Semicarbazone
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[[Image:Semicarbazone.png|thumb|right|General chemical structure of a semicarbazone]]
[[Image:Thiosemicarbazone.png|thumb|right|General chemical structure of a thiosemicarbazone]]
[[Image:Nitrofurazone.png|thumb|right|[[Nitrofurazone]] is a semicarbazone antibiotic]]
In [[organic chemistry]], a '''semicarbazone''' is a [[Derivative (chemistry)|derivative]] of an [[aldehyde]] or [[ketone]] formed by a [[condensation reaction]] between a [[ketone]] or [[aldehyde]] and [[semicarbazide]].
For ketones:
:H<sub>2</sub>NNHC(=O)NH<sub>2</sub> + RC(=O)R → R<sub>2</sub>C=NNHC(=O)NH<sub>2</sub>
For aldehydes:
:H<sub>2</sub>NNHC(=O)NH<sub>2</sub> + RCHO → RCH=NNHC(=O)NH<sub>2</sub>
For example, the semicarbazone of [[acetone]] would have the structure (CH<sub>3</sub>)<sub>2</sub>C=NNHC(=O)NH<sub>2</sub>.
A '''thiosemicarbazone''' is an analog of a semicarbazone which contains a [[sulfur]] atom in place of the oxygen atom.
Some semicarbazones, such as [[nitrofurazone]], and thiosemicarbazones are known to have anti-viral and anti-cancer activity, usually mediated through binding to copper or iron in cells. Many semicarbazones are crystalline solids, useful for the identification of the parent aldehydes/ketones by [[melting point]] analysis.<ref name=Williamson>{{cite book
| last = Williamson
| first = Kenneth L.
| title = Macroscale and Microscale Organic Experiments, 3rd ed.
| publisher = Houghton-Mifflin
| date = 1999
| location = Boston
| pages = 426-7
| isbn = 0-395-90220-7}}</ref>
==See also==
*[[Semicarbazide]]
*[[Carbazone]]
*[[Carbazide]]
== References ==
<references/>
==External links==
* [http://nlfaculty.dcccd.edu/logan/slides/chapter16/sld029.htm Description of derivatives at dcccd.edu]
* [http://www.acdlabs.com/iupac/nomenclature/79/r79_673.htm Compounds Containing a N-CO-N-N or More Complex Group]
[[Category:Functional groups]]
[[Category:Hydrazines]]
[[Category:Ureas]]
[[de:Semicarbazone]]