کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
43406 | 45968 | 2008 | 7 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
Quantum calculations on the acid catalyzed rearrangements of norborn-5-en-2-one, 7-oxanorborn-5-en-2-one and 7-azanorborn-5-en-2-one
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موضوعات مرتبط
مهندسی و علوم پایه
مهندسی شیمی
کاتالیزور
پیش نمایش صفحه اول مقاله
![عکس صفحه اول مقاله: Quantum calculations on the acid catalyzed rearrangements of norborn-5-en-2-one, 7-oxanorborn-5-en-2-one and 7-azanorborn-5-en-2-one Quantum calculations on the acid catalyzed rearrangements of norborn-5-en-2-one, 7-oxanorborn-5-en-2-one and 7-azanorborn-5-en-2-one](/preview/png/43406.png)
چکیده انگلیسی
Protonation of norborn-5-en-2-one gives 6-oxo-2-norbornyl cation (2) as most stable C7H9O+ cation. Quantum calculations at B3LYP/6-31G(d) level (gas phase, 1 atm, 25 °C) predict a CS-structure for 2 that can be represented as an intramolecular Ï-complex (Dewar Ï-complex model) of an acetylium ion with an alkene (cyclopent-3-enyl moiety). Isomeric 5-oxo-2-norbornyl (1) cation is calculated to be 16.7 kcal/mol less stable than 2. Part of the relatively high stability of 2 arises from the electron-releasing carbonyl group through n(CO) â Ï â 2p(C+) hyperconjugation. This effect is also present in more stable 6-oxo-3-oxa (14) and 6-oxo-3-aza-2-norbornyl cation (19) as these ions are calculated to be 7.4 and 3.3 kcal/mol, respectively, more stable than their 5-oxo isomers.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Applied Catalysis A: General - Volume 336, Issues 1â2, 1 March 2008, Pages 72-78
Journal: Applied Catalysis A: General - Volume 336, Issues 1â2, 1 March 2008, Pages 72-78
نویسندگان
José Ángel Sordo, Adrián Varela-Álvarez, Samuele Giani, Pierre Vogel,