Semicarbazone

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.

General chemical structure of a semicarbazone
Nitrofurazone is a semicarbazone used as an antiseptic

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.[1]

A thiosemicarbazone is an analog of a semicarbazone which contains a sulfur atom in place of the oxygen atom.

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See also


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