Издательство СО РАН

Издательство СО РАН

Адрес Издательства СО РАН: Россия, 630090, а/я 187
Новосибирск, Морской пр., 2

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Яндекс.Метрика

Поиск по журналу

Журнал структурной химии

2015 год, номер 4

A THEORETICAL STUDY OF THE THERMAL CURTIUS REARRANGEMENT OF SOME CINNAMOYL AZIDES USING THE DFT APPROACH

Rafie H. Abu-Eittah1, Walid M.I. Hassan1, W. Zordok2
1University of Cairo, Giza, Egypt
aboeittah@yahoo.com
2University of Zagazig, Zagazig, Egypt
Ключевые слова: Curtius rearrangement, cinnamoyl azides, DFT treatment, one stage mechanism
Страницы: 676-688
Подраздел: ТЕОРИЯ СТРОЕНИЯ МОЛЕКУЛ И ХИМИЧЕСКОЙ СВЯЗИ

Аннотация

The thermal Curtius rearrangement of cinnamoyl azide, 1-azido-3-phenylprop-2-ene-1-one, and the reactions of some of its derivatives is studied theoretically using the DFT (B3LYP-631G(d, p) approach. The potential energy surface profiles of the rearrangement are calculated. The transition state was located and confirmed. The Curtius rearrangement of the studied compounds is a one-stage, discrete reaction. A weak effect of substitution on the reaction rate is due to the unique, localized p system of the studied molecules; strong opposing dipoles span the whole molecule.

DOI: 10.15372/JSC20150404