Information conservation principle determines electrophilicity, nucleophilicity, and regioselectivity.
Electrophilic and nucleophilic reactions are important chemical transformations involving charge acceptance and donation, so chemical intuition suggests that atomic charges should be a reliable descriptor to determine electrophilicity, nucleophilicity, and regioselectivity. Nevertheless, no such theoretical framework has been established as of yet. Herein, we report that the Hirshfeld charge can be used for such purposes. We justify this usage by showing that it results from the Information Conservation Principle. This principle not only decides where electrophilic and nucleophilic attacks will preferably occur but also dictates the amount of the Hirshfeld charge distribution, which, as we will show here, remarkably strongly correlates with experimental scales of both electrophilicity and nucleophilicity.
Research Computing Center, University of North Carolina , Chapel Hill, North Carolina 27599-3420, United States.
Shubin
S
Liu
Chuying
C
Rong
Tian
T
Lu
D011789:Quantum Theory; D013237:Stereoisomerism