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Semicarbazone

From Wikipedia, the free encyclopedia
General chemical structure of a semicarbazone
Nitrofurazone is a semicarbazone used as an antiseptic

Inorganic chemistry, asemicarbazone is aderivative ofimines formed by acondensation reaction between aketone oraldehyde andsemicarbazide. 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 primaryamines.

Formation

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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 ofacetone would have the structure (CH3)2C=NNHC(=O)NH2.

Properties and uses

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Some semicarbazones, such asnitrofurazone, andthiosemicarbazones are known to haveanti-viral andanti-cancer activity, usually mediated through binding tocopper oriron in cells. Many semicarbazones are crystalline solids, useful for the identification of the parent aldehydes/ketones bymelting point analysis.[1]

Athiosemicarbazone is an analog of a semicarbazone which contains asulfur atom in place of the oxygen atom.

See also

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References

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  1. ^Williamson, Kenneth L. (1999).Macroscale and Microscale Organic Experiments, 3rd ed. Boston: Houghton-Mifflin. pp. 426–7.ISBN 0-395-90220-7.

External links

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