1165:
316:
330:
323:
309:
2394:
1147:
2358:
2997:
2848:
2916:
2753:
1156:
2382:
2370:
191:
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
1707:
1477:
1437:
929:
1638:
1613:
1603:
2009:
1337:
1278:
1186:
2098:
1914:
1849:
1789:
1717:
1623:
1517:
1387:
1342:
1013:
2178:
1643:
1487:
1457:
1573:
1553:
1226:
1598:
1236:
938:
867:
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.
2431:
1593:
922:
94:
1263:
1809:
1206:
1357:
444:
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
1268:
915:
2136:
1452:
433:, 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
884:
1668:
1427:
1347:
799:
855:
2049:
2424:
429:
The C−H bond in general is very strong, so it is relatively unreactive. In several compound classes, collectively called
424:
2301:
2201:
776:
2326:
2409:
901:
Yu-Ran Luo and Jin-Pei Cheng "Bond
Dissociation Energies" in CRC Handbook of Chemistry and Physics, 96th Edition
2417:
2251:
2286:
1482:
101:
difference between these two atoms is 0.35. Because of this small difference in electronegativities, the
3129:
2986:
2981:
2976:
2971:
2966:
2961:
2956:
2951:
2946:
2941:
2936:
2931:
2921:
2864:
2758:
2679:
2674:
2531:
3134:
3022:
2724:
2694:
2684:
2664:
2652:
2620:
2585:
2553:
2521:
2516:
2476:
2241:
2236:
1417:
3067:
3062:
3057:
3052:
3047:
3042:
3037:
3032:
3027:
3012:
3002:
2853:
2828:
2823:
2808:
2793:
2773:
2768:
2719:
2647:
2630:
2580:
2575:
2570:
2565:
2541:
2501:
2491:
2281:
742:
732:
3017:
3007:
2818:
2803:
2788:
2778:
2763:
2704:
2689:
2669:
2659:
2640:
2635:
2625:
2615:
2558:
2526:
2361:
399:
2926:
2841:
2783:
2746:
2741:
2729:
2709:
2699:
2605:
2600:
2595:
2536:
2511:
2496:
2486:
2216:
1181:
1091:
968:
963:
737:
727:
118:
766:
2734:
2546:
2481:
2471:
2271:
2246:
1884:
1502:
1049:
410:
188:
2813:
2798:
2610:
2590:
2332:
2316:
1941:
1312:
1283:
1164:
988:
438:
137:
113:
of molecules, the hydrogen atoms are often omitted. Compound classes consisting solely of
8:
2714:
2276:
2256:
2069:
1759:
1247:
1111:
1086:
1054:
973:
152:
315:
2374:
2296:
2266:
2211:
2088:
2064:
1563:
1497:
1362:
1322:
1173:
1136:
1096:
1075:
1018:
993:
193:
110:
888:
2321:
1904:
1804:
1774:
1692:
1432:
1317:
1273:
1221:
1028:
1023:
955:
829:
782:
772:
164:
98:
907:
807:
2398:
2386:
2306:
2206:
2111:
2059:
1492:
1367:
1332:
1253:
1241:
1201:
1106:
1039:
868:
59:
47:
147:
In
October 2016, astronomers reported that the very basic chemical ingredients of
2439:
1994:
1969:
1507:
1447:
1231:
1131:
1116:
1101:
1008:
998:
329:
322:
2231:
2196:
1979:
1869:
1834:
1819:
1754:
1749:
1648:
1548:
1467:
1442:
1407:
1352:
1327:
1196:
1044:
872:
171:, rather than in other ways, such as the result of turbulent events related to
67:
3123:
3086:
2261:
2116:
1999:
1974:
1955:
1899:
1779:
1737:
1732:
1472:
1462:
1422:
1297:
1191:
1146:
1121:
1003:
983:
786:
768:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd edition
78:
51:
35:
2337:
2191:
2044:
1984:
1964:
1936:
1864:
1744:
1727:
1682:
1633:
1538:
1258:
1211:
1059:
141:
2311:
2221:
2186:
2153:
2079:
2054:
1894:
1799:
1769:
1653:
1568:
1558:
1288:
1216:
762:
567:
499:
445:
430:
90:
82:
74:
55:
308:
2226:
2168:
2131:
2106:
2004:
1814:
1677:
547:
434:
176:
172:
63:
2158:
2023:
1859:
1663:
1543:
1397:
1372:
523:
230:
106:
20:
2126:
2038:
1839:
1702:
1687:
1658:
1527:
1302:
1126:
1070:
1064:
1033:
978:
946:
223:
43:
2291:
2121:
2074:
2033:
1989:
1931:
1926:
1889:
1879:
1874:
1829:
1824:
1764:
1697:
1588:
1583:
1533:
1412:
1402:
1155:
707:
583:
209:
2441:
2342:
2163:
2145:
1608:
1578:
1080:
830:"Building Blocks of Life's Building Blocks Come From Starlight"
659:
607:
475:
441:. Many enzymes are known, however, to effect these reactions.
297:
292:
287:
282:
216:
187:
The length of the carbonhydrogen bond varies slightly with the
133:
129:
125:
39:
887:. Organic Chemistry, Michigan State University. Archived from
1377:
1307:
631:
86:
834:
168:
148:
683:
437:(O, N, Si, etc.). Such bonds usually only participate in
16:
Covalent chemical bond between hydrogen and carbon atoms
937:
200:Comparison of bond lengths in simple hydrocarbons
3121:
2425:
923:
821:
761:
2432:
2418:
930:
916:
2444:with other elements in the periodic table
58:, meaning that carbon shares its outer
3122:
2461:
827:
460:Molar Bond Dissociation Energy (kcal)
151:—the carbon–hydrogen molecule (CH, or
2413:
911:
856:CRC Handbook of Chemistry and Physics
828:Landau, Elizabeth (12 October 2016).
379:Proportion of ethane C-H bond length
155:), the carbon–hydrogen positive ion (
3103:Academic research, no widespread use
755:
463:Molar Bond Dissociation Energy (kJ)
163:)—are the result, in large part, of
105:bond is generally regarded as being
196:of ethane, ethylene and acetylene.
13:
2302:Nexus for Exoplanet System Science
14:
3146:
2202:Atomic and molecular astrophysics
939:Molecules detected in outer space
140:. Collectively they are known as
62:with up to four hydrogens. This
2995:
2914:
2846:
2751:
2451:
2392:
2380:
2368:
2357:
2356:
1163:
1154:
1145:
328:
321:
314:
307:
46:atoms that can be found in many
2327:Polycyclic aromatic hydrocarbon
425:Carbon–hydrogen bond activation
396:Structure determination method
895:
877:
861:
849:
792:
182:
1:
2252:Extraterrestrial liquid water
748:
73:Carbon–hydrogen bonds have a
418:
7:
1483:Protonated hydrogen cyanide
800:"Life Sciences Cyberbridge"
721:
10:
3151:
873:10.1016/j.cbpa.2009.03.018
422:
97:—C (2.55) and H (2.2)—the
93:(see table below). Using
3078:
2992:
2911:
2463:
2459:
2449:
2351:
2242:Earliest known life forms
2237:Diffuse interstellar band
2177:
2097:
2022:
1913:
1848:
1788:
1716:
1708:Protonated cyanoacetylene
1622:
1516:
1478:Protonated carbon dioxide
1438:Hydromagnesium isocyanide
1386:
1172:
1143:
954:
945:
2287:Iron–sulfur world theory
2282:Photodissociation region
1985:Methyl-cyano-diacetylene
337:Hybridisation of carbon
2362:Category:Astrochemistry
1952:, fullerene, buckyball)
1639:Cyanobutadiynyl radical
1614:Silicon-carbide cluster
1604:Protonated formaldehyde
407:microwave spectroscopy
404:microwave spectroscopy
3098:Many uses in chemistry
3093:Core organic chemistry
2375:Outer space portal
2217:Circumstellar envelope
1182:Aluminium(I) hydroxide
1092:Phosphorus mononitride
969:Aluminium monofluoride
964:Aluminium monochloride
400:microwave spectroscopy
179:, as thought earlier.
159:) and the carbon ion (
70:, making them stable.
2272:Interplanetary medium
2247:Extraterrestrial life
1885:Octatetraynyl radical
1503:Tricarbon monosulfide
1050:Magnesium monohydride
411:infrared spectroscopy
138:aromatic hydrocarbons
2399:Chemistry portal
2387:Astronomy portal
2333:RNA world hypothesis
2317:PAH world hypothesis
2010:Heptatrienyl radical
1942:Buckminsterfullerene
1830:Methylcyanoacetylene
1338:Silicon carbonitride
1313:Methylidynephosphane
1279:Magnesium isocyanide
1187:Aluminium isocyanide
989:Carbon monophosphide
743:Carbon–fluorine bond
733:Carbon–nitrogen bond
457:Hydrocarbon radical
439:radical substitution
81:(1.09 × 10 m) and a
25:carbon–hydrogen bond
2277:Interstellar medium
2257:Forbidden mechanism
2070:Hydrogen isocyanide
1760:Hexatriynyl radical
1343:c-Silicon dicarbide
1248:Hydrogen isocyanide
1112:Silicon monosulfide
1087:Phosphorus monoxide
1055:Methylidyne radical
1014:Fluoromethylidynium
974:Aluminium(II) oxide
771:, New York: Wiley,
201:
153:methylidyne radical
111:structural formulas
2297:Molecules in stars
2267:Intergalactic dust
2212:Circumstellar dust
2154:Naphthalene cation
2089:Trihydrogen cation
2065:Hydrogen deuteride
1990:Methyltriacetylene
1825:Hexapentaenylidene
1644:E-Cyanomethanimine
1564:Cyclopropenylidene
1498:Tricarbon monoxide
1488:Silicon tricarbide
1458:Methylene amidogen
1448:Isothiocyanic acid
1363:Thioxoethenylidene
1323:Trihydrogen cation
1137:Titanium(II) oxide
1097:Potassium chloride
1076:Sulfur mononitride
1019:Helium hydride ion
994:Carbon monosulfide
891:on 29 August 2016.
738:Carbon–oxygen bond
728:Carbon–carbon bond
199:
194:molecular geometry
3130:Organic chemistry
3117:
3116:
3073:
3072:
2407:
2406:
2322:Pseudo-panspermia
2018:
2017:
1965:Cyanodecapentayne
1905:N-Methylformamide
1880:Methyldiacetylene
1805:Aminoacetonitrile
1775:Methyl isocyanate
1693:Methyl isocyanide
1574:Isocyanoacetylene
1554:Cyanoformaldehyde
1433:Hydrogen peroxide
1318:Potassium cyanide
1274:Magnesium cyanide
1227:Disilicon carbide
1222:Dicarbon monoxide
1029:Hydrogen fluoride
1024:Hydrogen chloride
719:
718:
684:tetrahydrofuranyl
416:
415:
165:ultraviolet light
99:electronegativity
60:valence electrons
50:. This bond is a
48:organic compounds
3142:
3135:Chemical bonding
3109:
3104:
3099:
3094:
2999:
2998:
2918:
2917:
2850:
2849:
2755:
2754:
2452:
2434:
2427:
2420:
2411:
2410:
2397:
2396:
2395:
2385:
2384:
2383:
2373:
2372:
2371:
2360:
2359:
2307:Organic compound
2207:Chemical formula
2112:Dihydroxyacetone
2060:Hydrogen cyanide
1745:Cyanodiacetylene
1599:Propadienylidene
1493:Thioformaldehyde
1368:Titanium dioxide
1333:Sodium hydroxide
1254:Hydrogen sulfide
1242:Hydrogen cyanide
1202:Carbonyl sulfide
1167:
1158:
1149:
1107:Silicon monoxide
1040:Hydroxyl radical
952:
951:
932:
925:
918:
909:
908:
902:
899:
893:
892:
881:
875:
865:
859:
853:
847:
846:
844:
842:
825:
819:
818:
816:
815:
806:. Archived from
796:
790:
789:
759:
451:
450:
354:C-H bond length
332:
325:
318:
311:
202:
198:
162:
158:
121:
116:
104:
31:
3150:
3149:
3145:
3144:
3143:
3141:
3140:
3139:
3120:
3119:
3118:
3113:
3112:
3107:
3102:
3097:
3092:
3074:
2996:
2915:
2847:
2752:
2445:
2438:
2408:
2403:
2393:
2391:
2381:
2379:
2369:
2367:
2347:
2173:
2149:
2140:
2093:
2083:
2026:
2014:
1995:Propionaldehyde
1970:Ethylene glycol
1959:
1951:
1947:
1918:
1916:
1909:
1865:Cyanohexatriyne
1851:
1844:
1791:
1784:
1719:
1712:
1672:
1625:
1618:
1589:Methoxy radical
1519:
1512:
1508:Thiocyanic acid
1389:
1382:
1292:
1232:Ethynyl radical
1168:
1162:
1161:
1160:
1159:
1153:
1152:
1151:
1150:
1141:
1132:Sulfur monoxide
1117:Sodium chloride
1102:Silicon carbide
1009:Diatomic carbon
999:Carbon monoxide
941:
936:
906:
905:
900:
896:
885:"Bond Energies"
883:
882:
878:
866:
862:
854:
850:
840:
838:
826:
822:
813:
811:
798:
797:
793:
779:
760:
756:
751:
724:
703:
699:
679:
675:
655:
651:
647:
627:
623:
603:
599:
563:
543:
539:
519:
515:
495:
491:
471:
427:
421:
274:
270:
264:
260:
254:
250:
244:
185:
160:
156:
119:
114:
102:
95:Pauling's scale
29:
17:
12:
11:
5:
3148:
3138:
3137:
3132:
3115:
3114:
3111:
3110:
3105:
3100:
3095:
3090:
3087:Chemical bonds
3083:
3082:
3080:
3076:
3075:
3071:
3070:
3065:
3060:
3055:
3050:
3045:
3040:
3035:
3030:
3025:
3020:
3015:
3010:
3005:
3000:
2993:
2990:
2989:
2984:
2979:
2974:
2969:
2964:
2959:
2954:
2949:
2944:
2939:
2934:
2929:
2924:
2919:
2912:
2909:
2908:
2904:
2903:
2900:
2897:
2894:
2891:
2888:
2885:
2882:
2879:
2876:
2873:
2870:
2867:
2862:
2859:
2856:
2851:
2844:
2839:
2835:
2834:
2831:
2826:
2821:
2816:
2811:
2806:
2801:
2796:
2791:
2786:
2781:
2776:
2771:
2766:
2761:
2756:
2749:
2744:
2738:
2737:
2732:
2727:
2722:
2717:
2712:
2707:
2702:
2697:
2692:
2687:
2682:
2677:
2672:
2667:
2662:
2657:
2655:
2650:
2644:
2643:
2638:
2633:
2628:
2623:
2618:
2613:
2608:
2603:
2598:
2593:
2588:
2583:
2578:
2573:
2568:
2563:
2561:
2556:
2550:
2549:
2544:
2539:
2534:
2529:
2524:
2519:
2514:
2508:
2507:
2504:
2499:
2494:
2489:
2484:
2479:
2474:
2468:
2467:
2464:
2462:
2460:
2458:
2450:
2447:
2446:
2437:
2436:
2429:
2422:
2414:
2405:
2404:
2402:
2401:
2389:
2377:
2365:
2352:
2349:
2348:
2346:
2345:
2340:
2335:
2330:
2324:
2319:
2314:
2309:
2304:
2299:
2294:
2289:
2284:
2279:
2274:
2269:
2264:
2259:
2254:
2249:
2244:
2239:
2234:
2232:Cosmochemistry
2229:
2224:
2219:
2214:
2209:
2204:
2199:
2197:Astrochemistry
2194:
2189:
2183:
2181:
2175:
2174:
2172:
2171:
2166:
2161:
2156:
2151:
2147:
2143:
2138:
2134:
2129:
2124:
2119:
2114:
2109:
2103:
2101:
2095:
2094:
2092:
2091:
2086:
2081:
2077:
2072:
2067:
2062:
2057:
2052:
2050:Formyl radical
2047:
2042:
2036:
2030:
2028:
2020:
2019:
2016:
2015:
2013:
2012:
2007:
2002:
1997:
1992:
1987:
1982:
1980:Methyl acetate
1977:
1972:
1967:
1962:
1957:
1953:
1949:
1945:
1939:
1934:
1929:
1923:
1921:
1911:
1910:
1908:
1907:
1902:
1897:
1892:
1887:
1882:
1877:
1872:
1870:Dimethyl ether
1867:
1862:
1856:
1854:
1846:
1845:
1843:
1842:
1837:
1835:Methyl formate
1832:
1827:
1822:
1820:Glycolaldehyde
1817:
1812:
1807:
1802:
1796:
1794:
1786:
1785:
1783:
1782:
1777:
1772:
1767:
1762:
1757:
1755:Glycolonitrile
1752:
1750:Ethylene oxide
1747:
1742:
1741:
1740:
1730:
1724:
1722:
1714:
1713:
1711:
1710:
1705:
1700:
1695:
1690:
1685:
1680:
1675:
1670:
1666:
1661:
1656:
1651:
1649:Cyclopropenone
1646:
1641:
1636:
1630:
1628:
1620:
1619:
1617:
1616:
1611:
1606:
1601:
1596:
1591:
1586:
1581:
1576:
1571:
1566:
1561:
1556:
1551:
1549:Cyanoacetylene
1546:
1541:
1536:
1531:
1524:
1522:
1514:
1513:
1511:
1510:
1505:
1500:
1495:
1490:
1485:
1480:
1475:
1470:
1468:Methyl radical
1465:
1460:
1455:
1450:
1445:
1443:Isocyanic acid
1440:
1435:
1430:
1425:
1420:
1415:
1410:
1408:Isocyanic acid
1405:
1400:
1394:
1392:
1384:
1383:
1381:
1380:
1375:
1370:
1365:
1360:
1355:
1353:Sulfur dioxide
1350:
1345:
1340:
1335:
1330:
1328:Sodium cyanide
1325:
1320:
1315:
1310:
1305:
1300:
1295:
1290:
1286:
1281:
1276:
1271:
1266:
1261:
1256:
1251:
1245:
1239:
1237:Formyl radical
1234:
1229:
1224:
1219:
1214:
1209:
1204:
1199:
1197:Carbon dioxide
1194:
1189:
1184:
1178:
1176:
1170:
1169:
1144:
1142:
1140:
1139:
1134:
1129:
1124:
1119:
1114:
1109:
1104:
1099:
1094:
1089:
1084:
1078:
1073:
1068:
1062:
1057:
1052:
1047:
1045:Iron(II) oxide
1042:
1037:
1031:
1026:
1021:
1016:
1011:
1006:
1001:
996:
991:
986:
981:
976:
971:
966:
960:
958:
949:
943:
942:
935:
934:
927:
920:
912:
904:
903:
894:
876:
860:
858:, 88th edition
848:
820:
804:Covalent Bonds
791:
777:
753:
752:
750:
747:
746:
745:
740:
735:
730:
723:
720:
717:
716:
713:
710:
705:
701:
697:
693:
692:
689:
686:
681:
677:
673:
669:
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665:
662:
657:
653:
649:
645:
641:
640:
637:
634:
629:
625:
621:
617:
616:
613:
610:
605:
601:
597:
593:
592:
589:
586:
581:
577:
576:
573:
570:
565:
561:
557:
556:
553:
550:
545:
541:
537:
533:
532:
529:
526:
521:
517:
513:
509:
508:
505:
502:
497:
493:
489:
485:
484:
481:
478:
473:
469:
465:
464:
461:
458:
455:
423:Main article:
420:
417:
414:
413:
408:
405:
402:
397:
393:
392:
389:
386:
383:
380:
376:
375:
370:
365:
360:
355:
351:
350:
347:
344:
341:
338:
334:
333:
326:
319:
312:
305:
301:
300:
295:
290:
285:
280:
276:
275:
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268:
265:
262:
258:
255:
252:
248:
245:
242:
239:
235:
234:
227:
220:
213:
206:
184:
181:
77:of about 1.09
66:both of their
15:
9:
6:
4:
3:
2:
3147:
3136:
3133:
3131:
3128:
3127:
3125:
3106:
3101:
3096:
3091:
3088:
3085:
3084:
3081:
3077:
3069:
3066:
3064:
3061:
3059:
3056:
3054:
3051:
3049:
3046:
3044:
3041:
3039:
3036:
3034:
3031:
3029:
3026:
3024:
3021:
3019:
3016:
3014:
3011:
3009:
3006:
3004:
3001:
2994:
2991:
2988:
2985:
2983:
2980:
2978:
2975:
2973:
2970:
2968:
2965:
2963:
2960:
2958:
2955:
2953:
2950:
2948:
2945:
2943:
2940:
2938:
2935:
2933:
2930:
2928:
2925:
2923:
2920:
2913:
2910:
2906:
2905:
2901:
2898:
2895:
2892:
2889:
2886:
2883:
2880:
2877:
2874:
2871:
2868:
2866:
2863:
2860:
2857:
2855:
2852:
2845:
2843:
2840:
2837:
2836:
2832:
2830:
2827:
2825:
2822:
2820:
2817:
2815:
2812:
2810:
2807:
2805:
2802:
2800:
2797:
2795:
2792:
2790:
2787:
2785:
2782:
2780:
2777:
2775:
2772:
2770:
2767:
2765:
2762:
2760:
2757:
2750:
2748:
2745:
2743:
2740:
2739:
2736:
2733:
2731:
2728:
2726:
2723:
2721:
2718:
2716:
2713:
2711:
2708:
2706:
2703:
2701:
2698:
2696:
2693:
2691:
2688:
2686:
2683:
2681:
2678:
2676:
2673:
2671:
2668:
2666:
2663:
2661:
2658:
2656:
2654:
2651:
2649:
2646:
2645:
2642:
2639:
2637:
2634:
2632:
2629:
2627:
2624:
2622:
2619:
2617:
2614:
2612:
2609:
2607:
2604:
2602:
2599:
2597:
2594:
2592:
2589:
2587:
2584:
2582:
2579:
2577:
2574:
2572:
2569:
2567:
2564:
2562:
2560:
2557:
2555:
2552:
2551:
2548:
2545:
2543:
2540:
2538:
2535:
2533:
2530:
2528:
2525:
2523:
2520:
2518:
2515:
2513:
2510:
2509:
2505:
2503:
2500:
2498:
2495:
2493:
2490:
2488:
2485:
2483:
2480:
2478:
2475:
2473:
2470:
2469:
2465:
2457:
2454:
2453:
2448:
2443:
2440:Compounds of
2435:
2430:
2428:
2423:
2421:
2416:
2415:
2412:
2400:
2390:
2388:
2378:
2376:
2366:
2364:
2363:
2354:
2353:
2350:
2344:
2341:
2339:
2336:
2334:
2331:
2328:
2325:
2323:
2320:
2318:
2315:
2313:
2310:
2308:
2305:
2303:
2300:
2298:
2295:
2293:
2290:
2288:
2285:
2283:
2280:
2278:
2275:
2273:
2270:
2268:
2265:
2263:
2262:Homochirality
2260:
2258:
2255:
2253:
2250:
2248:
2245:
2243:
2240:
2238:
2235:
2233:
2230:
2228:
2225:
2223:
2220:
2218:
2215:
2213:
2210:
2208:
2205:
2203:
2200:
2198:
2195:
2193:
2190:
2188:
2185:
2184:
2182:
2180:
2176:
2170:
2167:
2165:
2162:
2160:
2157:
2155:
2152:
2150:
2144:
2142:
2135:
2133:
2130:
2128:
2125:
2123:
2120:
2118:
2117:Methoxyethane
2115:
2113:
2110:
2108:
2105:
2104:
2102:
2100:
2096:
2090:
2087:
2085:
2078:
2076:
2073:
2071:
2068:
2066:
2063:
2061:
2058:
2056:
2053:
2051:
2048:
2046:
2043:
2040:
2037:
2035:
2032:
2031:
2029:
2025:
2021:
2011:
2008:
2006:
2003:
2001:
2000:Butyronitrile
1998:
1996:
1993:
1991:
1988:
1986:
1983:
1981:
1978:
1976:
1975:Ethyl formate
1973:
1971:
1968:
1966:
1963:
1961:
1954:
1943:
1940:
1938:
1935:
1933:
1930:
1928:
1925:
1924:
1922:
1920:
1912:
1906:
1903:
1901:
1900:Propionitrile
1898:
1896:
1893:
1891:
1888:
1886:
1883:
1881:
1878:
1876:
1873:
1871:
1868:
1866:
1863:
1861:
1858:
1857:
1855:
1853:
1847:
1841:
1838:
1836:
1833:
1831:
1828:
1826:
1823:
1821:
1818:
1816:
1813:
1811:
1808:
1806:
1803:
1801:
1798:
1797:
1795:
1793:
1787:
1781:
1780:Vinyl alcohol
1778:
1776:
1773:
1771:
1768:
1766:
1763:
1761:
1758:
1756:
1753:
1751:
1748:
1746:
1743:
1739:
1738:Vinyl cyanide
1736:
1735:
1734:
1733:Acrylonitrile
1731:
1729:
1726:
1725:
1723:
1721:
1715:
1709:
1706:
1704:
1701:
1699:
1698:Pentynylidyne
1696:
1694:
1691:
1689:
1686:
1684:
1681:
1679:
1676:
1674:
1667:
1665:
1662:
1660:
1657:
1655:
1652:
1650:
1647:
1645:
1642:
1640:
1637:
1635:
1632:
1631:
1629:
1627:
1621:
1615:
1612:
1610:
1607:
1605:
1602:
1600:
1597:
1595:
1594:Methylenimine
1592:
1590:
1587:
1585:
1582:
1580:
1577:
1575:
1572:
1570:
1567:
1565:
1562:
1560:
1557:
1555:
1552:
1550:
1547:
1545:
1542:
1540:
1537:
1535:
1532:
1529:
1526:
1525:
1523:
1521:
1515:
1509:
1506:
1504:
1501:
1499:
1496:
1494:
1491:
1489:
1486:
1484:
1481:
1479:
1476:
1474:
1473:Propynylidyne
1471:
1469:
1466:
1464:
1463:Methyl cation
1461:
1459:
1456:
1454:
1451:
1449:
1446:
1444:
1441:
1439:
1436:
1434:
1431:
1429:
1426:
1424:
1423:Fulminic acid
1421:
1419:
1416:
1414:
1411:
1409:
1406:
1404:
1401:
1399:
1396:
1395:
1393:
1391:
1385:
1379:
1376:
1374:
1371:
1369:
1366:
1364:
1361:
1359:
1356:
1354:
1351:
1349:
1346:
1344:
1341:
1339:
1336:
1334:
1331:
1329:
1326:
1324:
1321:
1319:
1316:
1314:
1311:
1309:
1306:
1304:
1301:
1299:
1298:Nitrous oxide
1296:
1294:
1287:
1285:
1282:
1280:
1277:
1275:
1272:
1270:
1267:
1265:
1262:
1260:
1257:
1255:
1252:
1249:
1246:
1243:
1240:
1238:
1235:
1233:
1230:
1228:
1225:
1223:
1220:
1218:
1215:
1213:
1210:
1208:
1205:
1203:
1200:
1198:
1195:
1193:
1192:Amino radical
1190:
1188:
1185:
1183:
1180:
1179:
1177:
1175:
1171:
1166:
1157:
1148:
1138:
1135:
1133:
1130:
1128:
1125:
1123:
1122:Sodium iodide
1120:
1118:
1115:
1113:
1110:
1108:
1105:
1103:
1100:
1098:
1095:
1093:
1090:
1088:
1085:
1082:
1079:
1077:
1074:
1072:
1069:
1066:
1063:
1061:
1058:
1056:
1053:
1051:
1048:
1046:
1043:
1041:
1038:
1035:
1032:
1030:
1027:
1025:
1022:
1020:
1017:
1015:
1012:
1010:
1007:
1005:
1004:Cyano radical
1002:
1000:
997:
995:
992:
990:
987:
985:
984:Carbon cation
982:
980:
977:
975:
972:
970:
967:
965:
962:
961:
959:
957:
953:
950:
948:
944:
940:
933:
928:
926:
921:
919:
914:
913:
910:
898:
890:
886:
880:
874:
870:
864:
857:
852:
837:
836:
831:
824:
810:on 2015-09-18
809:
805:
801:
795:
788:
784:
780:
778:9780471854722
774:
770:
769:
764:
758:
754:
744:
741:
739:
736:
734:
731:
729:
726:
725:
714:
711:
709:
706:
695:
694:
690:
687:
685:
682:
671:
670:
666:
663:
661:
658:
643:
642:
638:
635:
633:
630:
619:
618:
614:
611:
609:
606:
595:
594:
590:
587:
585:
582:
579:
578:
574:
571:
569:
566:
559:
558:
554:
551:
549:
546:
535:
534:
530:
527:
525:
522:
511:
510:
506:
503:
501:
498:
487:
486:
482:
479:
477:
474:
467:
466:
462:
459:
456:
453:
452:
449:
447:
442:
440:
436:
432:
426:
412:
409:
406:
403:
401:
398:
395:
394:
390:
387:
384:
381:
378:
377:
374:
371:
369:
366:
364:
361:
359:
356:
353:
352:
348:
345:
342:
339:
336:
335:
331:
327:
324:
320:
317:
313:
310:
306:
303:
302:
299:
296:
294:
291:
289:
286:
284:
281:
278:
277:
266:
256:
246:
240:
237:
236:
233:
232:
228:
226:
225:
221:
219:
218:
214:
212:
211:
207:
204:
203:
197:
195:
190:
189:hybridisation
180:
178:
174:
170:
166:
154:
150:
145:
143:
139:
135:
131:
127:
123:
112:
108:
100:
96:
92:
88:
85:of about 413
84:
80:
76:
71:
69:
65:
61:
57:
53:
49:
45:
41:
37:
36:chemical bond
33:
26:
22:
3108:Bond unknown
2455:
2355:
2338:Spectroscopy
2192:Astrobiology
2045:Formaldehyde
1937:Benzonitrile
1728:Acetaldehyde
1683:Methanethiol
1634:Acetonitrile
1539:Carbodiimide
1418:Formaldehyde
1413:Cyanoethynyl
1264:Iron cyanide
1259:Hydroperoxyl
1060:Nitric oxide
897:
889:the original
879:
863:
851:
839:. Retrieved
833:
823:
812:. Retrieved
808:the original
803:
794:
767:
763:March, Jerry
757:
443:
431:carbon acids
428:
372:
367:
362:
357:
229:
222:
215:
208:
186:
146:
142:hydrocarbons
72:
68:outer shells
28:
24:
18:
2312:Outer space
2222:Cosmic dust
2187:Abiogenesis
2099:Unconfirmed
2055:Heavy water
1895:Ethanethiol
1810:Cyanoallene
1800:Acetic acid
1770:Methylamine
1654:Diacetylene
1569:Formic acid
1559:Cyanomethyl
1217:Diazenylium
1207:CCP radical
1083:(molecular)
1067:(molecular)
1036:(molecular)
446:heteroatoms
183:Bond length
177:young stars
83:bond energy
75:bond length
56:single bond
3124:Categories
2227:Cosmic ray
2169:Silylidyne
2132:Hemolithin
2107:Anthracene
2024:Deuterated
2005:Pyrimidine
1815:Ethanimine
1678:Ketenimine
1534:Butadiynyl
1358:Thioformyl
1212:Chloronium
841:13 October
814:2015-09-15
749:References
548:tert-Butyl
435:heteroatom
304:Structure
173:supernovae
117:bonds and
3089:to carbon
2159:Phosphine
2027:molecules
1960:fullerene
1860:Acetamide
1664:Formamide
1544:Cyanamide
1398:Acetylene
1373:Tricarbon
1284:Methylene
1269:Isoformyl
1174:Triatomic
947:Molecules
787:642506595
524:Isopropyl
419:Reactions
231:Acetylene
205:Molecule
107:non-polar
64:completes
21:chemistry
2146:Linear C
2127:Graphene
2039:Ammonium
1840:Acrolein
1703:Propynal
1688:Methanol
1659:Ethylene
1528:Ammonium
1303:Nitroxyl
1127:Sulfanyl
1071:Imidogen
1065:Nitrogen
1034:Hydrogen
979:Argonium
956:Diatomic
765:(1985),
722:See also
708:acetonyl
238:Formula
224:Ethylene
52:covalent
44:hydrogen
38:between
2907:
2292:Kerogen
2179:Related
2122:Glycine
2075:Propyne
2034:Ammonia
1932:Benzene
1927:Acetone
1919:or more
1890:Propene
1875:Ethanol
1765:Propyne
1584:Methane
1453:Ketenyl
1403:Ammonia
584:ethynyl
580:HC≡C−H
373:1.060 Å
368:1.087 Å
363:1.094 Å
358:1.087 Å
210:Methane
134:alkynes
130:alkenes
126:alkanes
34:) is a
3079:Legend
2442:carbon
2343:Tholin
2164:Pyrene
1609:Silane
1579:Ketene
1081:Oxygen
785:
775:
700:C(O)CH
660:Benzyl
608:phenyl
564:=CH−H
476:Methyl
298:alkyne
293:alkene
288:alkane
283:alkane
279:Class
217:Ethane
136:, and
40:carbon
23:, the
2329:(PAH)
1917:atoms
1852:atoms
1792:atoms
1790:Eight
1720:atoms
1718:Seven
1626:atoms
1520:atoms
1390:atoms
1378:Water
1308:Ozone
1250:(HNC)
1244:(HCN)
632:Allyl
624:=CHCH
568:vinyl
520:HC−H
500:Ethyl
454:Bond
385:100%
169:stars
167:from
122:bonds
109:. In
1850:Nine
1518:Five
1428:HCCN
1388:Four
1348:SiNC
843:2016
835:NASA
783:OCLC
773:ISBN
715:400
691:380
667:360
639:370
615:460
612:110
591:560
588:133
575:470
572:112
555:390
544:C−H
531:400
507:410
483:440
480:104
391:97%
388:99%
382:99%
175:and
149:life
124:are
42:and
32:bond
3053:CEs
3048:CCf
3043:CBk
3038:CCm
3033:CAm
3028:CPu
3023:CNp
3013:CPa
3008:CTh
2987:CYb
2982:CTm
2977:CEr
2972:CHo
2967:CDy
2962:CTb
2957:CGd
2952:CEu
2947:CSm
2942:CPm
2937:CNd
2932:CPr
2927:CCe
2922:CLa
2902:Og
2899:Ts
2896:Lv
2893:Mc
2890:Fl
2887:Nh
2884:Cn
2881:Rg
2878:Ds
2875:Mt
2872:Hs
2869:Bh
2865:CSg
2861:Db
2858:Rf
2842:CRa
2838:Fr
2833:Rn
2829:CAt
2824:CPo
2819:CBi
2814:CPb
2809:CTl
2804:CHg
2799:CAu
2794:CPt
2789:CIr
2784:COs
2779:CRe
2769:CTa
2764:CHf
2759:CLu
2747:CBa
2742:CCs
2735:CXe
2725:CTe
2720:CSb
2715:CSn
2710:CIn
2705:CCd
2700:CAg
2695:CPd
2690:CRh
2685:CRu
2680:CTc
2675:CMo
2670:CNb
2665:CZr
2653:CSr
2648:CRb
2641:CKr
2636:CBr
2631:CSe
2626:CAs
2621:CGe
2616:CGa
2611:CZn
2606:CCu
2601:CNi
2596:CCo
2591:CFe
2586:CMn
2581:CCr
2571:CTi
2566:CSc
2559:CCa
2547:CAr
2542:CCl
2527:CSi
2522:CAl
2517:CMg
2512:CNa
2506:Ne
2477:CBe
2472:CLi
2466:He
2141:NCO
2041:ion
1948:, C
1915:Ten
1624:Six
1530:ion
869:doi
712:96
704:−H
688:92
680:−H
664:85
656:−H
636:88
628:−H
604:−H
552:93
536:(CH
528:95
512:(CH
504:98
496:−H
472:−H
349:sp
346:sp
343:sp
340:sp
120:C−C
115:C−H
103:C−H
91:mol
30:C−H
19:In
3126::
3068:No
3063:Md
3058:Fm
3018:CU
3003:Ac
2854:Lr
2774:CW
2730:CI
2660:CY
2576:CV
2554:CK
2537:CS
2532:CP
2502:CF
2497:CO
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2482:CB
2456:CH
1958:70
1950:60
1946:60
1944:(C
1669:HC
832:.
802:.
781:,
696:CH
672:OC
652:CH
620:CH
560:CH
468:CH
448:.
241:CH
157:CH
144:.
132:,
128:,
87:kJ
54:,
2433:e
2426:t
2419:v
2148:5
2139:2
2137:H
2084:D
2082:2
2080:N
1956:C
1673:N
1671:4
1293:H
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1289:N
931:e
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871::
845:.
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702:2
698:3
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646:6
644:C
626:2
622:2
602:5
600:H
598:6
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562:2
542:3
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538:3
518:2
516:)
514:3
494:5
492:H
490:2
488:C
470:3
273:2
271:H
269:2
267:C
263:4
261:H
259:2
257:C
253:6
251:H
249:2
247:C
243:4
161:C
89:/
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