See Also

Amide

n chemistry Chemistry

Chemistry is the science [i] of matter [i] at the atom [i]ic to molecular [i] scale, dealing primarily ... 

, an amide is one of two kinds of compounds: - the organic Organic chemistry

Organic chemistry is a specific discipline within the subject of chemistry [i]. ... 

 functional group Functional group

In organic chemistry [i] functional groups are specific groups of atom [i]s within molecule [i]s, that ... 

 characterized by a carbonyl Carbonyl

In organic chemistry [i], a carbonyl group is a functional group [i] composed of a carbon [i] atom [i] double-bonded [i] ... 

 group linked to a nitrogen Nitrogen

Nitrogen is a chemical element [i] which has the symbol N and atomic number [i] 7 in the periodic table [i] ... 

 atom , or a compound that contains this functional group Functional group

In organic chemistry [i] functional groups are specific groups of atom [i]s within molecule [i]s, that ... 

 ; or - a particular kind of nitrogen Nitrogen

Nitrogen is a chemical element [i] which has the symbol N and atomic number [i] 7 in the periodic table [i] ... 

 anion. Many chemists make a pronunciation distinction between the two, saying In the first sense referred to above, an amide is an amine Amine

Amines are organic compound [i]s and a type of functional group [i] that contain nitrogen [i] as the key ... 

 where one of the nitrogen Nitrogen

Nitrogen is a chemical element [i] which has the symbol N and atomic number [i] 7 in the periodic table [i] ... 

 substituents is an acyl group; it is generally represented by the formula: R1N Nitrogen

Nitrogen is a chemical element [i] which has the symbol N and atomic number [i] 7 in the periodic table [i] ... 

R2R3 , where either or both R2 and R3 may be hydrogen Hydrogen

|- | Triple point [i] || 13.8033 K, 7.042 kPa ... 

.

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Encyclopedia

In chemistry Chemistry

Chemistry is the science [i] of matter [i] at the atom [i]ic to molecular [i] scale, dealing primarily ... 

, an amide is one of two kinds of compounds:

- the organic Organic chemistry

Organic chemistry is a specific discipline within the subject of chemistry [i]. ... 

 functional group Functional group

In organic chemistry [i] functional groups are specific groups of atom [i]s within molecule [i]s, that ... 

 characterized by a carbonyl Carbonyl

In organic chemistry [i], a carbonyl group is a functional group [i] composed of a carbon [i] atom [i] double-bonded [i]... 

 group linked to a nitrogen Nitrogen

Nitrogen is a chemical element [i] which has the symbol N and atomic number [i] 7 in the periodic table [i] ... 

 atom , or a compound that contains this functional group Functional group

In organic chemistry [i] functional groups are specific groups of atom [i]s within molecule [i]s, that ... 

 ; or

- a particular kind of nitrogen Nitrogen

Nitrogen is a chemical element [i] which has the symbol N and atomic number [i] 7 in the periodic table [i] ... 

 anion.

Many chemists make a pronunciation distinction between the two, saying
In the first sense referred to above, an amide is an amine Amine

Amines are organic compound [i]s and a type of functional group [i] that contain nitrogen [i] as the key ... 

 where one of the nitrogen Nitrogen

Nitrogen is a chemical element [i] which has the symbol N and atomic number [i] 7 in the periodic table [i] ... 

 substituents is an acyl group; it is generally represented by the formula: R1N Nitrogen

Nitrogen is a chemical element [i] which has the symbol N and atomic number [i] 7 in the periodic table [i] ... 

R2R3 , where either or both R2 and R3 may be hydrogen Hydrogen

|-
| Triple point [i] || 13.8033 K, 7.042 kPa
... 

. Specifically, an amide can also be regarded as a derivative of a carboxylic acid Carboxylic acid

Carboxylic acids are organic acid [i]s characterized by the presence of a carboxyl group, which ha ... 

 in which the hydroxyl group has been replaced by an amine Amine

Amines are organic compound [i]s and a type of functional group [i] that contain nitrogen [i] as the key ... 

 or ammonia Ammonia

Ammonia is a compound [i] of nitrogen [i] and hydrogen [i] with the formula [i] ... 

.

Compounds in which a hydrogen Hydrogen

|-
| Triple point [i] || 13.8033 K, 7.042 kPa
... 

 atom Atom

In chemistry [i] and physics [i], an atom is the smallest possible particle of a chemical element [i] t ... 

 on nitrogen Nitrogen

Nitrogen is a chemical element [i] which has the symbol N and atomic number [i] 7 in the periodic table [i] ... 

 from ammonia Ammonia

Ammonia is a compound [i] of nitrogen [i] and hydrogen [i] with the formula [i] ... 

 or an amine Amine

Amines are organic compound [i]s and a type of functional group [i] that contain nitrogen [i] as the key ... 

 is replaced by a metal Metal

In chemistry, a metal is an element [i] that readily forms positive ion [i]s and has ... 

 cation are also known as amides or azanides.

The second sense of the word amide is the amide anion, which is a deprotonated form of ammonia Ammonia

Ammonia is a compound [i] of nitrogen [i] and hydrogen [i] with the formula [i] ... 

  or an amine Amine

Amines are organic compound [i]s and a type of functional group [i] that contain nitrogen [i] as the key ... 

. It is generally represented by the formula: [R1NR2]-, and is an extremely strong base, due to the extreme weakness of ammonia Ammonia

Ammonia is a compound [i] of nitrogen [i] and hydrogen [i] with the formula [i] ... 

 and its analogues as Brønsted acids.

The remainder of this article is about the carbonyl Carbonyl

In organic chemistry [i], a carbonyl group is a functional group [i] composed of a carbon [i] atom [i] double-bonded [i]... 

-nitrogen Nitrogen

Nitrogen is a chemical element [i] which has the symbol N and atomic number [i] 7 in the periodic table [i] ... 

 sense of amide. For examples of the anionic amide, see the articles Sodium amide Sodium amide

Sodium amide, also called sodamide, is NaNH2.... 

 and Lithium diisopropylamide Lithium diisopropylamide

Lithium diisopropylamide with the formula [(CH3)2CH]2NLi, is a strong base [i], widely used in organic chemistry [i] ... 

.

Amide synthesis

  • Amides are commonly formed from the reaction of a carboxylic acid Carboxylic acid

    Carboxylic acids are organic acid [i]s characterized by the presence of a carboxyl group, which ha ... 

     with an amine Amine

    Amines are organic compound [i]s and a type of functional group [i] that contain nitrogen [i] as the key ... 

    . This is the reaction Chemical reaction

    A chemical reaction is a process that results in the interconversion of chemical substance [i]s . ... 

     that forms peptide bond Peptide bond

    A peptide bond is a chemical bond [i] formed between two molecule [i]s when the carboxyl group [i] of on ... 

    s between amino acid Amino acid

    In chemistry [i], an amino acid is any molecule [i] that contains both amine [i] and carboxyl [i] functional group [i] ... 

    s. These amides can participate in hydrogen bond Hydrogen bond

    In chemistry [i], a hydrogen bond is a type of attractive intermolecular force [i] that exists between t ... 

    ing as hydrogen bond Hydrogen bond

    In chemistry [i], a hydrogen bond is a type of attractive intermolecular force [i] that exists between t ... 

     acceptors and donors, but do not ionize in aqueous solution Water

    Water is a taste [i]less, odor [i]less substance that is essential to all known forms of life [i] and i ... 

    , whereas their parent acids and amines are almost completely ionized in solution Solution



In chemistry [i], a solution is a homogeneous mixture [i] composed of one or more substances, known a ... 

 at neutral pH PH

pH is a measure of the acidity [i] of a solution [i], in terms of activity [i] of hydrogen [i] ... 

. Amide formation plays a role in the synthesis of some condensation polymer Condensation polymer

Condensation polymers are any class of polymers formed through a condensation reaction [i], releasing a ... 

s, such as nylon Nylon

Nylon [i] represents a family of synthetic polymer [i]s, a thermoplastic [i] material, fir ... 

 and Kevlar Kevlar

Kevlar is DuPont Company [i]'s brand name for a particular light but very strong aramid [i] fibre ... 

.


  • Cyclic amides are synthesized in the Beckmann rearrangement Beckmann rearrangement

    The Beckmann rearrangement, named after the German chemist Ernst Beckmann [i], is an acid-catalyzed [i] ... 

     from oxime Oxime

    [i]

[i]
[i]
... 

s.
  • Other amide-forming reaction Chemical reaction

    A chemical reaction is a process that results in the interconversion of chemical substance [i]s . ... 

    s are the Passerini reaction Passerini reaction

    The Passerini reaction is a chemical reaction [i] involving an isocyanide [i], an aldehyde [i], and a carboxylic acid [i] ... 

     and the Ugi reaction Ugi reaction

    The Ugi reaction is a multi-component reaction [i] in organic chemistry [i] involving a ketone [i] or aldehyde [i] ... 



Amide reactions

  • Amide breakdown is possible via amide hydrolysis.
  • In the Vilsmeier-Haack reaction Vilsmeier-Haack reaction

    The Vilsmeier-Haack reaction is the chemical reaction [i] of a substituted amide [i] with phosphorus oxychloride [i] ... 

     an amide is converted into an imine Imine

    An imine is a functional group [i] or chemical compound [i] containing a carbon [i]-nitrogen [i] double bond [i] ... 

    .
  • Hofmann rearrangement Hofmann rearrangement

    The Hofmann rearrangement is the organic [i] reaction of a primary amide [i] to a prim ... 

     of primary amides to primary amine Amine

    Amines are organic compound [i]s and a type of functional group [i] that contain nitrogen [i] as the key ... 

    s.

Amide properties

An amide linkage is kinetically stable to hydrolysis Hydrolysis

Hydrolysis is a chemical reaction [i] or process in which a molecule [i] is split into two parts by reac ... 

. However, it can be hydrolysed in boiling alkali, as well as in strong acidic conditions. Amide linkages in a biochemical Biochemistry

Biochemistry is the study of the chemical processes and chemical transformations in living organism [i]s ... 

 context are called peptide link Peptide bond

A peptide bond is a chemical bond [i] formed between two molecule [i]s when the carboxyl group [i] of on ... 

ages. Amide linkages constitute a defining molecular feature of protein Protein

Proteins are large organic compound [i]s made of amino acid [i]s arranged in a linear chain and joined b ... 

s, the secondary structure Secondary structure

Secondary structure in biochemistry [i] and structural biology [i] describes the general three-dimension ... 

 of which is due in part to the hydrogen bonding Hydrogen bond

In chemistry [i], a hydrogen bond is a type of attractive intermolecular force [i] that exists between t ... 

 abilities of amides.

Compared to amine Amine

Amines are organic compound [i]s and a type of functional group [i] that contain nitrogen [i] as the key ... 

s, amides are very weak bases. While the conjugate acid of an amine Amine

Amines are organic compound [i]s and a type of functional group [i] that contain nitrogen [i] as the key ... 

 has a pKa of about 9.5, the conjugate acid of an amide has a pKa around -0.5. Therefore amides don't have as clearly noticeable acid-base properties in water Water

Water is a taste [i]less, odor [i]less substance that is essential to all known forms of life [i] and i ... 

. This lack of basicity is discussed in the peptide bond Peptide bond

A peptide bond is a chemical bond [i] formed between two molecule [i]s when the carboxyl group [i] of on ... 

 article, and explained by the electron Electron

The electron is a fundamental [i] subatomic particle [i] that carries an electric charge [i]... 

-withdrawing nature of the carbonyl group Carbonyl

In organic chemistry [i], a carbonyl group is a functional group [i] composed of a carbon [i] atom [i] double-bonded [i]... 

 where the lone pair of electron Electron

The electron is a fundamental [i] subatomic particle [i] that carries an electric charge [i]... 

s on the nitrogen Nitrogen

Nitrogen is a chemical element [i] which has the symbol N and atomic number [i] 7 in the periodic table [i] ... 

 is delocalized by resonance, thus forming a partial double bond Covalent bond

Covalent bonding is an intramolecular form of chemical bond [i]ing characterized by the sharing of one o ... 

 with the carbonyl Carbonyl

In organic chemistry [i], a carbonyl group is a functional group [i] composed of a carbon [i] atom [i] double-bonded [i]... 

 carbon Carbon

Carbon is a chemical element [i] in the periodic table [i] that has the symbol [i] C' ... 

 and putting a negative charge on the oxygen Oxygen

Oxygen is a chemical element [i] with the chemical symbol O and atomic number [i] 8.... 

. On the other hand, amides are much stronger bases than carboxylic acid Carboxylic acid

Carboxylic acids are organic acid [i]s characterized by the presence of a carboxyl group, which ha ... 

s, ester Ester

In chemistry [i], esters are organic compound [i]s in which an organic group [i] replac ... 

s, aldehyde Aldehyde

An aldehyde is an organic compound containing
... 

s, and ketone Ketone

A ketone is either the functional group [i] characterized by a carbonyl [i] group linked to two other carbon [i]... 

s .

Derivatives

Sulfonamides are analogues of amides in which the atom double-bonded to oxygen Oxygen

Oxygen is a chemical element [i] with the chemical symbol O and atomic number [i] 8.... 

 is sulfur Sulfur

Sulfur or sulphur is the chemical element [i] in the periodic table [i] that has the symbol S' ... 

 rather than carbon Carbon

Carbon is a chemical element [i] in the periodic table [i] that has the symbol [i] C' ... 

.

Naming conventions

  • Example: CH3CONH2 is named acetamide or ethanamide
  • Other examples: propan-1-amide, N,N-dimethylpropanamide, acrylamide
  • For more detail see IUPAC nomenclature of organic chemistry - Amines and Amides IUPAC nomenclature of organic chemistry

    The IUPAC nomenclature of organic chemistry is a systematic [i] way of naming organic chemical compound [i] ... 



External links