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A theoretical study of the limits of the acidity of carbon acids in phase transfer catalysis in water and in liquid ammonia

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Alkorta I., Elguero J., Gallo R.

Open Chemistry

2013

vol. 11

issue 11

1711-1722

The acidities of a large number of carbon acids have been theoretically calculated for the gas-phase and for DMSO solution. The gas-phase values, both ΔH and ΔG, are very well correlated with the available experimental data. From the calculated ΔG values in DMSO and the pKas in the same solvent, a homogeneous set of pK a (DMSO) values was devised that was used to generate pK a (water). These last pK as were used to establish the limits of the acidity of carbon acids for reactions under PTC conditions both alkylations and H/D exchange. A step further led to the pK as in liquid ammonia and from them to the virtual use of PTC using liquid ammonia instead of water. [...]

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1 Open Chemistry

1 2013

1 Alkorta I.

1 Elguero J.

1 Gallo R.

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A theoretical study of the limits of the acidity of carbon acids in phase transfer catalysis in water and in liquid ammonia