text: The best Lewis structure for an oxocarbenium ion contains an oxygen–carbon double bond, with the oxygen atom attached to an additional group and consequently taking on a formal positive charge.  In the language of canonical structures (or "resonance"), the polarization of the π bond is described by a secondary carbocationic resonance form, with a formal positive charge on carbon (see above). In terms of frontier molecular orbital theory, the Lowest Unoccupied Molecular Orbital (LUMO) of the oxocarbenium ion is a π* orbital that has the large lobe on the carbon atom; the more electronegative oxygen contributes less to the LUMO. Consequently, in an event of a nucleophilic attack, the carbon is the electrophilic site. Compared to a ketone, the polarization of an oxocarbenium ion is accentuated: they more strongly resemble a "true" carbocation, and they are more reactive toward nucleophiles.  In organic reactions, ketones are commonly activated by the coordination of a Lewis acid or Brønsted acid to the oxygen to generate an oxocarbenium ion as an intermediate.
  Numerically, a typical partial charge (derived from Hartree-Fock computations) for the carbonyl carbon of a ketone RC=O (like acetone) is δ+ = 0.51. With the addition of an acidic hydrogen to the oxygen atom to produce [RC=OH], the partial charge increases to δ+ = 0.61.  In comparison, the nitrogen analogues of ketones and oxocarbenium ions, imines (RC=NR) and iminium ions ([RC=NRH]), respectively, have partial charges of δ+ = 0.33 and δ+ = 0.54, respectively. The order of partial positive charge on the carbonyl carbon is therefore imine < ketone < iminium < oxocarbenium. 
  This is also the order of electrophilicity for species containing C=X (X = O, NR) bonds.  This order is synthetically significant and explains, for example, why reductive aminations are often best carried out at pH = 5 to 6 using sodium cyanoborohydride (Na[HB(CN)]) or sodium triacetoxyborohydride (Na[HB(OAc)]) as a reagent.  Bearing an electron-withdrawing group, sodium cyanoborohydride and sodium triacetoxyborohydride are poorer reducing agents than sodium borohydride, and their direct reaction with ketones is generally a slow and inefficient process.  However, the iminium ion (but not the imine itself) formed in situ during a reductive amination reaction is a stronger electrophile than the ketone starting material and will react with the hydride source at a synthetically useful rate.  Importantly, the reaction is conducted under mildly acidic conditions that protonate the imine intermediate to a significant extent, forming the iminium ion, while not being strongly acidic enough to protonate the ketone, which would form the even more electrophilic oxocarbenium ion.  Thus, the reaction conditions and reagent ensure that amine is formed selectively from iminium reduction, instead of direct reduction of the carbonyl group (or its protonated form) to form an alcohol.