Download Amide Uses

Amide
An amide is one of three kinds of compounds:
 the organic functional group characterized by a carbonyl group (C=O) linked to a
nitrogen atom (N), or a compound that contains this functional group (pictured to the
right); or
 a particular kind of nitrogen anion.
 any organic compound derived by the replacement of a hydroxyl group by an amino
group.
Formation of amide :
O
∥
CH3—C—OH + NH3
O
∥
CH3—C—NH2 + H2O
Uses
Industrial:
Sodium amide (NaNH2), commonly called sodamide, is used in the industrial production of
indigo, hydrazine, and sodium cyanide. It is the reagent of choice for the drying of
ammonia (liquid or gaseous) and is also widely used as a strong base in organic chemistry,
often in liquid ammonia solution. One of the main advantages to the use of sodamide is that it
is an excellent base and rarely serves as a nucleophile. It is however poorly soluble and its
use has been superseded by the related reagents such as sodium hydride, sodium
bis(trimethylsilyl)amide (NaHMDS), and lithium diisopropylamide(LDA).
Dimethylformamide ((CH3)2NC(O)H), commonly abbreviated as DMF, colourless liquid
miscible with water and the majority of organic liquids. The primary use of
dimethylformamide is as a solvent with low evaporation rate. DMF is used in the
production of acrylic fibers and plastics. It is also used as a solvent in peptide coupling
for pharmaceuticals, in the development and production of pesticides, and in the
manufacture of adhesives, synthetic leathers, fibers, films, and surface coatings. It is used
as a reagent in the Bouveault aldehyde synthesis and in the Vilsmeier-Haack reaction,
another useful method of forming aldehydes. It is also a common catalyst used in the
synthesis of acyl halides, in particular the synthesis of acyl chlorides from carboxylic
acids using oxalyl or thionyl chloride. DMF penetrates most plastics and makes them swell.
This property makes it very suitable for solid phase peptide synthesis. It also frequently
occurs as a component of paint strippers for this purpose. DMF is very effective at separating
and suspending carbon nanotubes, and is recommended by the NIST for use in near
infrared spectroscopy of such. DMF can be utilized as a standard in proton NMR allowing for
a quantitative determination of an unknown chemical. DMF is used as a solvent to recover
olefins such as 1,3-butadiene via extractive distillation. It is also used in the
manufacturing of solvent dyes as an important raw material.
Deprotonation:
Lithium bis(trimethylsilyl)amide (commonly abbreviated as LiHMDS, Lithium
HexaMethylDiSilazide) is the organosilicon compound with the formula [(CH3)3Si]2NLi. This
colourless solid is a strong non-nucleophilic base used for deprotonation reactions and as
a ligand. When solvent-free, this compound is dimeric in solution, and trimeric in solid state.
Sodium bis(trimethylsilyl)amide is the chemical compound with the formula
((CH3)3Si)2NNa. This species, usually called NaHMDS (sodium hexamethyldisilazide), is a
strong base used for deprotonation reactions or base catalyzed reaction. Its advantages
are that it is available as a solid and it is soluble in a wide range of nonpolar solvents such as
THF, diethyl ether and benzene. NaHMDS is widely used as a base for C-H acids and N-H
acids.
Lithium diisopropylamide is the chemical compound with the formula [(CH3)2CH]2NLi.
Generally abbreviated LDA, it is a strong base used in organic chemistry for the
deprotonation of weakly acidic compounds. The reagent has been widely accepted because
it is soluble in non-polar organic solvents and it is non-pyrophoric. LDA can, however, act as
a nucleophile under certain conditions. For instance, it can react with tungsten
hexacarbonyl as part of the synthesis of a diisopropylaminocarbyne. If given the proper
conditions, LDA will act like any other nucleophile and perform condensation reactions.
Other uses:
Lithium amide (Li+NH2-) is a white solid with a tetragonal crystal structure. Lithium
amides are very reactive compounds and can act as strong bases. Unless the nitrogen atom is
hindered, as in the case of LDA, they can also act as nucleophiles.
Potassium amide (K+NH2-) is a yellowish brown solid. It is used as a pesticide which
intended for preventing, destroying, repelling or mitigating any pest.
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