553:
432:
470:
560:
425:
397:
502:
598:
591:
390:
463:
509:
637:
2808:
2659:
2727:
2564:
630:
669:
203:
is often described as consisting of two C=O double bonds, although in such delocalized systems, bond order is less distinct. As mentioned above, carbon forms triple bonds to oxygen in carbon monoxide and its derivatives, which includes acylium ions and
975:
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".
867:
Laniel, Dominique; Binck, Jannes; Winkler, Björn; Vogel, Sebastian; Fedotenko, Timofey; Chariton, Stella; Prakapenka, Vitali; Milman, Victor; Schnick, Wolfgang; Dubrovinsky, Leonid; Dubrovinskaia, Natalia (2021).
123:
with two carbon atoms, C–O–C, whereas in alcohols oxygen forms one single bond with carbon and one with hydrogen, C–O–H. In most organic carbonyl compounds, oxygen forms a covalent
2242:
319:, R–C≡O (typically 110-112 pm). Such triple bonds have a very high bond energy, even higher than N≡N triple bonds. Oxygen can also be trivalent, for example in
240:
of C–N or C–C bonds. Shortened single bonds are found with carboxylic acids (136 pm) due to partial double bond character and elongated bonds are found in
1122:
944:
Chevrier, B.; Carpentier, J. M. Le; Weiss, R. (1972). "Synthesis of two crystalline species of the
Friedel–Crafts intermediate antimony pentachloride-
1010:
1089:
931:
851:
800:
765:
2235:
135:, oxygen forms a single bond with carbon and accepts an electron from a metal to form an alkoxide anion, R–O, with three lone pairs. In
320:
1056:
882:
143:, >O– or =O– or ≡O, with one lone pair remaining. In carbon monoxide and acylium ions, oxygen forms a triple bond to carbon.
552:
2228:
2196:
1115:
431:
131:. In ethers, alcohols and carbonyl compounds, the four nonbonding electrons in oxygen's outer shell are nonbonding. In
469:
2797:
2792:
2787:
2782:
2777:
2772:
2767:
2762:
2757:
2752:
2747:
2742:
2732:
2675:
2569:
2490:
2485:
2342:
332:
2945:
2940:
2833:
2535:
2505:
2495:
2475:
2463:
2431:
2396:
2364:
2332:
2327:
2287:
1108:
2302:
2266:
2220:
1006:"Silicon Tetrakis(trifluoromethanesulfonate): A Simple Neutral Silane Acting as a Soft and Hard Lewis Superacid"
707:
702:
692:
248:
is also larger than C–N or C–C. For example, bond strengths are 91 kilocalories (380 kJ)/mol (at 298 K) in
2878:
2873:
2868:
2863:
2858:
2853:
2848:
2843:
2838:
2823:
2813:
2664:
2639:
2634:
2619:
2604:
2584:
2579:
2530:
2458:
2441:
2391:
2386:
2381:
2376:
2352:
2312:
978:
712:
2828:
2818:
2629:
2614:
2599:
2589:
2574:
2515:
2500:
2480:
2470:
2451:
2446:
2436:
2426:
2369:
2337:
559:
2297:
1971:
697:
636:
2737:
2652:
2594:
2557:
2552:
2540:
2520:
2510:
2416:
2411:
2406:
2347:
2322:
2168:
2154:
1383:
474:
291:, the oxygen atom contributes to pi-electron delocalization via its filled p-orbital and hence furans are
184:
1079:
597:
2545:
2357:
2292:
2282:
2182:
2098:
1582:
792:
1256:
1545:
2624:
2609:
2421:
2401:
2140:
2084:
2029:
2017:
1931:
1836:
1804:
1792:
1501:
1472:
1448:
1174:
2525:
2126:
2109:
1963:
1943:
1918:
1889:
1681:
1606:
1565:
1521:
1460:
1436:
1415:
1308:
1296:
1142:
501:
396:
377:
106:
with carbon, while a carbon atom can form up to four single bonds or two double bonds with oxygen.
75:
35:
590:
462:
1955:
1906:
1844:
1751:
1668:
1656:
1635:
1533:
1284:
1244:
508:
160:
51:
389:
2116:
2041:
2005:
1923:
1828:
1816:
1737:
1729:
1717:
1673:
1594:
1557:
1513:
1489:
1424:
1395:
1264:
1198:
1166:
1085:
1038:
901:
870:"Synthesis, crystal structure and structure–property relations of strontium orthocarbonate, Sr
847:
796:
761:
602:
217:
83:
629:
295:. Bond lengths of C=O bonds are around 123 pm in carbonyl compounds. The C=O bond length in
2070:
1988:
1877:
1780:
1768:
1742:
1647:
1577:
1484:
1407:
1375:
1362:
1186:
1131:
1028:
1018:
986:
957:
948:-toluoyl chloride. Crystal structures of the donor–acceptor complex and of the ionic salt".
909:
891:
831:
784:
687:
424:
344:
87:
71:
59:
199:, the carbonyl carbon forms one double bond and two single bonds to oxygen. The bonding in
2209:
2075:
2058:
1901:
1856:
1763:
1699:
1623:
1345:
1332:
1276:
1239:
1210:
1154:
571:
524:
312:
280:
192:
176:
151:
A carbon atom forms one single bond to oxygen in alcohols, ethers, and peroxides, two in
139:, one of oxygen's two lone pairs is used to form a third covalent bond which generates a
1618:
1337:
1222:
1033:
1005:
914:
869:
353:
296:
205:
200:
188:
128:
67:
1060:
2934:
2897:
1996:
1868:
1370:
1357:
839:
835:
668:
648:
436:
245:
196:
95:
2049:
1983:
1234:
17:
1708:
1690:
1075:
641:
564:
316:
304:
300:
292:
284:
264:
253:
237:
229:
172:
156:
136:
124:
120:
103:
743:
Advanced
Organic Chemistry Carey, Francis A., Sundberg, Richard J. 5th ed. 2007
102:, or a combination of the two. In neutral compounds, an oxygen atom can form a
896:
578:
358:
91:
905:
233:
63:
55:
1042:
1023:
307:
character and are consequently very short: 117 pm. Compounds with formal C
513:
485:
450:
268:
249:
164:
132:
961:
655:
612:
401:
241:
2252:
990:
489:
272:
257:
168:
152:
140:
47:
43:
1059:. Department of Chemistry, Michigan State University. Archived from
1100:
331:
Carbon–oxygen bond forming reactions are numerous. Promient is the
528:
443:
412:
288:
283:
and many more. Internal C=O bonds are found in positively charged
276:
180:
99:
79:
1081:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
39:
2224:
1104:
191:
forms one double bond and one single bond to oxygen. In
315:, which has a very short, strong bond (112.8 pm), and
2889:
232:for paraffinic C–O bonds are in the range of 143
1004:Hermannsdorfer, André; Driess, Matthias (2021).
1084:(6th ed.), New York: Wiley-Interscience,
94:by sharing electrons with other atoms to form
2236:
1116:
8:
271:compounds to which belong such compounds as
267:in functional groups collectively known as
256:, and 88 kilocalories (370 kJ)/mol in
2243:
2229:
2221:
1123:
1109:
1101:
216:The C–O bond is polarized towards oxygen (
163:. Carbon forms a double bond to oxygen in
2255:with other elements in the periodic table
1032:
1022:
913:
895:
846:(1st ed.). Oxford University Press.
826:
824:
822:
820:
818:
816:
814:
812:
779:
777:
343:Carbon–oxygen bonds are present in these
2202:
2198:
2188:
2184:
2174:
2170:
2160:
2156:
2146:
2142:
2132:
2128:
2118:
2100:
2090:
2086:
756:Smith, Michael B.; March, Jerry (2007).
688:Carbon compounds#Carbon-oxygen compounds
349:
50:. Carbon–oxygen bonds are found in many
760:(6th ed.). John Wiley & Sons.
751:
749:
724:
311:O triple bonds do not exist except for
252:, 87 kilocalories (360 kJ)/mol in
2272:
932:CRC Handbook of Chemistry and Physics
927:
925:
119:In ethers, oxygen forms two covalent
92:fill its outer shell with 8 electrons
7:
2914:Academic research, no widespread use
212:Electronegativities and bond lengths
758:March's Advanced Organic Chemistry
25:
321:triethyloxonium tetrafluoroborate
98:, accepting electrons to form an
2806:
2725:
2657:
2562:
2262:
667:
635:
628:
596:
589:
558:
551:
507:
500:
468:
461:
430:
423:
395:
388:
339:Functional groups with C-O bonds
263:Carbon and oxygen form terminal
1:
127:with carbon, C=O, known as a
570:many analogues are similar:
299:is 116 pm. The C=O bonds in
2962:
442:Many examples, inclluding
333:Williamson ether synthesis
2803:
2722:
2274:
2270:
2260:
1138:
897:10.1107/S2052520620016650
795:. pp. 292, 304–314.
789:Chemistry of the Elements
787:; Earnshaw, Alan (1997).
607:Many analogous compounds
1057:"Standard Bond Energies"
90:of its own and tends to
2909:Many uses in chemistry
2904:Core organic chemistry
1024:10.1002/anie.202103414
475:Di-tert-butyl peroxide
1011:Angew. Chem. Int. Ed.
793:Butterworth-Heinemann
785:Greenwood, Norman N.
335:and many oxidations.
734:John McMurry 2nd Ed.
708:Carbon–fluorine bond
703:Carbon–nitrogen bond
693:Carbon–hydrogen bond
189:carbonyl carbon atom
1074:Smith, Michael B.;
1017:(24): 13656–13660.
962:10.1021/ja00771a031
883:Acta Crystallogr. B
713:Silicon–oxygen bond
366:Structural Formula
52:inorganic compounds
36:polar covalent bond
1063:on 29 August 2016.
698:Carbon–carbon bond
618:1 & 1 & 1
244:(147 pm). The C–O
84:carbonyl compounds
32:carbon–oxygen bond
18:Carbon-oxygen bond
2928:
2927:
2884:
2883:
2218:
2217:
1091:978-0-471-72091-1
956:(16): 5718–5723.
853:978-0-19-850346-0
844:Organic Chemistry
834:; Greeves, Nick;
832:Clayden, Jonathan
802:978-0-08-037941-8
767:978-0-471-72091-1
732:Organic Chemistry
679:
678:
603:Phenyl isocyanate
497:RCHO and RC(O)R'
345:functional groups
218:electronegativity
147:Bonding at carbon
115:Bonding at oxygen
88:valence electrons
72:organic compounds
16:(Redirected from
2953:
2946:Chemical bonding
2941:Oxygen compounds
2920:
2915:
2910:
2905:
2810:
2809:
2729:
2728:
2661:
2660:
2566:
2565:
2263:
2245:
2238:
2231:
2222:
2206:
2192:
2178:
2164:
2150:
2136:
2122:
2112:
2105:
2094:
1328:
1327:
1326:
1318:
1317:
1132:Oxygen compounds
1125:
1118:
1111:
1102:
1095:
1094:
1071:
1065:
1064:
1053:
1047:
1046:
1036:
1026:
1001:
995:
994:
991:10.1039/B407654K
972:
966:
965:
950:J. Am. Chem. Soc
941:
935:
929:
920:
919:
917:
899:
864:
858:
857:
828:
807:
806:
791:(2nd ed.).
781:
772:
771:
753:
744:
741:
735:
729:
671:
639:
632:
600:
593:
572:Carbonate esters
562:
555:
525:Carboxylic acids
511:
504:
472:
465:
434:
427:
399:
392:
350:
281:carboxylic acids
193:carbonate esters
177:carboxylic acids
21:
2961:
2960:
2956:
2955:
2954:
2952:
2951:
2950:
2931:
2930:
2929:
2924:
2923:
2918:
2913:
2908:
2903:
2885:
2807:
2726:
2658:
2563:
2256:
2249:
2219:
2214:
2204:
2200:
2195:
2190:
2186:
2181:
2176:
2172:
2167:
2162:
2158:
2153:
2148:
2144:
2139:
2134:
2130:
2125:
2120:
2115:
2108:
2102:
2097:
2092:
2088:
2083:
2079:
2066:
2062:
2053:
2045:
2037:
2033:
2025:
2021:
2013:
2009:
2000:
1992:
1979:
1975:
1967:
1959:
1951:
1947:
1939:
1935:
1927:
1914:
1910:
1897:
1893:
1885:
1881:
1872:
1864:
1860:
1852:
1848:
1840:
1832:
1824:
1820:
1812:
1808:
1800:
1796:
1788:
1784:
1776:
1772:
1759:
1755:
1746:
1733:
1725:
1721:
1712:
1703:
1694:
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1660:
1651:
1643:
1639:
1631:
1627:
1614:
1610:
1602:
1598:
1590:
1586:
1573:
1569:
1561:
1553:
1549:
1541:
1537:
1529:
1525:
1517:
1509:
1505:
1497:
1493:
1480:
1476:
1468:
1464:
1456:
1452:
1444:
1440:
1432:
1428:
1419:
1411:
1403:
1399:
1391:
1387:
1379:
1366:
1353:
1349:
1341:
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1322:
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1320:
1316:
1313:
1312:
1311:
1309:
1304:
1300:
1292:
1288:
1280:
1272:
1268:
1260:
1252:
1248:
1230:
1226:
1218:
1214:
1206:
1202:
1194:
1190:
1182:
1178:
1170:
1162:
1158:
1150:
1146:
1134:
1129:
1099:
1098:
1092:
1073:
1072:
1068:
1055:
1054:
1050:
1003:
1002:
998:
974:
973:
969:
943:
942:
938:
930:
923:
877:
873:
866:
865:
861:
854:
830:
829:
810:
803:
783:
782:
775:
768:
755:
754:
747:
742:
738:
730:
726:
721:
684:
644:
640:
624:
601:
567:
563:
547:
543:
541:
537:
516:
512:
477:
473:
439:
435:
404:
400:
341:
329:
313:carbon monoxide
214:
206:metal carbonyls
161:orthocarbonates
149:
117:
112:
86:. Oxygen has 6
68:metal carbonyls
28:
23:
22:
15:
12:
11:
5:
2959:
2957:
2949:
2948:
2943:
2933:
2932:
2926:
2925:
2922:
2921:
2916:
2911:
2906:
2901:
2898:Chemical bonds
2894:
2893:
2891:
2887:
2886:
2882:
2881:
2876:
2871:
2866:
2861:
2856:
2851:
2846:
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2836:
2831:
2826:
2821:
2816:
2811:
2804:
2801:
2800:
2795:
2790:
2785:
2780:
2775:
2770:
2765:
2760:
2755:
2750:
2745:
2740:
2735:
2730:
2723:
2720:
2719:
2715:
2714:
2711:
2708:
2705:
2702:
2699:
2696:
2693:
2690:
2687:
2684:
2681:
2678:
2673:
2670:
2667:
2662:
2655:
2650:
2646:
2645:
2642:
2637:
2632:
2627:
2622:
2617:
2612:
2607:
2602:
2597:
2592:
2587:
2582:
2577:
2572:
2567:
2560:
2555:
2549:
2548:
2543:
2538:
2533:
2528:
2523:
2518:
2513:
2508:
2503:
2498:
2493:
2488:
2483:
2478:
2473:
2468:
2466:
2461:
2455:
2454:
2449:
2444:
2439:
2434:
2429:
2424:
2419:
2414:
2409:
2404:
2399:
2394:
2389:
2384:
2379:
2374:
2372:
2367:
2361:
2360:
2355:
2350:
2345:
2340:
2335:
2330:
2325:
2319:
2318:
2315:
2310:
2305:
2300:
2295:
2290:
2285:
2279:
2278:
2275:
2273:
2271:
2269:
2261:
2258:
2257:
2250:
2248:
2247:
2240:
2233:
2225:
2216:
2215:
2213:
2212:
2207:
2193:
2179:
2165:
2151:
2137:
2123:
2113:
2106:
2095:
2081:
2077:
2073:
2068:
2064:
2060:
2056:
2051:
2047:
2043:
2039:
2035:
2031:
2027:
2023:
2019:
2015:
2011:
2007:
2003:
1998:
1994:
1990:
1986:
1981:
1977:
1973:
1969:
1965:
1961:
1957:
1953:
1949:
1945:
1941:
1937:
1933:
1929:
1925:
1921:
1916:
1912:
1908:
1904:
1899:
1895:
1891:
1887:
1883:
1879:
1875:
1870:
1866:
1862:
1858:
1854:
1850:
1846:
1842:
1838:
1834:
1830:
1826:
1822:
1818:
1814:
1810:
1806:
1802:
1798:
1794:
1790:
1786:
1782:
1778:
1774:
1770:
1766:
1761:
1757:
1753:
1749:
1744:
1740:
1735:
1731:
1727:
1723:
1719:
1715:
1710:
1706:
1701:
1697:
1692:
1688:
1683:
1679:
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1671:
1666:
1662:
1658:
1654:
1649:
1645:
1641:
1637:
1633:
1629:
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1621:
1616:
1612:
1608:
1604:
1600:
1596:
1592:
1588:
1584:
1580:
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1571:
1567:
1563:
1559:
1555:
1551:
1547:
1543:
1539:
1535:
1531:
1527:
1523:
1519:
1515:
1511:
1507:
1503:
1499:
1495:
1491:
1487:
1482:
1478:
1474:
1470:
1466:
1462:
1458:
1454:
1450:
1446:
1442:
1438:
1434:
1430:
1426:
1422:
1417:
1413:
1409:
1405:
1401:
1397:
1393:
1389:
1385:
1381:
1377:
1373:
1368:
1364:
1360:
1355:
1351:
1347:
1343:
1339:
1335:
1330:
1323:
1314:
1306:
1302:
1298:
1294:
1290:
1286:
1282:
1278:
1274:
1270:
1266:
1262:
1258:
1254:
1250:
1246:
1242:
1237:
1232:
1228:
1224:
1220:
1216:
1212:
1208:
1204:
1200:
1196:
1192:
1188:
1184:
1180:
1176:
1172:
1168:
1164:
1160:
1156:
1152:
1148:
1144:
1139:
1136:
1135:
1130:
1128:
1127:
1120:
1113:
1105:
1097:
1096:
1090:
1066:
1048:
996:
967:
936:
921:
890:(1): 131–137.
875:
871:
859:
852:
840:Wothers, Peter
836:Warren, Stuart
808:
801:
773:
766:
745:
736:
723:
722:
720:
717:
716:
715:
710:
705:
700:
695:
690:
683:
680:
677:
676:
674:
672:
665:
662:
659:
652:
651:
649:Pyrylium salts
645:
633:
626:
622:
619:
616:
609:
608:
605:
594:
587:
584:
581:
575:
574:
568:
556:
549:
545:
539:
534:
531:
521:
520:
519:Many examples
517:
505:
498:
495:
492:
482:
481:
480:Many examples
478:
466:
459:
456:
453:
447:
446:
440:
428:
421:
418:
415:
409:
408:
407:Many examples
405:
393:
386:
383:
380:
374:
373:
370:
367:
364:
361:
356:
354:Chemical class
340:
337:
328:
325:
297:carbon dioxide
213:
210:
201:carbon dioxide
159:, and four in
148:
145:
129:carbonyl group
116:
113:
111:
110:Bonding motifs
108:
96:covalent bonds
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
2958:
2947:
2944:
2942:
2939:
2938:
2936:
2917:
2912:
2907:
2902:
2899:
2896:
2895:
2892:
2888:
2880:
2877:
2875:
2872:
2870:
2867:
2865:
2862:
2860:
2857:
2855:
2852:
2850:
2847:
2845:
2842:
2840:
2837:
2835:
2832:
2830:
2827:
2825:
2822:
2820:
2817:
2815:
2812:
2805:
2802:
2799:
2796:
2794:
2791:
2789:
2786:
2784:
2781:
2779:
2776:
2774:
2771:
2769:
2766:
2764:
2761:
2759:
2756:
2754:
2751:
2749:
2746:
2744:
2741:
2739:
2736:
2734:
2731:
2724:
2721:
2717:
2716:
2712:
2709:
2706:
2703:
2700:
2697:
2694:
2691:
2688:
2685:
2682:
2679:
2677:
2674:
2671:
2668:
2666:
2663:
2656:
2654:
2651:
2648:
2647:
2643:
2641:
2638:
2636:
2633:
2631:
2628:
2626:
2623:
2621:
2618:
2616:
2613:
2611:
2608:
2606:
2603:
2601:
2598:
2596:
2593:
2591:
2588:
2586:
2583:
2581:
2578:
2576:
2573:
2571:
2568:
2561:
2559:
2556:
2554:
2551:
2550:
2547:
2544:
2542:
2539:
2537:
2534:
2532:
2529:
2527:
2524:
2522:
2519:
2517:
2514:
2512:
2509:
2507:
2504:
2502:
2499:
2497:
2494:
2492:
2489:
2487:
2484:
2482:
2479:
2477:
2474:
2472:
2469:
2467:
2465:
2462:
2460:
2457:
2456:
2453:
2450:
2448:
2445:
2443:
2440:
2438:
2435:
2433:
2430:
2428:
2425:
2423:
2420:
2418:
2415:
2413:
2410:
2408:
2405:
2403:
2400:
2398:
2395:
2393:
2390:
2388:
2385:
2383:
2380:
2378:
2375:
2373:
2371:
2368:
2366:
2363:
2362:
2359:
2356:
2354:
2351:
2349:
2346:
2344:
2341:
2339:
2336:
2334:
2331:
2329:
2326:
2324:
2321:
2320:
2316:
2314:
2311:
2309:
2306:
2304:
2301:
2299:
2296:
2294:
2291:
2289:
2286:
2284:
2281:
2280:
2276:
2268:
2265:
2264:
2259:
2254:
2251:Compounds of
2246:
2241:
2239:
2234:
2232:
2227:
2226:
2223:
2211:
2208:
2205:
2194:
2191:
2180:
2177:
2166:
2163:
2152:
2149:
2138:
2135:
2124:
2121:
2114:
2111:
2107:
2104:
2096:
2093:
2082:
2080:
2074:
2072:
2069:
2067:
2057:
2055:
2048:
2046:
2040:
2038:
2028:
2026:
2016:
2014:
2004:
2002:
1995:
1993:
1987:
1985:
1982:
1980:
1970:
1968:
1962:
1960:
1954:
1952:
1942:
1940:
1930:
1928:
1922:
1920:
1917:
1915:
1905:
1903:
1900:
1898:
1888:
1886:
1876:
1874:
1867:
1865:
1855:
1853:
1843:
1841:
1835:
1833:
1827:
1825:
1815:
1813:
1803:
1801:
1791:
1789:
1779:
1777:
1767:
1765:
1762:
1760:
1750:
1748:
1741:
1739:
1736:
1734:
1728:
1726:
1716:
1714:
1707:
1705:
1698:
1696:
1689:
1687:
1680:
1678:
1672:
1670:
1667:
1665:
1655:
1653:
1646:
1644:
1634:
1632:
1622:
1620:
1617:
1615:
1605:
1603:
1593:
1591:
1581:
1579:
1576:
1574:
1564:
1562:
1556:
1554:
1544:
1542:
1532:
1530:
1520:
1518:
1512:
1510:
1500:
1498:
1488:
1486:
1483:
1481:
1471:
1469:
1459:
1457:
1447:
1445:
1435:
1433:
1423:
1421:
1414:
1412:
1406:
1404:
1394:
1392:
1382:
1380:
1374:
1372:
1369:
1367:
1361:
1359:
1356:
1354:
1344:
1342:
1336:
1334:
1331:
1329:
1307:
1305:
1295:
1293:
1283:
1281:
1275:
1273:
1263:
1261:
1255:
1253:
1243:
1241:
1238:
1236:
1233:
1231:
1221:
1219:
1209:
1207:
1197:
1195:
1185:
1183:
1173:
1171:
1165:
1163:
1153:
1151:
1141:
1140:
1137:
1133:
1126:
1121:
1119:
1114:
1112:
1107:
1106:
1103:
1093:
1087:
1083:
1082:
1077:
1070:
1067:
1062:
1058:
1052:
1049:
1044:
1040:
1035:
1030:
1025:
1020:
1016:
1013:
1012:
1007:
1000:
997:
992:
988:
985:: 1568–1574.
984:
981:
980:
971:
968:
963:
959:
955:
951:
947:
940:
937:
933:
928:
926:
922:
916:
911:
907:
903:
898:
893:
889:
885:
884:
879:
863:
860:
855:
849:
845:
841:
837:
833:
827:
825:
823:
821:
819:
817:
815:
813:
809:
804:
798:
794:
790:
786:
780:
778:
774:
769:
763:
759:
752:
750:
746:
740:
737:
733:
728:
725:
718:
714:
711:
709:
706:
704:
701:
699:
696:
694:
691:
689:
686:
685:
681:
675:
673:
670:
666:
663:
660:
657:
654:
653:
650:
646:
643:
638:
634:
631:
627:
620:
617:
614:
611:
610:
606:
604:
599:
595:
592:
588:
585:
582:
580:
577:
576:
573:
569:
566:
561:
557:
554:
550:
535:
532:
530:
526:
523:
522:
518:
515:
510:
506:
503:
499:
496:
493:
491:
487:
484:
483:
479:
476:
471:
467:
464:
460:
457:
454:
452:
449:
448:
445:
441:
438:
437:Diethyl ether
433:
429:
426:
422:
419:
416:
414:
411:
410:
406:
403:
398:
394:
391:
387:
384:
381:
379:
376:
375:
371:
368:
365:
362:
360:
357:
355:
352:
351:
348:
346:
338:
336:
334:
326:
324:
322:
318:
314:
310:
306:
303:have partial
302:
298:
294:
290:
286:
282:
278:
274:
270:
266:
261:
259:
255:
251:
247:
246:bond strength
243:
239:
235:
231:
227:
223:
219:
211:
209:
207:
202:
198:
197:carbonic acid
194:
190:
186:
182:
178:
174:
170:
166:
162:
158:
154:
146:
144:
142:
138:
134:
130:
126:
122:
114:
109:
107:
105:
101:
97:
93:
89:
85:
81:
77:
73:
69:
65:
61:
57:
56:carbon oxides
53:
49:
45:
41:
37:
33:
27:Chemical bond
19:
2919:Bond unknown
2307:
1080:
1076:March, Jerry
1069:
1061:the original
1051:
1014:
1009:
999:
982:
979:New J. Chem.
977:
970:
953:
949:
945:
939:
887:
881:
862:
843:
788:
757:
739:
731:
727:
642:Anthocyanins
542:H) and RCOOR
342:
330:
317:acylium ions
308:
301:acyl halides
285:oxonium ions
265:double bonds
262:
236:– less than
230:Bond lengths
225:
221:
215:
173:acyl halides
157:ortho esters
150:
137:oxonium ions
121:single bonds
118:
31:
29:
579:Isocyanates
565:Acetic acid
305:triple bond
254:methylamine
155:, three in
125:double bond
104:triple bond
2935:Categories
719:References
533:1 & 2
359:Bond order
185:anhydrides
64:carbonates
60:oxohalides
2900:to carbon
906:2052-5206
647:includes
486:Aldehydes
451:Peroxides
327:Chemistry
165:aldehydes
133:alkoxides
70:, and in
1078:(2007),
1043:33826216
934:65Th Ed.
842:(2001).
682:See also
514:Acrolein
378:Alcohols
372:Comment
369:Example
363:Formula
293:aromatic
269:carbonyl
250:methanol
242:epoxides
224:O, 2.55
76:alcohols
74:such as
54:such as
38:between
2718:
2210:more...
1034:8252640
915:7941283
656:Acylium
613:Oxonium
544:(or RCO
538:(or RCO
490:Ketones
402:Ethanol
273:ketones
228:3.44).
187:, each
169:ketones
153:acetals
2890:Legend
2253:carbon
1088:
1041:
1031:
912:
904:
850:
799:
764:
529:Esters
458:ROOR′
444:Furans
413:Ethers
289:furans
287:. In
277:esters
258:ethane
181:esters
141:cation
82:, and
80:ethers
48:oxygen
44:carbon
586:RNCO
536:RCOOH
420:ROR′
238:those
220:of C
175:. In
100:anion
40:atoms
34:is a
1086:ISBN
1039:PMID
902:ISSN
848:ISBN
797:ISBN
762:ISBN
664:RCO
658:ions
615:ions
527:and
488:and
385:ROH
195:and
183:and
171:and
66:and
58:and
46:and
2864:CEs
2859:CCf
2854:CBk
2849:CCm
2844:CAm
2839:CPu
2834:CNp
2824:CPa
2819:CTh
2798:CYb
2793:CTm
2788:CEr
2783:CHo
2778:CDy
2773:CTb
2768:CGd
2763:CEu
2758:CSm
2753:CPm
2748:CNd
2743:CPr
2738:CCe
2733:CLa
2713:Og
2710:Ts
2707:Lv
2704:Mc
2701:Fl
2698:Nh
2695:Cn
2692:Rg
2689:Ds
2686:Mt
2683:Hs
2680:Bh
2676:CSg
2672:Db
2669:Rf
2653:CRa
2649:Fr
2644:Rn
2640:CAt
2635:CPo
2630:CBi
2625:CPb
2620:CTl
2615:CHg
2610:CAu
2605:CPt
2600:CIr
2595:COs
2590:CRe
2580:CTa
2575:CHf
2570:CLu
2558:CBa
2553:CCs
2546:CXe
2536:CTe
2531:CSb
2526:CSn
2521:CIn
2516:CCd
2511:CAg
2506:CPd
2501:CRh
2496:CRu
2491:CTc
2486:CMo
2481:CNb
2476:CZr
2464:CSr
2459:CRb
2452:CKr
2447:CBr
2442:CSe
2437:CAs
2432:CGe
2427:CGa
2422:CZn
2417:CCu
2412:CNi
2407:CCo
2402:CFe
2397:CMn
2392:CCr
2382:CTi
2377:CSc
2370:CCa
2358:CAr
2353:CCl
2338:CSi
2333:CAl
2328:CMg
2323:CNa
2317:Ne
2288:CBe
2283:CLi
2277:He
2201:PtF
2076:NbO
2071:NbO
2042:NaO
1964:MoO
1956:MoO
1924:MnO
1919:MnO
1902:MgO
1829:IrO
1738:HgO
1730:HfO
1674:GeO
1669:GeO
1619:FeO
1578:CuO
1558:CsO
1514:CrO
1485:CoO
1408:ClO
1376:CeO
1371:CdO
1363:CaO
1358:CaO
1277:BrO
1257:BiO
1240:BeO
1235:BaO
1167:AmO
1029:PMC
1019:doi
987:doi
958:doi
910:PMC
892:doi
548:R)
42:of
2937::
2879:No
2874:Md
2869:Fm
2829:CU
2814:Ac
2665:Lr
2585:CW
2541:CI
2471:CY
2387:CV
2365:CK
2348:CS
2343:CP
2313:CF
2308:CO
2303:CN
2298:CC
2293:CB
2267:CH
2117:OF
2110:OF
2085:Nd
2059:Na
2050:Na
1989:NO
1984:NO
1972:Mo
1944:Mn
1932:Mn
1907:Mg
1890:Lu
1878:Li
1869:Li
1857:La
1837:KO
1817:In
1764:IO
1752:Ho
1743:Hg
1657:Ga
1648:Ga
1636:Fe
1624:Fe
1607:Eu
1595:Er
1583:Dy
1566:Cs
1552:12
1546:Cr
1534:Cr
1522:Cr
1502:Co
1490:Co
1473:Cl
1461:Cl
1449:Cl
1437:Cl
1425:Cl
1416:Cl
1396:Ce
1384:Ce
1338:CO
1333:CO
1310:Br
1297:Br
1285:Br
1265:Bi
1245:Bi
1211:Au
1199:As
1187:As
1175:Am
1155:Al
1143:Ag
1037:.
1027:.
1015:60
1008:.
983:28
954:94
952:.
924:^
908:.
900:.
888:77
886:.
880:.
874:CO
838:;
811:^
776:^
748:^
661:3
625:O
583:2
494:2
455:1
417:1
382:1
347::
323:.
279:,
275:,
260:.
234:pm
226:vs
222:vs
208:.
179:,
167:,
78:,
62:,
30:A
2244:e
2237:t
2230:v
2203:6
2199:2
2197:O
2189:2
2187:F
2185:6
2183:O
2175:2
2173:F
2171:5
2169:O
2161:2
2159:F
2157:4
2155:O
2147:2
2145:F
2143:3
2141:O
2133:2
2131:F
2129:2
2127:O
2119:2
2103:F
2101:2
2099:O
2091:3
2089:O
2087:2
2078:2
2065:2
2063:O
2061:2
2054:O
2052:2
2044:2
2036:5
2034:O
2032:2
2030:N
2024:4
2022:O
2020:2
2018:N
2012:3
2010:O
2008:2
2006:N
2001:O
1999:2
1997:N
1991:2
1978:3
1976:O
1974:2
1966:3
1958:2
1950:7
1948:O
1946:2
1938:3
1936:O
1934:2
1926:2
1913:3
1911:O
1909:2
1896:3
1894:O
1892:2
1884:2
1882:O
1880:2
1873:O
1871:2
1863:3
1861:O
1859:2
1851:2
1849:O
1847:2
1845:K
1839:2
1831:2
1823:3
1821:O
1819:2
1811:9
1809:O
1807:4
1805:I
1799:6
1797:O
1795:2
1793:I
1787:5
1785:O
1783:2
1781:I
1775:4
1773:O
1771:2
1769:I
1758:3
1756:O
1754:2
1747:O
1745:2
1732:2
1724:2
1722:O
1720:2
1718:H
1713:O
1711:2
1709:H
1704:O
1702:2
1700:H
1695:O
1693:2
1691:H
1686:O
1684:2
1682:H
1676:2
1663:3
1661:O
1659:2
1652:O
1650:2
1642:4
1640:O
1638:3
1630:3
1628:O
1626:2
1613:3
1611:O
1609:2
1601:3
1599:O
1597:2
1589:3
1587:O
1585:2
1572:3
1570:O
1568:2
1560:2
1550:O
1548:5
1540:5
1538:O
1536:2
1528:3
1526:O
1524:2
1516:3
1508:4
1506:O
1504:3
1496:3
1494:O
1492:2
1479:7
1477:O
1475:2
1467:6
1465:O
1463:2
1455:4
1453:O
1451:2
1443:3
1441:O
1439:2
1431:2
1429:O
1427:2
1420:O
1418:2
1410:2
1402:3
1400:O
1398:2
1390:4
1388:O
1386:3
1378:2
1365:2
1352:2
1350:O
1348:3
1346:C
1340:2
1324:8
1319:O
1315:3
1303:5
1301:O
1299:2
1291:3
1289:O
1287:2
1279:2
1271:5
1269:O
1267:2
1259:2
1251:3
1249:O
1247:2
1229:3
1227:O
1225:2
1223:B
1217:3
1215:O
1213:2
1205:5
1203:O
1201:2
1193:3
1191:O
1189:2
1181:3
1179:O
1177:2
1169:2
1161:3
1159:O
1157:2
1149:4
1147:O
1145:4
1124:e
1117:t
1110:v
1045:.
1021::
993:.
989::
964:.
960::
946:p
918:.
894::
878:"
876:4
872:2
856:.
805:.
770:.
623:3
621:R
546:2
540:2
309:≡
20:)
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