. Belyakov
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  5. M. V. Petrova
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  6. I. Ya. Gudele
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 489–498, April, 1993.

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Strakov, A.Y., Neiland, O.Y., Tonkikh, N.N. et al. 2-(1-Isonicotinoylhydrazinoalkylidene)-5,5-dimethyl-1,3-cyclohexanediones and their polychromism. A new type of compound with intramolecular charge transfer through the hydrazonocarbonyl bridge. Chem Heterocycl Compd 29, 414–422 (1993). https://doi.org/10.1007/BF00529880

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  • DOI: https://doi.org/10.1007/BF00529880

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