Hydrazinium

Hydrazinium is the cation with the formula N
2H+
5. It can be derived from hydrazine by protonation (treatment with a strong acid). Hydrazinium is a weak acid with pKa = 8.1.

Structures of hydrazinium N
2H+
5 and hydrazinediium N
2H2+
6.

Salts of hydrazinium are common reagents in chemistry and are often used in certain industrial processes.[1] Notable examples are hydrazinium hydrogensulfate, N
2H
6SO
4 or [N
2H+
5][HSO−
4], and hydrazinium azide, N
5H
5 or [N
2H+
5][N−
3]. In the common names of such salts, the cation is often called "hydrazine", as in "hydrazine sulfate" for hydrazinium hydrogensulfate.

The terms "hydrazinium" and "hydrazine" may also be used for the doubly protonated cation N
2H2+
6, more properly called hydrazinediium or hydrazinium(2+). This cation has an ethane-like structure. Salts of this cation include hydrazinediium sulfate [N
2H2+
6][SO2−
4][2] and hydrazinediium bis(6-carboxypyridazine-3-carboxylate), [N
2H2+
6][C
6H
3N
2O−
4]
2.[3]

See also

References
  1. Jean-Pierre Schirmann, Paul Bourdauducq "Hydrazine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a13_177.
  2. Klapötke, T.; Peter S. White; Inis C. Tornieporth-Oetting (1996). "Reaction of hydrazinium azide with sulfuric acid: the X-ray structure of [N
    2    H
    6    ][SO
    4    ]    ". Polyhedron. 15 (15): 2579–2582. doi:10.1016/0277-5387(95)00527-7.
  3. W. Starosta and J. Leciejewicz (2008), "Hydrazinediium bis(6-carboxypyridazine-3-carboxylate) dihydrate". Acta Crystallographica, volume E64, article o461. doi:10.1107/S1600536808001037
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