Halogen Bonding and Rearrangements in Complexes of <i>N</i>-Chlorosuccinimide with Halides.

ABSTRACT: The role of halogen bonding (HaB) in the reactions of N-chlorosuccinimide (SimCl), a versatile reagent in organic synthesis, was investigated through experimental and computational analyses of its interactions with halides. The reactions of SimCl with Br^- or I^- resulted in the crystallization of HaB complexes of chloride with N-iodosuccinimide (SimI) or N-bromosuccinimide (SimBr). Computational analysis revealed that halogen rearrangements, which occurred even at -73 °C, were facilitated by halogen bonding. The dissociation of SimCl∙Y^- (Y = I or Br) complexes into a Sim^- + ClY pair (followed by the rotation and re-binding of the interhalogen molecules) bypassed the formation of the high-energy Sim^- + Cl⁺

SUBMITTER: Hardin M 

PROVIDER: S-EPMC11819834 | biostudies-literature | 2025 Jan

REPOSITORIES: biostudies-literature