ArticleRSC advances2018
Insight into trifluoromethylation - experimental electron density for Togni reagent I.
Article in RSC advances, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- The Halogen Bond to Ethers - Prototypic Molecules and Experimental Electron Density.ACS omega · 2024Article
- The Relevance of Experimental Charge Density Analysis in Unraveling Noncovalent Interactions in Molecular Crystals.Molecules (Basel, Switzerland) · 2022Review
- Weaving a 2D net of hydrogen and halogen bonds: cocrystal of a pyrazolium bromide with tetrafluorodiiodobenzene.Acta crystallographica. Section C, Structural chemistry · 2022Article
- Exploring Orthogonality between Halogen and Hydrogen Bonding Involving Benzene.Molecules (Basel, Switzerland) · 2021Article
- Hydrogen-Bonded and Halogen-Bonded: Orthogonal Interactions for the Chloride Anion of a Pyrazolium Salt.Molecules (Basel, Switzerland) · 2021Article
- The many flavours of halogen bonds - message from experimental electron density and Raman spectroscopy.Acta crystallographica. Section C, Structural chemistry · 2019Article
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Authors and funding
3 authors.
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Abstract
3,3-Dimethyl-1-(trifluoromethyl)-1,3-dihydro-1-λ3,2-benziodoxole represents a popular reagent for trifluoromethylation. The σ hole on the hypervalent iodine atom in this "Togni reagent" is crucial for adduct formation between the reagent and a nucleophilic substrate. The electronic situation may be probed by high resolution X-ray diffraction: the experimental charge density thus derived shows that the short intermolecular contact of 3.0 Å between the iodine and a neighbouring oxygen atom is associated with a local charge depletion on the heavy halogen in the direction of the nucleophile and visible polarization of the O valence shell towards the iodine atom. In agreement with the expectation for λ3-iodanes, the intermolecular O⋯I-C
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