Add time:09/24/2019         Source:sciencedirect.com

Iodocytosine is deiodinated by specific hydrogen-ion attack on the neutral species to iodouracil, which is further transformed to uracil in acid solutions. The extent of the transformation of iodouracil to uracil is dependent on its concentration and is consistent with a postulated equilibration of iodouracil and two chloride ions with uracil and the complex anion ICl2- and thus is a function of hydrochloric acid concentration. There are pH-independent rates of solvolysis at high acidities, indicative of negligible hydrogen-ion-catalyzed solvolysis of protonated iodocytosine. In the neutral pH region, the iodocytosine solvolysis can be rationalized by general acid–base and water catalysis to cytosine, since it was shown that phosphate and carbonate buffers served as catalysts for the deiodination although acetate buffers did not. Hydroxide ion attacked both the neutral and anionic iodocytosine and produced 6-hydroxycytosine, which further degraded on hydroxide-ion attack, probably through a fast reacting barbituric acid intermediate. Arrhenius parameters were deter mined.

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