Thiohydantoins. VII. Ionization and ultraviolet spectra of 4-thiohydantoins and 2,4-dithiohydantoins
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The acid and base dissociation constants of 5,5-pentamethylene-4-thiohydantoin, 5,5-pentamethylene-2,4-dithiohydantoin, and their 1-methyl derivatives, have been determined by ultraviolet studies in basic and acid media. In aqueous sulfuric acid the 4-thiohydantoins are protonated on oxygen at the 2-position, so that the extent of protonation varies with the HA function of the acid solution, while the 2,4-dithiohydantoins are protonated on sulfur at the 2-position, so that the extent of their protonation varies with H0′′′. The importance of using acidity functions appropriate to the different types of compounds when comparing their basicities is emphasized.
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2013 ◽
Vol 58
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pp. 3009-3032
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1962 ◽
Vol 84
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pp. 3618-3622
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1995 ◽
Vol 27
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pp. 7-16
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2011 ◽
Vol 115
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pp. 13704-13716
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