Semicarbazone
Image:Nitrofurazone.png is a semicarbazone used as an antiseptic]]
In organic chemistry, a semicarbazone is a derivative of imines formed by a condensation reaction between a ketone or aldehyde and semicarbazide. They are classified as imine derivatives because they are formed from the reaction of an aldehyde or ketone with the terminal -NH2 group of semicarbazide, which behaves very similarly to primary amines.
Formation
;For ketones
:H2NNHC(=O)NH2 + RC(=O)R → R2C=NNHC(=O)NH2
;For aldehydes
:H2NNHC(=O)NH2 + RCHO → RCH=NNHC(=O)NH2
For example, the semicarbazone of acetone would have the structure (CH3)2C=NNHC(=O)NH2.
Properties and uses
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.{{cite book
| last = Williamson
| first = Kenneth L.
| title = Macroscale and Microscale Organic Experiments, 3rd ed.
| publisher = Houghton-Mifflin
| year = 1999
| location = Boston
| pages = 426–7
| isbn = 0-395-90220-7}}
A thiosemicarbazone is an analog of a semicarbazone which contains a sulfur atom in place of the oxygen atom.
See also
References
{{Reflist|2}}
External links
- [http://www.acdlabs.com/iupac/nomenclature/79/r79_673.htm Compounds Containing a N-CO-N-N or More Complex Group]
{{Hydrazines}}
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