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3-(2-Methylphenyl)-2-selenoxo-2,3-dihydroquinazolin-4(1H)-one and Its Complex with Cd(II): Synthesis and Molecular and Crystal Structures

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Abstract

The reaction of methyl anthranilate with 2-methylphenyl-iso-selenocyanate in boiling absolute ethanol affords a new compound: 3-(2-methylphenyl)-2-selenoxo-2,3-dihydroquinazolin-4(1Н)-one (HL). Free ligand HL, which is selone, is preliminarily transformed into the corresponding sodium selenolate [C15H11N2OSeNa] (I), which is then used without isolation in the reaction with cadmium chloride. This reaction leads to the formation of complex [Cd2(μ-L)2(L)2(C2H5OH)2] (II). The structures of the compounds are determined by X-ray diffraction (XRD) (CIF files CCDC nos. 2142342 (НL) and 2246014 (II)) and NMR spectroscopy (1Н, 13С, 15N, and 77Se). In the crystal, the molecules of HL form one-dimensional chains due to H…O and H…Se contacts and alternate in the syndiotactic order. Compound II is the centrosymmetric binuclear complex [C64H56Cd2N8O6Se4]. The cadmium atoms in complex II are hexacoordinated by two chelate anionic ligands L–. According to the NMR data, in a DMSO-d6 solution free ligand HL has the selone structure, whereas in cadmium complex II this ligand exists in the selenolate form, which is consistent with the XRD data on the crystal structures of the compounds.

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Funding

This work was supported by the Russian Science Foundation (interdisciplinary projects nos. 20-62-47038 and 20-63-47107).

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Authors and Affiliations

  1. Baku State University, Baku, Azerbaijan

    R. K. Askerov & A. M. Magerramov

  2. Nizhni Novgorod State Technical University, Nizhni Novgorod, Russia

    E. V. Chipinskii, V. K. Osmanov, Zh. V. Matsulevich, G. N. Borisova & A. V. Borisov

  3. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russia

    A. S. Peregudov

  4. Peoples’ Friendship University of Russia, Moscow, Russia

    V. N. Khrustalev

  5. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia

    V. N. Khrustalev

  6. National Research State University, Nizhni Novgorod, Russia

    O. N. Smirnova

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  1. R. K. Askerov
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  2. E. V. Chipinskii
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  3. A. S. Peregudov
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  4. V. K. Osmanov
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  7. V. N. Khrustalev
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  8. O. N. Smirnova
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  9. A. M. Magerramov
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  10. A. V. Borisov
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Correspondence to R. K. Askerov.

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Translated by E. Yablonskaya

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Askerov, R.K., Chipinskii, E.V., Peregudov, A.S. et al. 3-(2-Methylphenyl)-2-selenoxo-2,3-dihydroquinazolin-4(1H)-one and Its Complex with Cd(II): Synthesis and Molecular and Crystal Structures. Russ J Coord Chem 49, 841–855 (2023). https://doi.org/10.1134/S1070328423601061

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