Semicarbazone 5377788 225981204 2008-07-16T09:03:31Z Albambot 6552142 robot Adding: [[de:Semicarbazone]] [[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]]