Unique halogen-π association detected in single crystals of C-N atropisomeric <i>N</i>-(2-halophenyl)quinolin-2-one derivatives and the thione analogue.

ABSTRACT: In single crystals of C-N atropisomeric N-(2-halophenyl)quinolin-2-one and the thione analogue, a unique association based on a halogen-π interaction was detected. In racemic and optically pure N-(2-bromo- or 2-chlorophenyl)quinolin-2-ones, homochiral layered polymers, which consist of (P)- or (M)-atropisomers, were formed through intermolecular halogen-π association. The halogen-π association in the racemates is due to a halogen bond (C-X···π) between a σ-hole on the halogen atom and a π-electron on the quinolinone benzene ring, while that in optically pure forms is caused by an n-π* interaction between a lone electron pair on the halogen atom and a π* orbital of the quinolinone. In contrast to the formation of the homochiral layered polymer in quinolinones, in

SUBMITTER: Uchibori M 

PROVIDER: S-EPMC12415909 | biostudies-literature | 2025

REPOSITORIES: biostudies-literature