Abstract
Stabilization of carbocations through donation of π electrons from adjacent carbon orbitals results in well-known species such as the allyl and benzyl cations. Adjacent nonbonding (n) electrons on heteroatoms also can provide considerable stabilization, as in oxonium ions such as CH2dOCH3 and iminium ions such as CH2dN(CH3)2. Less well known is stabilization of carbocations by σ orbitals. In its most common example this interaction provides stabilization of tertiary over secondary over primary carbocations. According to the valence bond representation of this interaction, a filled σ orbital donates electrons to an empty π orbital, as in 1 and 2 (R ) H).
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