In
organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; ...
, a semicarbazone is a
derivative
In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. F ...
of
imines
In organic chemistry, an imine ( or ) is a functional group or organic compound containing a carbon–nitrogen double bond (). The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bo ...
formed by a
condensation reaction
In organic chemistry, a condensation reaction is a type of chemical reaction in which two molecules are combined to form a single molecule, usually with the loss of a small molecule such as water. If water is lost, the reaction is also known as a ...
between a
ketone
In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...
or
aldehyde
In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl grou ...
and
semicarbazide
Semicarbazide is the chemical compound with the formula OC(NH2)(N2H3). It is a water-soluble white solid. It is a derivative of urea.
Synthesis
The compound prepared by treating urea with hydrazine:Jean-Pierre Schirmann, Paul Bourdauducq "Hydrazi ...
. They are classified as imine derivatives because they are formed from the reaction of an aldehyde or ketone with the terminal -NH
2 group of semicarbazide, which behaves very similarly to primary
amines
In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent such ...
.
Formation
;For ketones
:H
2NNHC(=O)NH
2 + RC(=O)R → R
2C=NNHC(=O)NH
2
;For aldehydes
:H
2NNHC(=O)NH
2 + RCHO → RCH=NNHC(=O)NH
2
For example, the semicarbazone of
acetone
Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour.
Acetone is miscib ...
would have the structure (CH
3)
2C=NNHC(=O)NH
2.
Properties and uses
Some semicarbazones, such as
nitrofurazone
Nitrofurazone (INN, trade name Furacin) is an antimicrobial organic compound belonging to the nitrofuran class. It is most commonly used as a topical antibiotic ointment. It is effective against gram-positive bacteria, gram-negative bacteria, ...
, and
thiosemicarbazone
A thiosemicarbazone is an organosulfur compound with the formula H2NC(S)NHN=CR2. Many variations exist, including those where some or all of the N''H'' centers are substituted by organic groups. Thiosemicarbazones are usually produced by condens ...
s are known to have
anti-viral
Antiviral drugs are a class of medication used for treating viral infections. Most antivirals target specific viruses, while a broad-spectrum antiviral is effective against a wide range of viruses. Unlike most antibiotics, antiviral drugs do ...
and
anti-cancer
Cancer is a group of diseases involving abnormal cell growth with the potential to invade or spread to other parts of the body. These contrast with benign tumors, which do not spread. Possible signs and symptoms include a lump, abnormal ble ...
activity, usually mediated through binding to
copper
Copper is a chemical element with the symbol Cu (from la, cuprum) and atomic number 29. It is a soft, malleable, and ductile metal with very high thermal and electrical conductivity. A freshly exposed surface of pure copper has a pinkis ...
or
iron
Iron () is a chemical element with symbol Fe (from la, ferrum) and atomic number 26. It is a metal that belongs to the first transition series and group 8 of the periodic table. It is, by mass, the most common element on Earth, right in f ...
in cells. Many semicarbazones are crystalline solids, useful for the identification of the parent aldehydes/ketones by
melting point
The melting point (or, rarely, liquefaction point) of a substance is the temperature at which it changes state from solid to liquid. At the melting point the solid and liquid phase exist in equilibrium. The melting point of a substance depends ...
analysis.
A ''thiosemicarbazone'' is an analog of a semicarbazone which contains a
sulfur
Sulfur (or sulphur in British English) is a chemical element with the symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms form cyclic octatomic molecules with a chemical formula ...
atom in place of the oxygen atom.
See also
*
Carbazone
*
Carbazide
In chemistry, a carbazide is a functional group with the general formula RNH-NH(C=O)NH-NHR. They can be derived from the condensation reaction, condensation of carbonic acid with a hydrazine. Carbohydrazide is the simplest carbazide, with another ...
*
Thiosemicarbazone
A thiosemicarbazone is an organosulfur compound with the formula H2NC(S)NHN=CR2. Many variations exist, including those where some or all of the N''H'' centers are substituted by organic groups. Thiosemicarbazones are usually produced by condens ...
References
External links
Compounds Containing a N-CO-N-N or More Complex Group
{{Hydrazines
Functional groups
Semicarbazones