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between approximately 1600–1900 cm(5263 nm to 6250 nm). The exact location of the absorption is well understood with respect to the geometry of the molecule. This absorption is known as the "carbonyl stretch" when displayed on an infrared absorption spectrum. In addition, the
476:
The polarity of C=O bond also enhances the acidity of any adjacent C-H bonds. Due to the positive charge on carbon and the negative charge on oxygen, carbonyl groups are subject to additions and/or nucleophilic attacks. A variety of nucleophiles attack, breaking the carbon-oxygen
527:: the C=O double-bond exhibits different resonances depending on surrounding atoms, generally a downfield shift. The C NMR of a carbonyl carbon is in the range of 160â220 ppm.
485:. Nucleophiliic reactivity is often proportional to the basicity of the nucleophile and as nucleophilicity increases, the stability within a carbonyl compound decreases. The
847:
892:
829:
Mayo D.W., Miller F.A and Hannah R.W âCourse Notes On The
Interpretation of Infrared and Raman Spectraâ 1st Ed. John Wiley & Sons Inc, 2004: New Jersey.
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878:
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250:
1933:
125:
The remainder of this article concerns itself with the organic chemistry definition of carbonyl, such that carbon and oxygen share a double bond.
134:
482:
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937:
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818:
652:
619:
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961:
95:), as part of many larger functional groups. A compound containing a carbonyl group is often referred to as a carbonyl compound.
1002:
854:
1832:
981:
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1956:
1961:
1405:
995:
943:
524:
486:
292:
1442:
968:
1915:
635:
G. Berthier, J. Serre (1966). "General and
Theoretical Aspects of the Carbonyl Group". In Saul Patai (ed.).
465:Ď values are much greater when the substituents on the carbonyl group are more electronegative than carbon.
537:
1815:
557:
35:
1922:
1810:
509:
457:. Substituents can affect carbonyl groups by addition or subtraction of electron density by means of a
197:
1891:
1336:
813:
Ouellette, R.J. and Rawn, J.D. "Organic
Chemistry" 1st Ed. Prentice-Hall, Inc., 1996: New Jersey.
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183:
521:
ultraviolet-visible spectra of propanone in water gives an absorption of carbonyl at 257 nm.
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639:. PATAI'S Chemistry of Functional Groups. Vol. 1. John Wiley & Sons. pp. 1â77.
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119:
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383:
260:
139:
In organic chemistry, a carbonyl group characterizes the following types of compounds:
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111:
31:
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1207:
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Interactions between carbonyl groups and other substituents were found in a study of
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For organic compounds, the length of the C-O bond does not vary widely from 120
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606:. PATAI'S Chemistry of Functional Groups. Vol. 2. John Wiley & Sons.
581:. PATAI'S Chemistry of Functional Groups. Vol. 1. John Wiley & Sons.
517:
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at the C atom. It is common to several classes of organic compounds (such as
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446:(amides). A variety of nucleophiles attack, breaking the carbon-oxygen
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434:. A qualitative order of electrophilicity is RCHO (aldehydes) > R
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103:
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991:
769:"Thiol Addition to the Carbonyl Group. Equilibria and Kinetics"
947:
767:
Lienhard, Gustav E.; Jencks, William P. (September 1966).
970:(retrieved Sep 2006). Includes water solubility data.
730:"The Interaction of Carbonyl Groups with Substituents"
668:
Newberry, Robert W.; Raines, Ronald T. (2017-08-15).
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45:
A ketone compound containing a carbonyl group (C=O)
409:. Inorganic carbonyls have shorter C-O distances:
397:compounds, which can exhibit special properties.
382:. Examples of inorganic carbonyl compounds are
1003:
8:
1383:
1182:
1010:
996:
988:
393:A special group of carbonyl compounds are
701:
773:Journal of the American Chemical Society
241:
141:
955:IUPAC Nomenclature of Organic Chemistry
569:
877:: CS1 maint: archived copy as title (
870:
953:Advanced Chemistry Development, Inc.
7:
723:
721:
98:The term carbonyl can also refer to
25:
982:The MSDS Hyperglossary- Anhydride
899:. 20 October 2021. Archived from
728:Wiberg, Kenneth B. (1999-11-01).
430:The carbonyl carbon is typically
135:ι,β-Unsaturated carbonyl compound
962:VirtualText of Organic Chemistry
298:
291:
284:
277:
210:
203:
196:
189:
182:
512:: the C=O double bond absorbs
500:are 16.7 and 19 respectively,
483:addition-elimination reactions
30:For carboxyl as a ligand, see
1:
734:Accounts of Chemical Research
674:Accounts of Chemical Research
967:Purdue Chemistry Department
686:10.1021/acs.accounts.7b00121
339:Other organic carbonyls are
306:
271:
244:
218:
176:
144:
893:"NMR Spectroscopy. 13C NMR"
602:Jacob Zabicky, ed. (1970).
34:. For the web browser, see
1978:
944:Frostburg State University
927:Organic Chemistry, 5th ed.
525:Nuclear magnetic resonance
132:
29:
1905:
645:10.1002/9780470771051.ch1
897:organicchemistrydata.org
577:Saul Patai, ed. (1966).
401:Structure and reactivity
1916:chemical classification
973:William Reusch. (2004)
977:Retrieved 23 May 2005.
948:Organic Chemistry Help
946:Chemistry Department.
670:"The nâĎ* Interaction"
558:Electrophilic addition
473:
442:R' (esters) > RCONH
336:
46:
36:Carbonyl (web browser)
27:Functional group (C=O)
1923:chemical nomenclature
975:Aldehydes and Ketones
960:William Reusch. tara
612:10.1002/9780470771228
587:10.1002/9780470771051
510:Infrared spectroscopy
471:
438:CO (ketones) > RCO
347:, the derivatives of
334:
44:
1379:not C, H or O)
785:10.1021/ja00969a017
472:A carbonyl compound
1957:Carbonyl compounds
1821:Hypervalent iodine
637:The Carbonyl Group
604:The Carbonyl Group
579:The Carbonyl Group
538:Carbonâoxygen bond
474:
337:
325:RC(O)N(R')C(O)R''
312:RC(O)C(R')CR''R'''
129:Carbonyl compounds
47:
1962:Functional groups
1944:
1943:
1882:Sulfenyl chloride
1860:
1859:
1359:
1358:
1178:(only C, H and O)
1019:Functional groups
903:on 6 January 2024
779:(17): 3982â3995.
746:10.1021/ar990008h
553:Bridging carbonyl
543:Organic chemistry
481:, and leading to
329:
328:
240:
239:
166:Carboxylate ester
61:with the formula
51:organic chemistry
16:(Redirected from
1969:
1911:
1816:Trifluoromethoxy
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1005:
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853:. Archived from
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838:
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705:
680:(8): 1838â1846.
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548:Functional group
388:carbonyl sulfide
360:carbonate esters
302:
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93:carboxylic acids
79:atom, and it is
65:, composed of a
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59:functional group
21:
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1972:
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1947:
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1901:
1856:
1811:Trichloromethyl
1806:Trifluoromethyl
1780:
1757:
1719:
1696:
1591:
1560:Phosphine oxide
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1021:
1016:
925:L.G. Wade, Jr.
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920:Further reading
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848:"Archived copy"
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740:(11): 922â929.
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308:General formula
220:General formula
161:Carboxylic acid
137:
131:
120:nickel carbonyl
100:carbon monoxide
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1897:Sulfinylamines
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1877:Phosphoramides
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1872:Isothiocyanate
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1755:
1750:
1748:Selenenic acid
1745:
1743:Seleninic acid
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1738:Selenonic acid
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384:carbon dioxide
352:chloroformates
349:acyl chlorides
335:Carbon dioxide
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116:metal carbonyl
112:organometallic
55:carbonyl group
32:Metal carbonyl
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1776:Telluroketone
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1652:Sulfinic acid
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1648:
1647:Thiosulfonate
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1632:Sulfenic acid
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1587:Phosphaallene
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1577:Phosphaalkene
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1249:Ethylenedioxy
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938:0-13-033832-X
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930:Prentice Hall
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860:on 2015-08-24
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835:0-471-24823-1
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596:9780470771051
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432:electrophilic
428:
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73:double-bonded
71:
68:
60:
56:
52:
43:
37:
33:
19:
1921:
1914:
1828:Vinyl halide
1785:
1715:Borinic acid
1710:Boronic acid
1687:Thioxanthate
1263:
1027:Hydrocarbons
926:
905:. Retrieved
901:the original
896:
887:
862:. Retrieved
855:the original
842:
825:
809:
776:
772:
762:
737:
733:
677:
673:
663:
636:
630:
603:
578:
572:
504:Spectroscopy
494:acetaldehyde
475:
462:
452:
429:
404:
392:
376:hydroxamates
338:
307:
272:
245:
219:
177:
145:
138:
124:
97:
54:
48:
1892:Thiocyanate
1887:Sulfonamide
1852:Perchlorate
1840:Acyl halide
1801:Fluoroethyl
1682:Thionoester
1570:Phosphonium
1555:Phosphinate
1550:Phosphonous
1538:Phosphonate
1237:Hydroperoxy
1059:Cyclopropyl
518:wavenumbers
479:double bond
448:double bond
420:, 116; and
380:isocyanates
256:Acyl halide
114:complex (a
1951:Categories
1796:Haloalkane
1667:Thioketone
1622:Persulfide
1518:Phosphorus
1483:Isocyanate
1473:Isonitrile
1374:or oxygen
1372:hydrogen,
1368:not being
1349:Orthoester
1242:Dioxiranes
1220:Enol ether
1108:1-Propenyl
864:2015-07-11
564:References
492:values of
459:sigma bond
427:, 116 pm.
407:picometers
395:dicarbonyl
364:thioesters
345:carbamates
236:RCONR'R''
133:See also:
1929:inorganic
1763:Tellurium
1677:Thioester
1642:Sulfoxide
1627:Disulfide
1615:Sulfonium
1565:Phosphine
1543:Phosphite
1526:Phosphate
1458:Carbamate
1433:Hydrazone
1366:element,
1364:Only one
1337:Anhydride
1076:Methylene
907:6 January
793:0002-7863
754:0001-4842
694:0001-4842
516:light at
273:Structure
178:Structure
108:inorganic
85:aldehydes
1910:See also
1845:Chloride
1771:Tellurol
1725:Selenium
1692:Xanthate
1406:Ammonium
1388:Nitrogen
1370:carbon,
1327:Carboxyl
1294:Aldehyde
1282:Acryloyl
1264:carbonyl
1168:hydrogen
1123:Cumulene
932:, 2002.
873:cite web
712:28735540
532:See also
514:infrared
455:collagen
368:lactones
356:phosgene
343:and the
246:Compound
151:Aldehyde
146:Compound
81:divalent
18:Carbonyl
1934:organic
1733:Selenol
1657:Sulfone
1610:Sulfide
1508:NONOate
1503:Nitroso
1493:Nitrite
1488:Nitrate
1478:Cyanate
1468:Nitrile
1453:Amidine
1448:Imidate
1418:Nitrene
1413:Hydrazo
1401:Enamine
1332:Acetoxy
1320:carboxy
1287:Benzoyl
1225:Epoxide
1208:Methoxy
1198:Alcohol
1152:Carbene
1086:Methine
964:(2004).
957:(1997).
950:(2000).
801:5915153
703:5559721
498:acetone
413:, 113;
372:lactams
118:, e.g.
89:ketones
1833:Iodide
1753:Selone
1597:Sulfur
1306:Ketone
1299:Ketene
1277:Acetyl
1232:Peroxy
1203:Alkoxy
1193:Acetal
1174:oxygen
1163:carbon
1147:Alkyne
1140:Benzyl
1135:Phenyl
1118:Allene
1113:Crotyl
1093:Alkene
1081:Bridge
1069:Pentyl
1054:Propyl
1044:Methyl
936:
833:
817:
799:
791:
752:
710:
700:
692:
651:
618:
593:
378:, and
233:RCOOR'
156:Ketone
106:in an
104:ligand
77:oxygen
75:to an
67:carbon
1865:Other
1702:Boron
1672:Thial
1605:Thiol
1498:Nitro
1463:Imide
1443:Amide
1428:Oxime
1423:Imine
1396:Amine
1344:Ester
1311:Ynone
1215:Ether
1186:R-O-R
1161:Only
1103:Allyl
1098:Vinyl
1064:Butyl
1049:Ethyl
1039:Alkyl
858:(PDF)
851:(PDF)
318:(RCO)
266:Imide
251:Enone
230:RCOOH
227:RCOR'
171:Amide
102:as a
57:is a
1787:Halo
1272:Acyl
1172:and
1130:Aryl
942:The
934:ISBN
909:2024
879:link
831:ISBN
815:ISBN
797:PMID
789:ISSN
750:ISSN
708:PMID
690:ISSN
649:ISBN
616:ISBN
591:ISBN
496:and
422:COCl
386:and
354:and
341:urea
315:RCOX
224:RCHO
91:and
70:atom
53:, a
49:For
1438:Azo
781:doi
742:doi
698:PMC
682:doi
641:doi
608:doi
583:doi
461:. Î
122:).
110:or
63:C=O
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1170:,
1165:,
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875:}}
871:{{
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777:88
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748:.
738:32
736:.
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720:^
706:.
696:.
688:.
678:50
676:.
672:.
647:.
614:.
589:.
487:pK
450:.
415:CO
411:CO
390:.
374:,
370:,
366:,
362:,
358:,
87:,
1011:e
1004:t
997:v
984:.
911:.
881:)
867:.
837:.
803:.
783::
756:.
744::
714:.
684::
657:.
643::
624:.
610::
599:.
585::
489:a
463:H
444:2
440:2
436:2
424:2
417:2
322:O
320:2
38:.
20:)
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