Изучение таутомерии имино- производных госсипола
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| Title |
Изучение таутомерии имино- производных госсипола
STUDYING OF THE TAUTOMERISM OF IMINE- DERIVATIVES OF GOSSYPOL |
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| Creator |
Макарова, Р.А.
Илькевич, Н.С. Дикун, А.М. Чотий, К.Ю. Рыбаченко, В.И. |
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| Subject |
имино-производные госсипола
ИК-спектры таутомерия квантово-химический расчёт imine-derivatives of gossypol IR spectrum tautomerism quantum-chemical calculation |
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| Description |
In previous works devoted to the study of gossypol derivatives, we noted that the interest in studying of properties of gossypol and its derivatives are associated with the biological activity of these compounds, as well as the possibility of their use for the synthesis of the another substrates. The fact, that gossypol that has antitumor capacity and a number of other useful features can not be used as a drug because of its toxicity and the many side effects, stimulates the synthesis and studying of properties of its derivatives. Found that the substitution of two aldehyde groups in molecule of gossypol (namely their presences are explained its toxicity) - way to obtain more effective but less toxic drugs. Imine-derivatives of gossypol have such properties. Synthesis of novel derivatives of gossypol, the study of their structure, physico-chemical characteristics, reactivity ability are important both in scientific as in applied aspects. Has repeatedly been suggested link between the tautomeric form in which gossypol derivatives exist and their antioxidant properties. That is why the researches of tautomerism of gossypol derivatives by combination of IR spectroscopy and quantum chemical calculations were continued. PM3 semi-empirical method has been applied for quantum-chemical calculations of the structure and vibrational spectra of dienamine and diimine tautomers of three gossypol imine-derivatives: 4-methoxy- and 2,5- dimethoxydianiline of gossypol and diphenilhydrazone of gossypol. Comparison of experimental and theoretical spectra of the compounds studied allowed to establish the tautomeric forms prevailing in the solid state. The introduction of a scaling factor to adjust the calculated frequencies gave good agreement between experimental and theoretical frequencies. Analysis of the experimental IR spectra of derivatives of the dianiline of gossypol show that are realized dienamine forms, whereas spectrum of diphenilhydrazone of gossypol indicates the presence of diimine form in a solid state. Проведен квантово-химический расчёт структуры и колебательных спектров диенаминных и дииминных таутомерных форм трёх имино-производных госсипола (4-метокси- и 2,5-диметоксидианилиногоссиполов, а также дифенилгидразона госсипола) полуэмпирическим методом РМ3. Сравнение экспериментальных и теоретических спектров изученных соединений позволило установить таутомерные формы, преобладающие в твёрдом состоянии: производные анилиногоссипола существуют в диенаминной форме, а гидразон – в дииминной. Введение масштабирующих коэффициентов для корректировки рассчитанных частот дало достаточно хорошее совпадение экспериментальных и теоретических частот. |
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| Date |
2014-04-15T14:35:13Z
2014-04-15T14:35:13Z 2014 |
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| Type |
Article
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| Identifier |
УДК 547.57
http://ea.donntu.edu.ua/handle/123456789/25979 |
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| Language |
other
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| Publisher |
Наукові праці ДонНТУ. Серія: Хімія і хімічна технологія. - 2014. - Вип. 1(22). - С. 119-127
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