Semicarbazone

From Wikipedia, the free encyclopedia

In organic chemistry, a semicarbazone is a derivative of an aldehyde or ketone formed by the addition-elimination (condensation) reaction between a ketone (or aldehyde) and a semicarbazide.

For ketones: H₂NNHC(=O)NH₂ + RC(=O)R (ketone) --> R₂C=NNHC(=O)NH₂.

For aldehydes: H₂NNHC(=O)NH₂ + RCHO (aldehyde) --> RCH=NNHC(=O)NH₂.

For example, the semicarbazone of acetone would have the structure (CH₃)₂C=NNHC(=O)NH₂. A 'thiosemicarbazone' contains a sulfur thio atom (sulfur) in lieu of the carbonyl oxygen.

Both semicarbazones 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]

[edit] See also

• Semicarbazide
• Carbazone
• Carbazide

[edit] References

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

[edit] External links

• Overview at uni.edu
• Diagram at uic.edu
• "Kinetic vs. Equilibrium Control in Semicarbazone Formation", at msu.edu
• Description of derivatives at dcccd.edu
• Compounds Containing a N-CO-N-N or More Complex Group