کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5418702 | 1506968 | 2007 | 8 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
Loss of aromaticity and Ï-electron delocalization in the first step of the electrophilic aromatic nitration of benzene, phenol and benzonitrile
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کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی تئوریک و عملی
پیش نمایش صفحه اول مقاله
چکیده انگلیسی
In this paper, a computational study on the first stages of the nitration of benzene, phenol and benzonitrile is presented. It is found that at the B3LYP/6-31G* and B3LYP/6-31+G* levels of theory the Ï-complexes associated with these reactions show local diamagnetic effects of much less intensity than the aromaticity associated with ring currents. It is found that these diamagnetic effects are more important in the meta regioisomeric Ï-complexes. In the case of phenol, the meta-Ï-complex is the less stable one in good agreement with the experimental evidence available. In contrast, our results indicate that the meta-Ï-complex corresponding to the nitration of benzonitrile is not the most stable one. This situation does not change at the MP2/6-31+G*+ÎZPVE and G3B3 levels of theory or when solvent effects were included in the calculations.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Journal of Molecular Structure: THEOCHEM - Volume 811, Issues 1â3, 1 June 2007, Pages 19-26
Journal: Journal of Molecular Structure: THEOCHEM - Volume 811, Issues 1â3, 1 June 2007, Pages 19-26
نویسندگان
Ana Arrieta, Fernando P. Cossı´o,