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  1. {{Cite journal|doi=10.1021/ja0663024|title="Amide Resonance" Correlates with a Breadth of C−N Rotation Barriers|year=2007|last1=Kemnitz|first1=Carl R.|last2=Loewen|first2=Mark J.|journal=Journal of the American Chemical Society|volume=129|issue=9|pages=2521–8|pmid=17295481}}
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  2. {{Cite journal|doi=10.1016/j.jep.2012.05.038|title=Alkamid database: Chemistry, occurrence and functionality of plant ''N''-alkylamides|year=2012|last1=Boonen|first1=Jente|last2=Bronselaer|first2=Antoon|last3=Nielandt|first3=Joachim|last4=Veryser|first4=Lieselotte|last5=De Tré|first5=Guy|last6=De Spiegeleer|first6=Bart|journal=Journal of Ethnopharmacology|volume=142|issue=3|pages=563–90|pmid=22659196}}
  3. {{cite journal|title=Amide bond formation and peptide coupling |first1=Christian A. G. N. |last1=Montalbetti |first2=Virginie |last2=Falque |journal=Tetrahedron |volume=61 |issue=46 |date=14 November 2005 |pages=10827–10852 |doi=10.1016/j.tet.2005.08.031}}
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  4. {{cite journal|title=Amide bond formation: beyond the myth of coupling reagents |first1=Eric |last1=Valeur |first2=Mark |last2=Bradley |journal=Chem. Soc. Rev. |date=2009|volume=38 |pages=606–631 |doi=10.1039/B701677H}}
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  5. {{cite journal|last1=Wenner|first1=Wilhelm|title=Phenylacetamide|journal=Organic Syntheses|date=1952|volume=32|page=92|doi=10.15227/orgsyn.032.0092}}
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  6. {{Cite journal|title=none|author =Bodroux F.|journal=Bull. Soc. Chim. France|year= 1905|volume= 33|pages= 831}}
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  7. {{Cite journal|author1=Schulenberg, J. W. |author2=Archer, S. |title=The Chapman Rearrangement|journal=[[Organic Reactions|Org. React.]]|year=1965|volume=14|doi=10.1002/0471264180.or014.01}}
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  8. {{Cite journal|doi=10.1039/CT9252701992|title=CCLXIX.—Imino-aryl ethers. Part III. The molecular rearrangement of ''N''-phenylbenziminophenyl ether |year=1925|last1=Chapman|first1=Arthur William|journal=Journal of the Chemical Society, Transactions|volume=127|pages=1992}}
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  9. {{Cite journal|author = [[Rudolf Leuckart (chemist)|Leuckart, R.]] |journal=[[Berichte der deutschen chemischen Gesellschaft]]|doi=10.1002/cber.188501801182|title= Ueber einige Reaktionen der aromatischen Cyanate|year= 1885|volume= 18|pages= 873–877}}
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  10. {{cite journal|last1=Corson|first1=B. B.|last2=Scott|first2=R. W.|last3=Vose|first3=C. E.|title=Cyanoacetamide|journal=Organic Syntheses|date=1941|volume=1|page=179|doi=10.15227/orgsyn.009.0036}}
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  11. {{cite journal|last1=Jacobs|first1=W. A.|title=Chloroacetamide|journal=Organic Syntheses|date=1941|volume=1|page=153|doi=10.15227/orgsyn.007.0016}}
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  12. {{cite journal|last1=Kleinberg|first1=J.|last2=Audrieth|first2=L. F.|title=Lactamide|journal=Organic Syntheses|date=1955|volume=3|page=516|doi=10.15227/orgsyn.021.0071}}
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  13. {{Cite journal|doi=10.1126/science.1145295|title=Direct Synthesis of Amides from Alcohols and Amines with Liberation of H2|year=2007|last1=Gunanathan|first1=C.|last2=Ben-David|first2=Y.|last3=Milstein|first3=D.|journal=Science|volume=317|issue=5839|pages=790–2|pmid=17690291}}
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Wikicode diff

3737
38==Characterization==38==Characterization==
39The presence of the functional group is generally easily established, at least in small molecules. They are the most common non-basic functional group. They can be distinguished from nitro and cyano groups by their [[IR spectroscopy|IR spectra]]. Amides exhibit a moderately intense ''ν''<sub>CO</sub> band near 1650&nbsp;cm<sup>−1</sup>. By <sup>1</sup>H [[NMR spectroscopy]], CON'''H'''R signals occur at low fields. In X-ray crystallography, the C(O)N center together with the three immediately adjacent atoms characteristically define a plane.39The presence of the functional group is generally easily established, at least in small molecules. They are the most common non-basic functional group. They can be distinguished from nitro and cyano groups by their [[IR spectroscopy|IR spectra]]. Amides exhibit a moderately intense ''ν''<sub>CO</sub> band near 1650&nbsp;cm<sup>−1</sup>. By <sup>1</sup>H [[NMR spectroscopy]], CON'''H'''R signals occur at low fields. In X-ray crystallography, the C(O)N center together with the three immediately adjacent atoms characteristically define a plane.
4040
41==Applications and occurrence==41==Applications and occurrence==
t42Amides are pervasive in nature and technology as structural materials. The amide linkage is easily formed, confers structural rigidity, and resists [[hydrolysis]]. [[Nylon]]s are [[polyamide]]s, as are the very resilient materials [[Aramid]], [[Twaron]], and [[Kevlar]]. Amide linkages constitute a defining molecular feature of [[protein]]s, the [[secondary structure]] of which is due in part to the [[hydrogen bonding]] abilities of amides. Amide linkages in a [[biochemistry|biochemical]] context are called [[peptide bond]]s when they occur in the main chain of a protein and [[isopeptide bond]]s when they occur to a side-chain of the protein. Proteins can have structural roles, such as in [[hair]] or [[spider silk]], but also nearly all [[enzyme]]s are proteins. Low molecular weight amides, such as [[dimethylformamide]] (HC(O)N(CH<sub>3</sub>)<sub>2</sub>), are common solvents. Many drugs are amides, including [[paracetamol]], [[penicillin]] and [[LSD]]. Moreover, plant ''N''-alkylamides have a wide range of biological functionalities.<ref>{{Cite journal|doi=10.1016/j.jep.2012.05.038|title=Alkamid database: Chemistry, occurrence and functionality of plant ''N''-alkylamides|year=2012|last1=Boonen|first1=Jente|last2=Bronselaer|first2=Antoon|last3=Nielandt|first3=Joachim|last4=Veryser|first4=Lieselotte|last5=De Tré|first5=Guy|last6=De Spiegeleer|first6=Bart|journal=Journal of Ethnopharmacology|volume=142|issue=3|pages=563–90|pmid=22659196}}</ref>t42Amides are pervasive in nature and technology as structural materials. The amide linkage is easily formed, confers structural rigidity, and resists [[hydrolysis]]. [[Nylon]]s are [[polyamide]]s, as are the very resilient materials [[Aramid]], [[Twaron]], and [[Kevlar]]. Amide linkages constitute a defining molecular feature of [[protein]]s, the [[secondary structure]] of which is due in part to the [[hydrogen bonding]] abilities of amides. Amide linkages in a [[biochemistry|biochemical]] context are called [[peptide bond]]s when they occur in the main chain of a protein and [[isopeptide bond]]s when they occur to a side-chain of the protein. Proteins can have structural roles, such as in [[hair]] or [[spider silk]], but also nearly all [[enzyme]]s are proteins. Low molecular weight amides, such as [[dimethylformamide]] (HC(O)N(CH<sub>3</sub>)<sub>2</sub>), are common solvents. Many drugs are amides, including [[paracetamol]], [[penicillin]] and [[LSD]]. Moreover, plant ''N''-alkylamides have a wide range of biological functionalities.<ref>{{Cite journal|doi=10.1016/j.jep.2012.05.038|title=Alkamid database: Chemistry, occurrence and functionality of plant ''N''-alkylamides|year=2012|last1=Boonen|first1=Jente|last2=Bronselaer|first2=Antoon|last3=Nielandt|first3=Joachim|last4=Veryser|first4=Lieselotte|last5=De Tré|first5=Guy|last6=De Spiegeleer|first6=Bart|journal=Journal of Ethnopharmacology|volume=142|issue=3|pages=563–90|pmid=22659196|hdl=1854/LU-2133714}}</ref>
4343
44==Amide synthesis==<!-- This section is linked from [[Organic reaction]] -->44==Amide synthesis==<!-- This section is linked from [[Organic reaction]] -->
45Many methods exist in amide synthesis.<ref>{{cite journal|title=Amide bond formation and peptide coupling |first1=Christian A. G. N. |last1=Montalbetti |first2=Virginie |last2=Falque |journal=Tetrahedron |volume=61 |issue=46 |date=14 November 2005 |pages=10827–10852 |doi=10.1016/j.tet.2005.08.031}}</ref> On paper, the simplest method for making amides is by coupling a [[carboxylic acid]] with an [[amine]]. In general this reaction is thermodynamically favorable, however it suffers from a high [[activation energy]], largely due to the amine first deprotonating the carboxylic acid, which reduces its reactivity. As such the direct reaction often requires high temperatures.45Many methods exist in amide synthesis.<ref>{{cite journal|title=Amide bond formation and peptide coupling |first1=Christian A. G. N. |last1=Montalbetti |first2=Virginie |last2=Falque |journal=Tetrahedron |volume=61 |issue=46 |date=14 November 2005 |pages=10827–10852 |doi=10.1016/j.tet.2005.08.031}}</ref> On paper, the simplest method for making amides is by coupling a [[carboxylic acid]] with an [[amine]]. In general this reaction is thermodynamically favorable, however it suffers from a high [[activation energy]], largely due to the amine first deprotonating the carboxylic acid, which reduces its reactivity. As such the direct reaction often requires high temperatures.
4646
47:RCO<sub>2</sub>H + R′R″NH {{eqm}} {{chem|RCO|2|−}} + {{chem|R′R″NH|2|+}} {{eqm}} RC(O)NR′R″ + H<sub>2</sub>O47:RCO<sub>2</sub>H + R′R″NH {{eqm}} {{chem|RCO|2|−}} + {{chem|R′R″NH|2|+}} {{eqm}} RC(O)NR′R″ + H<sub>2</sub>O

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