Examples of stable organic cations [closed]








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What are examples of organic cations that are stable at room temperature, can be isolated and that cannot be easily deprotonated by $\ce{NaOH}$? My only guess are various compounds with tetravalent nitrogen (tetraalkylammonium, *N*-alkylpyridinium, *N*-alkylimidazolium, etc.).  

Are there some other examples?




The conjugate bases of some other stable cations, called **proton sponges** or **superbases**, is discussed [here[1]](https://core.ac.uk/download/62655280.pdf). Broadly, the compounds discussed have one or both of the following functions:


**1,8-diaminonaphthalenes.** In these compounds two nitrogen atoms are fixed into positions that allow a proton to be simultaneously covalent-bonded to one and hydrogen-bonded to the other (or symmetrically bonded between the two nitrogens), giving a conjugate-acid cation that may be weaker at redissociating the proton than water would be.


**Bis(dialkylamino)cyclopropenimines.** These have a structure similar to cyclopropenones, except the ligands on the ring carbon are all nitrogen atoms. The pi-donor character of the nitrogen atoms combined with the aromaticity of the cationic cyclopropenyl ring render the protonated molecule a strongly stabilized cation.


**Reference**


1. Lee Belding (2016). *Bis(cyclopropenimine) Substituted Proton Sponge Derivatives: Theory, Synthesis, and Applications*, Ph.D. thesis, Brock University, St. Catherine's, Ontario, Canada.


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