SYNTHESIS, CRYSTAL STRUCTURE, AND CONFORMATION OF N-ISONICOTINOYLPHTHALIMIDE

• Published in: Journal of structural chemistry 2021-08, Vol.62 (8), p.1279-1284
• Main Authors: Turdybekov, K. M., Nurkenov, O. A., Fazylov, S. D., Makhmutova, A. S., Turdybekov, D. M., Seilkhanov, T. M., Arinova, A. E.
• Format: Article
• Language: English
• Subjects: Acidic oxides; Atomic; Atomic/Molecular Structure and Spectra; Carbonyl groups; Carbonyls; Chemistry; Chemistry and Materials Science; Conjugation; Crystal structure; Inorganic Chemistry; Molecular; NMR spectroscopy; Optical and Plasma Physics; Physical Chemistry; Pyridines; Quantum chemistry; Rings (mathematics); Single crystals; Solid State Physics; Spectrum analysis
• ISSN: 0022-4766; 1573-8779
• DOI: 10.1134/S0022476621080151

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 1 H and 13 C NMR spectroscopy and from the data of two-dimensional ( 1 H– 1 H) COSY and ( 1 H– 13 C) 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.