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Halogen Bonding Helicates Encompassing Iodonium Cations.

ABSTRACT: The first halonium-ion-based helices were designed and synthesized using oligo-aryl/pyridylene-ethynylene backbones that fold around reactive iodonium ions. Halogen bonding interactions stabilize the iodonium ions within the helices. Remarkably, the distance between two iodonium ions within a helix is shorter than the sum of their van der Waals radii. The helical conformations were characterized by X-ray crystallography in the solid state, by NMR spectroscopy in solution and corroborated by DFT calculations. The helical complexes possess potential synthetic utility, as demonstrated by their ability to induce iodocyclization of 4-penten-1-ol.

SUBMITTER: Vanderkooy A

PROVIDER: S-EPMC6773207 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

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Halogen Bonding Helicates Encompassing Iodonium Cations.

Vanderkooy Alan A Gupta Arvind Kumar AK Földes Tamás T Lindblad Sofia S Orthaber Andreas A Pápai Imre I Erdélyi Máté M

Angewandte Chemie (International ed. in English) 20190606 27

The first halonium-ion-based helices were designed and synthesized using oligo-aryl/pyridylene-ethynylene backbones that fold around reactive iodonium ions. Halogen bonding interactions stabilize the iodonium ions within the helices. Remarkably, the distance between two iodonium ions within a helix is shorter than the sum of their van der Waals radii. The helical conformations were characterized by X-ray crystallography in the solid state, by NMR spectroscopy in solution and corroborated by DFT ...[more]

PMID: 31074942

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