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'''Azines''' are a [[functional class]] of [[organic compound]]s, formed from the [[condensation reaction]] of two [[equivalent (chemistry)|equivalent]]s of an [[aldehyde]] or [[ketone]] with one equivalent of [[hydrazine]].<ref>{{IUPAC class names 1995|page=1321}}.</ref><ref>{{GoldBookRef|title=azines|file=A00557|accessdate=2010-07-02}}.</ref> They may be further classified as '''aldazines''' or '''ketazines''', depending on the nature of the [[carbonyl compound]].<ref>{{IUPAC class names 1995|pages=1312, 1348}}.</ref><ref>{{GoldBookRef|title=aldazines|file=A00207|accessdate=2010-07-02}}. {{GoldBookRef|title=ketazines|file=K03377|accessdate=2010-07-02}}.</ref>

==Preparation==
Azines may be prepared by the direct reaction of a carbonyl compound with [[hydrazine hydrate]]:<ref name="OrgSynth">{{OrgSynth | first1 = A. C. | last1 = Day | first2 = M. C. | last2 = Whiting | title = Acetone hydrazone | collvol = 6 | collvolpages = 10 | volume = 50 | pages =3 | year = 1970 | prep = cv6p0010}}.</ref> the reaction is exothermic.<ref>{{citation | first = E. C. | last = Gilbert | title = Studies on Hydrazine. The Hydrolysis of Dimethylketazine and the Equilibrium between Hydrazine and Acetone | journal = J. Am. Chem. Soc. | year = 1929 | volume = 51 | issue = 11 | pages = 3394–3409 | doi = 10.1021/ja01386a032}}.</ref>

==Reactions and uses==
Azines have been used as sources of hydrazine produced ''in situ'', for example in the production of [[herbicide]] precursor [[1,2,4-triazole]].<ref>{{citation | inventor1-last = Nagata | inventor1-first = Nobuhiro | inventor2-last = Nishizawa | inventor2-first = Chiharu | inventor3-last = Kurai | inventor3-first = Toshikiyo | assignee = Mitsubishi Gas Chemical Co. | title = Method of producing 1,2,4-triazole | country-code = US | patent-number = 6002015 | issue-date = 1999-12-14}}.</ref>

==Nomenclature==
Azines may be named by [[substitutive nomenclature|substitutive]] or [[functional class nomenclature]].<ref>{{BlueBook1993|rule=5.6.6.3|page=105|url=http://www.acdlabs.com/iupac/nomenclature/93/r93_469.htm}}.</ref><ref>{{BlueBook2004|rule=68.3.1.2.3}}.</ref> In functional class nomenclature, the functional modifier "azine" is appended to the name of the carbonyl compound: hence, "[[acetone azine]]". In substitutive nomenclature, azines are named as derivatives of hydrazine: hence, "[[diisopropylidenehydrazine]]". In the presence of groups of higher seniority, the prefixes "hydrazinylidene" and "hydrazinediylidene" are used.<ref>{{BlueBook2004|rule=53.6.2}}.</ref>

Unsymmetrical azines, that is compounds of the type X=N–N=Y with X&nbsp;≠ Y, are not named as azines: in the absence of other functional groups having higher seniority, they can be named as substituted [[hydrazone]]s.<ref>{{BlueBook1979|rule=C-923.2|url=http://www.acdlabs.com/iupac/nomenclature/79/r79_623.htm}}.</ref>

==References==
{{reflist|2}}

[[Category:Azines| ]]
[[Category:Functional classes]]
[[Category:Hydrazine derivatives]]

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