Iminium

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The general structure of an iminium cation

An iminium salt or cation in organic chemistry has the general structure [R1R2C=NR3R4]+ and is as such a protonated or substituted imine.[1] Iminium ions are formed from the protonation of imines, which arise by the condensation of ketones or aldehydes with primary amines:

RN=CR'2 + H+ → [RNH=CR'2]+

They also are generated by the condensation of secondary amines with ketones or aldehydes:[2]

O=CR'2 + R2NH → [R2N=CR'2]+ + OH-

Reactions and reagents involving iminium species[edit]

Iminylium ions[edit]

Iminylium ions have the general structure R2C=N+. They form a subclass of nitrenium ions.[3]

See also[edit]

References[edit]

  1. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006–) "iminium compounds".
  2. ^ Anniina Erkkilä, Inkeri Majander, Petri M. Pihko (2007). "Iminium Catalysis". Chem. Rev. 107: 5416–5470. doi:10.1021/cr068388p.
  3. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006–) "iminylium ions".