Neighboring group’s effect in sigmatropic migration on indol rings. A theoretical study and NBO analysis
محورهای موضوعی : Journal of the Iranian Chemical Research
Saeed Jameh-Bozorghi
1
,
Zahra Javanshir
2
,
Fatemeh Naseri
3
,
Maryam Darvishpoor
4
1 - Chemistry Department, Faculty of science, Islamic Azad University, Arak Branch, Arak, Iran
2 - Chemistry Department, Faculty of science, Islamic Azad University, Arak Branch, Arak, Iran
3 - Chemistry Department, Faculty of science, Islamic Azad University, Arak Branch, Arak, Iran
4 - Chemistry Department, Faculty of Science, Razi University, Kermanshah, Iran
کلید واژه: DFT calculation, Borotropic shift, Prototropic shift, Indol,
چکیده مقاله :
Structural properties, energies behavior and NBO analysis was performed for1-5 prototrophic shift endinelboran where substitutions like H, CH3 and CF3 that were placed on Benzene were investigated by usingDFT-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. TheResults of calculations using B3LYP, HF and MP2 [basic seyies 6-311+G**] show that Ea for CF3substitutionis is lower than H substitution; also, this amount of activation energy for CH3 was lower thanCF3. But for prototrophic shift, activation energy changes, as will be shown in the following CF3, H and CH3tables. Finally, prototrophic shift activation energy in proportion to that of borotrophic shift is higher. Loweramount of activation energy in bortorphic shift show that rotation of bore on the cycle can happen in theambient temperature.
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