A Competing Hydrogen Bond Network Offers Access to a New Conformation in 24-Atom Triazine Macrocycles.

ABSTRACT: For a family of 24-atom triazine macrocycles, a single intramolecular hydrogen bond (IMHB) network leads to a conserved, hinge-like motif in solution. Modifications to the backbone of these macrocycles preserve this motif. Modifications to peripheral sites lead to conformational isomers due to hindered bond rotation while conserving the hinge motif. Here, a competitive IMHB network is introduced by the addition of a hydrogen bond donor on the periphery. Cyclization remains quantitative, but multiple conformers result. Three conformers are derived from the hinge motif. Three others are attributed to a new motif that utilizes the new IMHB network. Crystallographic analysis confirms this hypothesis and establishes that this new motif differs significantly from the original with respect to ove

SUBMITTER: Reddy KHV 

PROVIDER: S-EPMC12655256 | biostudies-literature | 2025 Nov

REPOSITORIES: biostudies-literature