A carbocation is a positively charged carbon-containing species with the positive charge associated with its carbon framework. A classical three-coordinate carbenium center has an electron-deficient carbon and an available acceptor orbital.
Resonance, hyperconjugation, and neighboring groups can stabilize or redistribute the charge. The resulting reactivity includes nucleophilic capture and possible rearrangement; a drawn localized charge need not describe the complete electronic structure.
A carbocation whose positively charged carbon is bonded to three carbon substituents.
A carbocation whose positively charged carbon is bonded to two carbon substituents.
Migration of a neighboring C–H bonding pair onto an electron-deficient carbon, moving the carbocation site.
An oxocarbenium ion is a cationic species stabilized by adjacent oxygen donation, commonly represented by carbon-cation and oxonium resonance contributors. Reversible acetal opening can expose a locally planar carbon for attack from either face.
An oxocarbenium ion at the anomeric carbon of a cyclic glycosyl fragment. Positive charge is delocalized between that carbon and the ring oxygen. A counterion can remain nearby and influence which face a nucleophile approaches.

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