Neighboring group’s effect in sigmatropic migration on indol rings. A theoretical study and NBO analysis

Journal of the Iranian Chemical Research

مقاله 3، دوره 5، شماره 2، شهریور 2012، صفحه 73-84   

نویسندگان

Saeed Jameh-Bozorghi^{* 1}؛ Zahra Javanshir¹؛ Fatemeh Naseri¹؛ Maryam Darvishpoor²

¹Chemistry Department, Faculty of science, Islamic Azad University, Arak Branch, Arak, Iran

²Chemistry Department, Faculty of Science, Razi University, Kermanshah, Iran

چکیده

Structural properties, energies behavior and NBO analysis was performed for1-5 prototrophic shift endinel
boran where substitutions like H, CH3 and CF3 that were placed on Benzene were investigated by using
DFT-B3LYP/6-311+G** level of theory. The Results show that, -BH2 shift doesn’t take place and a kind of
[1,3] shift for borotrophic occured. In prototrophic shift, however, [1,5] transition easily happened. The
Results of calculations using B3LYP, HF and MP2 [basic seyies 6-311+G**] show that Ea for CF3
substitutionis is lower than H substitution; also, this amount of activation energy for CH3 was lower than
CF3. But for prototrophic shift, activation energy changes, as will be shown in the following CF3, H and CH3
tables. Finally, prototrophic shift activation energy in proportion to that of borotrophic shift is higher. Lower
amount of activation energy in bortorphic shift show that rotation of bore on the cycle can happen in the
ambient temperature.

کلیدواژه‌ها

DFT calculation؛ Borotropic shift؛ Prototropic shift؛ Indol

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