Abstract
Hypervalent iodine (HVI) compounds feature electron deficient iodine centers that often establish significant intermolecular interactions with oxygen atoms from neighboring molecules (I⋯O) in the solid state. This report examines the impact of the introduction of nitro (–NO2) groups on the solid state aggregation of two common types of cyclic HVI compounds, diaryliodonium (DAI) salts, and bisdiaryliodoniuim (BDAI) salts. The results of four structural determinations on three different cyclic iodonium compounds reveal that while the NO2 substituent may increase the electrophilicity of the iodine center in the solid state, the intermolecular interactions with counterions (OTf−) or solvent molecules (THF, DMF, or DMSO) are mostly preferred.
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