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Tuning conformations of calix[4]tubes by weak intramolecular interactionsстатья
Информация о цитировании статьи получена из
Web of Science,
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 19 июля 2013 г.
- Авторы: Kirill Puchnin, Dmitry Cheshkov, Pavel Zaikin, Ivan Vatsouro, Vladimir Kovalev
- Журнал: New Journal of Chemistry
- Том: 37
- Номер: 2
- Год издания: 2013
- Издательство: Royal Society of Chemistry
- Местоположение издательства: United Kingdom
- Первая страница: 416
- Последняя страница: 424
- DOI: 10.1039/C2NJ40961E
- Аннотация: The conformational distribution in distally functionalized adamantylated calix[4]tubes was analyzed with NMR and quantum-chemical calculations. Without any intramolecular interactions, ester-, acid-, amino-, alcohol-, isocyanate-, phthalimide- and urea-substituted calixtubes preferred less sterically hindered flattened cone conformers in solution. In contrast, in a non-polar medium (CDCl3) for calixtubes bearing two 3-carboxymethyl-1-adamantyl or 3-(2-ureidoethyl)-1-adamantyl units, the less sterically preferable flattened cone conformation with bulky substituents connected by intramolecular hydrogen bonds was found to be more favorable. On the other hand, for a calixtube with two positively charged units, only the conformer with distanced substituents was exclusively detected. Thus, the conformational equilibrium in functionalized calix[4]tubes can be controlled by intramolecular hydrogen bonding between appropriately arranged carboxylic groups or urea moieties, or by electrostatic repulsion of positively charged substituents.
- Добавил в систему: Вацуро Иван Михайлович