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Heterocyclic superbases: retrospective and current trends

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Chemistry of Heterocyclic Compounds Aims and scope

The structural principles known to date serving as the basis for the design of heterocyclic compounds with anomalously high basicity (superbasicity) are reviewed. A general classification is given for such superbases as proton sponges, compounds that are similar to proton sponges but are not sponges (proton-sponge-like), and proton traps.

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Notes

  1. Here and subsequently, the pK a values given were measured in water at 25 °C except where otherwise indicated.

  2. *This value is maintained also in the gas phase, where basicity is given through proton affinity (PA) (see section 9). Kaljurand et al. [20] have proposed the term superbase to compounds with pK a ≥ 33 in acetonitrile, which corresponds to pK a ~26 for aqueous solutions.

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  1. Southern Federal University, 7 Zorge St., Rostov-on-Don, 344090, Russia

    A. F. Pozharskii, V. A. Ozeryanskii & E. A. Filatova

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 208–228, January, 2012.

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Pozharskii, A.F., Ozeryanskii, V.A. & Filatova, E.A. Heterocyclic superbases: retrospective and current trends. Chem Heterocycl Comp 48, 200–219 (2012). https://doi.org/10.1007/s10593-012-0983-5

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