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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Resumo

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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Sobre autores

R. Askerov

Baku State University

Autor responsável pela correspondência
Email: rizvankam@bk.ru
Azerbaijão, Baku

E. Chipinskii

Nizhni Novgorod State Technical University

Email: rizvankam@bk.ru
Rússia, Nizhni Novgorod

A. Peregudov

Nesmeyanov Institute of Organic Element Compounds, Russian Academy of Sciences

Email: rizvankam@bk.ru
Rússia, Moscow

V. Osmanov

Nizhni Novgorod State Technical University

Email: rizvankam@bk.ru
Rússia, Nizhni Novgorod

Zh. Matsulevich

Nizhni Novgorod State Technical University

Email: rizvankam@bk.ru
Rússia, Nizhni Novgorod

G. Borisova

Nizhni Novgorod State Technical University

Email: rizvankam@bk.ru
Rússia, Nizhni Novgorod

V. Khrustalev

Peoples’ Friendship University of Russia; Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences

Email: rizvankam@bk.ru
Rússia, Moscow; Moscow

O. Smirnova

National Research State University

Email: rizvankam@bk.ru
Rússia, Nizhni Novgorod

A. Magerramov

Baku State University

Email: rizvankam@bk.ru
Azerbaijão, Baku

A. Borisov

Nizhni Novgorod State Technical University

Email: rizvankam@bk.ru
Rússia, Nizhni Novgorod

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2. Scheme 1. Tautomeric forms of thiones and selons.

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3. Scheme 2.

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4. Scheme 3.

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5. Fig. 1. Molecular structure of the compound HL.

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6. Fig. 2. Fragment of crystal packing of compound HL: in projection x0u (a) and x0z (b). (a - dashed lines indicate H...O and H...Se contacts, conformer molecules are labelled with letters A and B; b - hydrogen atoms have been removed for clarity).

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7. Fig. 3. Molecular structure of complex II.

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8. Fig. 4. Fragment of the crystal packing of complex II (dashed lines show H...O and C...C contacts; for clarity, hydrogen atoms not participating in hydrogen bonds are not shown).

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9. Scheme 4.

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10. Fig. 5. 1H NMR spectrum of complex II at 25 (a) and 70°C (b).

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11. Fig. 6. 1H NMR spectrum of the HL ligand at 25°C.

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12. Fig. 7. 13C NMR spectrum of the HL ligand at 25°C recorded in JMODECHO mode.

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13. Fig. 8. 13C NMR spectra of complex II at 25°C (a) and 70°C (b) recorded in JMODECHO mode (a - numbers indicate broadened signals, asterisks - ethanol signals; b - numbers indicate narrowed signals).

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14. Fig. 9. 77Se NMR spectra of: ligand HL (a); complex II at 25°C (b); complex II at 70°C (c).

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15. Fig. 10. HMBC (1H,15N) spectrum of the HL ligand at 25°C.

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16. Fig. 11. HMBC (1H,15N) spectrum of complex II at 70°C.

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