Carbocation
A carbocation is an ion with a positively charged carbon atom. Among the simplest examples are the methenium CH+3, methanium CH+5 and vinyl C2H+3 cations. Occasionally, carbocations that bear more than one positively charged carbon atom are also encountered (e.g., C2H2+4). Until the early 1970s, all carbocations were called carbonium ions. In the present-day definition given by the IUPAC, a carbocation is any even-electron cation with significant partial positive charge on a carbon atom. They are further classified in two main categories according to the coordination number of the charged carbon: three in the carbenium ions and five in the carbonium ions. This nomenclature was proposed by G. A. Olah. Carbonium ions, as originally defined by Olah, are characterized by a three-center two-electron delocalized bonding scheme and are essentially synonymous with so-called 'non-classical carbocations', which are carbocations that contain bridging CβC or CβH Ο-bonds. However, others have more narrowly defined the term 'carbonium ion' as formally protonated or alkylated alkanes (CR+5, where R is H or alkyl), to the exclusion of non-classical carbocations like the 2-norbornyl cation. (Wikipedia).
