Onium Compounds - Onium Cations With Polyvalent Substitutions

Onium Cations With Polyvalent Substitutions

• secondary ammonium cations having one double-bonded substitution, R=NH₂+
  • diazenium, HN=NH₂+ (protonated diazene)

• quaternary ammonium cations having one double-bonded substitution and two single-bonded substitutions, R=NR₂+
  • iminium, R₂C=NR₂+ (substituted protonated imine)
  • diazenium, RN=NR₂+ (substituted protonated diazene)

• quaternary ammonium cations having two double-bonded substitutions, R=N=R+
  • nitronium, NO+
    2
  • bis(triphenylphosphine)iminium, ((C₆H₅)₃P)₂N+

• tertiary ammonium cations having one triple-bonded substitution, R≡NH+
  • nitrilium, RC≡NH+ (protonated nitrile)
  • diazonium, N≡NH+ (protonated nitrogen)

• tertiary ammonium cations having two partially double-bonded substitutions, R=-NH+=-R
  • pyridinium, C₅H₅NH+ (protonated pyridine)

• quaternary ammonium cations having one triple-bonded substitution and one single-bonded substitution, R≡NR+
  • diazonium, N≡NR+ (substituted protonated nitrogen)
  • nitrilium, RC≡NR+ (substituted protonated nitrile)

• tertiary oxonium cations having one triple-bonded substitution, R≡O+
  • nitrosonium, N≡O+

• tertiary oxonium cations having two partially double-bonded substitutions, R=-O+=-R
  • pyrylium, C₅H₅O+

• tertiary sulfonium cations having one triple-bonded substitution, R≡S+
  • thionitrosyl, N≡S+