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- W2071781277 abstract "The protonation of N,N-dimethylalkylthioamides in water—sulfuric acid media has been followed through nmr spectroscopy. Bunnett and Olsen treatment of the data gives (for protonation of the methyl derivative at 25 °C) pK = 2.7 and ø = 1.1. The ø value suggests protonation at the sulfur atom (øsulfides = −0.26/−0.35) rather than at the nitrogen atom (øamides = +0.42/+0.55) and wide delocalisation of the charge: On the other hand, two different N-methyl resonances are observed in water, which collapse into a single resonance upon protonation. This may suggest either a lowering of the rotational barrier upon protonation at nitrogen or protonation of sulfur with collapse of the signals due to a smaller N-methyl resonance difference in the protonated rather than in the free thioamide. Rational barriers have been calculated as a function of the medium acidity." @default.
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- W2071781277 date "1980-01-01" @default.
- W2071781277 modified "2023-09-23" @default.
- W2071781277 title "Protonation and solvation in aqueous systems of N,N-dimethylalkylthioamides" @default.
- W2071781277 doi "https://doi.org/10.1016/s0020-1693(00)92283-7" @default.
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