UC San Diego
The hydrogen bond acidity and other descriptors for oximes
- Author(s): Abraham, Michael H
- Gil-Lostes, Javier
- Cometto-Muniz, J. Enrique
- Cain, William S
- Poole, Colin F
- Atapattu, Sanka N
- Abraham, Raymond J
- Leonard, Paul
- et al.
Published Web Locationhttps://doi.org/10.1039/b811688a
The solvation descriptors for cyclohexanone oxime and acetone oxime have been obtained from measurements on water-solvent partitions, and gas-liquid chromatographic retention data. These yield values of 0.33 and 0.37 for the Abraham hydrogen bond acidity, A , in reasonable agreement with a value of 0.37 for cyclohexanone oxime obtained by our recent n.m.r. method. The other descriptors E, S , B, L and V have also been obtained for cyclohexanone oxime and acetone oxime, and have been estimated for a number of other oximes as well. The value for A, the overall or effective hydrogen bond acidity of the oximes is reasonably close to the 1:1 hydrogen bond acidity, α2 H = 0.39 to 0.46, that can be deduced from previous literature measurements on oximes, and to the 1:1 hydrogen bond acidity, α2 H = 0.43 for another NOH compound, N,N-dibenzylhydroxylamine, that again can be deduced from literature measurements.
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