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Prototropic Tautomerism of 3-Nitro- and 5-Nitrosalicylidene-3-picolylimines

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Abstract

Synthesis, X-ray diffraction and spectroscopic analysis (IR, 1H, 13C, 15N NMR) of azomethines derived from 3-nitro- and 5-nitrosalicylic aldehyde and 3-picolylamine were carried out. In crystals both molecules are realized in ketoamine (quinoid) tautomeric form. The structures of azomethines are stabilized by strong intramolecular hydrogen N1–H1···O2 bonds. In CDCl3 and DMSO-d6 solutions the obtained azomethines exist in enol-imine (benzoid) tautomeric form, stabilized by the N1···H1–O2 bond.

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ACKNOWLEDGMENTS

The authors are grateful to S.Yu. Savelyeva (Laboratory of Magnetic Tomography and Spectroscopy, Faculty of Fundamental Medicine, Lomonosov Moscow State University) for their help in recording and discussing the 1Н, 13С, and 15N NMR spectra of the synthesized compounds.

Funding

This work was carried out within the framework of the governmental task of the N.S. Kurnakov Institute of General and Inorganic Chemistry of RAS in the field of fundamental scientific research.

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Authors and Affiliations

  1. V. Dahl Lugansk State University, 91034, Lugansk, Ukraine

    V. L. Abramenko & S. G. Krivokolysko

  2. N.S. Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences, 119991, Moscow, Russia

    V. S. Sergienko & A. V. Churakov

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  1. V. L. Abramenko
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  2. V. S. Sergienko
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Abramenko, V.L., Sergienko, V.S., Churakov, A.V. et al. Prototropic Tautomerism of 3-Nitro- and 5-Nitrosalicylidene-3-picolylimines. Russ J Gen Chem 92, 750–758 (2022). https://doi.org/10.1134/S1070363222050024

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