I have an allylic organic compound that I’ll be deprotonating to make an allylic anion. This anion will have the lone pair delocalizing on 2 different (chemically non equivalent) carbons. I’m trying to rationalize the regioselectivity. Which carbon will be reacting with my electrophile? And why?
I want to do a DFT calculation using Gaussian software to find out which carbon will react? Maybe by calculating the HOMO orbitals energy of the 2 different carbons each carrying the lone pair in 2 separate instances.
I’m not an expert on the subject, so any sources or references for studies conducted for examples of this sort would be appreciated.
Thanks.
Dear Abdulrahman, you probably need to calculate the transition states for the electrophile attack on one carbon and on the other one. TS will tell to you which carbon reacts firts (kinetically faster). Other properties may help, as you mentioned, HOMO or atomic charges, but those values may only tell to you that the reaction is possible in both carbon atoms.
Pablo, thanks for your recommendation. Do you have any references that go over how to do this?
Thanks.
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