384:
1752:
20:
477:
1479:
2981:
1388:
1400:
1734:
2945:
1462:
1445:
1743:
95:
582:
495:
1428:
2969:
2957:
395:
or acrylic dispersion. Here the polycarbodiimide reacts with carboxylic acids, whose functional groups are often present in such aqueous resins, to form N-acyl urea. The result is the formation of covalent bonds between the polymer chains, making them crosslinked.
154:
to the molecule rotating and thereby converting quickly between its isomers, the actual isolation of one optical isomer of a carbodiimide is extremely difficult. It has been demonstrated at least once, in the case of conformationally restricted
572:, and repeated contact with skin increases the probability of sensitization to the compound. Clinical reports of individuals who cannot enter rooms where peptide coupling agents are used have been reported.
81:
upon standing at room temperature, though this mostly occurs with low melting point carbodiimides that are liquids at room temperature. Solid diaryl carbodiimides are more stable, but can slowly undergo
717:
The name carbodiimide, for HN=C=NH, is retained but only for general nomenclature; no substitution of any kind is allowed. The systematic name, methanediimine, is the preferred IUPAC name.
159:
carbodiimides; though there are other reports of one-handed axially chiral carbodiimides, their validity has since been called into question on experimental and computational grounds.
729:
McGuire, Brett A.; Loomis, Ryan A.; Charness, Cameron M.; Corby, Joanna F.; Blake, Geoffrey A.; Hollis, Jan M.; Lovas, Frank J.; Jewell, Philip R.; Remijan, Anthony J. (2012-10-20).
636:
EDC is a water-soluble carbodiimide reagent used for a wide range of purposes. Apart from uses similar to those of DCC and DIC, it is also used for various biochemical purposes as a
1190:
Li, Zhen; Mayer, Robert J.; Ofial, Armin R.; Mayr, Herbert (2020-04-27). "From
Carbodiimides to Carbon Dioxide: Quantification of the Electrophilic Reactivities of Heteroallenes".
138:, the central N=C=N angle is 170° and the C-N=C angles are within 1° of 126°. The C=N distances are short, nearly 120 pm, as is characteristic of double bonds. Carbodiimides are
2294:
2064:
2024:
1516:
1127:
Arnab K. Maity; Skye
Fortier; Leonel Griego; Alejandro J. Metta-Magaña (2014). "Synthesis of a "Super Bulky" Guanidinate Possessing an Expandable Coordination Pocket".
857:
Irngartinger, H.; Jäger, H.-U. (1978). "Kristall- und
Molekularstrukturen von zwei Carbodiimiden: Bis(diphenylmethyl)carbodiimid und Bis(p-methoxyphenyl)-carbodiimid".
276:
Compared to other heteroallenes, carbodiimides are very weak electrophiles and only react with nucleophiles in the presence of catalysts, such as acids. In this way,
2225:
2200:
2190:
211:
This reaction can often be conducted as stated, even though carbodiimides react with water. In some cases, a dehydrating agent is added to the reaction mixture.
2596:
1924:
1865:
1773:
2685:
2501:
2436:
2376:
2304:
2210:
2104:
1974:
1929:
1600:
2765:
2230:
2074:
2044:
2160:
2140:
1813:
2185:
565:
is mostly removed by filtration, but trace impurities can be difficult to remove. It is incompatible with traditional solid-phase peptide synthesis.
1823:
1525:
2180:
1509:
476:
1850:
2396:
1793:
631:
1944:
1855:
657:
641:
1502:
543:. DCC has achieved popularity mainly because of its high-yielding amide coupling reactions and the fact that it is quite inexpensive.
2723:
2039:
383:
360:, compounds containing the carbodiimide functionality are used as dehydration agents. Specifically they are often used to convert
2255:
2014:
1934:
404:
The formation of an amide using a carbodiimide is a common reaction, but carries the risk of several side reactions. The acid
1322:
Posthumus, W.; Derksen, A. J.; van den
Goorbergh, J. A. M.; Hesselmans, L. C. J. (2007). "Crosslinking by polycarbodiimides".
1100:
John C. Sheehan; Philip A. Cruickshank (1968). "1-Ethyl-3-(3-Dimethylamino)propylcarbodiimide
Hydrochloride and Methiodide".
1084:
710:
535:) was one of the first carbodiimides developed as a reagent. It is widely used for amide and ester formation, especially for
2636:
1416:
731:"Interstellar Carbodiimide (HNCNH): A New Astronomical Detection from the GBT Primos Survey Via Maser Emission Features"
2888:
2788:
522:
516:
499:
2913:
1434:
1233:
Tidwell, T. T. (1990). "Oxidation of
Alcohols by Activated Dimethyl Sulfoxide and Related Reactions: An Update".
609:
603:
586:
935:
Taniguchi, Tohru; Suzuki, Takahiro; Satoh, Haruka; Shichibu, Yukatsu; Konishi, Katsuaki; Monde, Kenji (2018).
2838:
2873:
1287:
Hesselmans, L. C. J.; Derksen, A. J.; van den
Goorbergh, J. A. M. (2006). "Polycarbodiimide crosslinkers".
1162:
Monagle, J. J. (1962). "Carbodiimides. III. Conversion of
Isocyanates to Carbodiimides. Catalyst Studies".
2069:
3016:
3011:
1378:
694:
2828:
2823:
2004:
416:
with an activated leaving group. The O-acylisourea will react with amines to give the desired amide
2868:
1359:
Coupling of substances containing a primary amine to hyaluronan via carbodiimide-mediated amidation
238:
66:
2948:
730:
546:
However, DCC does have some serious drawbacks, and its use is often avoided for several reasons:
392:
1126:
3006:
2803:
1768:
1678:
1555:
1550:
373:
130:
The N=C=N core is relatively linear and the C-N=C angles approach 120°. In the case of C(NCHPh
2858:
2833:
2471:
2089:
1636:
691:
Nomenclature of
Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)
622:) is a liquid. Its hydrolysis product, N,N'-diisopropylurea, is soluble in organic solvents.
536:
107:
1485:
2919:
2903:
2528:
1899:
1870:
1751:
1575:
752:
377:
234:
1468:
1451:
1040:
Frederick Kurzer; K. Douraghi-Zadeh (1967). "Advances in the
Chemistry of Carbodiimides".
8:
2863:
2843:
2656:
2346:
1834:
1698:
1673:
1641:
1560:
756:
2961:
2883:
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2150:
2084:
1949:
1909:
1760:
1723:
1683:
1662:
1605:
1580:
1215:
964:
797:
Andrew Williams; Ibrahim T. Ibrahim (1981). "Carbodiimide Chemistry: recent Advances".
776:
742:
297:
55:
764:
450:. The main undesired reaction pathway involves the rearrangement of the O-acylisourea
19:
2908:
2491:
2391:
2361:
2279:
2019:
1904:
1860:
1808:
1615:
1610:
1542:
1362:
1339:
1304:
1219:
1207:
1144:
1080:
1057:
1010:
956:
768:
706:
357:
293:
74:
70:
35:
1494:
968:
936:
780:
408:
will react with the carbodiimide to produce the key intermediate: the O-acylisourea
2985:
2973:
2893:
2793:
2698:
2646:
2079:
1954:
1919:
1840:
1828:
1788:
1693:
1626:
1392:
1335:
1331:
1300:
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1242:
1199:
1172:
1136:
1109:
1049:
1002:
948:
917:
866:
836:
806:
760:
698:
562:
341:
296:, a protocol for conversion of an alcohol to a carbonyl (ketone or aldehyde) using
47:
859:
Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry
2581:
2556:
2094:
2034:
1818:
1718:
1703:
1688:
1595:
1585:
990:
466:
361:
265:
156:
147:
702:
2818:
2783:
2566:
2456:
2421:
2406:
2341:
2336:
2235:
2135:
2054:
2029:
1994:
1939:
1914:
1783:
1631:
1404:
669:
440:
391:
Polycarbodiimides can also be used as crosslinkers for aqueous resins, such as
340:
Typically the sulfoxide and diimide are used in excess. The reaction generates
188:
151:
119:
870:
73:. Dialkylcarbodiimides are stable. Some diaryl derivatives tend to convert to
3000:
2848:
2703:
2586:
2561:
2542:
2486:
2366:
2324:
2319:
2059:
2049:
2009:
1884:
1778:
1733:
1708:
1590:
1570:
1366:
1343:
1308:
1273:
1164:
1113:
840:
772:
115:
2924:
2778:
2631:
2571:
2551:
2523:
2451:
2331:
2314:
2269:
2220:
1845:
1798:
1646:
1321:
1211:
1148:
1014:
960:
249:
Isocyanates can be converted to carbodiimides with loss of carbon dioxide:
1061:
280:
can be prepared. As weak bases, carbodiimides bind to Lewis acids to give
2898:
2808:
2773:
2740:
2666:
2641:
2481:
2386:
2356:
2240:
2155:
2145:
1875:
1803:
1246:
1203:
952:
921:
28:
27:-carbodiimides: The core functional group is shown in blue with attached
1176:
1053:
810:
2813:
2755:
2718:
2693:
2591:
2401:
2264:
637:
470:
83:
1399:
1140:
1006:
2745:
2610:
2446:
2250:
2130:
1984:
1959:
277:
167:
1099:
2713:
2625:
2426:
2289:
2274:
2245:
2114:
1889:
1713:
1657:
1651:
1620:
1565:
1533:
569:
459:
184:
163:
78:
1286:
884:
Vincent, A. T.; Wheatley, P. J. (1972). "Crystal Structure of Bis-
747:
380:, are often added to increase yields and decrease side reactions.
183:
A classic route to carbodiimides involves dehydrosulfurization of
2878:
2708:
2661:
2620:
2576:
2518:
2513:
2476:
2466:
2461:
2416:
2411:
2351:
2284:
2175:
2170:
2120:
1999:
1989:
1742:
1039:
796:
540:
94:
581:
494:
431:
produce both desired and undesired products. The O-acylisourea
122:. Three principal resonance structures describe carbodiimides:
2929:
2750:
2732:
2195:
2165:
1667:
281:
139:
937:"Preparation of Carbodiimides with One-Handed Axial Chirality"
827:
T. W. Campbell; J. J. Monagle (1963). "Diphenylcarbodiimide".
480:
The reaction mechanism of amide formation using a carbodiimide
1964:
1894:
1410:
465:. The use of solvents with low dielectric constants such as
413:
369:
365:
59:
51:
934:
826:
345:
728:
214:
The dehydration of N,N'-dialkylureas gives carbodiimides:
16:
Class of organic compounds with general structure RN=C=NR'
989:
Damrauer, Robert; Lin, Hai; Damrauer, Niels H. (2014).
656:-toluene sulfonate is a carbodiimide developed for the
914:
Journal of the Chemical Society, Perkin Transactions 2
1524:
1376:
162:
The parent compound, methanediimine, (HN=C=NH), is a
58:
the parent compound HN=C=NH has been detected by its
988:
652:
1-cyclohexyl-(2-morpholinoethyl)carbodiimide metho-
114:From the perspective of bonding, carbodiimides are
856:
2998:
1189:
1356:
1259:
883:
1232:
1161:
1510:
991:"Computational Studies of Carbodiimide Rings"
632:1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide
435:can react with an additional carboxylic acid
1074:
446:, which can react further to give the amide
427:The possible reactions of the O-acylisourea
178:
1517:
1503:
852:
850:
792:
790:
399:
1260:John G. Moffatt (1967). "Cholane-24-al".
1077:Chemistry and Technology of Carbodiimides
822:
820:
746:
1192:Journal of the American Chemical Society
941:Journal of the American Chemical Society
580:
493:
241:have been used as a dehydrating agents.
187:. A typical reagent for this process is
93:
89:
18:
847:
787:
387:Amide coupling utilizing a carbodiimide
54:they are exclusively synthetic, but in
2999:
1068:
817:
1498:
1417:
1035:
1033:
1031:
287:
86:in the presence of water over time.
292:Carbodiimides are reagents for the
244:
13:
2889:Nexus for Exoplanet System Science
1120:
475:
382:
351:
110:(color scheme: gray = C, blue = N)
14:
3028:
2789:Atomic and molecular astrophysics
1526:Molecules detected in outer space
1028:
658:chemical probing of RNA structure
473:can minimize this side reaction.
2979:
2967:
2955:
2944:
2943:
1750:
1741:
1732:
1477:
1460:
1443:
1426:
1398:
1386:
2914:Polycyclic aromatic hydrocarbon
1361:(Thesis). Uppsala Universitet.
1350:
1315:
1280:
1253:
1226:
1183:
1155:
1093:
268:. This reaction is reversible.
1336:10.1016/j.porgcoat.2006.09.031
1301:10.1016/j.porgcoat.2005.08.011
982:
928:
877:
722:
683:
647:
1:
2839:Extraterrestrial liquid water
676:
517:N,N'-Dicyclohexylcarbodiimide
264:The reaction is catalyzed by
65:A well known carbodiimide is
50:with the formula RN=C=NR. On
1324:Progress in Organic Coatings
1289:Progress in Organic Coatings
995:Journal of Organic Chemistry
604:N,N'-Diisopropylcarbodiimide
271:
173:
7:
2070:Protonated hydrogen cyanide
888:-nitrophenylcarbodiimide, O
765:10.1088/2041-8205/758/2/L33
703:10.1039/9781849733069-00372
663:
484:
412:, which can be viewed as a
126:RN=C=NR ↔ RN≡C-NR ↔ RN-C≡NR
10:
3033:
695:Royal Society of Chemistry
629:
601:
514:
150:. However, due to the low
2938:
2829:Earliest known life forms
2824:Diffuse interstellar band
2764:
2684:
2609:
2500:
2435:
2375:
2303:
2295:Protonated cyanoacetylene
2209:
2103:
2065:Protonated carbon dioxide
2025:Hydromagnesium isocyanide
1973:
1759:
1730:
1541:
1532:
871:10.1107/S0567740878010626
735:The Astrophysical Journal
608:In contrast to DCC, DIC (
533:-dicyclohexylcarbodiimide
510:-dicyclohexylcarbodiimide
2874:Iron–sulfur world theory
2869:Photodissociation region
2572:Methyl-cyano-diacetylene
1357:Hotan Mojarradi (2010).
1274:10.15227/orgsyn.047.0025
1114:10.15227/orgsyn.048.0083
841:10.15227/orgsyn.043.0031
620:-diisopropylcarbodiimide
597:-diisopropylcarbodiimide
393:polyurethane dispersions
300:as the oxidizing agent:
239:Toluenesulfonyl chloride
179:From thioureas and ureas
146:-symmetry and therefore
67:dicyclohexylcarbodiimide
42:(systematic IUPAC name:
2949:Category:Astrochemistry
2539:, fullerene, buckyball)
2226:Cyanobutadiynyl radical
2201:Silicon-carbide cluster
2191:Protonated formaldehyde
400:Amide formation pathway
2962:Outer space portal
2804:Circumstellar envelope
1769:Aluminium(I) hydroxide
1679:Phosphorus mononitride
1556:Aluminium monofluoride
1551:Aluminium monochloride
625:
599:
576:
512:
489:
481:
388:
374:N-hydroxybenzotriazole
372:. Additives, such as
111:
31:
2859:Interplanetary medium
2834:Extraterrestrial life
2472:Octatetraynyl radical
2090:Tricarbon monosulfide
1637:Magnesium monohydride
1075:Henri Ulrich (2008).
697:. 2014. p. 375.
672:- the sulfur analogue
584:
537:solid-phase synthesis
497:
479:
386:
108:X-ray crystallography
97:
90:Structure and bonding
23:General structure of
22:
2986:Chemistry portal
2974:Astronomy portal
2920:RNA world hypothesis
2904:PAH world hypothesis
2597:Heptatrienyl radical
2529:Buckminsterfullerene
2417:Methylcyanoacetylene
1925:Silicon carbonitride
1900:Methylidynephosphane
1866:Magnesium isocyanide
1774:Aluminium isocyanide
1576:Carbon monophosphide
1247:10.1055/s-1990-27036
1204:10.1021/jacs.0c01960
953:10.1021/jacs.8b08969
922:10.1039/P29720001567
378:N-hydroxysuccinimide
235:Phosphorus pentoxide
98:Structure of C(NCHPh
2864:Interstellar medium
2844:Forbidden mechanism
2657:Hydrogen isocyanide
2347:Hexatriynyl radical
1930:c-Silicon dicarbide
1835:Hydrogen isocyanide
1699:Silicon monosulfide
1674:Phosphorus monoxide
1642:Methylidyne radical
1601:Fluoromethylidynium
1561:Aluminium(II) oxide
1177:10.1021/jo01058a022
1054:10.1021/cr60246a001
947:(46): 15577−15581.
811:10.1021/cr00046a004
757:2012ApJ...758L..33M
69:, which is used in
2884:Molecules in stars
2854:Intergalactic dust
2799:Circumstellar dust
2741:Naphthalene cation
2676:Trihydrogen cation
2652:Hydrogen deuteride
2577:Methyltriacetylene
2412:Hexapentaenylidene
2231:E-Cyanomethanimine
2151:Cyclopropenylidene
2085:Tricarbon monoxide
2075:Silicon tricarbide
2045:Methylene amidogen
2035:Isothiocyanic acid
1950:Thioxoethenylidene
1910:Trihydrogen cation
1724:Titanium(II) oxide
1684:Potassium chloride
1663:Sulfur mononitride
1606:Helium hydride ion
1581:Carbon monosulfide
600:
513:
482:
389:
298:dimethyl sulfoxide
112:
56:interstellar space
32:
3017:Functional groups
3012:Organic chemistry
2994:
2993:
2909:Pseudo-panspermia
2605:
2604:
2552:Cyanodecapentayne
2492:N-Methylformamide
2467:Methyldiacetylene
2392:Aminoacetonitrile
2362:Methyl isocyanate
2280:Methyl isocyanide
2161:Isocyanoacetylene
2141:Cyanoformaldehyde
2020:Hydrogen peroxide
1905:Potassium cyanide
1861:Magnesium cyanide
1814:Disilicon carbide
1809:Dicarbon monoxide
1616:Hydrogen fluoride
1611:Hydrogen chloride
1198:(18): 8383–8402.
1171:(11): 3851–3855.
1141:10.1021/ic501219q
1135:(15): 8155–8164.
1086:978-0-470-06510-5
1007:10.1021/jo4026435
916:(11): 1567–1571.
865:(11): 3262–3265.
712:978-0-85404-182-4
693:. Cambridge: The
660:in biochemistry.
521:DCC (acronym for
358:organic synthesis
294:Moffatt oxidation
288:Moffatt oxidation
106:as determined by
71:peptide synthesis
36:organic chemistry
3024:
2984:
2983:
2982:
2972:
2971:
2970:
2960:
2959:
2958:
2947:
2946:
2894:Organic compound
2794:Chemical formula
2699:Dihydroxyacetone
2647:Hydrogen cyanide
2332:Cyanodiacetylene
2186:Propadienylidene
2080:Thioformaldehyde
1955:Titanium dioxide
1920:Sodium hydroxide
1841:Hydrogen sulfide
1829:Hydrogen cyanide
1789:Carbonyl sulfide
1754:
1745:
1736:
1694:Silicon monoxide
1627:Hydroxyl radical
1539:
1538:
1519:
1512:
1505:
1496:
1495:
1490:
1489:from Wikiversity
1482:
1481:
1480:
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1403:
1402:
1391:
1390:
1389:
1382:
1371:
1370:
1354:
1348:
1347:
1330:(2–3): 231–236.
1319:
1313:
1312:
1284:
1278:
1277:
1257:
1251:
1250:
1230:
1224:
1223:
1187:
1181:
1180:
1159:
1153:
1152:
1124:
1118:
1117:
1097:
1091:
1090:
1072:
1066:
1065:
1048:(2): ee107–152.
1037:
1026:
1025:
1023:
1021:
1001:(9): 3781−3788.
986:
980:
979:
977:
975:
932:
926:
925:
881:
875:
874:
854:
845:
844:
824:
815:
814:
794:
785:
784:
750:
726:
720:
719:
687:
619:
596:
568:DCC is a potent
563:dicyclohexylurea
560:
532:
509:
414:carboxylic ester
362:carboxylic acids
342:dimethyl sulfide
266:phosphine oxides
245:From isocyanates
48:functional group
3032:
3031:
3027:
3026:
3025:
3023:
3022:
3021:
2997:
2996:
2995:
2990:
2980:
2978:
2968:
2966:
2956:
2954:
2934:
2760:
2736:
2727:
2680:
2670:
2613:
2601:
2582:Propionaldehyde
2557:Ethylene glycol
2546:
2538:
2534:
2505:
2503:
2496:
2452:Cyanohexatriyne
2438:
2431:
2378:
2371:
2306:
2299:
2259:
2212:
2205:
2176:Methoxy radical
2106:
2099:
2095:Thiocyanic acid
1976:
1969:
1879:
1819:Ethynyl radical
1755:
1749:
1748:
1747:
1746:
1740:
1739:
1738:
1737:
1728:
1719:Sulfur monoxide
1704:Sodium chloride
1689:Silicon carbide
1596:Diatomic carbon
1586:Carbon monoxide
1528:
1523:
1493:
1483:
1478:
1476:
1466:
1461:
1459:
1449:
1444:
1442:
1432:
1427:
1425:
1422:
1418:sister projects
1415:at Knowledge's
1409:
1397:
1387:
1385:
1377:
1375:
1374:
1355:
1351:
1320:
1316:
1285:
1281:
1258:
1254:
1241:(10): 857–870.
1231:
1227:
1188:
1184:
1160:
1156:
1125:
1121:
1098:
1094:
1087:
1073:
1069:
1038:
1029:
1019:
1017:
987:
983:
973:
971:
933:
929:
911:
907:
903:
899:
895:
891:
882:
878:
855:
848:
825:
818:
795:
788:
727:
723:
713:
689:
688:
684:
679:
666:
650:
634:
628:
617:
606:
594:
579:
558:
530:
519:
507:
492:
487:
467:dichloromethane
402:
354:
352:Coupling agents
348:as byproducts.
335:
331:
327:
323:
319:
315:
311:
307:
290:
274:
260:
256:
253:2 RN=C=O → (RN)
247:
229:
225:
221:
206:
202:
199:CS + HgO → (RN)
198:
181:
176:
148:axial chirality
145:
137:
133:
105:
101:
92:
17:
12:
11:
5:
3030:
3020:
3019:
3014:
3009:
2992:
2991:
2989:
2988:
2976:
2964:
2952:
2939:
2936:
2935:
2933:
2932:
2927:
2922:
2917:
2911:
2906:
2901:
2896:
2891:
2886:
2881:
2876:
2871:
2866:
2861:
2856:
2851:
2846:
2841:
2836:
2831:
2826:
2821:
2819:Cosmochemistry
2816:
2811:
2806:
2801:
2796:
2791:
2786:
2784:Astrochemistry
2781:
2776:
2770:
2768:
2762:
2761:
2759:
2758:
2753:
2748:
2743:
2738:
2734:
2730:
2725:
2721:
2716:
2711:
2706:
2701:
2696:
2690:
2688:
2682:
2681:
2679:
2678:
2673:
2668:
2664:
2659:
2654:
2649:
2644:
2639:
2637:Formyl radical
2634:
2629:
2623:
2617:
2615:
2607:
2606:
2603:
2602:
2600:
2599:
2594:
2589:
2584:
2579:
2574:
2569:
2567:Methyl acetate
2564:
2559:
2554:
2549:
2544:
2540:
2536:
2532:
2526:
2521:
2516:
2510:
2508:
2498:
2497:
2495:
2494:
2489:
2484:
2479:
2474:
2469:
2464:
2459:
2457:Dimethyl ether
2454:
2449:
2443:
2441:
2433:
2432:
2430:
2429:
2424:
2422:Methyl formate
2419:
2414:
2409:
2407:Glycolaldehyde
2404:
2399:
2394:
2389:
2383:
2381:
2373:
2372:
2370:
2369:
2364:
2359:
2354:
2349:
2344:
2342:Glycolonitrile
2339:
2337:Ethylene oxide
2334:
2329:
2328:
2327:
2317:
2311:
2309:
2301:
2300:
2298:
2297:
2292:
2287:
2282:
2277:
2272:
2267:
2262:
2257:
2253:
2248:
2243:
2238:
2236:Cyclopropenone
2233:
2228:
2223:
2217:
2215:
2207:
2206:
2204:
2203:
2198:
2193:
2188:
2183:
2178:
2173:
2168:
2163:
2158:
2153:
2148:
2143:
2138:
2136:Cyanoacetylene
2133:
2128:
2123:
2118:
2111:
2109:
2101:
2100:
2098:
2097:
2092:
2087:
2082:
2077:
2072:
2067:
2062:
2057:
2055:Methyl radical
2052:
2047:
2042:
2037:
2032:
2030:Isocyanic acid
2027:
2022:
2017:
2012:
2007:
2002:
1997:
1995:Isocyanic acid
1992:
1987:
1981:
1979:
1971:
1970:
1968:
1967:
1962:
1957:
1952:
1947:
1942:
1940:Sulfur dioxide
1937:
1932:
1927:
1922:
1917:
1915:Sodium cyanide
1912:
1907:
1902:
1897:
1892:
1887:
1882:
1877:
1873:
1868:
1863:
1858:
1853:
1848:
1843:
1838:
1832:
1826:
1824:Formyl radical
1821:
1816:
1811:
1806:
1801:
1796:
1791:
1786:
1784:Carbon dioxide
1781:
1776:
1771:
1765:
1763:
1757:
1756:
1731:
1729:
1727:
1726:
1721:
1716:
1711:
1706:
1701:
1696:
1691:
1686:
1681:
1676:
1671:
1665:
1660:
1655:
1649:
1644:
1639:
1634:
1632:Iron(II) oxide
1629:
1624:
1618:
1613:
1608:
1603:
1598:
1593:
1588:
1583:
1578:
1573:
1568:
1563:
1558:
1553:
1547:
1545:
1536:
1530:
1529:
1522:
1521:
1514:
1507:
1499:
1492:
1491:
1474:
1472:from Wikibooks
1457:
1455:from Wikiquote
1440:
1411:
1408:
1407:
1395:
1373:
1372:
1349:
1314:
1295:(2): 142–148.
1279:
1252:
1225:
1182:
1154:
1119:
1092:
1085:
1067:
1027:
981:
927:
909:
905:
901:
897:
893:
889:
876:
846:
816:
805:(6): 589–636.
786:
721:
711:
681:
680:
678:
675:
674:
673:
670:Sulfur diimide
665:
662:
649:
646:
642:chemical probe
630:Main article:
627:
624:
602:Main article:
578:
575:
574:
573:
566:
550:The byproduct
515:Main article:
491:
488:
486:
483:
454:to the stable
441:acid anhydride
401:
398:
353:
350:
338:
337:
333:
329:
325:
321:
317:
313:
309:
305:
289:
286:
273:
270:
262:
261:
258:
254:
246:
243:
232:
231:
227:
223:
219:
209:
208:
204:
200:
196:
189:mercuric oxide
180:
177:
175:
172:
152:energy barrier
143:
142:, possessing C
135:
131:
128:
127:
120:carbon dioxide
103:
99:
91:
88:
44:methanediimine
15:
9:
6:
4:
3:
2:
3029:
3018:
3015:
3013:
3010:
3008:
3007:Carbodiimides
3005:
3004:
3002:
2987:
2977:
2975:
2965:
2963:
2953:
2951:
2950:
2941:
2940:
2937:
2931:
2928:
2926:
2923:
2921:
2918:
2915:
2912:
2910:
2907:
2905:
2902:
2900:
2897:
2895:
2892:
2890:
2887:
2885:
2882:
2880:
2877:
2875:
2872:
2870:
2867:
2865:
2862:
2860:
2857:
2855:
2852:
2850:
2849:Homochirality
2847:
2845:
2842:
2840:
2837:
2835:
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:
2771:
2769:
2767:
2763:
2757:
2754:
2752:
2749:
2747:
2744:
2742:
2739:
2737:
2731:
2729:
2722:
2720:
2717:
2715:
2712:
2710:
2707:
2705:
2704:Methoxyethane
2702:
2700:
2697:
2695:
2692:
2691:
2689:
2687:
2683:
2677:
2674:
2672:
2665:
2663:
2660:
2658:
2655:
2653:
2650:
2648:
2645:
2643:
2640:
2638:
2635:
2633:
2630:
2627:
2624:
2622:
2619:
2618:
2616:
2612:
2608:
2598:
2595:
2593:
2590:
2588:
2587:Butyronitrile
2585:
2583:
2580:
2578:
2575:
2573:
2570:
2568:
2565:
2563:
2562:Ethyl formate
2560:
2558:
2555:
2553:
2550:
2548:
2541:
2530:
2527:
2525:
2522:
2520:
2517:
2515:
2512:
2511:
2509:
2507:
2499:
2493:
2490:
2488:
2487:Propionitrile
2485:
2483:
2480:
2478:
2475:
2473:
2470:
2468:
2465:
2463:
2460:
2458:
2455:
2453:
2450:
2448:
2445:
2444:
2442:
2440:
2434:
2428:
2425:
2423:
2420:
2418:
2415:
2413:
2410:
2408:
2405:
2403:
2400:
2398:
2395:
2393:
2390:
2388:
2385:
2384:
2382:
2380:
2374:
2368:
2367:Vinyl alcohol
2365:
2363:
2360:
2358:
2355:
2353:
2350:
2348:
2345:
2343:
2340:
2338:
2335:
2333:
2330:
2326:
2325:Vinyl cyanide
2323:
2322:
2321:
2320:Acrylonitrile
2318:
2316:
2313:
2312:
2310:
2308:
2302:
2296:
2293:
2291:
2288:
2286:
2285:Pentynylidyne
2283:
2281:
2278:
2276:
2273:
2271:
2268:
2266:
2263:
2261:
2254:
2252:
2249:
2247:
2244:
2242:
2239:
2237:
2234:
2232:
2229:
2227:
2224:
2222:
2219:
2218:
2216:
2214:
2208:
2202:
2199:
2197:
2194:
2192:
2189:
2187:
2184:
2182:
2181:Methylenimine
2179:
2177:
2174:
2172:
2169:
2167:
2164:
2162:
2159:
2157:
2154:
2152:
2149:
2147:
2144:
2142:
2139:
2137:
2134:
2132:
2129:
2127:
2124:
2122:
2119:
2116:
2113:
2112:
2110:
2108:
2102:
2096:
2093:
2091:
2088:
2086:
2083:
2081:
2078:
2076:
2073:
2071:
2068:
2066:
2063:
2061:
2060:Propynylidyne
2058:
2056:
2053:
2051:
2050:Methyl cation
2048:
2046:
2043:
2041:
2038:
2036:
2033:
2031:
2028:
2026:
2023:
2021:
2018:
2016:
2013:
2011:
2010:Fulminic acid
2008:
2006:
2003:
2001:
1998:
1996:
1993:
1991:
1988:
1986:
1983:
1982:
1980:
1978:
1972:
1966:
1963:
1961:
1958:
1956:
1953:
1951:
1948:
1946:
1943:
1941:
1938:
1936:
1933:
1931:
1928:
1926:
1923:
1921:
1918:
1916:
1913:
1911:
1908:
1906:
1903:
1901:
1898:
1896:
1893:
1891:
1888:
1886:
1885:Nitrous oxide
1883:
1881:
1874:
1872:
1869:
1867:
1864:
1862:
1859:
1857:
1854:
1852:
1849:
1847:
1844:
1842:
1839:
1836:
1833:
1830:
1827:
1825:
1822:
1820:
1817:
1815:
1812:
1810:
1807:
1805:
1802:
1800:
1797:
1795:
1792:
1790:
1787:
1785:
1782:
1780:
1779:Amino radical
1777:
1775:
1772:
1770:
1767:
1766:
1764:
1762:
1758:
1753:
1744:
1735:
1725:
1722:
1720:
1717:
1715:
1712:
1710:
1709:Sodium iodide
1707:
1705:
1702:
1700:
1697:
1695:
1692:
1690:
1687:
1685:
1682:
1680:
1677:
1675:
1672:
1669:
1666:
1664:
1661:
1659:
1656:
1653:
1650:
1648:
1645:
1643:
1640:
1638:
1635:
1633:
1630:
1628:
1625:
1622:
1619:
1617:
1614:
1612:
1609:
1607:
1604:
1602:
1599:
1597:
1594:
1592:
1591:Cyano radical
1589:
1587:
1584:
1582:
1579:
1577:
1574:
1572:
1571:Carbon cation
1569:
1567:
1564:
1562:
1559:
1557:
1554:
1552:
1549:
1548:
1546:
1544:
1540:
1537:
1535:
1531:
1527:
1520:
1515:
1513:
1508:
1506:
1501:
1500:
1497:
1488:
1487:
1475:
1471:
1470:
1458:
1454:
1453:
1441:
1437:
1436:
1424:
1423:
1420:
1414:
1406:
1401:
1396:
1394:
1384:
1383:
1380:
1368:
1364:
1360:
1353:
1345:
1341:
1337:
1333:
1329:
1325:
1318:
1310:
1306:
1302:
1298:
1294:
1290:
1283:
1275:
1271:
1267:
1263:
1256:
1248:
1244:
1240:
1236:
1229:
1221:
1217:
1213:
1209:
1205:
1201:
1197:
1193:
1186:
1178:
1174:
1170:
1167:
1166:
1165:J. Org. Chem.
1158:
1150:
1146:
1142:
1138:
1134:
1130:
1123:
1115:
1111:
1107:
1103:
1096:
1088:
1082:
1079:. Wiley-VCH.
1078:
1071:
1063:
1059:
1055:
1051:
1047:
1043:
1036:
1034:
1032:
1016:
1012:
1008:
1004:
1000:
996:
992:
985:
970:
966:
962:
958:
954:
950:
946:
942:
938:
931:
923:
919:
915:
887:
880:
872:
868:
864:
860:
853:
851:
842:
838:
834:
830:
823:
821:
812:
808:
804:
800:
793:
791:
782:
778:
774:
770:
766:
762:
758:
754:
749:
744:
740:
736:
732:
725:
718:
714:
708:
704:
700:
696:
692:
686:
682:
671:
668:
667:
661:
659:
655:
645:
643:
639:
633:
623:
621:
616:
612:
605:
598:
593:
589:
585:Structure of
583:
571:
567:
564:
557:
553:
549:
548:
547:
544:
542:
538:
534:
529:
525:
518:
511:
506:
502:
498:Structure of
496:
478:
474:
472:
468:
464:
461:
457:
453:
449:
445:
442:
438:
434:
430:
425:
423:
419:
415:
411:
407:
397:
394:
385:
381:
379:
375:
371:
367:
363:
359:
349:
347:
343:
303:
302:
301:
299:
295:
285:
283:
279:
269:
267:
252:
251:
250:
242:
240:
236:
217:
216:
215:
212:
194:
193:
192:
190:
186:
171:
169:
165:
160:
158:
153:
149:
141:
125:
124:
123:
121:
117:
116:isoelectronic
109:
96:
87:
85:
80:
76:
72:
68:
63:
61:
57:
53:
49:
45:
41:
37:
30:
26:
21:
2942:
2925:Spectroscopy
2779:Astrobiology
2632:Formaldehyde
2524:Benzonitrile
2315:Acetaldehyde
2270:Methanethiol
2221:Acetonitrile
2126:Carbodiimide
2125:
2005:Formaldehyde
2000:Cyanoethynyl
1851:Iron cyanide
1846:Hydroperoxyl
1647:Nitric oxide
1484:
1467:
1450:
1438:from Commons
1433:
1413:Carbodiimide
1412:
1358:
1352:
1327:
1323:
1317:
1292:
1288:
1282:
1265:
1261:
1255:
1238:
1234:
1228:
1195:
1191:
1185:
1168:
1163:
1157:
1132:
1128:
1122:
1105:
1101:
1095:
1076:
1070:
1045:
1041:
1018:. Retrieved
998:
994:
984:
972:. Retrieved
944:
940:
930:
913:
885:
879:
862:
858:
832:
828:
802:
798:
738:
734:
724:
716:
690:
685:
653:
651:
635:
614:
610:
607:
591:
587:
555:
551:
545:
527:
523:
520:
504:
500:
462:
455:
451:
447:
443:
436:
432:
428:
426:
421:
417:
409:
405:
403:
390:
355:
339:
291:
275:
263:
248:
233:
213:
210:
182:
161:
129:
113:
64:
43:
40:carbodiimide
39:
33:
24:
2899:Outer space
2809:Cosmic dust
2774:Abiogenesis
2686:Unconfirmed
2642:Heavy water
2482:Ethanethiol
2397:Cyanoallene
2387:Acetic acid
2357:Methylamine
2241:Diacetylene
2156:Formic acid
2146:Cyanomethyl
1804:Diazenylium
1794:CCP radical
1670:(molecular)
1654:(molecular)
1623:(molecular)
1129:Inorg. Chem
648:CMCT or CMC
638:crosslinker
439:to give an
222:CO → (RN)
203:C + HgS + H
62:emissions.
3001:Categories
2814:Cosmic ray
2756:Silylidyne
2719:Hemolithin
2694:Anthracene
2611:Deuterated
2592:Pyrimidine
2402:Ethanimine
2265:Ketenimine
2121:Butadiynyl
1945:Thioformyl
1799:Chloronium
1452:Quotations
1262:Org. Synth
1102:Org. Synth
829:Org. Synth
741:(2): L33.
677:References
471:chloroform
328:S + (CyNH)
320:CHOH → (CH
312:SO + (CyN)
278:guanidines
84:hydrolysis
2746:Phosphine
2614:molecules
2547:fullerene
2447:Acetamide
2251:Formamide
2131:Cyanamide
1985:Acetylene
1960:Tricarbon
1871:Methylene
1856:Isoformyl
1761:Triatomic
1534:Molecules
1486:Resources
1469:Textbooks
1393:Chemistry
1367:1650-8297
1344:0300-9440
1309:0300-9440
1235:Synthesis
1220:216557447
1042:Chem. Rev
1020:18 August
974:18 August
799:Chem. Rev
773:2041-8205
748:1209.1590
420:and urea
272:Reactions
185:thioureas
174:Synthesis
168:cyanamide
2733:Linear C
2714:Graphene
2626:Ammonium
2427:Acrolein
2290:Propynal
2275:Methanol
2246:Ethylene
2115:Ammonium
1890:Nitroxyl
1714:Sulfanyl
1658:Imidogen
1652:Nitrogen
1621:Hydrogen
1566:Argonium
1543:Diatomic
1212:32338511
1149:25029088
1015:24716711
969:53231838
961:30398863
900:·N:C:N·C
781:26146516
664:See also
570:allergen
541:peptides
485:Examples
460:acylurea
164:tautomer
79:polymers
29:R groups
2879:Kerogen
2766:Related
2709:Glycine
2662:Propyne
2621:Ammonia
2519:Benzene
2514:Acetone
2506:or more
2477:Propene
2462:Ethanol
2352:Propyne
2171:Methane
2040:Ketenyl
1990:Ammonia
1405:Science
1379:Portals
1062:4859920
753:Bibcode
282:adducts
218:(R(H)N)
195:(R(H)N)
46:) is a
2930:Tholin
2751:Pyrene
2196:Silane
2166:Ketene
1668:Oxygen
1365:
1342:
1307:
1268:: 25.
1218:
1210:
1147:
1108:: 83.
1083:
1060:
1013:
967:
959:
835:: 31.
779:
771:
709:
370:esters
366:amides
344:and a
332:CO + R
257:C + CO
237:and p-
226:C + H
157:cyclic
140:chiral
75:dimers
2916:(PAH)
2504:atoms
2439:atoms
2379:atoms
2377:Eight
2307:atoms
2305:Seven
2213:atoms
2107:atoms
1977:atoms
1965:Water
1895:Ozone
1837:(HNC)
1831:(HCN)
1435:Media
1216:S2CID
965:S2CID
777:S2CID
743:arXiv
618:'
595:'
559:'
531:'
508:'
316:C + R
118:with
60:maser
52:Earth
25:trans
2437:Nine
2105:Five
2015:HCCN
1975:Four
1935:SiNC
1363:ISSN
1340:ISSN
1305:ISSN
1239:1990
1208:PMID
1145:PMID
1081:ISBN
1058:PMID
1022:2020
1011:PMID
976:2020
957:PMID
769:ISSN
707:ISBN
346:urea
77:and
38:, a
2728:NCO
2628:ion
2535:, C
2502:Ten
2211:Six
2117:ion
1332:doi
1297:doi
1270:doi
1243:doi
1200:doi
1196:142
1173:doi
1137:doi
1110:doi
1050:doi
1003:doi
949:doi
945:140
918:doi
912:".
908:·NO
892:N·C
867:doi
837:doi
807:doi
761:doi
739:758
699:doi
640:or
626:EDC
577:DIC
539:of
490:DCC
469:or
376:or
368:or
364:to
356:In
336:C=O
304:(CH
166:of
34:In
3003::
2545:70
2537:60
2533:60
2531:(C
2256:HC
1338:.
1328:58
1326:.
1303:.
1293:55
1291:.
1266:47
1264:.
1237:.
1214:.
1206:.
1194:.
1169:27
1143:.
1133:53
1131:.
1106:48
1104:.
1056:.
1046:67
1044:.
1030:^
1009:.
999:79
997:.
993:.
963:.
955:.
943:.
939:.
863:34
861:.
849:^
833:43
831:.
819:^
803:81
801:.
789:^
775:.
767:.
759:.
751:.
737:.
733:.
715:.
705:.
644:.
424:.
284:.
191::
170:.
2735:5
2726:2
2724:H
2671:D
2669:2
2667:N
2543:C
2260:N
2258:4
1880:H
1878:2
1876:N
1518:e
1511:t
1504:v
1421::
1381::
1369:.
1346:.
1334::
1311:.
1299::
1276:.
1272::
1249:.
1245::
1222:.
1202::
1179:.
1175::
1151:.
1139::
1116:.
1112::
1089:.
1064:.
1052::
1024:.
1005::
978:.
951::
924:.
920::
910:2
906:4
904:H
902:6
898:4
896:H
894:6
890:2
886:p
873:.
869::
843:.
839::
813:.
809::
783:.
763::
755::
745::
701::
654:p
615:N
613:,
611:N
592:N
590:,
588:N
561:-
556:N
554:,
552:N
528:N
526:,
524:N
505:N
503:,
501:N
463:6
458:-
456:N
452:2
448:3
444:5
437:1
433:2
429:2
422:4
418:3
410:2
406:1
334:2
330:2
326:2
324:)
322:3
318:2
314:2
310:2
308:)
306:3
259:2
255:2
230:O
228:2
224:2
220:2
207:O
205:2
201:2
197:2
144:2
136:2
134:)
132:2
104:2
102:)
100:2
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