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Regioselectivity in the reactions of the acetonate ion with electron-deficient arenesстатья
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: 18 июля 2013 г.
- Авторы: Alifanova E.N., Chudakov P.V., Kaminsky A.Y., Mamaev V.M., Gloriozov I.P., Akhmedov N.G., Grudtsyn Y.D., Borbulevych O.Y., Shishkin O.V., Antipin M.Y., Atroshchenko Y.M., Gitis S.S.
- Журнал: Russian Chemical Bulletin
- Том: 50
- Номер: 6
- Год издания: 2001
- Издательство: Springer Nature
- Местоположение издательства: Switzerland
- Первая страница: 1056
- Последняя страница: 1063
- DOI: 10.1023/A:1011381605400
- Аннотация: The reactions of the acetonate ion with 1,3-dinitro-5-X-, 1.3-X-2-5-nitro- (X = NO2, CN, COOCH3, CONH2, COO-, and H), and 1,3,5-tricyanobenzenes were studied by H-1 NMR and electronic absorption spectroscopy and by quantum-chemical methods. The kinetic factor is decisive for the initial attack of the carbanion on the C(2) atom of unsymmetrical arenes. However, sigma-adducts in which a nucleophile is added to the C(4) atom are more stable thermodynamically. In the case of 1,3-X-2-5-nitrobenzenes (X = CN, COOCH3, or CONH2), the sigma-adducts with the acetonate group in para-position to the X group unexpectedly proved to be very stable. The structures of the sigma-adducts based on trinitro- and 1,3-dinitro-5-cyanobenzenes were determined by X-ray diffraction analysis. Quantum-chemical calculations (the AM1 and PM3 semiempirical methods and the density functional method) were used to interpret the reaction regioselectivity and the molecular and electronic structures of the sigma-adducts.
- Добавил в систему: Глориозов Игорь Павлович