The electronic and spatial structures of a broad spectrum of neutral compounds with X-Hal (X = N, O, Cl; Hal = Cl, Br, I) bonds and their protonated forms and of differ ent electronic states of triiodide cation, I 3 + , were determined from density functional B3LYP/6 311G* quantum chemical calculations. The effects of the structure of these com pounds on the parameters of electrophilic reactivity were revealed and the thermochemical characteristics of homolytic and heterolytic X-Hal bond dissociation and of iodine transfer in hydroxyl containing solvents were calculated. Due to low homolytic bond dissociation ener gies of X-I, the formation of molecular iodine and triiodide cation I 3 + becomes thermody namically favorable and the cation should act as iodinating agent alternative to acylhypoiodites and N iodoimides. The solvation effects of MeOH and CH 2 Cl 2 on the X-Hal bond homolysis and heterolysis were determined using the PCM model.

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