Onium ion In chemistry , an onium ion is a cation formally obtained by the protonation of mononuclear parent hydride of a pnictogen , chalcogen , or halogen . The oldest-known onium ion, and the namesake for the class, is ammonium , NH, the protonated derivative of ammonia , NH3 . The name onium is also used for cations that would result from the substitution of hydrogen atoms in those ions by other groups, such as organic radicals, or halogens; such as tetraphenylphosphonium , 4 P+ . The substituent groups may be divalent or trivalent, yielding ions such as iminium and nitrilium . A simple onium ion has a charge of +1. A larger ion that has two onium ion subgroups is called a double onium ion , and has a charge of +2. A triple onium ion has a charge of +3, and so on. Compounds of an onium cation and some other anion are known as onium compounds or onium salts . Onium ions and onium compounds are inversely analogous to -ate ions and ate complexes:Lewis bases form onium ions when the central atom gains one more bond and becomes a positive cation. Lewis acids form -ate ions when the central atom gains one more bond and becomes a negative anion.Simple onium cations (hydrides with no substitutions) [Group 15 ] (pnictogen) onium cationsammonium, phosphonium, arsonium, stibonium, bismuthonium,[Group 16 ] (chalcogen) onium cations oxonium, sulfonium, selenonium, telluronium, fluoronium, chloronium, bromonium, iodonium, aminodiazonium, hydrocyanonium,[Group 14 ] (carbon group) onium cations carbonium ions, protonated hydrocarbons, having a pentavalent carbon atom with a +1 charge *alkanium cations, **methanium, **ethanium, **propanium, ***propylium, or propan-1-ylium ***propan-2-ylium **butanium, ***n -butanium ****n -butylium, or n -butan-1-ylium ****n -butan-2-ylium ***isobutanium ****isobutylium, or isobutan-1-ylium ****isobutan-2-ylium **octonium or octanium, *alkenium cations, **ethenium, *alkynium cations, **ethynium, silanium, further silanium cations, *disilanium, germonium, stannonium, plumbonium,[Group 13 ] (boron group) onium cations boronium cation, further boronium cations,[Group 18 ] (noble gas) onium cations hydrohelium or helonium , better known as helium hydride ion , HeH + neonium, NeH+ argonium, ArH+ kryptonium, KrH+ xenonium, XeH+ hydrogenonium, better known as trihydrogen cation , H, found in ionized hydrogen and interstellar space Onium cations with monovalent substitutions primary ammonium cations, RH3 N+ or RNH *hydroxylammonium, NH3 OH+ *methylammonium, CH3 NH *ethylammonium, C2 H5 NH *hydrazinium, or diazanium , NH2 NH secondary ammonium cations, R2 NH *dimethylammonium 2 NH *diethylammonium 2 NH *ethylmethylammonium, C2 H5 CH3 NH *diethanolammonium, 2 NH tertiary ammonium cations, R3 NH+ *trimethylammonium 3 NH+ *triethylammonium 3 NH+ quaternary ammonium cations, R4 N+ or NR *tetramethylammonium, 4 N+ *tetraethylammonium, 4 N+ *tetrapropylammonium, *tetrabutylammonium, 4 N+ or abbreviated Bu4 N+ *trimethyl ammonium compounds, 3 RN+ *didecyldimethylammonium, 2 2 N+ *pentamethylhydrazinium, N2 N *tetrafluoroammonium, NF quaternary phosphonium cations, R4 P+ or PR *tetraphenylphosphonium, 4 P+ secondary sulfonium cations, R2 SH+ *dimethylsulfonium, 2 SH+ tertiary sulfonium cations, R3 S+ *trimethylsulfonium, 3 S+ secondary fluoronium cations, R2 F+ *dichlorofluoronium, Cl2 F+ trifluoroxenonium, XeFOnium cations with polyvalent substitutions secondary ammonium cations having one double-bonded substitution, R=NH2 + *diazenium, HN=NH2 + *guanidinium, 2 C=NH2 + quaternary ammonium cations having one double-bonded substitution and two single-bonded substitutions, R=NR2 + *iminium, R2 C=NR2 + *diazenium, RN=NR2 + quaternary ammonium cations having two double-bonded substitutions, R=N=R+ *nitronium, NO *bisiminium, 2 N+ tertiary ammonium cations having one triple-bonded substitution, R≡NH+ *nitrilium, RC≡NH+ *diazonium, N≡NH+ tertiary ammonium cations having two partially double-bonded substitutions, RNH+ R *pyridinium, C5 H5 NH+ quaternary ammonium cations having one triple-bonded substitution and one single-bonded substitution, R≡NR+ *diazonium, N≡NR+ *nitrilium, RC≡NR+ tertiary oxonium cations having one triple-bonded substitution, R≡O+ *nitrosonium, N≡O+ tertiary oxonium cations having two partially double-bonded substitutions, RO+ R *pyrylium, C5 H5 O+ tertiary sulfonium cations having one triple-bonded substitution, R≡S+ *thionitrosyl, N≡S+ Double onium dications hydrazinediium or hydrazinium dication , + H3 NNH diazenediium cation, + H2 N=NH diazynediium cation, + HN≡NH+ Enium cations The extra bond is added to a less-common parent hydride , a carbene analog , typically named -ene or -ylene , which is neutral with 2 fewer bonds than the more-common hydride, typically named -ane or -ine .borenium cations, carbenium cations, *methenium cation, silylium cations, nitrenium cations, phosphinidenium cations, mercurinium cations,Ynium cations carbynium ions, protonated carbynes, have a divalent carbon atom with a +1 charge *methynium cation,
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