Synthesis and Study of New N-Substituted Hydrazones of Ni(II) Complexes of beta-Octaethylporphyrin and Coproporphyrin I Tetraethyl Esterстатья
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Дата последнего поиска статьи во внешних источниках: 7 марта 2018 г.
Аннотация:N-substituted hydrazones of nickel complexes of beta-octaethylporphyrin and tetraethyl ester of coproporphyrin I were obtained. These compounds can serve as intermediate compounds for the preparation of meso-functionalized derivatives of porphyrins by means of various reactions. In the first stage Vilsmeier-Haack reaction was carried out by the interaction of nickel complexes of beta-octaethylporphyrin and tetraethyl ester of coproporphyrin I with N,N-dimethylformamide and phosphorus(V) oxochloride forming the so-called "phosphorus complex", which was hydrolyzed with saturated solution of sodium acetate. The corresponding meso-formyl derivatives of metal porphyrins were obtained as a result. Synthesis of the hydrazones was carried out by the reactions of meso-formyl derivatives with the hydrazines using trifluoroacetic acid as a catalyst. The result of the reaction was formation of hydrazones in the form of a mixture of E-and Z-isomers, which were separated using preparative thin layer chromatography. Thus a series of hydrazones with different substituents at the nitrogen atom was obtained. The structures of all obtained compounds were determined using the methods of NMR spectroscopy, electronic absorption spectroscopy and mass spectrometry. For nickel complex of tosylhydrazone derivative of beta-octaethylporphyrin the crystal structure was determined using X-ray diffraction. X-ray analysis shows that porphyrin molecules in the crystal form dimers bonded by two hydrogen bonds between the hydrogen atom of the NH-group of hydrazone and the oxygen atom of the sulfonate groups.