Semicarbazone

General chemical structure of a semicarbazone

General chemical structure of a thiosemicarbazone

Nitrofurazone 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.^[1]

Thiosemicarbazone

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

See also

• Carbazone
• Carbazide

References

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

• Compounds Containing a N-CO-N-N or More Complex Group