The basicities of aliphatic amides

descriptionPublicationkeyboard_double_arrow_right Article 01 Nov 1983 English Publisher:CSIRO PublishingJournal:Australian Journal of Chemistry, volume 36, pages 2,211-2,218 (issn: 0004-9425, eissn: 1445-0038,

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Authors: HM Grant; P Mctigue; DG Ward;

doi: 10.1071/ch9832211

The basicities of aliphatic amides

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Abstract

We report pKa values in aqueous solution at 298 K of the protonated forms of several aliphatic amides, viz., acetamide (pKa = -0.62 ± 0.07), N -methylacetamide (-0.42 ± 0.03), N,N -dimethyl-acetamide (-0.28 ± 0.03), N,N -dimethylformamide (-1.2 + 0.5), urea (0.053 ± 0.002) and thiourea (-0.9 ± :O.l). pKa values are also reported for protonated acetamide and urea in aqueous solution in the temperature range 5-40ºC and in D2O. A previously described conductimetric method was used for all measurements.

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