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• W2090922284 endingPage "11768" @default.
• W2090922284 startingPage "11756" @default.
• W2090922284 abstract "The values of Ka, ΔSa, and ΔHa for deprotonation of hydroxyurea (HU) and N-methylhydroxyurea (NMHU), as targeted compounds, and for betainohydroxamic acid, were potentiometrically determined. Although NMHU has two and HU even three deprotonation sites, the measurements confirm that they behave as weak acids with a single pKa ≈ 10. Comparison with analogous thermodynamic parameters previously determined for series of monohydroxamic acids reveals deviations from a ΔSa, vs ΔHa plot for HU and NMHU, raising the question of the dissociation site of hydroxureas in water. In addition to the deprotonation of the hydroxyl oxygen, ab initio calculations performed at the MP2/6−311++G(d,p) level of theory for these two compounds indicate a notable participation of the nitrogen deprotonation site in HU. The calculations for the isolated, monohydrate, trihydrate, and decahydrate molecular and anionic forms of hydroxyureas support the importance of hydrogen bonding in the gas and aqueous phases. The hydroxylamino nitrogen in HU is the most acidic site in water, contributing ∼94% to the overall deprotonation process at 25 °C. On the contrary, the hydroxylamino oxygen is by far the most favored deprotonation site in NMHU, contributing almost 100% in aqueous medium. The predicted participations of two deprotonation sites in HU, calculated at the MP2/6−311++G(d,p) level of theory, combined with the calculated relative reaction enthalpy and entropy for the deprotonation, satisfactorily explain the observed deviation from linearity of ΔHa vs ΔSa, plot. There is no such a simple explanation for acid−base behavior of NMHU." @default.
• W2090922284 created "2016-06-24" @default.
• W2090922284 creator A5010261267 @default.
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• W2090922284 date "2008-10-25" @default.
• W2090922284 modified "2023-09-25" @default.
• W2090922284 title "Acido-Base Behavior of Hydroxamic Acids: Experimental and Ab Initio Studies on Hydroxyureas" @default.
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• W2090922284 doi "https://doi.org/10.1021/jp804925b" @default.
• W2090922284 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/18950143" @default.
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