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Neutral Superacids in the Gas-phase and in DMSO Solution

A superacid is any acid stronger than 100% sulfuric acid. There is an ongoing interest in chemistry for compounds exhibiting extreme acidity since neutral superacids are the most important catalysts in chemical transformations. Beside that, very stable anions produced upon deprotonation of strong acids proved useful in isolation of chemically very important and very reactive cations like HC60+, C6H7+, Me3C+ and Xe2+. We developed a useful strategy in designing exceptionally strong neutral superacids. As evidenced by their corresponding deprotonation enthalpies in the gas-phase or by pKa values in DMSO, they surpass the acidity of sulfuric acid by 30-50 orders of magnitude. The proposed compounds include polycyano derivatives of well known organic systems (cyclopentadiene, azatriquinanes, Rees’ molecules etc.) or derivatives of inorganic carboranes. It is expected that the conjugate base anions of these superacids possess some useful properties like low nucleophilicity, weak coordinating ability and high solubility in organic solvents, which should make them useful in everyday chemical applications.

superacids; polycyano derivatives; carboranes

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