Prediction on chemoselectivity for selected organocatalytic reactions by the DFT version of the Huckel-defined free valence index

Developing reliable indexes for the prediction of the actual chemical active site of substrates is one of the most challenging tasks in the chemistry field. Herein, we suggested a general method for predicting the possible active sites of intermediates or substrates by computing the DFT version of the Huckel-defined free valence index (HFV) and then validated the reliability of this method through several case studies. The calculated results indicate that the active site with a higher HFV index should correspond to the favorable chemoselective pathway in these cases. Therefore, this HFV computing method is of great significance for predicting the chemoselectivity for a wide range of organocatalytic reactions.

Automated summary

This study proposes a method for predicting the active sites of substrates by calculating the HFV index and validates its reliability through case studies. The results indicate that higher HFV index corresponds to favorable chemoselective pathways.