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{{Short description|Chemical compound as a cyclicCyclic amide}}
[[Image:Lactams General Formulae V.1.png|thumb|right|450px|From left to right, the above are general structures of a [[β-lactam]], a [[γ-lactam]], a [[δ-lactam]], and an [[ε-lactam]]. TheTheir specificcommon structuresnames are β-propiolactam, γ-butyrolactam, δ-valerolactam, and ε-caprolactam.]]
 
A '''lactam''' is a [[Cyclic compound|cyclic]] [[amide]], formally derived from an [[amino]] [[alkanoic acid]] through [[cyclization]] reactions. The term is a [[portmanteau]] of the words ''[[lactone]]'' + ''[[amide]]''.
 
==Nomenclature==
[[Greek_alphabet#Letters|Greek prefixesprefix]]es in alphabetical order indicate ring size:.
 
{| {{table}}
* α-Lactam (3-atom rings)
! Ring size<br />(number of atoms in the ring)
* [[β-Lactam]] (4-atom rings)
! {{nobr|[[Systematic name]]}}
* [[2-Pyrrolidone|γ-Lactam]] (5-atom rings)
! [[IUPAC name]]
* [[2-Piperidinone|δ-Lactam]] (6-atom rings)
! {{nobr|[[Trivial name|Common name]]}}(s)
* [[Caprolactam|ε-Lactam]] (7-atom rings)
! Structure
|-
|3
|[[α-Lactam]]
|Aziridin-2-one
|α-Acetolactam
|[[File:Α-Lactam structure.svg|thumb|100px]]
|-
|4
* |[[β-Lactam]] (4-atom rings)
|Azetidin-2-one
|β-Propiolactam
|[[File:Beta-lactam.svg|thumb|100px]]
|-
|5
|[[γ-Lactam]]
|Pyrrolidin-2-one
|{{ubl|γ-Butyrolactam|2-Pyrrolidone}}
|[[File:Structural formula of 2-pyrrolidone.svg|thumb|100px]]
|-
|6
|[[δ-Lactam]]
|Piperidin-2-one
|{{ubl|δ-Valerolactam|2-Piperidinone|2-piperidone}}
|[[File:2-piperidinone.svg|thumb|100px]]
|-
|7
|[[ε-Lactam]]
|Azepan-2-one
|{{ubl|ε-Caprolactam|Caprolactam}}
|[[File:Caprolactam-2D-skeletal.png|thumb|100px]]
|}
 
This ring-size nomenclature stems from the fact that a [[hydrolysis|hydrolyzed]] of an α-Lactamlactam leads togives an α-[[amino acid]] and that of a β-Lactam togives a β-amino acid, ''etc''and so on.
 
==Synthesis==<!-- This section is linked from [[Organic reaction]] -->
General synthetic methods existare used for the [[organic synthesis]] of lactams.
 
===Beckmann rearrangement===
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===Schmidt reaction===
Lactams form from [[cyclic ketones]] and [[hydrazoic acid]] in the [[Schmidt reaction]]. Cyclohexanone with hydrazoic acid, forms [[Caprolactam|ε - Caprolactum]], which upon treatment with excess acid forms [[Pentylenetetrazol|Cardiazole]], a heart stimulant.
 
===Cyclization of amino acids===
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:[[File:Preparation_of_gamma_and_beta_lactams.svg|400px|Preparation of VL and beta lactam]]
 
==Lactam–lactim tautomerism==
==Tautomerization to lactims==
A '''lactim''' is a cyclic [[Imidic acid|carboximidicimidic acid]] compound characterized by an endocyclic carbon-nitrogen [[double bond]]. They are formed when lactams undergo [[tautomer]]ization.
 
:[[File:Lactam-Lactim-Tautomerie.svg|thumb|320px|&nbsp;&nbsp;&nbsp;Lactam&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Lactim]]
:[[File:Lactam-Lactim-Tautomerie.svg|frameless]]
 
==Reactions==<!-- This section is linked from [[Organic reaction]] -->
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==References==
{{Reflist}}
<references />
 
==External links==
*{{CommonscatinlineCommons category-inline|Lactams}}
 
{{Authority control}}
 
[[Category:Functional groups]]