Cyclopropenimine as a hydrogen bond acceptor-towards the strongest non-phosphorus superbases

Utilizing dialkylamino cyclopropenimines as hydrogen bond acceptors in tri-substituted guanidines and cyclopropenimines, we computationally designed the most basic superbases possessing intramolecular hydrogen bonds (IHB-superbases) so far. The values of proton affinity in the gas phase range between 296.6 and 306 kcal mol−1, with estimated pKa values in acetonitrile between 35.5 and 39.7. The obtained PAs of five new IHB-superbases surpass the basicity of the paradigmatic P4-tBu Schwesinger phosphazene, whereas pKa values come close to that of P4-tBu. None of the designed superbases contain phosphorus, which puts them among few most basic non-phosphorus superbases desiged so far.

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