КВАНТОВО-ХИМИЧЕСКИЙ РАСЧЁТ КОЛЕБАТЕЛЬНЫХ СПЕКТРОВ АЛЬДИМИНОВ ГОССИПОЛА
Електронний архів E-archive DonNTU – (Electronic archive Donetsk National Technical University)
Переглянути архів Інформація| Поле | Співвідношення | |
| Title |
КВАНТОВО-ХИМИЧЕСКИЙ РАСЧЁТ КОЛЕБАТЕЛЬНЫХ СПЕКТРОВ АЛЬДИМИНОВ ГОССИПОЛА
QUANTUM CHEMICAL CALCULATION OF THE GOSSYPOL ALDIMINES VIBRATIONAL SPECTRA |
|
| Creator |
Рыбаченко, Владимир Иванович
Макарова, Раиса Александровна Илькевич, Наталья Сергеевна Чотий, Константин Юрьевич Гребенюк, Людмила Владимировна |
|
| Subject |
таутомерия
квантово-химический расчёт альдимины госсипола ИК-спектры tautomerism quantum-chemical calculation gossypol aldimines IR spectra |
|
| Description |
Проведен квантово-химический расчёт структуры и колебательных спектров диенаминных и дииминных таутомерных форм трёх альдиминов госсипола полуэмпирическим методом РМ3. Сравнение экспериментальных и теоретических спектров изученных соединений позволило установить таутомерные формы, преобладающие в твёрдом состоянии. Введение масштабирующих коэффициентов для корректировки рассчитанных частот дало хорошее согласие между экспериментальными и теоретическими частотами.
This message is a continuation of a series of studies on the synthesis and study of the derivatives of natural polyphenol gossypol (2,2`-bis(8-formyl-1,6,7-trihydroxy-5-isopropyl-3-methyl naphthalene). Interest in this class of compounds is caused by the fact that these compounds are biologically active substances. Is known the ability of gossypol to suppress tumor cells and the possibility for its use in the treatment of infertility. However, the use of gossypol as a drug is limited because of its toxicity and the many side effects. Its toxicity is directly related to the presence of two aldehyde groups that are blocked during the formation of imine-derivatives. Since Schiff bases and hydrazones of gossypol are less toxic and retain biological activity. Some of them have anti-malarial activity. Others are more efficient than gossypol in inhibiting the replication of HIV in vitro and show cytotoxic effect toward human cancer cells. Thus, the synthesis of new derivatives of gossypol, the study of their structure, physical and chemical characteristics, reactivity, search of correlations structure - property are important both in scientific as applied aspects. 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 aldimines: GDFA - diimine with p-fluoroaniline, GAMI - diimine with 3-amino-5 - methylisoxazole and also GDTA - diimine with [2 - (3,5-dimethyl-1H-1,2,4-triazole-1-yl)-1-methylethyl] amine. 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 GDFA and GDTA shows that realized, in generally, only enamine form, whereas GAMI spectrum indicates the presence of both tautomers in a solid form. |
|
| Date |
2013-04-13T13:16:59Z
2013-04-13T13:16:59Z 2013 |
|
| Type |
Article
|
|
| Identifier |
2074-6652
http://ea.donntu.edu.ua/handle/123456789/18467 |
|
| Relation |
Наукові праці ДонНТУ;Серія: Хімія і хімічна технологія, 2013. - Вип.2(21). - С.97-102
|
|
| Publisher |
Донецк, ДонНТУ
|
|