Pushing the limits of the hydrogen bond enhanced halogen bond-the case of the C-H hydrogen bond.

ABSTRACT: C-H hydrogen bonds have remarkable impacts on various chemical systems. Here we consider the influence of C-H hydrogen bonds to iodine atoms. Positioning a methyl group between two iodine halogen bond donors of the receptor engendered intramolecular C-H hydrogen bonding (HBing) to the electron-rich belt of both halogen bond donors. When coupled with control molecules, the role of the C-H hydrogen bond was evaluated. Gas-phase density functional theory studies indicated that methyl C-H hydrogen bonds help bias a bidentate binding conformation. Interaction energy analysis suggested that the charged C-H donors augment the halogen bond interaction-producing a >10 kcal mol^-1 enhancement over a control lacking the C-H⋯I-C interaction. X-ray crystallographic analysis demonstrated C-H h

SUBMITTER: Decato DA 

PROVIDER: S-EPMC9516949 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature