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Amide

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Amide
Formamide-MO-3D-balls.pngAmide-general.png
General
Systematic name Amide
Molecular formula -CONH2 group
Molar mass Molar mass::16.0226 g/mol
Appearance Gas
CAS number CAS number::17655-31-1
Properties
Solubility in water Low, Lower than Amines
Melting point [[Melting point::Generally high,
depends on size of the molecule ]]
Boiling point [[Boiling point::Generally high,
depends on size of the molecule]]
Basicity (pKb) Stronger Basicity than a hydroxide anion
Structure
Molecular shape Triangular Pyramid
Related compounds
Other anions Sodium Amide, Lithium diisopropylamide
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Disclaimer and references

Amides are a class of chemical compounds that contain the -CONH2 group. They are derived from carboxylic acids. A carboxylic acid contains the -COOH group, and in an amide the -OH part of that group is replaced by an -NH2 group resulting in -CONH2. The amide linkage has some interesting properties that may not be obvious from other chemical classes.[1]

Amide can also refer to the conjugate base of ammonia (the anion H2N−) or of an organic amine (an anion R2N−).[2]

Properties

The amide is neutral ion. The amide is gas therefore there is no known physical property of it. For chemical property, Amides are either highly basic or weak base because the conjugate acid of amide has pKa is around -0.5 when Amine is around 9.5 pKa. Also, another reason for amide is not strong base is, amides are part of Carbonyl group which gives electron and has one pair of electron and Nitrogen. [3]

Synthesis

Amide Bonds

The amide is usually formed by reaction between Carboxylic acid and amine. To Form amide, it needs a different type of reaction which is Schotten-Baumann reaction, which is conversion of the acid to the acid chloride.[4] Not only Schotten-Baumann reaction, passerini Reaction, Ritter Reaction and Ugi Reaction can also can be used to form Amide.[5] Also Amide can be produced when converting carboxylic acid to ammonium salt.[6]

Uses

Sodium bis(trimethylsilyl)amide

There are several different ways to use amide in industries. One way to use amide is to make nylon 66. It is called nylon 66 because to make this fiber we need hexamethylene diamine and adipic acid and each of them has six carbon atoms, so it is called nylon 66. [7] Nylon 66 is used to make conveyor belts, hoses, several machine parts and frame of weapons because nylon 66 has higher melting points and wear resistant. [8] Another way to use amide is to make reagent. Sodium amide is used as reagent for drying ammonia and it is a good base because it is sometimes nucleophile, which is a chemical that donates an electron pair to an electrophile. [9] Also amide can be used to prevent plastic and acrylic fibers from pesticide. Dimethylformamide also called DMF is used to form aldehydes and acyl halides. DMF usually separate carbon nano tubes and penetrate plastics and make them swell up. [10]

Sodium Amide

3D structure of Sodium Amide

Sodium Amide's molecular formula is NaNH2. Sodium Amide is a strong base which eliminate reactions and also "deprotonate alkynes, alcohol, and any substance with acidity. [11] Sodium Amide is also called Sodamide, it is solid and it is extremely hazardous, may cause irritation when it touches skin or eyes and also may cause inhalation. Sodamine has melting point of 210°C and it's color is grey-white.[12] Sodamine can be made by reacting Sodium with ammonia Gas but usually scientists use ammonia and Iron (III)nitrate to speed up the process and also it is highly reactive to water and also highly conductive. [13]

Video

Amines and amides: naming, drawing and reactions.

References

  1. Amides UC Davis ChemWiki Web. Accessed May 21, 2015.
  2. Amide Wikipedia. Web. Last Modified 22 March 2015.
  3. Unknown Author. Amide Wikipedia. Web. Last Modified 22 March 2015.
  4. Fung Ka Chun, Kwok Chun Sing, Shing Ming Fung, Wong Chun Yin. Synthesis of Amide Amide. Web. Accessed 5 May 2015.
  5. Unknown Author. Synthesis of Amide Organic Chemistry. Web. Accessed 5 May 2015.
  6. Clark.Jim. Synthesis of Amide Making Amides. Web. 2004.
  7. Newton, David. Amide Amides- Important synthetic Amides. Web. Accessed 20 April 2015.
  8. Unknown Author. Nylon 66 Plastics International . Web. Accessed 20 April 2015.
  9. Unknown Author. Amide uses Amide. Web. Accessed 20 April 2015.
  10. Unknown Author. Amide uses Amide. Web. Accessed 20 April 2015.
  11. James. Sodium Amide Reagent Friday: Sodium Amide (NaNH2). Web. Last modified 19 February 2015.
  12. Unknown Author. [www.sciencelab.com/msds.php?msdsId=9927587 Sodium Amide] Material Safety Data Sheet Sodium Amide MSDS. Web. Last modified 21 May 2013.
  13. Unknown Author. [1] Wikipedia. Web. Last modified 11 February 2015.