Semicarbazone


Semicarbazone

In organic chemistry, a semicarbazone is a derivative of an aldehyde or ketone formed by a condensation reaction between a ketone or aldehyde and semicarbazide.

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.

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

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
date = 1999
location = Boston
pages = 426-7
isbn = 0-395-90220-7
]

ee also

*Semicarbazide
*Carbazone
*Carbazide

References

External links

* [http://nlfaculty.dcccd.edu/logan/slides/chapter16/sld029.htm Description of derivatives at dcccd.edu]
* [http://www.acdlabs.com/iupac/nomenclature/79/r79_673.htm Compounds Containing a N-CO-N-N or More Complex Group]


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  • Semicarbazone — Allgemeine Struktur der Semicarbazone; R1 bis R5 können beliebige organische Reste oder Wasserstoff sein. Semicarbazone sind organische chemische Verbindungen, die als funktionelle Gruppe die Gruppierung C = N − NH − CO − NH2 enthalten. Ein …   Deutsch Wikipedia

  • Semicarbazone — Structure générale d un semicarbazone Structure générale d une thiosemicarbazone …   Wikipédia en Français

  • semicarbazone — noun The reaction product of an aldehyde or ketone with semicarbazide; they have the general formula RRC=N NH CO NH …   Wiktionary

  • semicarbazone — semi·car·ba·zone kär bə .zōn n any of a class of usu. well crystallized compounds having the general formula RR C=NNHCONH2 and formed by the action of semicarbazide on an aldehyde or ketone …   Medical dictionary

  • semicarbazone — semi·car·ba·zone …   English syllables

  • semicarbazone — “+ˈkärbəˌzōn noun ( s) Etymology: International Scientific Vocabulary semicarbazide + one : any of a class of usually well crystallized compounds having the general formula RR′C . NNHCONH2 and formed by the action of semicarbazide on an aldehyde… …   Useful english dictionary

  • Semicarbazid — Strukturformel Allgemeines Name Semicarbazid Andere Namen …   Deutsch Wikipedia

  • Groupe fonctionnel — En chimie organique, un groupe fonctionnel est une structure sub moléculaire constituée d un assemblage d atomes donnés qui confère une réactivité propre à la molécule qui le contient. Cette manière de considérer les molécules comme étant un… …   Wikipédia en Français

  • Semicarbazid — Se|mi|car|b|a|zid [Kurzw. aus ↑ semi , ↑ Carbamid u. ↑ Hydrazid], das; s: H2N C(O) NH NH2; farblose krist. Verb., Smp. 96 °C, die mit Aldehyden u. Ketonen schwer lösliche u. gut krist., zur Isolierung u. Identifizierung der Carbonylverb.… …   Universal-Lexikon

  • nitrofurazone — ˌ ̷ ̷ ̷ ̷ˈfyu̇rəˌzōn noun ( s) Etymology: nitr + fur + semicarbazone : a pale yellow crystalline compound O2NC4H2OCH . NNHCONH2 used chiefly externally as a bacteriostatic or bactericidal dressing (as for wounds and infections); 5 nitro 2… …   Useful english dictionary


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