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

Abstract

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