Ion Pair pKs of Some Amines: Extension
of the Computed Lithium pK Scale

Streitwieser, Andrew; Facchetti, Antonio; Xie, Linfeng; Zhang, Xingyue; Wu, Eric C.

doi:10.1021/jo202253q.s001

Ion Pair pKs of Some Amines: Extension of the Computed Lithium pK Scale

https://doi.org/10.1021/jo202253q.s001
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journal contribution

posted on 2012-01-20, 00:00 authored by Andrew Streitwieser, Antonio Facchetti, Linfeng Xie, Xingyue Zhang, Eric C. Wu

The pK of p-(methylamino)biphenyl, 1, on our Li scale, pK(Li) = 22.09, compared to the cesium scale, pK(Cs) = 28.60. For hexamethyldisilazane, HMDS, pK(Li) = 23.05, pK(Cs) = 29.26. These results are those for the monomers in THF; corrections were made for dimers present in some cases. The pK(Li) of these two amines fit well the previously found correlation with Hartree–Fock calculations at 6-31+g(d) using RLi coordinated with three dimethyl ethers as a computational model for RLi in THF. The results are also compared with earlier pK(Li)s reported from equilibria with lithium amides in which aggregation was not considered.