Effect of the solvent nature and the number of electrophilic substituents in the molecule on hydration of nitro derivatives of phenanthrene-9,10-quinone

Solvates (1 : 2) of 10,10-dihydroxy-2,4,7-trinitro-9,10-dihydrophenanthren-9-one with DMSO and of 10,10-dihydroxy-2,7-dinitro-9,10-dihydrophenanthren-9-one with HMPA were prepared. The crystal structure of 2,5-dinitrophenanthrene-9,10-quinone was established. The results of X-ray diffraction analysis and IR spectroscopy of a series of mono-, di-, and trinitro derivatives of phenanthrene-9,10-quinone demonstrated that the ability of carbonyl groups to participate in nucleophilic addition of water increases as the number of nitro groups in substituted phenanthrene-9,10-quinone increases. The nature of the solvent (HMPA, DMF, or DMSO) affects hydration of phenanthrenequinones primarily due to the difference in the strength of intermolecular hydrogen bonds stabilizing di- and tetrahydroxydihydrophenanthrenes.

Авторы
Linko R.V. 1 , Soldatkina V.A. 1 , Zaitsev B.E. 1 , Sokol V.I.2 , Davydov V.V. 1
Редакторы
-
Издательство
-
Номер выпуска
4
Язык
Английский
Страницы
734-738
Статус
Опубликовано
Подразделение
-
Номер
-
Том
48
Год
1999
Организации
  • 1 Russ. Peoples' Friendship University, 6 ul. Miklukho-Maklaya, 117198 Moscow, Russian Federation
  • 2 N. S. Kurnakov Inst. of Gen. and I., Russian Academy of Sciences, 31 Leninsky prosp., 117907 Moscow, Russian Federation
Ключевые слова
10,10-dihydroxy-2,4,7-trinitro-9,10-dihydrophenanthren-9-one; 10,10-dihydroxy-2,7-dinitro-9,10-dihydrophenanthren-9-one; 2,5-dinitrophenanthrene-9,10-quinone; Hydration; IR spectroscopy; Solvate; X-ray diffraction study
Дата создания
19.10.2018
Дата изменения
19.10.2018
Постоянная ссылка
https://repository.rudn.ru/ru/records/article/record/609/