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SYNTHESIS, CRYSTAL STRUCTURE, AND CONFORMATION OF N-ISONICOTINOYLPHTHALIMIDE

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Abstract

The reaction of phthalic acid anhydride with isonicotinoylhydrazide is carried out under severe conditions with the formation of cyclic phthalic acid imide N-isonicotinoylphthalimide. The structure of the compound is determined by 1H and 13C NMR spectroscopy and from the data of two-dimensional (1H–1H) COSY and (1H–13C) HMQC spectra. The spatial structure and conformation of N-isonicotinoylphthalimide is investigated by single crystal XRD and a semi-empirical quantum chemical method. It is found that π-conjugation between the phenyl and carbonyl groups is practically absent in the free N-isonicotinoylphthalimide molecule and a rotation of the pyridine ring relative to the amide group in the crystal is determined by the π–π interaction between the pyridine rings.

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Funding

The work was supported by the Science Committee of the Ministry of Education and Science of the Republic of Kazakhstan (grant No. AR051311054).

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Authors and Affiliations

  1. Buketov Karaganda University, Karaganda, Republic of Kazakhstan

    K. M. Turdybekov

  2. Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, Karaganda, Republic of Kazakhstan

    O. A. Nurkenov, S. D. Fazylov & A. E. Arinova

  3. Medical University of Karaganda, Karaganda, Republic of Kazakhstan

    A. S. Makhmutova

  4. Karaganda Technical University, Karaganda, Republic of Kazakhstan

    O. A. Nurkenov & D. M. Turdybekov

  5. Ualikhanov Kokshetau University, Kokshetau, Republic of Kazakhstan

    T. M. Seilkhanov

Authors
  1. K. M. Turdybekov
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  2. O. A. Nurkenov
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  3. S. D. Fazylov
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  4. A. S. Makhmutova
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  5. D. M. Turdybekov
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  6. T. M. Seilkhanov
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  7. A. E. Arinova
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Correspondence to K. M. Turdybekov.

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Additional information

Russian Text © The Author(s), 2021, published in Zhurnal Strukturnoi Khimii, 2021, Vol. 62, No. 8, pp. 1366-1371.https://doi.org/10.26902/JSC_id78509

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Turdybekov, K.M., Nurkenov, O.A., Fazylov, S.D. et al. SYNTHESIS, CRYSTAL STRUCTURE, AND CONFORMATION OF N-ISONICOTINOYLPHTHALIMIDE. J Struct Chem 62, 1279–1284 (2021). https://doi.org/10.1134/S0022476621080151

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  • DOI: https://doi.org/10.1134/S0022476621080151

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