213:
1316:
1388:
1354:
402:
272:
300:
356:
31:
385:
309:
328:
1804:
365:
519:
337:
281:
421:
for rotation about an amide bond is 75–85 kJ/mol (18–20 kcal/mol), much larger than values observed for normal single bonds. For example, the C–C bond in ethane has an energy barrier of only 12 kJ/mol (3 kcal/mol). Once a nucleophile attacks and a tetrahedral intermediate is formed, the energetically
425:
Esters exhibit less resonance stabilization than amides, so the formation of a tetrahedral intermediate and subsequent loss of resonance is not as energetically unfavorable. Anhydrides experience even weaker resonance stabilization, since the resonance is split between two carbonyl groups, and are
1278:
and as a result, nucleophilic acyl substitution reactions are equilibrium processes. Because the equilibrium will favor the product containing the best nucleophile, the leaving group must be a comparatively poor nucleophile in order for a reaction to be practical.
796:
bonds. Metal acyls also arise from reactions involving acyl chlorides with low-valence metal complexes or by the reaction of organolithium compounds with metal carbonyls. Metal acyls are often described by two resonance structures, one of which emphasizes the
207:
ions are essentially unreactive towards nucleophilic substitution, since they possess no leaving group. The reactivity of these five classes of compounds covers a broad range; the relative reaction rates of acid chlorides and amides differ by a factor of 10.
1311:. Because the last step involves the loss of a proton, nucleophilic acyl substitution reactions are considered catalytic in acid. Also note that under acidic conditions, a nucleophile will typically exist in its protonated form (i.e. H−Z instead of Z).
1387:
212:
426:
more reactive than esters and amides. In acid halides, there is very little resonance, so the energetic penalty for forming a tetrahedral intermediate is small. This helps explain why acid halides are the most reactive acyl derivatives.
1274:. As a result of this two-step addition/elimination process, the nucleophile takes the place of the leaving group on the carbonyl compound by way of an intermediate state that does not contain a carbonyl. Both steps are
1587:
Davlieva, Milya G.; Lindeman, Sergey V.; Neretin, Ivan S.; Kochi, Jay K. (2004). "Structural effects of carbon monoxide coordination to carbon centers. π and σ bindings in aliphatic acyl versus aromatic aroylcations".
1342:. While nucleophilic acyl substitution reactions can be base-catalyzed, the reaction will not occur if the leaving group is a stronger base than the nucleophile (i.e. the leaving group must have a higher p
218:
A major factor in determining the reactivity of acyl derivatives is leaving group ability, which is related to acidity. Weak bases are better leaving groups than strong bases; a species with a strong
413:. Amides exhibit two main resonance forms. Both are major contributors to the overall structure, so much so that the amide bond between the carbonyl carbon and the amide nitrogen has significant
1315:
1353:
1556:
Chevrier, B.; Carpentier, J. M. Le; Weiss, R. (1972). "Synthesis of two crystalline species of the
Friedel–Crafts intermediate antimony pentachloride-
1526:
1449:
175:. In the most common arrangement, acyl groups are attached to a larger molecular fragment, in which case the carbon and oxygen atoms are linked by a
167:. Although the term is almost always applied to organic compounds, acyl groups can in principle be derived from other types of acids such as
1349:
than the nucleophile). Unlike acid-catalyzed processes, both the nucleophile and the leaving group exist as anions under basic conditions.
1836:
636:
are almost always unstable—usually too unstable to be exploited synthetically. They readily react with the neutral aldehyde to form an
238:. The reactivity of acyl compounds towards nucleophiles decreases as the basicity of the leaving group increases, as the table shows.
2755:
2760:
1622:
841:
1270:. After the tetrahedral intermediate forms, it collapses, recreating the carbonyl C=O bond and ejecting the leaving group in an
1677:
1227:
Acyl compounds react with nucleophiles via an addition mechanism: the nucleophile attacks the carbonyl carbon, forming a
1743:
690:, the most common derivative, serves as an acyl donor in many biosynthetic transformations. Such acyl compounds are
422:
favorable resonance effect is lost. This helps explain why amides are one of the least reactive acyl derivatives.
1829:
775:
1618:"Silicon Tetrakis(trifluoromethanesulfonate): A Simple Neutral Silane Acting as a Soft and Hard Lewis Superacid"
1783:
1497:
648:, as surrogates. However, as a partial exception, hindered dialkylformamides (e.g., diisopropylformamide, HCON
2659:
1808:
1291:
is protonated, which activates it towards nucleophilic attack. In the second step, the protonated carbonyl
729:
581:
1303:, which then collapses to eject the protonated leaving group (H−X), giving protonated carbonyl compound
2788:
2232:
1822:
788:
reactions, which are important in some catalytic reactions. Metal acyls arise usually via insertion of
554:
2269:
1590:
1413:
1228:
657:
1247:
and therefore more reactive nucleophile. The tetrahedral intermediate itself can be an alcohol or
2742:
1489:
1483:
737:
733:
2642:
1338:. The intermediate collapses and expels the leaving group (X) to give the substitution product
741:
618:
are readily generated from aldehydes by hydrogen-atom abstraction. However, they undergo rapid
1775:
1769:
2749:
2637:
745:
589:
562:
558:
410:
1560:-toluoyl chloride. Crystal structures of the donor–acceptor complex and of the ionic salt".
2783:
2718:
2163:
1271:
676:
there are many instances of acyl groups, in all major categories of biochemical molecules.
17:
8:
2024:
1402:
groups the acyl group is bonded to oxygen: R−C(=O)−O−R′ where R−C(=O) is the acyl group.
1275:
615:
49:
1645:
1617:
93:
2708:
2678:
2436:
2058:
1779:
1739:
1716:
1673:
1650:
1493:
756:
418:
223:
136:
1536:
1459:
409:
Another factor that plays a role in determining the reactivity of acyl compounds is
2413:
1907:
1845:
1706:
1640:
1630:
1598:
1569:
1540:
1531:
1463:
1454:
1430:
1372:
1364:
1360:
1327:
1240:
798:
585:
447:
293:
458:
COCl). These compounds, which are treated as sources of acylium cations, are good
2632:
2391:
2386:
2369:
2352:
2153:
1902:
939:
861:
845:
826:
806:
789:
748:(5′-uridylic acid) are adenylyl, guanylyl, cytidylyl, and uridylyl respectively.
619:
543:
439:
265:
226:) will be a better leaving group than a species with a weak conjugate acid (e.g.
172:
152:
1330:
conditions, a nucleophile (Nuc) attacks the carbonyl group of the acyl compound
2703:
2698:
2574:
2569:
2564:
2357:
2324:
2108:
2090:
2080:
1376:
1123:
1060:
592:. Salts containing acylium ions can be generated by removal of the halide from
219:
105:
401:
2777:
2723:
2671:
2602:
2488:
2478:
2473:
2463:
2458:
2408:
2403:
2319:
2314:
2304:
2158:
2113:
2075:
2063:
2034:
1912:
1720:
1535:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
1458:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
1267:
1202:
1186:
1177:
785:
539:
435:
321:
168:
116:
1774:(4th ed.). Pacific Grove, CA: Brooks/Cole Publishing Company. pp.
1544:
1467:
2654:
2541:
2536:
2513:
2264:
2103:
2029:
1966:
1961:
1939:
1895:
1880:
1870:
1654:
1635:
1236:
1210:
1197:
1137:
1095:
1043:
1011:
969:
915:
895:
887:
818:
752:
673:
570:
271:
128:
1299:. Proton transfer from the nucleophile (Z) to the leaving group (X) gives
2713:
2666:
2627:
2508:
2396:
2381:
2376:
2364:
1929:
1924:
1890:
1885:
1875:
1853:
1405:
1263:
1078:
1025:
1006:
988:
925:
899:
891:
875:
853:
593:
547:
535:
414:
235:
227:
204:
188:
176:
1573:
355:
299:
2622:
2613:
2493:
2448:
2344:
2309:
2299:
2239:
2175:
2046:
763:
698:
687:
683:
2589:
2503:
2468:
2453:
2441:
2284:
2259:
2068:
1602:
1425:
1368:
691:
661:
565:
bearing a formal positive charge on the oxygen (rather than carbon):
349:
192:
85:
1814:
1711:
1694:
1295:
is attacked by a nucleophile (H−Z) to give tetrahedral intermediate
2597:
2551:
2518:
2214:
2120:
1994:
1949:
1934:
1248:
1163:
1113:
907:
679:
645:
640:
dimer. Hence, synthetic chemists have developed various acyl anion
580:
Acylium ions are common reactive intermediates, for example in the
503:
491:
231:
164:
124:
97:
73:
53:
656:) can undergo deprotonation at low temperature (−78 °C) with
2559:
2483:
2334:
2329:
2294:
2279:
2274:
2244:
2227:
2051:
1978:
1944:
1695:"Direct Formation of the Carbonyl Anion of Diisopropyl Formamide"
1380:
1287:
Under acidic conditions, the carbonyl group of the acyl compound
871:
The acyls are between the hydrocarbyls and the carboxylic acids.
710:
641:
637:
499:
459:
377:
160:
101:
69:
30:
384:
308:
2647:
2579:
2423:
2132:
2125:
2019:
2000:
1989:
1973:
1919:
1803:
1409:
1155:
974:
903:
883:
781:
718:
714:
574:
527:
507:
483:
109:
45:
41:
364:
327:
2528:
2498:
2431:
2289:
2254:
2249:
2222:
2170:
2137:
2041:
1865:
1244:
879:
793:
722:
633:
475:
463:
200:
196:
148:
140:
61:
57:
1586:
769:
1956:
1259:
1232:
911:
336:
280:
112:
518:
513:
191:
are the most reactive towards nucleophiles, followed by
1555:
1307:. The loss of a proton gives the substitution product,
1252:
1375:(NaOH), the oxygen-18 label is completely absent from
821:
of acyl groups are derived typically by replacing the
878:
group names that end in -yl are not acyl groups, but
1693:
Fraser, Robert R.; Hubert, Patrick R. (1974-01-01).
1615:
848:
of acyl groups are derived exactly by replacing the
553:
The carbon centres of acylium ions generally have a
542:(110-112 pm), which is shorter than the 112.8 pm of
569:. They are characteristic fragments observed in EI-
1266:attached to the central carbon that can act as a
462:for attaching acyl groups to various substrates.
2775:
1616:Hermannsdorfer, André; Driess, Matthias (2021).
1488:(6th ed.). New York: McGraw-Hill. pp.
1412:of the formula R−C≡O. They are intermediates in
187:There are five main types of acyl derivatives.
1830:
1733:
1692:
482:OR′) are classes of acyl compounds, as are
1837:
1823:
1334:to give tetrahedral alkoxide intermediate
405:The two major resonance forms of an amide.
1710:
1644:
1634:
1235:conditions, which make the carbonyl more
770:In organometallic chemistry and catalysis
1443:
1209:
1201:
1196:
1112:
1077:
1042:
1005:
968:
517:
400:
29:
1767:
1761:
1513:
1511:
1509:
1477:
1475:
842:IUPAC nomenclature of organic chemistry
14:
2776:
1371:-labeled ethoxy group is treated with
1231:. This reaction can be accelerated by
1222:
96:derived by the removal of one or more
1844:
1818:
1667:
1481:
514:Acylium cations, radicals, and anions
1506:
1472:
1282:
664:anion stable at these temperatures.
182:
1672:. Hoboken, NJ: Wiley. p. 857.
1321:
1258:The tetrahedral intermediate of an
522:Resonance structures of acylium ion
234:ion is a better leaving group than
155:, in which case it has the formula
24:
1670:March's Advanced Organic Chemistry
1532:Compendium of Chemical Terminology
1455:Compendium of Chemical Terminology
667:
538:in these cations is near 1.1
434:Well-known acyl compounds are the
383:
363:
354:
335:
326:
307:
298:
279:
270:
25:
2800:
1796:
1243:conditions, which provide a more
805:-alkylation of metal acyls gives
709:. For example, the acyl group of
1802:
1386:
1379:and is found exclusively in the
1352:
1314:
837:), as shown in the table below.
682:are acyl derivatives formed via
561:, and are best represented by a
211:
1752:
1727:
1393:
1359:This mechanism is supported by
902:), alkenyl groups derived from
868:, as shown in the table below.
812:
776:Transition metal acyl complexes
1686:
1661:
1609:
1580:
1549:
1520:
856:group's systemic name (or the
108:. It contains a double-bonded
13:
1:
1699:Canadian Journal of Chemistry
1436:
730:ribonucleoside monophosphates
622:to afford the alkyl radical:
498:H), where R and R′ stand for
1159:
1154:
860:suffix of the corresponding
852:suffix of the corresponding
825:suffix of the corresponding
701:are formed by replacing the
627:RC(H)=O → RC=O → R + C≡O
429:
151:) is usually derived from a
7:
1419:
10:
2805:
1734:Elschenbroich, C. (2006).
1668:Smith, Michael B. (2013).
1482:Carey, Francis A. (2006).
784:are intermediates in many
773:
44:(top left), as an acylium
2732:
2691:
2611:
2588:
2550:
2527:
2422:
2343:
2213:
2190:
2146:
2089:
2012:
1987:
1852:
1414:Friedel-Crafts acylations
937:
932:
923:
759:is called phosphatidyl-.
744:(5′-cytidylic acid), and
252:
48:(top centre), as an acyl
1229:tetrahedral intermediate
728:Names of acyl groups of
697:Names of acyl groups of
658:lithium diisopropylamide
582:Friedel–Crafts acylation
159:, where R represents an
147:if the organyl group is
2743:chemical classification
1758:Wade 2010, pp. 996–997.
1738:. Weinheim: Wiley-VCH.
1545:10.1351/goldbook.A00129
1517:Wade 2010, pp. 998–999.
1468:10.1351/goldbook.A00123
864:'s systemic name) with
1768:McMurry, John (1996).
1636:10.1002/anie.202103414
801:of the oxygen center.
660:as the base to form a
523:
406:
388:
368:
359:
340:
331:
312:
303:
284:
275:
81:
34:A general acyl group (
27:Chemical group (R–C=O)
2750:chemical nomenclature
1623:Angew. Chem. Int. Ed.
642:synthetic equivalents
605:→ [RCO][SbCl
590:Hayashi rearrangement
521:
404:
387:
367:
358:
339:
330:
311:
302:
283:
274:
33:
1811:at Wikimedia Commons
1272:elimination reaction
1262:compound contains a
882:groups derived from
829:'s common name with
755:, the acyl group of
740:(5′-guanylic acid),
736:(5′-adenylic acid),
559:atomic hybridization
534:. The carbon–oxygen
2206:not C, H or O)
1629:(24): 13656–13660.
1574:10.1021/ja00771a031
1251:, depending on the
1223:Reaction mechanisms
563:resonance structure
60:(bottom centre) or
2648:Hypervalent iodine
1363:experiments. When
524:
407:
389:
369:
360:
341:
332:
313:
304:
285:
276:
260:of Conjugate Acid
139:, the acyl group (
82:
2789:Functional groups
2771:
2770:
2709:Sulfenyl chloride
2687:
2686:
2186:
2185:
2005:(only C, H and O)
1846:Functional groups
1807:Media related to
1771:Organic Chemistry
1679:978-0-470-46259-1
1568:(16): 5718–5723.
1485:Organic Chemistry
1283:Acidic conditions
1255:of the reaction.
1220:
1219:
757:phosphatidic acid
586:organic reactions
526:Acylium ions are
399:
398:
224:hydrochloric acid
183:Reactivity trends
137:organic chemistry
64:(bottom right). (
16:(Redirected from
2796:
2738:
2643:Trifluoromethoxy
2211:
2210:
2207:
2010:
2009:
2006:
1859:
1839:
1832:
1825:
1816:
1815:
1806:
1790:
1789:
1765:
1759:
1756:
1750:
1749:
1731:
1725:
1724:
1714:
1690:
1684:
1683:
1665:
1659:
1658:
1648:
1638:
1613:
1607:
1606:
1603:10.1039/B407654K
1584:
1578:
1577:
1562:J. Am. Chem. Soc
1553:
1547:
1524:
1518:
1515:
1504:
1503:
1479:
1470:
1447:
1431:Functional group
1390:
1373:sodium hydroxide
1365:ethyl propionate
1361:isotope labeling
1356:
1322:Basic conditions
1318:
921:
920:
846:systematic names
628:
610:
568:
533:
448:benzoyl chloride
294:Acetic anhydride
241:
240:
215:
173:phosphonic acids
158:
134:
122:
79:
67:
52:(top right), an
39:
21:
2804:
2803:
2799:
2798:
2797:
2795:
2794:
2793:
2774:
2773:
2772:
2767:
2736:
2728:
2683:
2638:Trichloromethyl
2633:Trifluoromethyl
2607:
2584:
2546:
2523:
2418:
2387:Phosphine oxide
2339:
2205:
2203:
2202:
2200:
2198:
2196:
2194:
2192:
2182:
2142:
2085:
2004:
2003:
1998:
1993:
1983:
1857:
1856:
1848:
1843:
1799:
1794:
1793:
1786:
1766:
1762:
1757:
1753:
1746:
1736:Organometallics
1732:
1728:
1712:10.1139/v74-029
1691:
1687:
1680:
1666:
1662:
1614:
1610:
1585:
1581:
1554:
1550:
1525:
1521:
1516:
1507:
1500:
1480:
1473:
1448:
1444:
1439:
1422:
1396:
1348:
1324:
1285:
1225:
943:
940:carboxylic acid
934:
933:Acyl group name
929:
910:, butenyl), or
862:carboxylic acid
827:carboxylic acid
815:
807:Fischer carbene
790:carbon monoxide
778:
772:
670:
668:In biochemistry
655:
626:
620:decarbonylation
608:
604:
600:
584:and many other
566:
555:linear geometry
544:carbon monoxide
531:
530:of the formula
516:
506:in the case of
473:
457:
453:
445:
440:acetyl chloride
432:
417:character. The
266:Acetyl chloride
258:
185:
156:
153:carboxylic acid
132:
127:in the case of
120:
106:inorganic acids
100:groups from an
77:
76:in the case of
72:substituent or
65:
56:(bottom left),
35:
28:
23:
22:
15:
12:
11:
5:
2802:
2792:
2791:
2786:
2769:
2768:
2766:
2765:
2764:
2763:
2758:
2746:
2739:
2733:
2730:
2729:
2727:
2726:
2724:Sulfinylamines
2721:
2716:
2711:
2706:
2704:Phosphoramides
2701:
2699:Isothiocyanate
2695:
2693:
2689:
2688:
2685:
2684:
2682:
2681:
2676:
2675:
2674:
2664:
2663:
2662:
2652:
2651:
2650:
2645:
2640:
2635:
2630:
2619:
2617:
2609:
2608:
2606:
2605:
2600:
2594:
2592:
2586:
2585:
2583:
2582:
2577:
2575:Selenenic acid
2572:
2570:Seleninic acid
2567:
2565:Selenonic acid
2562:
2556:
2554:
2548:
2547:
2545:
2544:
2539:
2533:
2531:
2525:
2524:
2522:
2521:
2516:
2511:
2506:
2501:
2496:
2491:
2486:
2481:
2476:
2471:
2466:
2461:
2456:
2451:
2446:
2445:
2444:
2434:
2428:
2426:
2420:
2419:
2417:
2416:
2411:
2406:
2401:
2400:
2399:
2389:
2384:
2379:
2374:
2373:
2372:
2362:
2361:
2360:
2358:Phosphodiester
2349:
2347:
2341:
2340:
2338:
2337:
2332:
2327:
2322:
2317:
2312:
2307:
2302:
2297:
2292:
2287:
2282:
2277:
2272:
2267:
2262:
2257:
2252:
2247:
2242:
2237:
2236:
2235:
2230:
2219:
2217:
2208:
2204:(one element,
2188:
2187:
2184:
2183:
2181:
2180:
2179:
2178:
2168:
2167:
2166:
2161:
2150:
2148:
2144:
2143:
2141:
2140:
2135:
2130:
2129:
2128:
2118:
2117:
2116:
2111:
2106:
2095:
2093:
2087:
2086:
2084:
2083:
2081:Methylenedioxy
2078:
2073:
2072:
2071:
2066:
2056:
2055:
2054:
2049:
2039:
2038:
2037:
2027:
2022:
2016:
2014:
2007:
1985:
1984:
1982:
1981:
1976:
1971:
1970:
1969:
1964:
1954:
1953:
1952:
1947:
1942:
1937:
1932:
1927:
1917:
1916:
1915:
1910:
1900:
1899:
1898:
1893:
1888:
1883:
1878:
1873:
1862:
1860:
1858:(only C and H)
1850:
1849:
1842:
1841:
1834:
1827:
1819:
1813:
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766:are acylated.
762:Finally, many
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2655:Vinyl halide
2612:
2542:Borinic acid
2537:Boronic acid
2514:Thioxanthate
2098:
1854:Hydrocarbons
1770:
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1591:New J. Chem.
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1537:Acyl species
1530:
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1406:Acylium ions
1404:
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1394:Acyl species
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822:
819:common names
816:
813:Nomenclature
802:
779:
761:
750:
727:
706:
705:suffix with
702:
696:
686:metabolism.
678:
674:biochemistry
671:
649:
631:
613:
594:acyl halides
588:such as the
579:
571:mass spectra
552:
525:
495:
487:
479:
467:
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424:
408:
254:
217:
210:
189:Acid halides
186:
144:
129:formyl group
104:, including
89:
83:
36:
2784:Acyl groups
2719:Thiocyanate
2714:Sulfonamide
2679:Perchlorate
2667:Acyl halide
2628:Fluoroethyl
2509:Thionoester
2397:Phosphonium
2382:Phosphinate
2377:Phosphonous
2365:Phosphonate
2064:Hydroperoxy
1886:Cyclopropyl
1809:Acyl groups
1460:Acyl groups
1264:substituent
964:systematic
926:hydrocarbyl
876:hydrocarbyl
854:hydrocarbyl
809:complexes.
792:into metal–
764:saccharides
699:amino acids
567:[R−C≡O]
550:character.
548:triple-bond
536:bond length
415:double bond
236:acetate ion
228:acetic acid
205:Carboxylate
177:double bond
68:stands for
2778:Categories
2623:Haloalkane
2494:Thioketone
2449:Persulfide
2345:Phosphorus
2310:Isocyanate
2300:Isonitrile
2201:or oxygen
2199:hydrogen,
2195:not being
2176:Orthoester
2069:Dioxiranes
2047:Enol ether
1935:1-Propenyl
1785:0534238327
1499:0072828374
1437:References
1276:reversible
958:systematic
952:systematic
928:group name
692:thioesters
688:Acetyl-CoA
684:fatty acid
644:, such as
446:COCl) and
438:, such as
247:Structure
193:anhydrides
90:acyl group
66:R, R and R
2756:inorganic
2590:Tellurium
2504:Thioester
2469:Sulfoxide
2454:Disulfide
2442:Sulfonium
2392:Phosphine
2370:Phosphite
2353:Phosphate
2285:Carbamate
2260:Hydrazone
2193:element,
2191:Only one
2164:Anhydride
1903:Methylene
1721:0008-4042
1426:Acylation
1369:oxygen-18
944:RC(O)O-H
858:-oic acid
717:, and of
680:Acyl-CoAs
662:carbamoyl
646:dithianes
492:aldehydes
430:Compounds
411:resonance
350:Acetamide
230:). Thus,
163:group or
86:chemistry
2737:See also
2672:Chloride
2598:Tellurol
2552:Selenium
2519:Xanthate
2233:Ammonium
2215:Nitrogen
2197:carbon,
2154:Carboxyl
2121:Aldehyde
2109:Acryloyl
2091:carbonyl
1995:hydrogen
1950:Cumulene
1655:33826216
1420:See also
1367:with an
1249:alkoxide
1114:propenyl
914:groups (
908:propenyl
823:-ic acid
799:basicity
732:such as
616:radicals
504:hydrogen
490:R′) and
460:reagents
232:chloride
165:hydrogen
157:R−C(=O)−
145:alkanoyl
125:hydrogen
98:hydroxyl
74:hydrogen
54:aldehyde
2761:organic
2560:Selenol
2484:Sulfone
2437:Sulfide
2335:NONOate
2330:Nitroso
2320:Nitrite
2315:Nitrate
2305:Cyanate
2295:Nitrile
2280:Amidine
2275:Imidate
2245:Nitrene
2240:Hydrazo
2228:Enamine
2159:Acetoxy
2147:carboxy
2114:Benzoyl
2052:Epoxide
2035:Methoxy
2025:Alcohol
1979:Carbene
1913:Methine
1776:820–821
1646:8252640
1490:866–868
1410:cations
1400:acyloxy
1381:ethanol
1245:anionic
1160:butenyl
1061:propion
1048:propion
935:RC(O)–
904:alkenes
884:alkanes
840:In the
782:ligands
711:glycine
638:acyloin
575:ketones
557:and sp
528:cations
500:organyl
484:ketones
378:Acetate
161:organyl
115:and an
102:oxoacid
70:organyl
50:radical
40:) in a
2660:Iodide
2580:Selone
2424:Sulfur
2133:Ketone
2126:Ketene
2104:Acetyl
2059:Peroxy
2030:Alkoxy
2020:Acetal
2001:oxygen
1990:carbon
1974:Alkyne
1967:Benzyl
1962:Phenyl
1945:Allene
1940:Crotyl
1920:Alkene
1908:Bridge
1896:Pentyl
1881:Propyl
1871:Methyl
1782:
1742:
1719:
1676:
1653:
1643:
1496:
1326:Under
1233:acidic
1198:benzyl
1178:croton
1164:croton
1156:crotyl
1146:propen
1131:propen
1069:propan
1054:propan
1044:propyl
997:methan
982:methan
970:methyl
961:common
955:common
949:common
916:benzyl
896:propyl
888:methyl
844:, the
719:lysine
715:glycyl
634:anions
508:formyl
476:esters
474:) and
464:Amides
380:anion
222:(e.g.
201:amides
199:, and
197:esters
135:). In
110:oxygen
94:moiety
46:cation
42:ketone
2692:Other
2529:Boron
2499:Thial
2432:Thiol
2325:Nitro
2290:Imide
2270:Amide
2255:Oxime
2250:Imine
2223:Amine
2171:Ester
2138:Ynone
2042:Ether
2013:R-O-R
1988:Only
1930:Allyl
1925:Vinyl
1891:Butyl
1876:Ethyl
1866:Alkyl
1527:IUPAC
1450:IUPAC
1328:basic
1241:basic
1239:, or
1187:buten
1171:buten
1150:acid
1138:acryl
1124:acryl
1118:acryl
1108:acid
1104:butan
1096:butyr
1089:butan
1083:butyr
1079:butyl
1073:acid
1038:acid
1034:ethan
1019:ethan
1007:ethyl
1001:acid
900:butyl
892:ethyl
880:alkyl
794:alkyl
780:Acyl
723:lysyl
632:Acyl
614:Acyl
496:RC(O)
488:RC(O)
480:RC(O)
468:RC(O)
344:15.9
316:4.76
149:alkyl
143:name
141:IUPAC
133:H−C=O
123:) or
121:R−C=O
92:is a
88:, an
62:amide
58:ester
2614:Halo
2099:Acyl
1999:and
1957:Aryl
1780:ISBN
1740:ISBN
1717:ISSN
1674:ISBN
1651:PMID
1494:ISBN
1408:are
1260:acyl
1215:acid
1211:benz
1203:benz
1191:acid
1182:acid
1142:acid
1100:acid
1065:acid
1030:acid
1026:acet
1012:acet
993:acid
989:form
975:form
942:name
930:RC–
912:aryl
874:The
866:-oyl
835:-oyl
833:(or
817:The
703:-ine
502:(or
395:N/a
392:N/a
171:and
113:atom
37:blue
18:Acyl
2265:Azo
1707:doi
1641:PMC
1631:doi
1599:doi
1570:doi
1541:doi
1539:".
1464:doi
1462:".
1398:In
1213:oic
1205:oyl
1189:oic
1173:oyl
1148:oic
1133:oyl
1126:oyl
1122:or
1106:oic
1091:oyl
1071:oic
1056:oyl
1036:oic
1021:oyl
999:oic
984:oyl
918:).
850:-yl
831:-yl
751:In
746:UMP
742:CMP
738:GMP
734:AMP
721:is
713:is
707:-yl
672:In
573:of
532:RCO
510:).
470:NR′
442:(CH
372:38
288:−7
84:In
2780::
1997:,
1992:,
1778:.
1715:.
1703:52
1701:.
1697:.
1649:.
1639:.
1627:60
1620:.
1595:28
1566:94
1564:.
1529:,
1508:^
1492:.
1474:^
1452:,
1416:.
1383:.
1253:pH
1180:ic
1166:yl
1140:ic
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