Molecular Rotors as Reactivity Probes: Predicting Electrophilicity from the Speed of Rotation.

ABSTRACT: A new empirical electrophilicity reactivity parameter, E_RB, was developed based on the rotational barriers of a series of N-phenylimide molecular rotors containing various electrophilic groups. In the bond rotation transition state, these electrophilic groups form close contact with an electronegative C═O oxygen. Thus, strong electrophilic groups significantly lowered the rotational barrier. As a result, the rotational barriers were inversely correlated with the strengths of the electrophiles. The rotational barriers were measured by dynamic NMR (EXSY), enabling the quantification across a wide range of types of electrophiles. Computational analysis confirmed that the observed variations arose from intramolecular interactions in the transition state, where the C═O oxygen served

SUBMITTER: Liu H 

PROVIDER: S-EPMC12402875 | biostudies-literature | 2025 Sep

REPOSITORIES: biostudies-literature