Short I⋯O Interactions in the Crystal Structures of Two 2-Iodo-Phenyl Methyl-Amides as Substrates for Radical Translocation Reactions

Ahtsham Ishaq, John M. D. Storey, William T. A. Harrison* (Corresponding Author)

*Corresponding author for this work

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Abstract

Radical translocation reactions are finding various uses in organic synthesis, in particular the stereospecific formation of complex natural products. In this work, the syntheses and single-crystal structures of two substituted 2-iodo-phenyl methyl-amides are reported, namely cyclo-propane carboxylic acid (2-iodo-phenyl)-methyl-amide, C11H12INO (1), and cyclo-heptane carboxylic acid (2-iodo-phenyl)-methyl-amide, C15H20INO (2). In each case, the methyl-amide group has a syn conformation, and this grouping is perpendicular to the plane of the benzene ring: these solid-state conformations appear to be well setup to allow an intramolecular hydrogen atom transfer to take place as part of a radical translocation reaction. Short intermolecular I⋯O halogen bonds occur in each crystal structure, leading to [010] chains in 1 [I⋯O = 3.012 (2) Å] and isolated dimers in 2 [I⋯O = 3.024 (4) and 3.057 (4) Å]. The intermolecular interactions are further quantified by Hirshfeld surface analyses.
Original languageEnglish
Pages (from-to)1233–1242
Number of pages10
JournalChemistry
Volume5
Issue number2
Early online date12 May 2023
DOIs
Publication statusPublished - 12 May 2023

Bibliographical note

Acknowledgments
We thank the EPSRC National Crystallography Service (University of Southampton, England) for the X-ray data collection for 2.
Funding
This research received no external funding.

Keywords

  • methyl-amides
  • halogen bonds
  • conformational analysis

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