1176:
327:
341:
334:
320:
2405:
1158:
2369:
3008:
2859:
2927:
2764:
1167:
2393:
2381:
202:
of the carbon atom. A bond between a hydrogen atom and an sp hybridised carbon atom is about 0.6% shorter than between hydrogen and sp hybridised carbon. A bond between hydrogen and sp hybridised carbon is shorter still, about 3% shorter than sp C-H. This trend is illustrated by the
1718:
1488:
1448:
940:
1649:
1624:
1614:
2020:
1348:
1289:
1197:
2109:
1925:
1860:
1800:
1728:
1634:
1528:
1398:
1353:
1024:
2189:
1654:
1498:
1468:
1584:
1564:
1237:
1609:
1247:
949:
878:
Bollinger, J. M. Jr., Broderick, J. B. "Frontiers in enzymatic C-H-bond activation" Current
Opinion in Chemical Biology 2009, vol. 13, page 51-7.
2442:
1604:
933:
105:
1274:
1820:
1217:
1368:
455:
Although the C−H bond is one of the strongest, it varies over 30% in magnitude for fairly stable organic compounds, even in the absence of
1279:
926:
2147:
1463:
444:, the C−H bond can be sufficiently acidic for proton removal. Unactivated C−H bonds are found in alkanes and are not adjacent to a
895:
1679:
1438:
1358:
810:
866:
2060:
17:
2435:
440:
The C−H bond in general is very strong, so it is relatively unreactive. In several compound classes, collectively called
435:
2312:
2212:
787:
2337:
2420:
912:
Yu-Ran Luo and Jin-Pei Cheng "Bond
Dissociation Energies" in CRC Handbook of Chemistry and Physics, 96th Edition
2428:
2262:
2297:
1493:
112:
difference between these two atoms is 0.35. Because of this small difference in electronegativities, the
3140:
2997:
2992:
2987:
2982:
2977:
2972:
2967:
2962:
2957:
2952:
2947:
2942:
2932:
2875:
2769:
2690:
2685:
2542:
3145:
3033:
2735:
2705:
2695:
2675:
2663:
2631:
2596:
2564:
2532:
2527:
2487:
2252:
2247:
1428:
3078:
3073:
3068:
3063:
3058:
3053:
3048:
3043:
3038:
3023:
3013:
2864:
2839:
2834:
2819:
2804:
2784:
2779:
2730:
2658:
2641:
2591:
2586:
2581:
2576:
2552:
2512:
2502:
2292:
753:
743:
3028:
3018:
2829:
2814:
2799:
2789:
2774:
2715:
2700:
2680:
2670:
2651:
2646:
2636:
2626:
2569:
2537:
2372:
410:
2937:
2852:
2794:
2757:
2752:
2740:
2720:
2710:
2616:
2611:
2606:
2547:
2522:
2507:
2497:
2227:
1192:
1102:
979:
974:
748:
738:
129:
777:
2745:
2557:
2492:
2482:
2282:
2257:
1895:
1513:
1060:
421:
199:
2824:
2809:
2621:
2601:
2343:
2327:
1952:
1323:
1294:
1175:
999:
449:
148:
124:
of molecules, the hydrogen atoms are often omitted. Compound classes consisting solely of
8:
2725:
2287:
2267:
2080:
1770:
1258:
1122:
1097:
1065:
984:
163:
326:
2385:
2307:
2277:
2222:
2099:
2075:
1574:
1508:
1373:
1333:
1184:
1147:
1107:
1086:
1029:
1004:
204:
121:
899:
2332:
1915:
1815:
1785:
1703:
1443:
1328:
1284:
1232:
1039:
1034:
966:
840:
793:
783:
175:
109:
918:
818:
2409:
2397:
2317:
2217:
2122:
2070:
1503:
1378:
1343:
1264:
1252:
1212:
1117:
1050:
879:
70:
58:
158:
In
October 2016, astronomers reported that the very basic chemical ingredients of
2450:
2005:
1980:
1518:
1458:
1242:
1142:
1127:
1112:
1019:
1009:
340:
333:
2242:
2207:
1990:
1880:
1845:
1830:
1765:
1760:
1659:
1559:
1478:
1453:
1418:
1363:
1338:
1207:
1055:
883:
182:, rather than in other ways, such as the result of turbulent events related to
78:
3134:
3097:
2272:
2127:
2010:
1985:
1966:
1910:
1790:
1748:
1743:
1483:
1473:
1433:
1308:
1202:
1157:
1132:
1014:
994:
797:
779:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd edition
89:
62:
46:
2348:
2202:
2055:
1995:
1975:
1947:
1875:
1755:
1738:
1693:
1644:
1549:
1269:
1222:
1070:
152:
2322:
2232:
2197:
2164:
2090:
2065:
1905:
1810:
1780:
1664:
1579:
1569:
1299:
1227:
773:
578:
510:
456:
441:
101:
93:
85:
66:
319:
2237:
2179:
2142:
2117:
2015:
1825:
1688:
558:
445:
187:
183:
74:
2169:
2034:
1870:
1674:
1554:
1408:
1383:
534:
241:
117:
31:
2137:
2049:
1850:
1713:
1698:
1669:
1538:
1313:
1137:
1081:
1075:
1044:
989:
957:
234:
54:
2302:
2132:
2085:
2044:
2000:
1942:
1937:
1900:
1890:
1885:
1840:
1835:
1775:
1708:
1599:
1594:
1544:
1423:
1413:
1166:
718:
594:
220:
2452:
2353:
2174:
2156:
1619:
1589:
1091:
841:"Building Blocks of Life's Building Blocks Come From Starlight"
670:
618:
486:
452:. Many enzymes are known, however, to effect these reactions.
308:
303:
298:
293:
227:
198:
The length of the carbonhydrogen bond varies slightly with the
144:
140:
136:
50:
898:. Organic Chemistry, Michigan State University. Archived from
1388:
1318:
642:
97:
845:
179:
159:
694:
448:(O, N, Si, etc.). Such bonds usually only participate in
27:
Covalent chemical bond between hydrogen and carbon atoms
948:
211:Comparison of bond lengths in simple hydrocarbons
3132:
2436:
934:
832:
772:
2443:
2429:
941:
927:
2455:with other elements in the periodic table
69:, meaning that carbon shares its outer
14:
3133:
2472:
838:
471:Molar Bond Dissociation Energy (kcal)
162:—the carbon–hydrogen molecule (CH, or
2424:
922:
867:CRC Handbook of Chemistry and Physics
839:Landau, Elizabeth (12 October 2016).
390:Proportion of ethane C-H bond length
166:), the carbon–hydrogen positive ion (
3114:Academic research, no widespread use
766:
474:Molar Bond Dissociation Energy (kJ)
174:)—are the result, in large part, of
116:bond is generally regarded as being
207:of ethane, ethylene and acetylene.
24:
2313:Nexus for Exoplanet System Science
25:
3157:
2213:Atomic and molecular astrophysics
950:Molecules detected in outer space
151:. Collectively they are known as
73:with up to four hydrogens. This
3006:
2925:
2857:
2762:
2462:
2403:
2391:
2379:
2368:
2367:
1174:
1165:
1156:
339:
332:
325:
318:
57:atoms that can be found in many
2338:Polycyclic aromatic hydrocarbon
436:Carbon–hydrogen bond activation
407:Structure determination method
906:
888:
872:
860:
803:
193:
13:
1:
2263:Extraterrestrial liquid water
759:
84:Carbon–hydrogen bonds have a
429:
7:
1494:Protonated hydrogen cyanide
811:"Life Sciences Cyberbridge"
732:
10:
3162:
884:10.1016/j.cbpa.2009.03.018
433:
108:—C (2.55) and H (2.2)—the
104:(see table below). Using
3089:
3003:
2922:
2474:
2470:
2460:
2362:
2253:Earliest known life forms
2248:Diffuse interstellar band
2188:
2108:
2033:
1924:
1859:
1799:
1727:
1719:Protonated cyanoacetylene
1633:
1527:
1489:Protonated carbon dioxide
1449:Hydromagnesium isocyanide
1397:
1183:
1154:
965:
956:
2298:Iron–sulfur world theory
2293:Photodissociation region
1996:Methyl-cyano-diacetylene
348:Hybridisation of carbon
2373:Category:Astrochemistry
1963:, fullerene, buckyball)
1650:Cyanobutadiynyl radical
1625:Silicon-carbide cluster
1615:Protonated formaldehyde
418:microwave spectroscopy
415:microwave spectroscopy
3109:Many uses in chemistry
3104:Core organic chemistry
2386:Outer space portal
2228:Circumstellar envelope
1193:Aluminium(I) hydroxide
1103:Phosphorus mononitride
980:Aluminium monofluoride
975:Aluminium monochloride
411:microwave spectroscopy
190:, as thought earlier.
170:) and the carbon ion (
81:, making them stable.
2283:Interplanetary medium
2258:Extraterrestrial life
1896:Octatetraynyl radical
1514:Tricarbon monosulfide
1061:Magnesium monohydride
422:infrared spectroscopy
149:aromatic hydrocarbons
2410:Chemistry portal
2398:Astronomy portal
2344:RNA world hypothesis
2328:PAH world hypothesis
2021:Heptatrienyl radical
1953:Buckminsterfullerene
1841:Methylcyanoacetylene
1349:Silicon carbonitride
1324:Methylidynephosphane
1290:Magnesium isocyanide
1198:Aluminium isocyanide
1000:Carbon monophosphide
754:Carbon–fluorine bond
744:Carbon–nitrogen bond
468:Hydrocarbon radical
450:radical substitution
92:(1.09 × 10 m) and a
36:carbon–hydrogen bond
18:Carbon-hydrogen bond
2288:Interstellar medium
2268:Forbidden mechanism
2081:Hydrogen isocyanide
1771:Hexatriynyl radical
1354:c-Silicon dicarbide
1259:Hydrogen isocyanide
1123:Silicon monosulfide
1098:Phosphorus monoxide
1066:Methylidyne radical
1025:Fluoromethylidynium
985:Aluminium(II) oxide
782:, New York: Wiley,
212:
164:methylidyne radical
122:structural formulas
2308:Molecules in stars
2278:Intergalactic dust
2223:Circumstellar dust
2165:Naphthalene cation
2100:Trihydrogen cation
2076:Hydrogen deuteride
2001:Methyltriacetylene
1836:Hexapentaenylidene
1655:E-Cyanomethanimine
1575:Cyclopropenylidene
1509:Tricarbon monoxide
1499:Silicon tricarbide
1469:Methylene amidogen
1459:Isothiocyanic acid
1374:Thioxoethenylidene
1334:Trihydrogen cation
1148:Titanium(II) oxide
1108:Potassium chloride
1087:Sulfur mononitride
1030:Helium hydride ion
1005:Carbon monosulfide
902:on 29 August 2016.
749:Carbon–oxygen bond
739:Carbon–carbon bond
210:
205:molecular geometry
3141:Organic chemistry
3128:
3127:
3084:
3083:
2418:
2417:
2333:Pseudo-panspermia
2029:
2028:
1976:Cyanodecapentayne
1916:N-Methylformamide
1891:Methyldiacetylene
1816:Aminoacetonitrile
1786:Methyl isocyanate
1704:Methyl isocyanide
1585:Isocyanoacetylene
1565:Cyanoformaldehyde
1444:Hydrogen peroxide
1329:Potassium cyanide
1285:Magnesium cyanide
1238:Disilicon carbide
1233:Dicarbon monoxide
1040:Hydrogen fluoride
1035:Hydrogen chloride
730:
729:
695:tetrahydrofuranyl
427:
426:
176:ultraviolet light
110:electronegativity
71:valence electrons
61:. This bond is a
59:organic compounds
16:(Redirected from
3153:
3146:Chemical bonding
3120:
3115:
3110:
3105:
3010:
3009:
2929:
2928:
2861:
2860:
2766:
2765:
2463:
2445:
2438:
2431:
2422:
2421:
2408:
2407:
2406:
2396:
2395:
2394:
2384:
2383:
2382:
2371:
2370:
2318:Organic compound
2218:Chemical formula
2123:Dihydroxyacetone
2071:Hydrogen cyanide
1756:Cyanodiacetylene
1610:Propadienylidene
1504:Thioformaldehyde
1379:Titanium dioxide
1344:Sodium hydroxide
1265:Hydrogen sulfide
1253:Hydrogen cyanide
1213:Carbonyl sulfide
1178:
1169:
1160:
1118:Silicon monoxide
1051:Hydroxyl radical
963:
962:
943:
936:
929:
920:
919:
913:
910:
904:
903:
892:
886:
876:
870:
864:
858:
857:
855:
853:
836:
830:
829:
827:
826:
817:. Archived from
807:
801:
800:
770:
462:
461:
365:C-H bond length
343:
336:
329:
322:
213:
209:
173:
169:
132:
127:
115:
42:
21:
3161:
3160:
3156:
3155:
3154:
3152:
3151:
3150:
3131:
3130:
3129:
3124:
3123:
3118:
3113:
3108:
3103:
3085:
3007:
2926:
2858:
2763:
2456:
2449:
2419:
2414:
2404:
2402:
2392:
2390:
2380:
2378:
2358:
2184:
2160:
2151:
2104:
2094:
2037:
2025:
2006:Propionaldehyde
1981:Ethylene glycol
1970:
1962:
1958:
1929:
1927:
1920:
1876:Cyanohexatriyne
1862:
1855:
1802:
1795:
1730:
1723:
1683:
1636:
1629:
1600:Methoxy radical
1530:
1523:
1519:Thiocyanic acid
1400:
1393:
1303:
1243:Ethynyl radical
1179:
1173:
1172:
1171:
1170:
1164:
1163:
1162:
1161:
1152:
1143:Sulfur monoxide
1128:Sodium chloride
1113:Silicon carbide
1020:Diatomic carbon
1010:Carbon monoxide
952:
947:
917:
916:
911:
907:
896:"Bond Energies"
894:
893:
889:
877:
873:
865:
861:
851:
849:
837:
833:
824:
822:
809:
808:
804:
790:
771:
767:
762:
735:
714:
710:
690:
686:
666:
662:
658:
638:
634:
614:
610:
574:
554:
550:
530:
526:
506:
502:
482:
438:
432:
285:
281:
275:
271:
265:
261:
255:
196:
171:
167:
130:
125:
113:
106:Pauling's scale
40:
28:
23:
22:
15:
12:
11:
5:
3159:
3149:
3148:
3143:
3126:
3125:
3122:
3121:
3116:
3111:
3106:
3101:
3098:Chemical bonds
3094:
3093:
3091:
3087:
3086:
3082:
3081:
3076:
3071:
3066:
3061:
3056:
3051:
3046:
3041:
3036:
3031:
3026:
3021:
3016:
3011:
3004:
3001:
3000:
2995:
2990:
2985:
2980:
2975:
2970:
2965:
2960:
2955:
2950:
2945:
2940:
2935:
2930:
2923:
2920:
2919:
2915:
2914:
2911:
2908:
2905:
2902:
2899:
2896:
2893:
2890:
2887:
2884:
2881:
2878:
2873:
2870:
2867:
2862:
2855:
2850:
2846:
2845:
2842:
2837:
2832:
2827:
2822:
2817:
2812:
2807:
2802:
2797:
2792:
2787:
2782:
2777:
2772:
2767:
2760:
2755:
2749:
2748:
2743:
2738:
2733:
2728:
2723:
2718:
2713:
2708:
2703:
2698:
2693:
2688:
2683:
2678:
2673:
2668:
2666:
2661:
2655:
2654:
2649:
2644:
2639:
2634:
2629:
2624:
2619:
2614:
2609:
2604:
2599:
2594:
2589:
2584:
2579:
2574:
2572:
2567:
2561:
2560:
2555:
2550:
2545:
2540:
2535:
2530:
2525:
2519:
2518:
2515:
2510:
2505:
2500:
2495:
2490:
2485:
2479:
2478:
2475:
2473:
2471:
2469:
2461:
2458:
2457:
2448:
2447:
2440:
2433:
2425:
2416:
2415:
2413:
2412:
2400:
2388:
2376:
2363:
2360:
2359:
2357:
2356:
2351:
2346:
2341:
2335:
2330:
2325:
2320:
2315:
2310:
2305:
2300:
2295:
2290:
2285:
2280:
2275:
2270:
2265:
2260:
2255:
2250:
2245:
2243:Cosmochemistry
2240:
2235:
2230:
2225:
2220:
2215:
2210:
2208:Astrochemistry
2205:
2200:
2194:
2192:
2186:
2185:
2183:
2182:
2177:
2172:
2167:
2162:
2158:
2154:
2149:
2145:
2140:
2135:
2130:
2125:
2120:
2114:
2112:
2106:
2105:
2103:
2102:
2097:
2092:
2088:
2083:
2078:
2073:
2068:
2063:
2061:Formyl radical
2058:
2053:
2047:
2041:
2039:
2031:
2030:
2027:
2026:
2024:
2023:
2018:
2013:
2008:
2003:
1998:
1993:
1991:Methyl acetate
1988:
1983:
1978:
1973:
1968:
1964:
1960:
1956:
1950:
1945:
1940:
1934:
1932:
1922:
1921:
1919:
1918:
1913:
1908:
1903:
1898:
1893:
1888:
1883:
1881:Dimethyl ether
1878:
1873:
1867:
1865:
1857:
1856:
1854:
1853:
1848:
1846:Methyl formate
1843:
1838:
1833:
1831:Glycolaldehyde
1828:
1823:
1818:
1813:
1807:
1805:
1797:
1796:
1794:
1793:
1788:
1783:
1778:
1773:
1768:
1766:Glycolonitrile
1763:
1761:Ethylene oxide
1758:
1753:
1752:
1751:
1741:
1735:
1733:
1725:
1724:
1722:
1721:
1716:
1711:
1706:
1701:
1696:
1691:
1686:
1681:
1677:
1672:
1667:
1662:
1660:Cyclopropenone
1657:
1652:
1647:
1641:
1639:
1631:
1630:
1628:
1627:
1622:
1617:
1612:
1607:
1602:
1597:
1592:
1587:
1582:
1577:
1572:
1567:
1562:
1560:Cyanoacetylene
1557:
1552:
1547:
1542:
1535:
1533:
1525:
1524:
1522:
1521:
1516:
1511:
1506:
1501:
1496:
1491:
1486:
1481:
1479:Methyl radical
1476:
1471:
1466:
1461:
1456:
1454:Isocyanic acid
1451:
1446:
1441:
1436:
1431:
1426:
1421:
1419:Isocyanic acid
1416:
1411:
1405:
1403:
1395:
1394:
1392:
1391:
1386:
1381:
1376:
1371:
1366:
1364:Sulfur dioxide
1361:
1356:
1351:
1346:
1341:
1339:Sodium cyanide
1336:
1331:
1326:
1321:
1316:
1311:
1306:
1301:
1297:
1292:
1287:
1282:
1277:
1272:
1267:
1262:
1256:
1250:
1248:Formyl radical
1245:
1240:
1235:
1230:
1225:
1220:
1215:
1210:
1208:Carbon dioxide
1205:
1200:
1195:
1189:
1187:
1181:
1180:
1155:
1153:
1151:
1150:
1145:
1140:
1135:
1130:
1125:
1120:
1115:
1110:
1105:
1100:
1095:
1089:
1084:
1079:
1073:
1068:
1063:
1058:
1056:Iron(II) oxide
1053:
1048:
1042:
1037:
1032:
1027:
1022:
1017:
1012:
1007:
1002:
997:
992:
987:
982:
977:
971:
969:
960:
954:
953:
946:
945:
938:
931:
923:
915:
914:
905:
887:
871:
869:, 88th edition
859:
831:
815:Covalent Bonds
802:
788:
764:
763:
761:
758:
757:
756:
751:
746:
741:
734:
731:
728:
727:
724:
721:
716:
712:
708:
704:
703:
700:
697:
692:
688:
684:
680:
679:
676:
673:
668:
664:
660:
656:
652:
651:
648:
645:
640:
636:
632:
628:
627:
624:
621:
616:
612:
608:
604:
603:
600:
597:
592:
588:
587:
584:
581:
576:
572:
568:
567:
564:
561:
556:
552:
548:
544:
543:
540:
537:
532:
528:
524:
520:
519:
516:
513:
508:
504:
500:
496:
495:
492:
489:
484:
480:
476:
475:
472:
469:
466:
434:Main article:
431:
428:
425:
424:
419:
416:
413:
408:
404:
403:
400:
397:
394:
391:
387:
386:
381:
376:
371:
366:
362:
361:
358:
355:
352:
349:
345:
344:
337:
330:
323:
316:
312:
311:
306:
301:
296:
291:
287:
286:
283:
279:
276:
273:
269:
266:
263:
259:
256:
253:
250:
246:
245:
238:
231:
224:
217:
195:
192:
88:of about 1.09
77:both of their
26:
9:
6:
4:
3:
2:
3158:
3147:
3144:
3142:
3139:
3138:
3136:
3117:
3112:
3107:
3102:
3099:
3096:
3095:
3092:
3088:
3080:
3077:
3075:
3072:
3070:
3067:
3065:
3062:
3060:
3057:
3055:
3052:
3050:
3047:
3045:
3042:
3040:
3037:
3035:
3032:
3030:
3027:
3025:
3022:
3020:
3017:
3015:
3012:
3005:
3002:
2999:
2996:
2994:
2991:
2989:
2986:
2984:
2981:
2979:
2976:
2974:
2971:
2969:
2966:
2964:
2961:
2959:
2956:
2954:
2951:
2949:
2946:
2944:
2941:
2939:
2936:
2934:
2931:
2924:
2921:
2917:
2916:
2912:
2909:
2906:
2903:
2900:
2897:
2894:
2891:
2888:
2885:
2882:
2879:
2877:
2874:
2871:
2868:
2866:
2863:
2856:
2854:
2851:
2848:
2847:
2843:
2841:
2838:
2836:
2833:
2831:
2828:
2826:
2823:
2821:
2818:
2816:
2813:
2811:
2808:
2806:
2803:
2801:
2798:
2796:
2793:
2791:
2788:
2786:
2783:
2781:
2778:
2776:
2773:
2771:
2768:
2761:
2759:
2756:
2754:
2751:
2750:
2747:
2744:
2742:
2739:
2737:
2734:
2732:
2729:
2727:
2724:
2722:
2719:
2717:
2714:
2712:
2709:
2707:
2704:
2702:
2699:
2697:
2694:
2692:
2689:
2687:
2684:
2682:
2679:
2677:
2674:
2672:
2669:
2667:
2665:
2662:
2660:
2657:
2656:
2653:
2650:
2648:
2645:
2643:
2640:
2638:
2635:
2633:
2630:
2628:
2625:
2623:
2620:
2618:
2615:
2613:
2610:
2608:
2605:
2603:
2600:
2598:
2595:
2593:
2590:
2588:
2585:
2583:
2580:
2578:
2575:
2573:
2571:
2568:
2566:
2563:
2562:
2559:
2556:
2554:
2551:
2549:
2546:
2544:
2541:
2539:
2536:
2534:
2531:
2529:
2526:
2524:
2521:
2520:
2516:
2514:
2511:
2509:
2506:
2504:
2501:
2499:
2496:
2494:
2491:
2489:
2486:
2484:
2481:
2480:
2476:
2468:
2465:
2464:
2459:
2454:
2451:Compounds of
2446:
2441:
2439:
2434:
2432:
2427:
2426:
2423:
2411:
2401:
2399:
2389:
2387:
2377:
2375:
2374:
2365:
2364:
2361:
2355:
2352:
2350:
2347:
2345:
2342:
2339:
2336:
2334:
2331:
2329:
2326:
2324:
2321:
2319:
2316:
2314:
2311:
2309:
2306:
2304:
2301:
2299:
2296:
2294:
2291:
2289:
2286:
2284:
2281:
2279:
2276:
2274:
2273:Homochirality
2271:
2269:
2266:
2264:
2261:
2259:
2256:
2254:
2251:
2249:
2246:
2244:
2241:
2239:
2236:
2234:
2231:
2229:
2226:
2224:
2221:
2219:
2216:
2214:
2211:
2209:
2206:
2204:
2201:
2199:
2196:
2195:
2193:
2191:
2187:
2181:
2178:
2176:
2173:
2171:
2168:
2166:
2163:
2161:
2155:
2153:
2146:
2144:
2141:
2139:
2136:
2134:
2131:
2129:
2128:Methoxyethane
2126:
2124:
2121:
2119:
2116:
2115:
2113:
2111:
2107:
2101:
2098:
2096:
2089:
2087:
2084:
2082:
2079:
2077:
2074:
2072:
2069:
2067:
2064:
2062:
2059:
2057:
2054:
2051:
2048:
2046:
2043:
2042:
2040:
2036:
2032:
2022:
2019:
2017:
2014:
2012:
2011:Butyronitrile
2009:
2007:
2004:
2002:
1999:
1997:
1994:
1992:
1989:
1987:
1986:Ethyl formate
1984:
1982:
1979:
1977:
1974:
1972:
1965:
1954:
1951:
1949:
1946:
1944:
1941:
1939:
1936:
1935:
1933:
1931:
1923:
1917:
1914:
1912:
1911:Propionitrile
1909:
1907:
1904:
1902:
1899:
1897:
1894:
1892:
1889:
1887:
1884:
1882:
1879:
1877:
1874:
1872:
1869:
1868:
1866:
1864:
1858:
1852:
1849:
1847:
1844:
1842:
1839:
1837:
1834:
1832:
1829:
1827:
1824:
1822:
1819:
1817:
1814:
1812:
1809:
1808:
1806:
1804:
1798:
1792:
1791:Vinyl alcohol
1789:
1787:
1784:
1782:
1779:
1777:
1774:
1772:
1769:
1767:
1764:
1762:
1759:
1757:
1754:
1750:
1749:Vinyl cyanide
1747:
1746:
1745:
1744:Acrylonitrile
1742:
1740:
1737:
1736:
1734:
1732:
1726:
1720:
1717:
1715:
1712:
1710:
1709:Pentynylidyne
1707:
1705:
1702:
1700:
1697:
1695:
1692:
1690:
1687:
1685:
1678:
1676:
1673:
1671:
1668:
1666:
1663:
1661:
1658:
1656:
1653:
1651:
1648:
1646:
1643:
1642:
1640:
1638:
1632:
1626:
1623:
1621:
1618:
1616:
1613:
1611:
1608:
1606:
1605:Methylenimine
1603:
1601:
1598:
1596:
1593:
1591:
1588:
1586:
1583:
1581:
1578:
1576:
1573:
1571:
1568:
1566:
1563:
1561:
1558:
1556:
1553:
1551:
1548:
1546:
1543:
1540:
1537:
1536:
1534:
1532:
1526:
1520:
1517:
1515:
1512:
1510:
1507:
1505:
1502:
1500:
1497:
1495:
1492:
1490:
1487:
1485:
1484:Propynylidyne
1482:
1480:
1477:
1475:
1474:Methyl cation
1472:
1470:
1467:
1465:
1462:
1460:
1457:
1455:
1452:
1450:
1447:
1445:
1442:
1440:
1437:
1435:
1434:Fulminic acid
1432:
1430:
1427:
1425:
1422:
1420:
1417:
1415:
1412:
1410:
1407:
1406:
1404:
1402:
1396:
1390:
1387:
1385:
1382:
1380:
1377:
1375:
1372:
1370:
1367:
1365:
1362:
1360:
1357:
1355:
1352:
1350:
1347:
1345:
1342:
1340:
1337:
1335:
1332:
1330:
1327:
1325:
1322:
1320:
1317:
1315:
1312:
1310:
1309:Nitrous oxide
1307:
1305:
1298:
1296:
1293:
1291:
1288:
1286:
1283:
1281:
1278:
1276:
1273:
1271:
1268:
1266:
1263:
1260:
1257:
1254:
1251:
1249:
1246:
1244:
1241:
1239:
1236:
1234:
1231:
1229:
1226:
1224:
1221:
1219:
1216:
1214:
1211:
1209:
1206:
1204:
1203:Amino radical
1201:
1199:
1196:
1194:
1191:
1190:
1188:
1186:
1182:
1177:
1168:
1159:
1149:
1146:
1144:
1141:
1139:
1136:
1134:
1133:Sodium iodide
1131:
1129:
1126:
1124:
1121:
1119:
1116:
1114:
1111:
1109:
1106:
1104:
1101:
1099:
1096:
1093:
1090:
1088:
1085:
1083:
1080:
1077:
1074:
1072:
1069:
1067:
1064:
1062:
1059:
1057:
1054:
1052:
1049:
1046:
1043:
1041:
1038:
1036:
1033:
1031:
1028:
1026:
1023:
1021:
1018:
1016:
1015:Cyano radical
1013:
1011:
1008:
1006:
1003:
1001:
998:
996:
995:Carbon cation
993:
991:
988:
986:
983:
981:
978:
976:
973:
972:
970:
968:
964:
961:
959:
955:
951:
944:
939:
937:
932:
930:
925:
924:
921:
909:
901:
897:
891:
885:
881:
875:
868:
863:
848:
847:
842:
835:
821:on 2015-09-18
820:
816:
812:
806:
799:
795:
791:
789:9780471854722
785:
781:
780:
775:
769:
765:
755:
752:
750:
747:
745:
742:
740:
737:
736:
725:
722:
720:
717:
706:
705:
701:
698:
696:
693:
682:
681:
677:
674:
672:
669:
654:
653:
649:
646:
644:
641:
630:
629:
625:
622:
620:
617:
606:
605:
601:
598:
596:
593:
590:
589:
585:
582:
580:
577:
570:
569:
565:
562:
560:
557:
546:
545:
541:
538:
536:
533:
522:
521:
517:
514:
512:
509:
498:
497:
493:
490:
488:
485:
478:
477:
473:
470:
467:
464:
463:
460:
458:
453:
451:
447:
443:
437:
423:
420:
417:
414:
412:
409:
406:
405:
401:
398:
395:
392:
389:
388:
385:
382:
380:
377:
375:
372:
370:
367:
364:
363:
359:
356:
353:
350:
347:
346:
342:
338:
335:
331:
328:
324:
321:
317:
314:
313:
310:
307:
305:
302:
300:
297:
295:
292:
289:
288:
277:
267:
257:
251:
248:
247:
244:
243:
239:
237:
236:
232:
230:
229:
225:
223:
222:
218:
215:
214:
208:
206:
201:
200:hybridisation
191:
189:
185:
181:
177:
165:
161:
156:
154:
150:
146:
142:
138:
134:
123:
119:
111:
107:
103:
99:
96:of about 413
95:
91:
87:
82:
80:
76:
72:
68:
64:
60:
56:
52:
48:
47:chemical bond
44:
37:
33:
19:
3119:Bond unknown
2466:
2366:
2349:Spectroscopy
2203:Astrobiology
2056:Formaldehyde
1948:Benzonitrile
1739:Acetaldehyde
1694:Methanethiol
1645:Acetonitrile
1550:Carbodiimide
1429:Formaldehyde
1424:Cyanoethynyl
1275:Iron cyanide
1270:Hydroperoxyl
1071:Nitric oxide
908:
900:the original
890:
874:
862:
850:. Retrieved
844:
834:
823:. Retrieved
819:the original
814:
805:
778:
774:March, Jerry
768:
454:
442:carbon acids
439:
383:
378:
373:
368:
240:
233:
226:
219:
197:
157:
153:hydrocarbons
83:
79:outer shells
39:
35:
29:
2323:Outer space
2233:Cosmic dust
2198:Abiogenesis
2110:Unconfirmed
2066:Heavy water
1906:Ethanethiol
1821:Cyanoallene
1811:Acetic acid
1781:Methylamine
1665:Diacetylene
1580:Formic acid
1570:Cyanomethyl
1228:Diazenylium
1218:CCP radical
1094:(molecular)
1078:(molecular)
1047:(molecular)
457:heteroatoms
194:Bond length
188:young stars
94:bond energy
86:bond length
67:single bond
3135:Categories
2238:Cosmic ray
2180:Silylidyne
2143:Hemolithin
2118:Anthracene
2035:Deuterated
2016:Pyrimidine
1826:Ethanimine
1689:Ketenimine
1545:Butadiynyl
1369:Thioformyl
1223:Chloronium
852:13 October
825:2015-09-15
760:References
559:tert-Butyl
446:heteroatom
315:Structure
184:supernovae
128:bonds and
3100:to carbon
2170:Phosphine
2038:molecules
1971:fullerene
1871:Acetamide
1675:Formamide
1555:Cyanamide
1409:Acetylene
1384:Tricarbon
1295:Methylene
1280:Isoformyl
1185:Triatomic
958:Molecules
798:642506595
535:Isopropyl
430:Reactions
242:Acetylene
216:Molecule
118:non-polar
75:completes
32:chemistry
2157:Linear C
2138:Graphene
2050:Ammonium
1851:Acrolein
1714:Propynal
1699:Methanol
1670:Ethylene
1539:Ammonium
1314:Nitroxyl
1138:Sulfanyl
1082:Imidogen
1076:Nitrogen
1045:Hydrogen
990:Argonium
967:Diatomic
776:(1985),
733:See also
719:acetonyl
249:Formula
235:Ethylene
63:covalent
55:hydrogen
49:between
2918:
2303:Kerogen
2190:Related
2133:Glycine
2086:Propyne
2045:Ammonia
1943:Benzene
1938:Acetone
1930:or more
1901:Propene
1886:Ethanol
1776:Propyne
1595:Methane
1464:Ketenyl
1414:Ammonia
595:ethynyl
591:HC≡C−H
384:1.060 Å
379:1.087 Å
374:1.094 Å
369:1.087 Å
221:Methane
145:alkynes
141:alkenes
137:alkanes
45:) is a
3090:Legend
2453:carbon
2354:Tholin
2175:Pyrene
1620:Silane
1590:Ketene
1092:Oxygen
796:
786:
711:C(O)CH
671:Benzyl
619:phenyl
575:=CH−H
487:Methyl
309:alkyne
304:alkene
299:alkane
294:alkane
290:Class
228:Ethane
147:, and
51:carbon
34:, the
2340:(PAH)
1928:atoms
1863:atoms
1803:atoms
1801:Eight
1731:atoms
1729:Seven
1637:atoms
1531:atoms
1401:atoms
1389:Water
1319:Ozone
1261:(HNC)
1255:(HCN)
643:Allyl
635:=CHCH
579:vinyl
531:HC−H
511:Ethyl
465:Bond
396:100%
180:stars
178:from
133:bonds
120:. In
1861:Nine
1529:Five
1439:HCCN
1399:Four
1359:SiNC
854:2016
846:NASA
794:OCLC
784:ISBN
726:400
702:380
678:360
650:370
626:460
623:110
602:560
599:133
586:470
583:112
566:390
555:C−H
542:400
518:410
494:440
491:104
402:97%
399:99%
393:99%
186:and
160:life
135:are
53:and
43:bond
3064:CEs
3059:CCf
3054:CBk
3049:CCm
3044:CAm
3039:CPu
3034:CNp
3024:CPa
3019:CTh
2998:CYb
2993:CTm
2988:CEr
2983:CHo
2978:CDy
2973:CTb
2968:CGd
2963:CEu
2958:CSm
2953:CPm
2948:CNd
2943:CPr
2938:CCe
2933:CLa
2913:Og
2910:Ts
2907:Lv
2904:Mc
2901:Fl
2898:Nh
2895:Cn
2892:Rg
2889:Ds
2886:Mt
2883:Hs
2880:Bh
2876:CSg
2872:Db
2869:Rf
2853:CRa
2849:Fr
2844:Rn
2840:CAt
2835:CPo
2830:CBi
2825:CPb
2820:CTl
2815:CHg
2810:CAu
2805:CPt
2800:CIr
2795:COs
2790:CRe
2780:CTa
2775:CHf
2770:CLu
2758:CBa
2753:CCs
2746:CXe
2736:CTe
2731:CSb
2726:CSn
2721:CIn
2716:CCd
2711:CAg
2706:CPd
2701:CRh
2696:CRu
2691:CTc
2686:CMo
2681:CNb
2676:CZr
2664:CSr
2659:CRb
2652:CKr
2647:CBr
2642:CSe
2637:CAs
2632:CGe
2627:CGa
2622:CZn
2617:CCu
2612:CNi
2607:CCo
2602:CFe
2597:CMn
2592:CCr
2582:CTi
2577:CSc
2570:CCa
2558:CAr
2553:CCl
2538:CSi
2533:CAl
2528:CMg
2523:CNa
2517:Ne
2488:CBe
2483:CLi
2477:He
2152:NCO
2052:ion
1959:, C
1926:Ten
1635:Six
1541:ion
880:doi
723:96
715:−H
699:92
691:−H
675:85
667:−H
647:88
639:−H
615:−H
563:93
547:(CH
539:95
523:(CH
515:98
507:−H
483:−H
360:sp
357:sp
354:sp
351:sp
131:C−C
126:C−H
114:C−H
102:mol
41:C−H
30:In
3137::
3079:No
3074:Md
3069:Fm
3029:CU
3014:Ac
2865:Lr
2785:CW
2741:CI
2671:CY
2587:CV
2565:CK
2548:CS
2543:CP
2513:CF
2508:CO
2503:CN
2498:CC
2493:CB
2467:CH
1969:70
1961:60
1957:60
1955:(C
1680:HC
843:.
813:.
792:,
707:CH
683:OC
663:CH
631:CH
571:CH
479:CH
459:.
252:CH
168:CH
155:.
143:,
139:,
98:kJ
65:,
2444:e
2437:t
2430:v
2159:5
2150:2
2148:H
2095:D
2093:2
2091:N
1967:C
1684:N
1682:4
1304:H
1302:2
1300:N
942:e
935:t
928:v
882::
856:.
828:.
713:2
709:3
689:7
687:H
685:4
665:2
661:5
659:H
657:6
655:C
637:2
633:2
613:5
611:H
609:6
607:C
573:2
553:3
551:)
549:3
529:2
527:)
525:3
505:5
503:H
501:2
499:C
481:3
284:2
282:H
280:2
278:C
274:4
272:H
270:2
268:C
264:6
262:H
260:2
258:C
254:4
172:C
100:/
90:Å
38:(
20:)
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