The arenium ion is no longer an aromatic species; however it is relatively stable due to delocalization: the positive charge is delocalized over 5 carbon atoms via the π system, as depicted on the following resonance structures: Another contribution to the stability of arenium ions is the energy gain resulting from the strong bond between the benzene and the complexed electrophile. The smallest arenium ion is protonated benzene, . The benzenium ion can be isolated as a stable compound when benzene is protonated by the carborane superacid, H(CB11H(CH3)5Br6). The benzenium salt is crystalline with thermal stability up to 150 °C. Bond lengths deduced from X-ray crystallography are consistent with a cyclohexadienyl cation structure. An acylium ion is a cation with the formula RCO+. The structure is described as R−C≡O+ or R−=O. It is the synthetic and reactive equivalent of an acyl carbocation, but the actual structure has the oxygen and carbon linked by a triple bond. Such species are common reactive intermediates, for example, in the Friedel−Crafts acylations also in many other organic reactions such as the Hayashi rearrangement. Salts containing acylium ions can be generated by removal of the halide from acyl halides:  The C–O distance in these cations is near 1.1 ångströms, even shorter than that in carbon monoxide. Acylium cations are characteristic fragments observed in EI-mass spectra of ketones.