hydrazoniumn.

1876 Jrnl. Chem. Soc. ii. 528 The author [sc. E. Fischer] has isolated a body of the formula C₆H₅.N₂H₂(C₂H₅)(C₂H₅ Br), which he names phenyldiethylhydrazoniumbromide.]

1949 Chem. & Industry 26 Feb. 134/2 The ions derived from hydrazine are also troublesome. The one most commonly encountered, N₂H₅⁺, is called hydrazinium in the 1940 Rules but hydrazonium in Chemical Abstracts (1945). Since the ion is essentially a substituted ammonium, the latter is strictly the more correct, but neither affords a means of distinguishing N₂H₅⁺ from N₂H₆⁺⁺, which occurs in a few compounds. The two names could be used in fact for this purpose, but the distinction is best achieved, without confusion, by writing N₂H₅⁺Hydrazonium (I) or (+ 1)N₂H₆⁺⁺Hydrazonium (II) or (+ 2).

1953 C. C. Clark Hydrazine iii. 36 The asymmetric dialkyl hydrazines are also strong bases. They react quantitatively with active alkyl chlorides to form water soluble hydrazonium salts: R₂NNH₂ + R′X → R₂NNH₂.R′X.

1954 Chem. & Engin. News 6 Sept. 3548/3 As a name for the ion H₂N.NH₃⁺ there has been some division of usage between ‘hydrazonium’ and ‘hydrazinium’; and some have applied one or other of these names to the ion ⁺H₃N.NH₃⁺ as well as to the ion of single charge. The newly revised inorganic rules propose to settle the question by naming N₂H₅⁺ ‘hydrazinium (1⁺)’ and N₂H₆²⁺ ‘hydrazinium (2⁺)’. This does not seem to us an ideal solution, to give two different ions (which are not isomers) the same name except for an affixed numeral. Might not the name ‘hydrazinium’ be retained for N₂H₅⁺ and some such name as ‘hydrazidiinium’ coined for N₂H₆²⁺?

1955 Chem. & Engin. News 3 Jan. 70/3 A.C. Nixon..suggests that ‘ hydrazonium’ be retained for H₂NONH₃⁺[sic] and ‘hydrazinium’ be applied to ⁺H₃N·NH₃⁺.

1957 Chem. Rev. 57 1022 The cation having the formula R₃+NNR₂ has been given many names. Emil Fischer called the first known representative of this type a ‘hydrazonium bromide’ but later referred to the same compound as an ‘azonium bromide’. Chemical Abstracts has used the names ‘azinium’, ‘azonium’, ‘hydrazinium’, and, most commonly of late, ‘hydrazonium’ for the same type. As a logical extension of the recommendations recently made for naming [H₃NNH₂]⁺, it is suggested that the name ‘hydrazinium’ be adopted... It is suggested here that the name ‘hydrazonium’ be restricted to salts of hydrazones (including quaternary salts).

1957 Chem. Rev. 57 1022 The cation having the formula R₃+NNR₂ has been given many names. Emil Fischer called the first known representative of this type a ‘hydrazonium bromide’ but later referred to the same compound as an ‘azonium bromide’. Chemical Abstracts has used the names ‘azinium’, ‘azonium’, ‘hydrazinium’, and, most commonly of late, ‘hydrazonium’ for the same type. As a logical extension of the recommendations recently made for naming [H₃NNH₂]⁺, it is suggested that the name ‘hydrazinium’ be adopted... It is suggested here that the name ‘hydrazonium’ be restricted to salts of hydrazones (including quaternary salts).

1966 P. A. S. Smith Chem. Open-chain Org. Nitrogen Compounds II. ix. 149 Quaternary hydrazinium salts can also be obtained by the hydrolysis of quaternary hydrazonium salts (R₃+N—N = CR₂X⁻).