Thermodynamics of protonation of N,N-dimethylthioamides in aqueous sulfuric acid
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The protonation (m* and [Formula: see text]) and thermodynamic (ΔG°, ΔH°, ΔS°) parameters of ionization of four thioamides RCSNMe2 (R = Me, Et, i-Pr, t-Bu) have been determined in aqueous sulfuric acid in the 25–60 °C temperature range with a UV technique. The title compounds are relatively strong bases; 100% protonation is reached in 47% H2SO4. Their solvation is lower than for primary thioamides and sulfides, as indicated by the higher values of m*, and close to the range of carbon bases. Base strengths are discussed in terms of the competition between internal and external stabilization. Keywords: basicity, protonation, solvation, thermodynamics, thioamides.
2013 ◽
Vol 58
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pp. 3009-3032
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2005 ◽
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pp. E212
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1990 ◽
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pp. 2227-2227
1977 ◽
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pp. 621-623
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1971 ◽
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pp. 7315-7315
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1998 ◽
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pp. 225-231
2009 ◽
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pp. 107-112
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