395:
1763:
31:
488:
1490:
2992:
1399:
1411:
1745:
2956:
1473:
1456:
1754:
106:
593:
506:
1439:
2980:
2968:
406:
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.
165:
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
583:, 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.
92:
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
728:
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.
170:
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.
740:
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).
647:
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
1201:
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".
149:, 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
2305:
2075:
2035:
1527:
1138:
Arnab K. Maity; Skye
Fortier; Leonel Griego; Alejandro J. Metta-Magaña (2014). "Synthesis of a "Super Bulky" Guanidinate Possessing an Expandable Coordination Pocket".
868:
Irngartinger, H.; Jäger, H.-U. (1978). "Kristall- und
Molekularstrukturen von zwei Carbodiimiden: Bis(diphenylmethyl)carbodiimid und Bis(p-methoxyphenyl)-carbodiimid".
287:
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,
2236:
2211:
2201:
222:
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.
2607:
1935:
1876:
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2512:
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1985:
1940:
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2085:
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2151:
1824:
2196:
576:
is mostly removed by filtration, but trace impurities can be difficult to remove. It is incompatible with traditional solid-phase peptide synthesis.
1834:
1536:
2191:
1520:
487:
1861:
2407:
1804:
642:
1955:
1866:
668:
652:
1513:
554:. DCC has achieved popularity mainly because of its high-yielding amide coupling reactions and the fact that it is quite inexpensive.
2734:
2050:
394:
371:, compounds containing the carbodiimide functionality are used as dehydration agents. Specifically they are often used to convert
2266:
2025:
1945:
415:
The formation of an amide using a carbodiimide is a common reaction, but carries the risk of several side reactions. The acid
1333:
Posthumus, W.; Derksen, A. J.; van den
Goorbergh, J. A. M.; Hesselmans, L. C. J. (2007). "Crosslinking by polycarbodiimides".
1111:
John C. Sheehan; Philip A. Cruickshank (1968). "1-Ethyl-3-(3-Dimethylamino)propylcarbodiimide
Hydrochloride and Methiodide".
1095:
721:
546:) was one of the first carbodiimides developed as a reagent. It is widely used for amide and ester formation, especially for
2647:
1427:
742:"Interstellar Carbodiimide (HNCNH): A New Astronomical Detection from the GBT Primos Survey Via Maser Emission Features"
2899:
2799:
533:
527:
510:
2924:
1445:
1244:
Tidwell, T. T. (1990). "Oxidation of
Alcohols by Activated Dimethyl Sulfoxide and Related Reactions: An Update".
620:
614:
597:
946:
Taniguchi, Tohru; Suzuki, Takahiro; Satoh, Haruka; Shichibu, Yukatsu; Konishi, Katsuaki; Monde, Kenji (2018).
2849:
17:
2884:
1298:
Hesselmans, L. C. J.; Derksen, A. J.; van den
Goorbergh, J. A. M. (2006). "Polycarbodiimide crosslinkers".
1173:
Monagle, J. J. (1962). "Carbodiimides. III. Conversion of
Isocyanates to Carbodiimides. Catalyst Studies".
2080:
3027:
3022:
1389:
705:
2839:
2834:
2015:
427:
with an activated leaving group. The O-acylisourea will react with amines to give the desired amide
2879:
1370:
Coupling of substances containing a primary amine to hyaluronan via carbodiimide-mediated amidation
249:
77:
2959:
741:
557:
However, DCC does have some serious drawbacks, and its use is often avoided for several reasons:
403:
1137:
3017:
2814:
1779:
1689:
1566:
1561:
384:
141:
The N=C=N core is relatively linear and the C-N=C angles approach 120°. In the case of C(NCHPh
2869:
2844:
2482:
2100:
1647:
702:
Nomenclature of
Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)
633:) is a liquid. Its hydrolysis product, N,N'-diisopropylurea, is soluble in organic solvents.
547:
118:
1496:
2930:
2914:
2539:
1910:
1881:
1762:
1586:
763:
388:
245:
1479:
1462:
1051:
Frederick Kurzer; K. Douraghi-Zadeh (1967). "Advances in the
Chemistry of Carbodiimides".
8:
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1226:
975:
808:
Andrew Williams; Ibrahim T. Ibrahim (1981). "Carbodiimide Chemistry: recent Advances".
787:
753:
308:
66:
775:
461:. The main undesired reaction pathway involves the rearrangement of the O-acylisourea
30:
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2502:
2402:
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2030:
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1819:
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1021:
967:
779:
717:
368:
304:
85:
81:
46:
1505:
979:
947:
791:
419:
will react with the carbodiimide to produce the key intermediate: the O-acylisourea
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2904:
2804:
2709:
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1965:
1930:
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959:
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847:
817:
771:
709:
573:
352:
307:, a protocol for conversion of an alcohol to a carbonyl (ketone or aldehyde) using
58:
870:
Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry
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2105:
2045:
1829:
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2005:
1950:
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1794:
1642:
1415:
680:
451:
402:
Polycarbodiimides can also be used as crosslinkers for aqueous resins, such as
351:
Typically the sulfoxide and diimide are used in excess. The reaction generates
199:
162:
130:
881:
84:. Dialkylcarbodiimides are stable. Some diaryl derivatives tend to convert to
3011:
2859:
2714:
2597:
2572:
2553:
2497:
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2335:
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2020:
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1222:
1159:
1025:
971:
260:
Isocyanates can be converted to carbodiimides with loss of carbon dioxide:
1072:
291:
can be prepared. As weak bases, carbodiimides bind to Lewis acids to give
2909:
2819:
2784:
2751:
2677:
2652:
2492:
2397:
2367:
2251:
2166:
2156:
1886:
1814:
1257:
1214:
963:
932:
39:
38:-carbodiimides: The core functional group is shown in blue with attached
1187:
1064:
821:
2824:
2766:
2729:
2704:
2602:
2412:
2275:
648:
481:
94:
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1995:
1970:
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580:
470:
195:
174:
89:
1297:
895:
Vincent, A. T.; Wheatley, P. J. (1972). "Crystal Structure of Bis-
758:
391:, are often added to increase yields and decrease side reactions.
194:
A classic route to carbodiimides involves dehydrosulfurization of
2889:
2719:
2672:
2631:
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2529:
2524:
2487:
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2472:
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2131:
2010:
2000:
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105:
592:
505:
442:
produce both desired and undesired products. The O-acylisourea
133:. Three principal resonance structures describe carbodiimides:
2940:
2761:
2743:
2206:
2176:
1678:
292:
150:
948:"Preparation of Carbodiimides with One-Handed Axial Chirality"
838:
T. W. Campbell; J. J. Monagle (1963). "Diphenylcarbodiimide".
491:
The reaction mechanism of amide formation using a carbodiimide
1975:
1905:
1421:
476:. The use of solvents with low dielectric constants such as
424:
380:
376:
70:
62:
945:
837:
356:
739:
225:
The dehydration of N,N'-dialkylureas gives carbodiimides:
27:
Class of organic compounds with general structure RN=C=NR'
1000:
Damrauer, Robert; Lin, Hai; Damrauer, Niels H. (2014).
667:-toluene sulfonate is a carbodiimide developed for the
925:
Journal of the Chemical Society, Perkin Transactions 2
1535:
1387:
173:
The parent compound, methanediimine, (HN=C=NH), is a
69:
the parent compound HN=C=NH has been detected by its
999:
663:
1-cyclohexyl-(2-morpholinoethyl)carbodiimide metho-
125:From the perspective of bonding, carbodiimides are
867:
3009:
1200:
1367:
1270:
894:
1243:
1172:
1521:
1002:"Computational Studies of Carbodiimide Rings"
643:1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide
446:can react with an additional carboxylic acid
1085:
457:, which can react further to give the amide
438:The possible reactions of the O-acylisourea
189:
1528:
1514:
863:
861:
803:
801:
410:
1271:John G. Moffatt (1967). "Cholane-24-al".
1088:Chemistry and Technology of Carbodiimides
833:
831:
757:
1203:Journal of the American Chemical Society
952:Journal of the American Chemical Society
591:
504:
252:have been used as a dehydrating agents.
198:. A typical reagent for this process is
104:
100:
29:
858:
798:
398:Amide coupling utilizing a carbodiimide
65:they are exclusively synthetic, but in
14:
3010:
1079:
828:
1509:
1428:
1046:
1044:
1042:
298:
97:in the presence of water over time.
303:Carbodiimides are reagents for the
255:
24:
2900:Nexus for Exoplanet System Science
1131:
486:
393:
362:
121:(color scheme: gray = C, blue = N)
25:
3039:
2800:Atomic and molecular astrophysics
1537:Molecules detected in outer space
1039:
669:chemical probing of RNA structure
484:can minimize this side reaction.
2990:
2978:
2966:
2955:
2954:
1761:
1752:
1743:
1488:
1471:
1454:
1437:
1409:
1397:
2925:Polycyclic aromatic hydrocarbon
1372:(Thesis). Uppsala Universitet.
1361:
1326:
1291:
1264:
1237:
1194:
1166:
1104:
279:. This reaction is reversible.
1347:10.1016/j.porgcoat.2006.09.031
1312:10.1016/j.porgcoat.2005.08.011
993:
939:
888:
733:
694:
658:
13:
1:
2850:Extraterrestrial liquid water
687:
528:N,N'-Dicyclohexylcarbodiimide
275:The reaction is catalyzed by
76:A well known carbodiimide is
61:with the formula RN=C=NR. On
1335:Progress in Organic Coatings
1300:Progress in Organic Coatings
1006:Journal of Organic Chemistry
615:N,N'-Diisopropylcarbodiimide
282:
184:
7:
2081:Protonated hydrogen cyanide
899:-nitrophenylcarbodiimide, O
776:10.1088/2041-8205/758/2/L33
714:10.1039/9781849733069-00372
674:
495:
423:, which can be viewed as a
137:RN=C=NR ↔ RN≡C-NR ↔ RN-C≡NR
10:
3044:
706:Royal Society of Chemistry
640:
612:
525:
161:. However, due to the low
2949:
2840:Earliest known life forms
2835:Diffuse interstellar band
2775:
2695:
2620:
2511:
2446:
2386:
2314:
2306:Protonated cyanoacetylene
2220:
2114:
2076:Protonated carbon dioxide
2036:Hydromagnesium isocyanide
1984:
1770:
1741:
1552:
1543:
882:10.1107/S0567740878010626
746:The Astrophysical Journal
619:In contrast to DCC, DIC (
544:-dicyclohexylcarbodiimide
521:-dicyclohexylcarbodiimide
2885:Iron–sulfur world theory
2880:Photodissociation region
2583:Methyl-cyano-diacetylene
1368:Hotan Mojarradi (2010).
1285:10.15227/orgsyn.047.0025
1125:10.15227/orgsyn.048.0083
852:10.15227/orgsyn.043.0031
631:-diisopropylcarbodiimide
608:-diisopropylcarbodiimide
404:polyurethane dispersions
311:as the oxidizing agent:
250:Toluenesulfonyl chloride
190:From thioureas and ureas
157:-symmetry and therefore
78:dicyclohexylcarbodiimide
53:(systematic IUPAC name:
2960:Category:Astrochemistry
2550:, fullerene, buckyball)
2237:Cyanobutadiynyl radical
2212:Silicon-carbide cluster
2202:Protonated formaldehyde
411:Amide formation pathway
2973:Outer space portal
2815:Circumstellar envelope
1780:Aluminium(I) hydroxide
1690:Phosphorus mononitride
1567:Aluminium monofluoride
1562:Aluminium monochloride
636:
610:
587:
523:
500:
492:
399:
385:N-hydroxybenzotriazole
383:. Additives, such as
122:
42:
2870:Interplanetary medium
2845:Extraterrestrial life
2483:Octatetraynyl radical
2101:Tricarbon monosulfide
1648:Magnesium monohydride
1086:Henri Ulrich (2008).
708:. 2014. p. 375.
683:- the sulfur analogue
595:
548:solid-phase synthesis
508:
490:
397:
119:X-ray crystallography
108:
101:Structure and bonding
34:General structure of
33:
2997:Chemistry portal
2985:Astronomy portal
2931:RNA world hypothesis
2915:PAH world hypothesis
2608:Heptatrienyl radical
2540:Buckminsterfullerene
2428:Methylcyanoacetylene
1936:Silicon carbonitride
1911:Methylidynephosphane
1877:Magnesium isocyanide
1785:Aluminium isocyanide
1587:Carbon monophosphide
1258:10.1055/s-1990-27036
1215:10.1021/jacs.0c01960
964:10.1021/jacs.8b08969
933:10.1039/P29720001567
389:N-hydroxysuccinimide
246:Phosphorus pentoxide
109:Structure of C(NCHPh
2875:Interstellar medium
2855:Forbidden mechanism
2668:Hydrogen isocyanide
2358:Hexatriynyl radical
1941:c-Silicon dicarbide
1846:Hydrogen isocyanide
1710:Silicon monosulfide
1685:Phosphorus monoxide
1653:Methylidyne radical
1612:Fluoromethylidynium
1572:Aluminium(II) oxide
1188:10.1021/jo01058a022
1065:10.1021/cr60246a001
958:(46): 15577−15581.
822:10.1021/cr00046a004
768:2012ApJ...758L..33M
80:, which is used in
2895:Molecules in stars
2865:Intergalactic dust
2810:Circumstellar dust
2752:Naphthalene cation
2687:Trihydrogen cation
2663:Hydrogen deuteride
2588:Methyltriacetylene
2423:Hexapentaenylidene
2242:E-Cyanomethanimine
2162:Cyclopropenylidene
2096:Tricarbon monoxide
2086:Silicon tricarbide
2056:Methylene amidogen
2046:Isothiocyanic acid
1961:Thioxoethenylidene
1921:Trihydrogen cation
1735:Titanium(II) oxide
1695:Potassium chloride
1674:Sulfur mononitride
1617:Helium hydride ion
1592:Carbon monosulfide
611:
524:
493:
400:
309:dimethyl sulfoxide
123:
67:interstellar space
43:
3028:Functional groups
3023:Organic chemistry
3005:
3004:
2920:Pseudo-panspermia
2616:
2615:
2563:Cyanodecapentayne
2503:N-Methylformamide
2478:Methyldiacetylene
2403:Aminoacetonitrile
2373:Methyl isocyanate
2291:Methyl isocyanide
2172:Isocyanoacetylene
2152:Cyanoformaldehyde
2031:Hydrogen peroxide
1916:Potassium cyanide
1872:Magnesium cyanide
1825:Disilicon carbide
1820:Dicarbon monoxide
1627:Hydrogen fluoride
1622:Hydrogen chloride
1209:(18): 8383–8402.
1182:(11): 3851–3855.
1152:10.1021/ic501219q
1146:(15): 8155–8164.
1097:978-0-470-06510-5
1018:10.1021/jo4026435
927:(11): 1567–1571.
876:(11): 3262–3265.
723:978-0-85404-182-4
704:. Cambridge: The
671:in biochemistry.
532:DCC (acronym for
369:organic synthesis
305:Moffatt oxidation
299:Moffatt oxidation
117:as determined by
82:peptide synthesis
47:organic chemistry
16:(Redirected from
3035:
2995:
2994:
2993:
2983:
2982:
2981:
2971:
2970:
2969:
2958:
2957:
2905:Organic compound
2805:Chemical formula
2710:Dihydroxyacetone
2658:Hydrogen cyanide
2343:Cyanodiacetylene
2197:Propadienylidene
2091:Thioformaldehyde
1966:Titanium dioxide
1931:Sodium hydroxide
1852:Hydrogen sulfide
1840:Hydrogen cyanide
1800:Carbonyl sulfide
1765:
1756:
1747:
1705:Silicon monoxide
1638:Hydroxyl radical
1550:
1549:
1530:
1523:
1516:
1507:
1506:
1501:
1500:from Wikiversity
1493:
1492:
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1341:(2–3): 231–236.
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1323:
1295:
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1241:
1235:
1234:
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1164:
1163:
1135:
1129:
1128:
1108:
1102:
1101:
1083:
1077:
1076:
1059:(2): ee107–152.
1048:
1037:
1036:
1034:
1032:
1012:(9): 3781−3788.
997:
991:
990:
988:
986:
943:
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855:
835:
826:
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805:
796:
795:
761:
737:
731:
730:
698:
630:
607:
579:DCC is a potent
574:dicyclohexylurea
571:
543:
520:
425:carboxylic ester
373:carboxylic acids
353:dimethyl sulfide
277:phosphine oxides
256:From isocyanates
59:functional group
21:
3043:
3042:
3038:
3037:
3036:
3034:
3033:
3032:
3008:
3007:
3006:
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2945:
2771:
2747:
2738:
2691:
2681:
2624:
2612:
2593:Propionaldehyde
2568:Ethylene glycol
2557:
2549:
2545:
2516:
2514:
2507:
2463:Cyanohexatriyne
2449:
2442:
2389:
2382:
2317:
2310:
2270:
2223:
2216:
2187:Methoxy radical
2117:
2110:
2106:Thiocyanic acid
1987:
1980:
1890:
1830:Ethynyl radical
1766:
1760:
1759:
1758:
1757:
1751:
1750:
1749:
1748:
1739:
1730:Sulfur monoxide
1715:Sodium chloride
1700:Silicon carbide
1607:Diatomic carbon
1597:Carbon monoxide
1539:
1534:
1504:
1494:
1489:
1487:
1477:
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1433:
1429:sister projects
1426:at Knowledge's
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1269:
1265:
1252:(10): 857–870.
1242:
1238:
1199:
1195:
1171:
1167:
1136:
1132:
1109:
1105:
1098:
1084:
1080:
1049:
1040:
1030:
1028:
998:
994:
984:
982:
944:
940:
922:
918:
914:
910:
906:
902:
893:
889:
866:
859:
836:
829:
806:
799:
738:
734:
724:
700:
699:
695:
690:
677:
661:
645:
639:
628:
617:
605:
590:
569:
541:
530:
518:
503:
498:
478:dichloromethane
413:
365:
363:Coupling agents
359:as byproducts.
346:
342:
338:
334:
330:
326:
322:
318:
301:
285:
271:
267:
264:2 RN=C=O → (RN)
258:
240:
236:
232:
217:
213:
210:CS + HgO → (RN)
209:
192:
187:
159:axial chirality
156:
148:
144:
116:
112:
103:
28:
23:
22:
15:
12:
11:
5:
3041:
3031:
3030:
3025:
3020:
3003:
3002:
3000:
2999:
2987:
2975:
2963:
2950:
2947:
2946:
2944:
2943:
2938:
2933:
2928:
2922:
2917:
2912:
2907:
2902:
2897:
2892:
2887:
2882:
2877:
2872:
2867:
2862:
2857:
2852:
2847:
2842:
2837:
2832:
2830:Cosmochemistry
2827:
2822:
2817:
2812:
2807:
2802:
2797:
2795:Astrochemistry
2792:
2787:
2781:
2779:
2773:
2772:
2770:
2769:
2764:
2759:
2754:
2749:
2745:
2741:
2736:
2732:
2727:
2722:
2717:
2712:
2707:
2701:
2699:
2693:
2692:
2690:
2689:
2684:
2679:
2675:
2670:
2665:
2660:
2655:
2650:
2648:Formyl radical
2645:
2640:
2634:
2628:
2626:
2618:
2617:
2614:
2613:
2611:
2610:
2605:
2600:
2595:
2590:
2585:
2580:
2578:Methyl acetate
2575:
2570:
2565:
2560:
2555:
2551:
2547:
2543:
2537:
2532:
2527:
2521:
2519:
2509:
2508:
2506:
2505:
2500:
2495:
2490:
2485:
2480:
2475:
2470:
2468:Dimethyl ether
2465:
2460:
2454:
2452:
2444:
2443:
2441:
2440:
2435:
2433:Methyl formate
2430:
2425:
2420:
2418:Glycolaldehyde
2415:
2410:
2405:
2400:
2394:
2392:
2384:
2383:
2381:
2380:
2375:
2370:
2365:
2360:
2355:
2353:Glycolonitrile
2350:
2348:Ethylene oxide
2345:
2340:
2339:
2338:
2328:
2322:
2320:
2312:
2311:
2309:
2308:
2303:
2298:
2293:
2288:
2283:
2278:
2273:
2268:
2264:
2259:
2254:
2249:
2247:Cyclopropenone
2244:
2239:
2234:
2228:
2226:
2218:
2217:
2215:
2214:
2209:
2204:
2199:
2194:
2189:
2184:
2179:
2174:
2169:
2164:
2159:
2154:
2149:
2147:Cyanoacetylene
2144:
2139:
2134:
2129:
2122:
2120:
2112:
2111:
2109:
2108:
2103:
2098:
2093:
2088:
2083:
2078:
2073:
2068:
2066:Methyl radical
2063:
2058:
2053:
2048:
2043:
2041:Isocyanic acid
2038:
2033:
2028:
2023:
2018:
2013:
2008:
2006:Isocyanic acid
2003:
1998:
1992:
1990:
1982:
1981:
1979:
1978:
1973:
1968:
1963:
1958:
1953:
1951:Sulfur dioxide
1948:
1943:
1938:
1933:
1928:
1926:Sodium cyanide
1923:
1918:
1913:
1908:
1903:
1898:
1893:
1888:
1884:
1879:
1874:
1869:
1864:
1859:
1854:
1849:
1843:
1837:
1835:Formyl radical
1832:
1827:
1822:
1817:
1812:
1807:
1802:
1797:
1795:Carbon dioxide
1792:
1787:
1782:
1776:
1774:
1768:
1767:
1742:
1740:
1738:
1737:
1732:
1727:
1722:
1717:
1712:
1707:
1702:
1697:
1692:
1687:
1682:
1676:
1671:
1666:
1660:
1655:
1650:
1645:
1643:Iron(II) oxide
1640:
1635:
1629:
1624:
1619:
1614:
1609:
1604:
1599:
1594:
1589:
1584:
1579:
1574:
1569:
1564:
1558:
1556:
1547:
1541:
1540:
1533:
1532:
1525:
1518:
1510:
1503:
1502:
1485:
1483:from Wikibooks
1468:
1466:from Wikiquote
1451:
1422:
1419:
1418:
1406:
1384:
1383:
1360:
1325:
1306:(2): 142–148.
1290:
1263:
1236:
1193:
1165:
1130:
1103:
1096:
1078:
1038:
992:
938:
920:
916:
912:
908:
904:
900:
887:
857:
827:
816:(6): 589–636.
797:
732:
722:
692:
691:
689:
686:
685:
684:
681:Sulfur diimide
676:
673:
660:
657:
653:chemical probe
641:Main article:
638:
635:
613:Main article:
589:
586:
585:
584:
577:
561:The byproduct
526:Main article:
502:
499:
497:
494:
465:to the stable
452:acid anhydride
412:
409:
364:
361:
349:
348:
344:
340:
336:
332:
328:
324:
320:
316:
300:
297:
284:
281:
273:
272:
269:
265:
257:
254:
243:
242:
238:
234:
230:
220:
219:
215:
211:
207:
200:mercuric oxide
191:
188:
186:
183:
163:energy barrier
154:
153:, possessing C
146:
142:
139:
138:
131:carbon dioxide
114:
110:
102:
99:
55:methanediimine
26:
9:
6:
4:
3:
2:
3040:
3029:
3026:
3024:
3021:
3019:
3018:Carbodiimides
3016:
3015:
3013:
2998:
2988:
2986:
2976:
2974:
2964:
2962:
2961:
2952:
2951:
2948:
2942:
2939:
2937:
2934:
2932:
2929:
2926:
2923:
2921:
2918:
2916:
2913:
2911:
2908:
2906:
2903:
2901:
2898:
2896:
2893:
2891:
2888:
2886:
2883:
2881:
2878:
2876:
2873:
2871:
2868:
2866:
2863:
2861:
2860:Homochirality
2858:
2856:
2853:
2851:
2848:
2846:
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:
2782:
2780:
2778:
2774:
2768:
2765:
2763:
2760:
2758:
2755:
2753:
2750:
2748:
2742:
2740:
2733:
2731:
2728:
2726:
2723:
2721:
2718:
2716:
2715:Methoxyethane
2713:
2711:
2708:
2706:
2703:
2702:
2700:
2698:
2694:
2688:
2685:
2683:
2676:
2674:
2671:
2669:
2666:
2664:
2661:
2659:
2656:
2654:
2651:
2649:
2646:
2644:
2641:
2638:
2635:
2633:
2630:
2629:
2627:
2623:
2619:
2609:
2606:
2604:
2601:
2599:
2598:Butyronitrile
2596:
2594:
2591:
2589:
2586:
2584:
2581:
2579:
2576:
2574:
2573:Ethyl formate
2571:
2569:
2566:
2564:
2561:
2559:
2552:
2541:
2538:
2536:
2533:
2531:
2528:
2526:
2523:
2522:
2520:
2518:
2510:
2504:
2501:
2499:
2498:Propionitrile
2496:
2494:
2491:
2489:
2486:
2484:
2481:
2479:
2476:
2474:
2471:
2469:
2466:
2464:
2461:
2459:
2456:
2455:
2453:
2451:
2445:
2439:
2436:
2434:
2431:
2429:
2426:
2424:
2421:
2419:
2416:
2414:
2411:
2409:
2406:
2404:
2401:
2399:
2396:
2395:
2393:
2391:
2385:
2379:
2378:Vinyl alcohol
2376:
2374:
2371:
2369:
2366:
2364:
2361:
2359:
2356:
2354:
2351:
2349:
2346:
2344:
2341:
2337:
2336:Vinyl cyanide
2334:
2333:
2332:
2331:Acrylonitrile
2329:
2327:
2324:
2323:
2321:
2319:
2313:
2307:
2304:
2302:
2299:
2297:
2296:Pentynylidyne
2294:
2292:
2289:
2287:
2284:
2282:
2279:
2277:
2274:
2272:
2265:
2263:
2260:
2258:
2255:
2253:
2250:
2248:
2245:
2243:
2240:
2238:
2235:
2233:
2230:
2229:
2227:
2225:
2219:
2213:
2210:
2208:
2205:
2203:
2200:
2198:
2195:
2193:
2192:Methylenimine
2190:
2188:
2185:
2183:
2180:
2178:
2175:
2173:
2170:
2168:
2165:
2163:
2160:
2158:
2155:
2153:
2150:
2148:
2145:
2143:
2140:
2138:
2135:
2133:
2130:
2127:
2124:
2123:
2121:
2119:
2113:
2107:
2104:
2102:
2099:
2097:
2094:
2092:
2089:
2087:
2084:
2082:
2079:
2077:
2074:
2072:
2071:Propynylidyne
2069:
2067:
2064:
2062:
2061:Methyl cation
2059:
2057:
2054:
2052:
2049:
2047:
2044:
2042:
2039:
2037:
2034:
2032:
2029:
2027:
2024:
2022:
2021:Fulminic acid
2019:
2017:
2014:
2012:
2009:
2007:
2004:
2002:
1999:
1997:
1994:
1993:
1991:
1989:
1983:
1977:
1974:
1972:
1969:
1967:
1964:
1962:
1959:
1957:
1954:
1952:
1949:
1947:
1944:
1942:
1939:
1937:
1934:
1932:
1929:
1927:
1924:
1922:
1919:
1917:
1914:
1912:
1909:
1907:
1904:
1902:
1899:
1897:
1896:Nitrous oxide
1894:
1892:
1885:
1883:
1880:
1878:
1875:
1873:
1870:
1868:
1865:
1863:
1860:
1858:
1855:
1853:
1850:
1847:
1844:
1841:
1838:
1836:
1833:
1831:
1828:
1826:
1823:
1821:
1818:
1816:
1813:
1811:
1808:
1806:
1803:
1801:
1798:
1796:
1793:
1791:
1790:Amino radical
1788:
1786:
1783:
1781:
1778:
1777:
1775:
1773:
1769:
1764:
1755:
1746:
1736:
1733:
1731:
1728:
1726:
1723:
1721:
1720:Sodium iodide
1718:
1716:
1713:
1711:
1708:
1706:
1703:
1701:
1698:
1696:
1693:
1691:
1688:
1686:
1683:
1680:
1677:
1675:
1672:
1670:
1667:
1664:
1661:
1659:
1656:
1654:
1651:
1649:
1646:
1644:
1641:
1639:
1636:
1633:
1630:
1628:
1625:
1623:
1620:
1618:
1615:
1613:
1610:
1608:
1605:
1603:
1602:Cyano radical
1600:
1598:
1595:
1593:
1590:
1588:
1585:
1583:
1582:Carbon cation
1580:
1578:
1575:
1573:
1570:
1568:
1565:
1563:
1560:
1559:
1557:
1555:
1551:
1548:
1546:
1542:
1538:
1531:
1526:
1524:
1519:
1517:
1512:
1511:
1508:
1499:
1498:
1486:
1482:
1481:
1469:
1465:
1464:
1452:
1448:
1447:
1435:
1434:
1431:
1425:
1417:
1412:
1407:
1405:
1395:
1394:
1391:
1379:
1375:
1371:
1364:
1356:
1352:
1348:
1344:
1340:
1336:
1329:
1321:
1317:
1313:
1309:
1305:
1301:
1294:
1286:
1282:
1278:
1274:
1267:
1259:
1255:
1251:
1247:
1240:
1232:
1228:
1224:
1220:
1216:
1212:
1208:
1204:
1197:
1189:
1185:
1181:
1178:
1177:
1176:J. Org. Chem.
1169:
1161:
1157:
1153:
1149:
1145:
1141:
1134:
1126:
1122:
1118:
1114:
1107:
1099:
1093:
1090:. Wiley-VCH.
1089:
1082:
1074:
1070:
1066:
1062:
1058:
1054:
1047:
1045:
1043:
1027:
1023:
1019:
1015:
1011:
1007:
1003:
996:
981:
977:
973:
969:
965:
961:
957:
953:
949:
942:
934:
930:
926:
898:
891:
883:
879:
875:
871:
864:
862:
853:
849:
845:
841:
834:
832:
823:
819:
815:
811:
804:
802:
793:
789:
785:
781:
777:
773:
769:
765:
760:
755:
751:
747:
743:
736:
729:
725:
719:
715:
711:
707:
703:
697:
693:
682:
679:
678:
672:
670:
666:
656:
654:
650:
644:
634:
632:
627:
623:
616:
609:
604:
600:
596:Structure of
594:
582:
578:
575:
568:
564:
560:
559:
558:
555:
553:
549:
545:
540:
536:
529:
522:
517:
513:
509:Structure of
507:
489:
485:
483:
479:
475:
472:
468:
464:
460:
456:
453:
449:
445:
441:
436:
434:
430:
426:
422:
418:
408:
405:
396:
392:
390:
386:
382:
378:
374:
370:
360:
358:
354:
314:
313:
312:
310:
306:
296:
294:
290:
280:
278:
263:
262:
261:
253:
251:
247:
228:
227:
226:
223:
205:
204:
203:
201:
197:
182:
180:
176:
171:
169:
164:
160:
152:
136:
135:
134:
132:
128:
127:isoelectronic
120:
107:
98:
96:
91:
87:
83:
79:
74:
72:
68:
64:
60:
56:
52:
48:
41:
37:
32:
19:
18:Carbodiimides
2953:
2936:Spectroscopy
2790:Astrobiology
2643:Formaldehyde
2535:Benzonitrile
2326:Acetaldehyde
2281:Methanethiol
2232:Acetonitrile
2137:Carbodiimide
2136:
2016:Formaldehyde
2011:Cyanoethynyl
1862:Iron cyanide
1857:Hydroperoxyl
1658:Nitric oxide
1495:
1478:
1461:
1449:from Commons
1444:
1424:Carbodiimide
1423:
1369:
1363:
1338:
1334:
1328:
1303:
1299:
1293:
1276:
1272:
1266:
1249:
1245:
1239:
1206:
1202:
1196:
1179:
1174:
1168:
1143:
1139:
1133:
1116:
1112:
1106:
1087:
1081:
1056:
1052:
1029:. Retrieved
1009:
1005:
995:
983:. Retrieved
955:
951:
941:
924:
896:
890:
873:
869:
843:
839:
813:
809:
749:
745:
735:
727:
701:
696:
664:
662:
646:
625:
621:
618:
602:
598:
566:
562:
556:
538:
534:
531:
515:
511:
473:
466:
462:
458:
454:
447:
443:
439:
437:
432:
428:
420:
416:
414:
401:
366:
350:
302:
286:
274:
259:
244:
224:
221:
193:
172:
140:
124:
75:
54:
51:carbodiimide
50:
44:
35:
2910:Outer space
2820:Cosmic dust
2785:Abiogenesis
2697:Unconfirmed
2653:Heavy water
2493:Ethanethiol
2408:Cyanoallene
2398:Acetic acid
2368:Methylamine
2252:Diacetylene
2167:Formic acid
2157:Cyanomethyl
1815:Diazenylium
1805:CCP radical
1681:(molecular)
1665:(molecular)
1634:(molecular)
1140:Inorg. Chem
659:CMCT or CMC
649:crosslinker
450:to give an
233:CO → (RN)
214:C + HgS + H
73:emissions.
3012:Categories
2825:Cosmic ray
2767:Silylidyne
2730:Hemolithin
2705:Anthracene
2622:Deuterated
2603:Pyrimidine
2413:Ethanimine
2276:Ketenimine
2132:Butadiynyl
1956:Thioformyl
1810:Chloronium
1463:Quotations
1273:Org. Synth
1113:Org. Synth
840:Org. Synth
752:(2): L33.
688:References
482:chloroform
339:S + (CyNH)
331:CHOH → (CH
323:SO + (CyN)
289:guanidines
95:hydrolysis
2757:Phosphine
2625:molecules
2558:fullerene
2458:Acetamide
2262:Formamide
2142:Cyanamide
1996:Acetylene
1971:Tricarbon
1882:Methylene
1867:Isoformyl
1772:Triatomic
1545:Molecules
1497:Resources
1480:Textbooks
1404:Chemistry
1378:1650-8297
1355:0300-9440
1320:0300-9440
1246:Synthesis
1231:216557447
1053:Chem. Rev
1031:18 August
985:18 August
810:Chem. Rev
784:2041-8205
759:1209.1590
431:and urea
283:Reactions
196:thioureas
185:Synthesis
179:cyanamide
2744:Linear C
2725:Graphene
2637:Ammonium
2438:Acrolein
2301:Propynal
2286:Methanol
2257:Ethylene
2126:Ammonium
1901:Nitroxyl
1725:Sulfanyl
1669:Imidogen
1663:Nitrogen
1632:Hydrogen
1577:Argonium
1554:Diatomic
1223:32338511
1160:25029088
1026:24716711
980:53231838
972:30398863
911:·N:C:N·C
792:26146516
675:See also
581:allergen
552:peptides
496:Examples
471:acylurea
175:tautomer
90:polymers
40:R groups
2890:Kerogen
2777:Related
2720:Glycine
2673:Propyne
2632:Ammonia
2530:Benzene
2525:Acetone
2517:or more
2488:Propene
2473:Ethanol
2363:Propyne
2182:Methane
2051:Ketenyl
2001:Ammonia
1416:Science
1390:Portals
1073:4859920
764:Bibcode
293:adducts
229:(R(H)N)
206:(R(H)N)
57:) is a
2941:Tholin
2762:Pyrene
2207:Silane
2177:Ketene
1679:Oxygen
1376:
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1024:
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790:
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381:esters
377:amides
355:and a
343:CO + R
268:C + CO
248:and p-
237:C + H
168:cyclic
151:chiral
86:dimers
2927:(PAH)
2515:atoms
2450:atoms
2390:atoms
2388:Eight
2318:atoms
2316:Seven
2224:atoms
2118:atoms
1988:atoms
1976:Water
1906:Ozone
1848:(HNC)
1842:(HCN)
1446:Media
1227:S2CID
976:S2CID
788:S2CID
754:arXiv
629:'
606:'
570:'
542:'
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327:C + R
129:with
71:maser
63:Earth
36:trans
2448:Nine
2116:Five
2026:HCCN
1986:Four
1946:SiNC
1374:ISSN
1351:ISSN
1316:ISSN
1250:1990
1219:PMID
1156:PMID
1092:ISBN
1069:PMID
1033:2020
1022:PMID
987:2020
968:PMID
780:ISSN
718:ISBN
357:urea
88:and
49:, a
2739:NCO
2639:ion
2546:, C
2513:Ten
2222:Six
2128:ion
1343:doi
1308:doi
1281:doi
1254:doi
1211:doi
1207:142
1184:doi
1148:doi
1121:doi
1061:doi
1014:doi
960:doi
956:140
929:doi
923:".
919:·NO
903:N·C
878:doi
848:doi
818:doi
772:doi
750:758
710:doi
651:or
637:EDC
588:DIC
550:of
501:DCC
480:or
387:or
379:or
375:to
367:In
347:C=O
315:(CH
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563:N
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333:3
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231:2
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155:2
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143:2
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111:2
20:)
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