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Can Conventional Bases and Unsaturated Hydrocarbons Be Converted into Gas-Phase Superacids That Are Stronger than Most of the Known Oxyacids? The Role of Beryllium Bonds

AuthorsYáñez, Manuel; Mó, Otilia; Alkorta, Ibon ; Elguero, José
superacidic systems
Issue Date2013
CitationChemistry - A European Journal 19 : 11637 – 11643 (2013)
AbstractThe association of BeX2 (X: H, F, Cl) derivatives with azoles leads to a dramatic increase of their intrinsic acidity. Hence, whereas 1H-tetrazole can be considered as a typical N base in the gas phase, the complex 1H-tetrazole– BeCl2 is predicted to be, through the use of high-level G4 ab initio calculations, a nitrogen acid stronger than perchloric acid. This acidity enhancement is due to a more favorable stabilization of the deprotonated species after the beryllium bond is formed, because the deprotonated anion is a much better electron donor than the neutral species. Consequently, this is a general phenomenon that should be observed for any Lewis base, including those in which the basic site is a hydroxy group, an amino group, a carbonyl group, an aromatic N atom, a second-row atom, or the p system of unsaturated hydrocarbons. The consequence is that typical bases like aniline or formamide lead to BeX2 complexes that are stronger acids than phosphoric or chloric acids. Similarly, water, methanol, and SH2 become stronger acids than sulfuric acid, pyridine becomes a C acid almost as strong as acetic acid, and unsaturated hydrocarbons such as ethylene and acetylene become acids as strong as nitric and sulfuric acids, respectively.
Publisher version (URL)http://dx.doi.org/10.1002/chem.201300808
Appears in Collections:(IQM) Artículos
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