2299:
3528:
2281:
413:
3492:
31:
2290:
3516:
3504:
747:, a major component of steel, places it within this broad definition of organometallic, yet steel and other carbon-containing alloys are seldom regarded as organic compounds. Thus, it is unclear whether the definition of organometallic should be narrowed, whether these considerations imply that organometallic compounds are not necessarily organic, or both.
404:. Urea had long been considered an "organic" compound, as it was known to occur only in the urine of living organisms. Wöhler's experiments were followed by many others, in which increasingly complex "organic" substances were produced from "inorganic" ones without the involvement of any living organism, thus disproving vitalism.
488:
classes of substances traditionally considered "inorganic". The list of substances so excluded varies from author to author. Still, it is generally agreed upon that there are (at least) a few carbon-containing compounds that should not be considered organic. For instance, almost all authorities would require the exclusion of
487:
As described in detail below, any definition of organic compound that uses simple, broadly-applicable criteria turns out to be unsatisfactory, to varying degrees. The modern, commonly accepted definition of organic compound essentially amounts to any carbon-containing compound, excluding several
238:, which are themselves formed from the high pressure and temperature degradation of organic matter underground over geological timescales. This ultimate derivation notwithstanding, organic compounds are no longer defined as compounds originating in living things, as they were historically.
854:
A slightly broader definition of the organic compound includes all compounds bearing C-H or C-C bonds. This would still exclude urea. Moreover, this definition still leads to somewhat arbitrary divisions in sets of carbon-halogen compounds. For example,
742:
covers all compounds that contain at least one carbon to metal covalent bond; it is unknown whether organometallic compounds form a subset of organic compounds. For example, the evidence of covalent Fe-C bonding in
362:). Vitalism taught that formation of these "organic" compounds were fundamentally different from the "inorganic" compounds that could be obtained from the elements by chemical manipulations in laboratories.
728:) and other metal carbonyls are often volatile liquids, like many organic compounds, yet they contain only carbon bonded to a transition metal and to oxygen, and are often prepared directly from metal and
918:
Organic compounds may be classified in a variety of ways. One major distinction is between natural and synthetic compounds. Organic compounds can also be classified or subdivided by the presence of
206:, they are of central importance because all known life is based on organic compounds. Living things incorporate inorganic carbon compounds into organic compounds through a network of processes (
960:
refer to those that are produced by plants or animals. Many of these are still extracted from natural sources because they would be more expensive to produce artificially. Examples include most
454:
is any compound that contains a significant amount of carbonâeven though many of the organic compounds known today have no connection to any substance found in living organisms. The term
354:
argued that a regulative force must exist within living bodies. Berzelius also contended that compounds could be distinguished by whether they required any organisms in their
775:
The relatively narrow definition of organic compounds as those containing C-H bonds excludes compounds that are (historically and practically) considered organic. Neither
2841:
2611:
2571:
2063:
803:
on organic nomenclature specifically mentions urea and oxalic acid as organic compounds. Other compounds lacking C-H bonds but traditionally considered organic include
1354:
2772:
2747:
2737:
1340:
is usually considered a branch of organic chemistry. The methods of organic synthesis have been applied to the rational synthesis of fullerenes and carbon nanotubes.
3143:
2471:
2412:
2320:
3232:
3048:
2983:
2923:
2851:
2757:
2651:
2521:
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2147:
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343:
was a widespread conception that substances found in organic nature are formed from the chemical elements by the action of a "vital force" or "life-force" (
2777:
2621:
2591:
2015:
2707:
2687:
2360:
171:), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as
2732:
1303:
2370:
2072:
2727:
2056:
1687:
2397:
1135:. Structures and a large diversity of physical and chemical properties are available for each substance, with reference to original literature.
2943:
2340:
2491:
2402:
1959:
64:; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-containing compounds such as
2049:
1660:
1635:
1131:
contains information on 9.8 million substances, covers the scientific literature from 1771 to the present, and is today accessible via
3270:
2586:
1282:
1995:
1528:
2802:
2561:
2481:
3183:
1350:
199:
on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive.
1185:
438:, showing features typical of organic compounds. Carbon atoms are in black, hydrogens gray, oxygens red, and nitrogen blue.
1825:
3435:
1787:
78:) and its derivatives are universally considered organic, but many others are sometimes considered inorganic, such as
3335:
1249:
800:
17:
1058:". They may be either compounds that are already found in plants/animals or those artificial compounds that do not
1572:
Jiang, C.; Srinivasan, S. G.; Caro, A.; Maloy, S. A. (2008). "Structural, elastic, and electronic properties of Fe
317:
are also excluded because they are simple substances composed of a single element and so not generally considered
3460:
1952:
1118:
545:
3385:
3420:
2616:
230:) or other sources of energy. Most synthetically-produced organic compounds are ultimately derived from
3558:
3553:
1945:
1578:
1112:
1489:"VitalismâA Worldview Revisited: A Critique Of Vitalism And Its Implications For Integrative Medicine"
3375:
3370:
2551:
2030:
1212:
931:
799:
are organic by this definition, yet they were two key compounds in the vitalism debate. However, the
553:). Other compounds and materials that are considered 'inorganic' by most authorities include: metal
3415:
1657:"IUPAC Blue Book, Table 28(a) Carboxylic acids and related groups. Unsubstituted parent structures"
1554:
1217:
739:
481:
57:
1097:
of an organism is altered to express compounds not ordinarily produced by the organism. Many such
3495:
1160:
923:
734:
913:
442:
Although vitalism has been discredited, scientific nomenclature retains the distinction between
351:
3350:
2315:
2225:
2102:
2097:
769:
665:
477:
61:
1151:
A great number of more specialized databases exist for diverse branches of organic chemistry.
3405:
3380:
3018:
2636:
2183:
1189:
1177:
1116:
database is the most comprehensive repository for data on organic compounds. The search tool
260:
For historical reasons discussed below, a few types of carbon-containing compounds, such as
3466:
3450:
3075:
2446:
2417:
2298:
2122:
1858:
1696:
1656:
1631:
1597:
1414:
865:
812:
718:
693:
656:
91:
83:
1093:âare manufactured industrially using organisms such as bacteria and yeast. Typically, the
8:
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3203:
2893:
2381:
2245:
2220:
2188:
2107:
1337:
1144:
1059:
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3198:
2697:
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2152:
2127:
1889:
1846:
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1613:
1587:
1505:
1488:
1472:
1447:
1201:
1127:
1055:
856:
824:
751:
697:
294:
87:
904:
would be organic, though these compounds share many physical and chemical properties.
3455:
3038:
2938:
2908:
2826:
2566:
2451:
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2162:
2157:
2089:
2010:
1969:
1894:
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1817:
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1682:
1510:
1459:
1255:
1245:
1237:
1207:
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Vitalism survived for a short period after the formulation of modern ideas about the
318:
172:
124:
53:
2041:
1783:
1617:
1313:
3532:
3520:
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2387:
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2240:
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2005:
1990:
1884:
1866:
1845:
Borysov, Stanislav S.; Geilhufe, R. Matthias; Balatsky, Alexander V. (2017-02-09).
1755:
1714:
1704:
1605:
1500:
1467:
1422:
1317:
1308:
1173:
1015:
957:
941:
Another distinction, based on the size of organic compounds, distinguishes between
892:
642:
638:
609:
508:), as well as other metal and semimetal carbides (including "ionic" carbides, e.g,
401:
394:
370:
273:
203:
188:
117:
1680:
3128:
3103:
2641:
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2132:
2025:
1871:
729:
575:
562:
541:
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314:
277:
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1937:
983:
complicated molecules present in reasonable concentrations in living organisms.
3365:
3330:
3113:
3003:
2968:
2953:
2888:
2883:
2782:
2682:
2601:
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2541:
2486:
2461:
2330:
2178:
1809:
1426:
942:
808:
689:
566:
281:
227:
215:
210:) that begins with the conversion of carbon dioxide and a hydrogen source like
191:
despite the fact it contains a carbon-hydrogen bond), are generally considered
184:
135:
1927:
1759:
1521:
1143:
contains 18.4 million entries on compounds and especially covers the field of
175:. For historical reasons, a few classes of carbon-containing compounds (e.g.,
3547:
3395:
3250:
3133:
3108:
3089:
3033:
2913:
2871:
2866:
2606:
2596:
2556:
2431:
2325:
2280:
2255:
2137:
2117:
1985:
1880:
1767:
1553:
1463:
1312:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
1259:
1170:
1098:
1043:
816:
531:
366:
242:
231:
1847:"Organic materials database: An open-access online database for data mining"
1743:
1375:
1321:
819:, which contains no C-H bonds, is considered a possible organic compound in
3471:
3325:
3178:
3118:
3098:
3070:
2998:
2878:
2861:
2816:
2767:
2672:
2392:
2345:
2193:
2020:
1898:
1821:
1775:
1728:
1709:
1514:
1019:
995:
987:
980:
804:
355:
207:
3445:
3355:
3320:
3287:
3213:
3188:
3028:
2933:
2903:
2787:
2702:
2692:
2422:
2350:
1980:
1915:(Fourth, Revised and Enlarged Edition). Springer-Verlag Berlin Heidelberg
1054:
Compounds that are prepared by reaction of other compounds are known as "
973:
790:
459:
378:
249:
235:
412:
3360:
3302:
3265:
3240:
3138:
2948:
2811:
1274:
1166:
1031:
1011:
935:
919:
883:
874:
588:
554:
470:
417:
298:
164:
1609:
750:
Metal complexes with organic ligands but no carbon-metal bonds (e.g.,
3292:
3157:
2993:
2797:
2677:
2531:
2506:
969:
744:
712:
685:
497:
310:
265:
223:
176:
145:
30:
3260:
3172:
2973:
2836:
2821:
2792:
2661:
2436:
2260:
2204:
2198:
2167:
2112:
2080:
965:
674:
621:
600:
592:
484:, as well as covalent bonds from carbon to oxygen and to nitrogen.
382:
340:
335:
306:
219:
101:
1592:
3425:
3255:
3208:
3167:
3123:
3065:
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3023:
3013:
3008:
2963:
2958:
2898:
2831:
2722:
2717:
2667:
2546:
2536:
2289:
1681:
S. A. Benner; K. G. Devine; L. N. Matveeva; D. H. Powell (2000).
1139:
1090:
1086:
1070:
1066:
1039:
1027:
1023:
1003:
991:
946:
828:
613:
302:
290:
261:
196:
180:
109:
79:
69:
34:
1368:
3476:
3297:
3279:
2742:
2712:
2214:
1132:
1074:
1035:
999:
558:
489:
105:
65:
768:) are not considered organometallic; instead, they are called
476:
molecule presents some features typical of organic compounds:
202:
Although organic compounds make up only a small percentage of
2511:
2441:
1007:
961:
927:
509:
493:
321:.The word "organic" in this context does not mean "natural".
211:
195:. Other than those just named, little consensus exists among
1911:
Ernö Pretsch, Philippe BĂŒhlmann, Martin
Badertscher (2009),
873:
would be considered by this rule to be "inorganic", whereas
1204: â Chemical compound without any carbon-hydrogen bonds
820:
776:
390:
381:, a compound known to occur only in living organisms, from
168:
1101:-engineered compounds did not previously exist in nature.
1932:
1742:
Korpi, Anne; JĂ€rnberg, Jill; Pasanen, Anna-Liisa (2009).
1094:
1807:
1571:
1402:
979:, and, in general, those natural products with large or
407:
245:, frequently represented by the letter R, refers to any
1844:
1242:
1632:"IUPAC Blue Book, Urea and Its Derivatives Rule C-971"
1220: â Study of organic compounds containing metal(s)
2071:
1487:
Coulter, Ian; Snider, Pamela; Neil, Amy (June 2019).
1077:) are organic synthetic or semi-synthetic compounds.
732:. Nickel tetracarbonyl is typically classified as an
595:
derivatives not containing an organic residue (e.g.,
1741:
655:
solvent). Halides of carbon without hydrogen (e.g.,
715:are also considered inorganic by some authorities.
1808:Durland, Justin; Ahmadian-Moghadam, Hamid (2022),
1400:
1967:
1486:
1401:Naylor, R. L.; Martin, J. D.; Staley, R. (2023).
466:, but this neologism remains relatively obscure.
3545:
1816:, Treasure Island (FL): StatPearls Publishing,
1688:Proceedings of the National Academy of Sciences
1279:American Fuel & Petrochemical Manufacturers
1236:
2057:
1953:
544:, and graphite intercalation compounds, e.g.
373:. It first came under question in 1824, when
358:(organic compounds) or whether they did not (
1913:Structure Determination of Organic Compounds
1336:are more frequently considered organic, and
823:soil. Terrestrially, it, and its anhydride,
620:, etc.), and heavier analogs thereof (e.g.,
183:), along with a few other exceptions (e.g.,
1493:Integrative Medicine: A Clinician's Journal
1480:
934:, which feature bonds between carbon and a
926:, which feature bonds between carbon and a
2064:
2050:
1960:
1946:
1394:
1154:
738:as it satisfies the broad definition that
44:) is among the simplest organic compounds.
1888:
1870:
1718:
1708:
1591:
1504:
1471:
1445:
986:Further compounds of prime importance in
1561:. Harvard University Press. p. 309.
1085:Many organic compoundsâtwo examples are
411:
252:whose open valence is on a carbon atom.
100:), and certain compounds of carbon with
29:
1683:"The missing organic molecules on Mars"
14:
3546:
1744:"Microbial volatile organic compounds"
1285:from the original on 11 September 2021
1049:
347:) that only living organisms possess.
2045:
1941:
1559:A Source Book in Chemistry, 1400-1900
1376:"Life Force, Naturalism & Holism"
408:Modern classification and ambiguities
1533:Routledge Encyclopedia of Philosophy
1244:. Thomson Brooks/Cole. p. 342.
952:
48:Some chemical authorities define an
1529:"Vitalism: Physiological Chemistry"
1230:
914:Organic chemistry § compounds
772:(and might be considered organic).
27:Carbon-containing chemical compound
24:
3436:Nexus for Exoplanet System Science
1309:Compendium of Chemical Terminology
827:, are associated with the mineral
25:
3570:
3336:Atomic and molecular astrophysics
2073:Molecules detected in outer space
1921:
1272:
907:
450:compounds. The modern meaning of
3526:
3514:
3502:
3491:
3490:
2297:
2288:
2279:
1557:; Herbert S. Klickstein (1951).
1080:
3461:Polycyclic aromatic hydrocarbon
1905:
1838:
1828:from the original on 2023-07-09
1801:
1790:from the original on 2023-01-04
1735:
1674:
1663:from the original on 2021-06-28
1649:
1638:from the original on 2021-05-06
1624:
1565:
1547:
1448:"History of Clinical Chemistry"
1357:from the original on 2022-09-16
1240:; Slabaugh, Michael R. (2004).
492:that contain carbon, including
167:(form chains with other carbon
1748:Critical Reviews in Toxicology
1439:
1343:
1326:
1297:
1266:
1069:(a category that includes all
530:and "covalent" carbides, e.g.
13:
1:
3386:Extraterrestrial liquid water
1446:Wilkinson, Ian (2002-06-10).
1224:
255:
241:In chemical nomenclature, an
1872:10.1371/journal.pone.0171501
1104:
972:, certain nutrients such as
7:
2617:Protonated hydrogen cyanide
1195:
462:as a modern alternative to
385:. A further experiment was
329:
163:Due to carbon's ability to
10:
3575:
1933:Organic Materials Database
1928:Organic Compounds Database
1579:Journal of Applied Physics
1576:C from first principles".
1427:10.1007/s00016-023-00297-z
1208:List of chemical compounds
1158:
932:organophosphorus compounds
911:
333:
324:
301:) of pure carbon, such as
3485:
3376:Earliest known life forms
3371:Diffuse interstellar band
3311:
3231:
3156:
3047:
2982:
2922:
2850:
2842:Protonated cyanoacetylene
2756:
2650:
2612:Protonated carbon dioxide
2572:Hydromagnesium isocyanide
2520:
2306:
2277:
2088:
2079:
2031:List of organic compounds
1976:
1760:10.1080/10408440802291497
1213:List of organic compounds
293:are generally considered
3421:Ironâsulfur world theory
3416:Photodissociation region
3119:Methyl-cyano-diacetylene
1555:Henry Marshall Leicester
1218:Organometallic chemistry
924:organometallic compounds
740:organometallic chemistry
3496:Category:Astrochemistry
3086:, fullerene, buckyball)
2773:Cyanobutadiynyl radical
2748:Silicon-carbide cluster
2738:Protonated formaldehyde
1810:"Genetics, Mutagenesis"
1380:Encyclopedia Britannica
1322:10.1351/goldbook.O04329
1161:Structure determination
1155:Structure determination
770:metal-organic compounds
735:organometallic compound
651:is often classed as an
387:Wöhler's 1828 synthesis
3509:Outer space portal
3351:Circumstellar envelope
2316:Aluminium(I) hydroxide
2226:Phosphorus mononitride
2103:Aluminium monofluoride
2098:Aluminium monochloride
1710:10.1073/pnas.040539497
1586:(4): 043502â043502â8.
1407:Physics in Perspective
439:
45:
3406:Interplanetary medium
3381:Extraterrestrial life
3019:Octatetraynyl radical
2637:Tricarbon monosulfide
2184:Magnesium monohydride
1190:X-ray crystallography
482:carbonâhydrogen bonds
469:The organic compound
458:has been proposed by
415:
234:consisting mainly of
224:autotrophic organisms
33:
3533:Chemistry portal
3521:Astronomy portal
3467:RNA world hypothesis
3451:PAH world hypothesis
3144:Heptatrienyl radical
3076:Buckminsterfullerene
2964:Methylcyanoacetylene
2472:Silicon carbonitride
2447:Methylidynephosphane
2413:Magnesium isocyanide
2321:Aluminium isocyanide
2123:Carbon monophosphide
813:carbon tetrachloride
719:Nickel tetracarbonyl
711:), and other exotic
694:nickel tetracarbonyl
352:Jöns Jacob Berzelius
92:carbon tetrachloride
3411:Interstellar medium
3391:Forbidden mechanism
3204:Hydrogen isocyanide
2894:Hexatriynyl radical
2477:c-Silicon dicarbide
2382:Hydrogen isocyanide
2246:Silicon monosulfide
2221:Phosphorus monoxide
2189:Methylidyne radical
2148:Fluoromethylidynium
2108:Aluminium(II) oxide
1863:2017PLoSO..1271501B
1701:2000PNAS...97.2425B
1602:2008JAP...103d3502J
1419:2023PhP....25....1N
1351:"Organic Chemistry"
1338:fullerene chemistry
1186:UV/Vis Spectroscopy
1165:The main tools are
1145:medicinal chemistry
1050:Synthetic compounds
981:stereoisometrically
478:carbonâcarbon bonds
393:from the inorganic
360:inorganic compounds
297:. Different forms (
295:inorganic compounds
88:carbon-carbon bonds
3431:Molecules in stars
3401:Intergalactic dust
3346:Circumstellar dust
3288:Naphthalene cation
3223:Trihydrogen cation
3199:Hydrogen deuteride
3124:Methyltriacetylene
2959:Hexapentaenylidene
2778:E-Cyanomethanimine
2698:Cyclopropenylidene
2632:Tricarbon monoxide
2622:Silicon tricarbide
2592:Methylene amidogen
2582:Isothiocyanic acid
2497:Thioxoethenylidene
2457:Trihydrogen cation
2271:Titanium(II) oxide
2231:Potassium chloride
2210:Sulfur mononitride
2153:Helium hydride ion
2128:Carbon monosulfide
1238:Seager, Spencer L.
1202:Inorganic compound
1128:Beilstein database
825:mellitic anhydride
698:mellitic anhydride
440:
319:chemical compounds
218:and other organic
82:of carbon without
62:carbonâcarbon bond
46:
3559:Organic chemistry
3554:Organic compounds
3541:
3540:
3456:Pseudo-panspermia
3152:
3151:
3099:Cyanodecapentayne
3039:N-Methylformamide
3014:Methyldiacetylene
2939:Aminoacetonitrile
2909:Methyl isocyanate
2827:Methyl isocyanide
2708:Isocyanoacetylene
2688:Cyanoformaldehyde
2567:Hydrogen peroxide
2452:Potassium cyanide
2408:Magnesium cyanide
2361:Disilicon carbide
2356:Dicarbon monoxide
2163:Hydrogen fluoride
2158:Hydrogen chloride
2039:
2038:
2011:Organic synthesis
2006:Organic reactions
2001:Organic compounds
1991:Functional groups
1970:organic chemistry
1610:10.1063/1.2884529
1182:Mass spectrometry
1016:neurotransmitters
958:Natural compounds
953:Natural compounds
473:
420:
398:potassium cyanate
371:chemical elements
173:organic chemistry
125:chloroformic acid
54:chemical compound
18:Organic compounds
16:(Redirected from
3566:
3531:
3530:
3529:
3519:
3518:
3517:
3507:
3506:
3505:
3494:
3493:
3441:Organic compound
3341:Chemical formula
3246:Dihydroxyacetone
3194:Hydrogen cyanide
2879:Cyanodiacetylene
2733:Propadienylidene
2627:Thioformaldehyde
2502:Titanium dioxide
2467:Sodium hydroxide
2388:Hydrogen sulfide
2376:Hydrogen cyanide
2336:Carbonyl sulfide
2301:
2292:
2283:
2241:Silicon monoxide
2174:Hydroxyl radical
2086:
2085:
2066:
2059:
2052:
2043:
2042:
1986:Covalent bonding
1962:
1955:
1948:
1939:
1938:
1916:
1909:
1903:
1902:
1892:
1874:
1842:
1836:
1835:
1834:
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1805:
1799:
1798:
1796:
1795:
1739:
1733:
1732:
1722:
1712:
1695:(6): 2425â2430.
1678:
1672:
1671:
1669:
1668:
1653:
1647:
1646:
1644:
1643:
1628:
1622:
1621:
1595:
1569:
1563:
1562:
1551:
1545:
1544:
1542:
1540:
1535:. March 10, 2024
1525:
1519:
1518:
1508:
1484:
1478:
1477:
1475:
1443:
1437:
1436:
1434:
1433:
1398:
1392:
1391:
1389:
1387:
1372:
1366:
1365:
1363:
1362:
1347:
1341:
1330:
1324:
1301:
1295:
1294:
1292:
1290:
1275:"Petrochemicals"
1270:
1264:
1263:
1234:
1174:NMR spectroscopy
902:
889:
880:
871:
862:
850:
798:
788:
766:
727:
710:
683:
671:
662:
650:
643:carbon disulfide
635:
627:
619:
606:
585:
574:, and arguably,
572:
551:
538:
528:
519:
507:
496:(which contains
471:
452:organic compound
437:
418:
402:ammonium sulfate
375:Friedrich Wöhler
315:carbon nanotubes
287:
274:oxides of carbon
270:carbonate esters
208:the carbon cycle
189:hydrogen cyanide
159:
158:
157:
154:
143:
133:
122:
118:hydrogen cyanide
115:
99:
77:
56:that contains a
50:organic compound
43:
21:
3574:
3573:
3569:
3568:
3567:
3565:
3564:
3563:
3544:
3543:
3542:
3537:
3527:
3525:
3515:
3513:
3503:
3501:
3481:
3307:
3283:
3274:
3227:
3217:
3160:
3148:
3129:Propionaldehyde
3104:Ethylene glycol
3093:
3085:
3081:
3052:
3050:
3043:
2999:Cyanohexatriyne
2985:
2978:
2925:
2918:
2853:
2846:
2806:
2759:
2752:
2723:Methoxy radical
2653:
2646:
2642:Thiocyanic acid
2523:
2516:
2426:
2366:Ethynyl radical
2302:
2296:
2295:
2294:
2293:
2287:
2286:
2285:
2284:
2275:
2266:Sulfur monoxide
2251:Sodium chloride
2236:Silicon carbide
2143:Diatomic carbon
2133:Carbon monoxide
2075:
2070:
2040:
2035:
2026:Stereochemistry
1972:
1966:
1924:
1919:
1910:
1906:
1857:(2): e0171501.
1843:
1839:
1831:
1829:
1806:
1802:
1793:
1791:
1740:
1736:
1679:
1675:
1666:
1664:
1655:
1654:
1650:
1641:
1639:
1630:
1629:
1625:
1575:
1570:
1566:
1552:
1548:
1538:
1536:
1527:
1526:
1522:
1485:
1481:
1444:
1440:
1431:
1429:
1403:"Vital Physics"
1399:
1395:
1385:
1383:
1382:. July 20, 1998
1374:
1373:
1369:
1360:
1358:
1349:
1348:
1344:
1331:
1327:
1302:
1298:
1288:
1286:
1271:
1267:
1252:
1235:
1231:
1227:
1198:
1178:IR Spectroscopy
1163:
1157:
1107:
1083:
1060:occur naturally
1052:
977:
955:
943:small molecules
916:
910:
901:
897:
893:
888:
884:
879:
875:
870:
866:
861:
857:
848:
844:
840:
836:
832:
801:IUPAC Blue Book
797:
793:
787:
783:
779:
764:
760:
756:
752:
730:carbon monoxide
726:
722:
709:
705:
701:
690:metal carbonyls
682:
678:
670:
666:
661:
657:
649:
645:
634:
630:
625:
617:
605:
601:
584:
580:
576:
571:
567:
550:
546:
536:
532:
527:
523:
518:
514:
510:
505:
501:
436:
432:
428:
424:
410:
338:
332:
327:
286:
282:
258:
177:carbonate salts
155:
152:
151:
149:
142:
138:
131:
127:
120:
113:
98:
94:
84:carbon-hydrogen
76:
72:
58:carbonâhydrogen
42:
38:
28:
23:
22:
15:
12:
11:
5:
3572:
3562:
3561:
3556:
3539:
3538:
3536:
3535:
3523:
3511:
3499:
3486:
3483:
3482:
3480:
3479:
3474:
3469:
3464:
3458:
3453:
3448:
3443:
3438:
3433:
3428:
3423:
3418:
3413:
3408:
3403:
3398:
3393:
3388:
3383:
3378:
3373:
3368:
3366:Cosmochemistry
3363:
3358:
3353:
3348:
3343:
3338:
3333:
3331:Astrochemistry
3328:
3323:
3317:
3315:
3309:
3308:
3306:
3305:
3300:
3295:
3290:
3285:
3281:
3277:
3272:
3268:
3263:
3258:
3253:
3248:
3243:
3237:
3235:
3229:
3228:
3226:
3225:
3220:
3215:
3211:
3206:
3201:
3196:
3191:
3186:
3184:Formyl radical
3181:
3176:
3170:
3164:
3162:
3154:
3153:
3150:
3149:
3147:
3146:
3141:
3136:
3131:
3126:
3121:
3116:
3114:Methyl acetate
3111:
3106:
3101:
3096:
3091:
3087:
3083:
3079:
3073:
3068:
3063:
3057:
3055:
3045:
3044:
3042:
3041:
3036:
3031:
3026:
3021:
3016:
3011:
3006:
3004:Dimethyl ether
3001:
2996:
2990:
2988:
2980:
2979:
2977:
2976:
2971:
2969:Methyl formate
2966:
2961:
2956:
2954:Glycolaldehyde
2951:
2946:
2941:
2936:
2930:
2928:
2920:
2919:
2917:
2916:
2911:
2906:
2901:
2896:
2891:
2889:Glycolonitrile
2886:
2884:Ethylene oxide
2881:
2876:
2875:
2874:
2864:
2858:
2856:
2848:
2847:
2845:
2844:
2839:
2834:
2829:
2824:
2819:
2814:
2809:
2804:
2800:
2795:
2790:
2785:
2783:Cyclopropenone
2780:
2775:
2770:
2764:
2762:
2754:
2753:
2751:
2750:
2745:
2740:
2735:
2730:
2725:
2720:
2715:
2710:
2705:
2700:
2695:
2690:
2685:
2683:Cyanoacetylene
2680:
2675:
2670:
2665:
2658:
2656:
2648:
2647:
2645:
2644:
2639:
2634:
2629:
2624:
2619:
2614:
2609:
2604:
2602:Methyl radical
2599:
2594:
2589:
2584:
2579:
2577:Isocyanic acid
2574:
2569:
2564:
2559:
2554:
2549:
2544:
2542:Isocyanic acid
2539:
2534:
2528:
2526:
2518:
2517:
2515:
2514:
2509:
2504:
2499:
2494:
2489:
2487:Sulfur dioxide
2484:
2479:
2474:
2469:
2464:
2462:Sodium cyanide
2459:
2454:
2449:
2444:
2439:
2434:
2429:
2424:
2420:
2415:
2410:
2405:
2400:
2395:
2390:
2385:
2379:
2373:
2371:Formyl radical
2368:
2363:
2358:
2353:
2348:
2343:
2338:
2333:
2331:Carbon dioxide
2328:
2323:
2318:
2312:
2310:
2304:
2303:
2278:
2276:
2274:
2273:
2268:
2263:
2258:
2253:
2248:
2243:
2238:
2233:
2228:
2223:
2218:
2212:
2207:
2202:
2196:
2191:
2186:
2181:
2179:Iron(II) oxide
2176:
2171:
2165:
2160:
2155:
2150:
2145:
2140:
2135:
2130:
2125:
2120:
2115:
2110:
2105:
2100:
2094:
2092:
2083:
2077:
2076:
2069:
2068:
2061:
2054:
2046:
2037:
2036:
2034:
2033:
2028:
2023:
2018:
2013:
2008:
2003:
1998:
1993:
1988:
1983:
1977:
1974:
1973:
1965:
1964:
1957:
1950:
1942:
1936:
1935:
1930:
1923:
1922:External links
1920:
1918:
1917:
1904:
1837:
1800:
1754:(2): 139â193.
1734:
1673:
1648:
1623:
1573:
1564:
1546:
1520:
1479:
1458:(4): 114â118.
1438:
1393:
1367:
1342:
1325:
1314:Organyl groups
1296:
1265:
1250:
1228:
1226:
1223:
1222:
1221:
1215:
1210:
1205:
1197:
1194:
1159:Main article:
1156:
1153:
1149:
1148:
1136:
1123:
1106:
1103:
1082:
1079:
1051:
1048:
975:
954:
951:
912:Main article:
909:
908:Classification
906:
899:
895:
886:
877:
868:
859:
846:
842:
838:
834:
809:mesoxalic acid
795:
785:
781:
762:
758:
754:
724:
707:
703:
680:
668:
659:
647:
632:
603:
582:
578:
569:
548:
534:
525:
516:
512:
503:
434:
430:
426:
409:
406:
350:In the 1810s,
334:Main article:
331:
328:
326:
323:
284:
276:(for example,
257:
254:
232:petrochemicals
228:photosynthesis
185:carbon dioxide
140:
136:carbon dioxide
129:
96:
74:
40:
26:
9:
6:
4:
3:
2:
3571:
3560:
3557:
3555:
3552:
3551:
3549:
3534:
3524:
3522:
3512:
3510:
3500:
3498:
3497:
3488:
3487:
3484:
3478:
3475:
3473:
3470:
3468:
3465:
3462:
3459:
3457:
3454:
3452:
3449:
3447:
3444:
3442:
3439:
3437:
3434:
3432:
3429:
3427:
3424:
3422:
3419:
3417:
3414:
3412:
3409:
3407:
3404:
3402:
3399:
3397:
3396:Homochirality
3394:
3392:
3389:
3387:
3384:
3382:
3379:
3377:
3374:
3372:
3369:
3367:
3364:
3362:
3359:
3357:
3354:
3352:
3349:
3347:
3344:
3342:
3339:
3337:
3334:
3332:
3329:
3327:
3324:
3322:
3319:
3318:
3316:
3314:
3310:
3304:
3301:
3299:
3296:
3294:
3291:
3289:
3286:
3284:
3278:
3276:
3269:
3267:
3264:
3262:
3259:
3257:
3254:
3252:
3251:Methoxyethane
3249:
3247:
3244:
3242:
3239:
3238:
3236:
3234:
3230:
3224:
3221:
3219:
3212:
3210:
3207:
3205:
3202:
3200:
3197:
3195:
3192:
3190:
3187:
3185:
3182:
3180:
3177:
3174:
3171:
3169:
3166:
3165:
3163:
3159:
3155:
3145:
3142:
3140:
3137:
3135:
3134:Butyronitrile
3132:
3130:
3127:
3125:
3122:
3120:
3117:
3115:
3112:
3110:
3109:Ethyl formate
3107:
3105:
3102:
3100:
3097:
3095:
3088:
3077:
3074:
3072:
3069:
3067:
3064:
3062:
3059:
3058:
3056:
3054:
3046:
3040:
3037:
3035:
3034:Propionitrile
3032:
3030:
3027:
3025:
3022:
3020:
3017:
3015:
3012:
3010:
3007:
3005:
3002:
3000:
2997:
2995:
2992:
2991:
2989:
2987:
2981:
2975:
2972:
2970:
2967:
2965:
2962:
2960:
2957:
2955:
2952:
2950:
2947:
2945:
2942:
2940:
2937:
2935:
2932:
2931:
2929:
2927:
2921:
2915:
2914:Vinyl alcohol
2912:
2910:
2907:
2905:
2902:
2900:
2897:
2895:
2892:
2890:
2887:
2885:
2882:
2880:
2877:
2873:
2872:Vinyl cyanide
2870:
2869:
2868:
2867:Acrylonitrile
2865:
2863:
2860:
2859:
2857:
2855:
2849:
2843:
2840:
2838:
2835:
2833:
2832:Pentynylidyne
2830:
2828:
2825:
2823:
2820:
2818:
2815:
2813:
2810:
2808:
2801:
2799:
2796:
2794:
2791:
2789:
2786:
2784:
2781:
2779:
2776:
2774:
2771:
2769:
2766:
2765:
2763:
2761:
2755:
2749:
2746:
2744:
2741:
2739:
2736:
2734:
2731:
2729:
2728:Methylenimine
2726:
2724:
2721:
2719:
2716:
2714:
2711:
2709:
2706:
2704:
2701:
2699:
2696:
2694:
2691:
2689:
2686:
2684:
2681:
2679:
2676:
2674:
2671:
2669:
2666:
2663:
2660:
2659:
2657:
2655:
2649:
2643:
2640:
2638:
2635:
2633:
2630:
2628:
2625:
2623:
2620:
2618:
2615:
2613:
2610:
2608:
2607:Propynylidyne
2605:
2603:
2600:
2598:
2597:Methyl cation
2595:
2593:
2590:
2588:
2585:
2583:
2580:
2578:
2575:
2573:
2570:
2568:
2565:
2563:
2560:
2558:
2557:Fulminic acid
2555:
2553:
2550:
2548:
2545:
2543:
2540:
2538:
2535:
2533:
2530:
2529:
2527:
2525:
2519:
2513:
2510:
2508:
2505:
2503:
2500:
2498:
2495:
2493:
2490:
2488:
2485:
2483:
2480:
2478:
2475:
2473:
2470:
2468:
2465:
2463:
2460:
2458:
2455:
2453:
2450:
2448:
2445:
2443:
2440:
2438:
2435:
2433:
2432:Nitrous oxide
2430:
2428:
2421:
2419:
2416:
2414:
2411:
2409:
2406:
2404:
2401:
2399:
2396:
2394:
2391:
2389:
2386:
2383:
2380:
2377:
2374:
2372:
2369:
2367:
2364:
2362:
2359:
2357:
2354:
2352:
2349:
2347:
2344:
2342:
2339:
2337:
2334:
2332:
2329:
2327:
2326:Amino radical
2324:
2322:
2319:
2317:
2314:
2313:
2311:
2309:
2305:
2300:
2291:
2282:
2272:
2269:
2267:
2264:
2262:
2259:
2257:
2256:Sodium iodide
2254:
2252:
2249:
2247:
2244:
2242:
2239:
2237:
2234:
2232:
2229:
2227:
2224:
2222:
2219:
2216:
2213:
2211:
2208:
2206:
2203:
2200:
2197:
2195:
2192:
2190:
2187:
2185:
2182:
2180:
2177:
2175:
2172:
2169:
2166:
2164:
2161:
2159:
2156:
2154:
2151:
2149:
2146:
2144:
2141:
2139:
2138:Cyano radical
2136:
2134:
2131:
2129:
2126:
2124:
2121:
2119:
2118:Carbon cation
2116:
2114:
2111:
2109:
2106:
2104:
2101:
2099:
2096:
2095:
2093:
2091:
2087:
2084:
2082:
2078:
2074:
2067:
2062:
2060:
2055:
2053:
2048:
2047:
2044:
2032:
2029:
2027:
2024:
2022:
2019:
2017:
2014:
2012:
2009:
2007:
2004:
2002:
1999:
1997:
1994:
1992:
1989:
1987:
1984:
1982:
1979:
1978:
1975:
1971:
1963:
1958:
1956:
1951:
1949:
1944:
1943:
1940:
1934:
1931:
1929:
1926:
1925:
1914:
1908:
1900:
1896:
1891:
1886:
1882:
1878:
1873:
1868:
1864:
1860:
1856:
1852:
1848:
1841:
1827:
1823:
1819:
1815:
1811:
1804:
1789:
1785:
1781:
1777:
1773:
1769:
1765:
1761:
1757:
1753:
1749:
1745:
1738:
1730:
1726:
1721:
1716:
1711:
1706:
1702:
1698:
1694:
1690:
1689:
1684:
1677:
1662:
1658:
1652:
1637:
1633:
1627:
1619:
1615:
1611:
1607:
1603:
1599:
1594:
1589:
1585:
1581:
1580:
1568:
1560:
1556:
1550:
1534:
1530:
1524:
1516:
1512:
1507:
1502:
1498:
1494:
1490:
1483:
1474:
1469:
1465:
1461:
1457:
1453:
1449:
1442:
1428:
1424:
1420:
1416:
1412:
1408:
1404:
1397:
1381:
1377:
1371:
1356:
1352:
1346:
1339:
1335:
1329:
1323:
1319:
1315:
1311:
1310:
1305:
1300:
1284:
1280:
1276:
1273:Smith, Cory.
1269:
1261:
1257:
1253:
1251:9780534399696
1247:
1243:
1239:
1233:
1229:
1219:
1216:
1214:
1211:
1209:
1206:
1203:
1200:
1199:
1193:
1191:
1187:
1183:
1179:
1175:
1172:
1168:
1162:
1152:
1146:
1142:
1141:
1137:
1134:
1130:
1129:
1124:
1121:
1120:
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1114:
1109:
1108:
1102:
1100:
1099:biotechnology
1096:
1092:
1088:
1081:Biotechnology
1078:
1076:
1072:
1068:
1063:
1061:
1057:
1047:
1045:
1044:fats and oils
1041:
1037:
1033:
1029:
1025:
1021:
1020:nucleic acids
1017:
1013:
1009:
1005:
1001:
997:
996:carbohydrates
993:
989:
984:
982:
978:
971:
967:
963:
959:
950:
948:
944:
939:
937:
933:
929:
925:
921:
915:
905:
903:
890:
881:
872:
863:
852:
830:
826:
822:
818:
817:Mellitic acid
814:
810:
806:
802:
792:
778:
773:
771:
767:
748:
746:
741:
737:
736:
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520:
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495:
491:
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449:
445:
422:
414:
405:
403:
399:
396:
392:
388:
384:
380:
376:
372:
368:
367:atomic theory
363:
361:
357:
353:
348:
346:
342:
337:
322:
320:
316:
312:
308:
304:
300:
296:
292:
288:
279:
275:
271:
267:
263:
253:
251:
248:
244:
243:organyl group
239:
237:
233:
229:
226:using light (
225:
221:
217:
216:simple sugars
213:
209:
205:
204:Earth's crust
200:
198:
194:
190:
186:
182:
181:cyanide salts
178:
174:
170:
166:
161:
147:
137:
126:
119:
111:
107:
103:
93:
89:
85:
81:
71:
67:
63:
59:
55:
51:
36:
32:
19:
3489:
3472:Spectroscopy
3440:
3326:Astrobiology
3179:Formaldehyde
3071:Benzonitrile
2862:Acetaldehyde
2817:Methanethiol
2768:Acetonitrile
2673:Carbodiimide
2552:Formaldehyde
2547:Cyanoethynyl
2398:Iron cyanide
2393:Hydroperoxyl
2194:Nitric oxide
2021:Spectroscopy
2016:Publications
2000:
1996:Nomenclature
1968:Concepts in
1912:
1907:
1854:
1850:
1840:
1830:, retrieved
1813:
1803:
1792:. Retrieved
1751:
1747:
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1651:
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1626:
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1532:
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1278:
1268:
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1232:
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1111:
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988:biochemistry
985:
956:
940:
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805:benzenehexol
774:
749:
733:
717:
652:
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468:
463:
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377:synthesized
364:
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344:
339:
259:
240:
236:hydrocarbons
201:
162:
49:
47:
3446:Outer space
3356:Cosmic dust
3321:Abiogenesis
3233:Unconfirmed
3189:Heavy water
3029:Ethanethiol
2944:Cyanoallene
2934:Acetic acid
2904:Methylamine
2788:Diacetylene
2703:Formic acid
2693:Cyanomethyl
2351:Diazenylium
2341:CCP radical
2217:(molecular)
2201:(molecular)
2170:(molecular)
1981:Aromaticity
1334:derivatives
1289:18 December
1122:is offered.
1032:amino acids
1012:fatty acids
920:heteroatoms
791:oxalic acid
641:; although
591:of carbon,
561:of carbon (
474:-isoleucine
460:E. J. Corey
421:-isoleucine
379:oxalic acid
345:vis vitalis
268:(excluding
250:substituent
187:, and even
3548:Categories
3361:Cosmic ray
3303:Silylidyne
3266:Hemolithin
3241:Anthracene
3158:Deuterated
3139:Pyrimidine
2949:Ethanimine
2812:Ketenimine
2668:Butadiynyl
2492:Thioformyl
2346:Chloronium
1832:2023-01-04
1814:StatPearls
1794:2023-01-04
1667:2009-11-22
1642:2009-11-22
1432:2024-03-10
1361:2022-08-25
1332:Fullerene
1225:References
970:terpenoids
936:phosphorus
713:oxocarbons
686:carboranes
589:allotropes
555:carbonates
456:carbogenic
423:molecule,
311:fullerenes
299:allotropes
272:), simple
266:carbonates
256:Definition
247:monovalent
3293:Phosphine
3161:molecules
3094:fullerene
2994:Acetamide
2798:Formamide
2678:Cyanamide
2532:Acetylene
2507:Tricarbon
2418:Methylene
2403:Isoformyl
2308:Triatomic
2081:Molecules
1881:1932-6203
1768:1547-6898
1593:0711.1528
1539:March 10,
1464:1650-3414
1386:March 10,
1260:155910842
1171:carbon-13
1119:SciFinder
1105:Databases
1056:synthetic
974:vitamin B
966:alkaloids
845:·16H
745:cementite
557:, simple
498:cementite
448:inorganic
356:synthesis
220:molecules
193:inorganic
146:carbonate
3280:Linear C
3261:Graphene
3173:Ammonium
2974:Acrolein
2837:Propynal
2822:Methanol
2793:Ethylene
2662:Ammonium
2437:Nitroxyl
2261:Sulfanyl
2205:Imidogen
2199:Nitrogen
2168:Hydrogen
2113:Argonium
2090:Diatomic
1899:28182744
1851:PLOS ONE
1826:archived
1822:32809354
1788:Archived
1784:98688955
1776:19204852
1729:10706606
1661:Archived
1636:Archived
1618:94576016
1515:32549817
1355:Archived
1283:Archived
1196:See also
1071:plastics
1067:polymers
1040:vitamins
1028:peptides
1024:proteins
1004:hormones
992:antigens
947:polymers
922:, e.g.,
675:phosgene
622:cyaphide
383:cyanogen
341:Vitalism
336:Vitalism
330:Vitalism
307:graphite
291:cyanides
262:carbides
197:chemists
165:catenate
102:nitrogen
3426:Kerogen
3313:Related
3256:Glycine
3209:Propyne
3168:Ammonia
3066:Benzene
3061:Acetone
3053:or more
3024:Propene
3009:Ethanol
2899:Propyne
2718:Methane
2587:Ketenyl
2537:Ammonia
1890:5300202
1859:Bibcode
1697:Bibcode
1598:Bibcode
1506:7217401
1473:6208063
1415:Bibcode
1140:PubChem
1091:insulin
1087:ethanol
1075:rubbers
1036:lectins
1000:enzymes
964:, some
829:mellite
821:Martian
692:(e.g.,
653:organic
614:cyanate
593:cyanide
587:), the
464:organic
444:organic
325:History
303:diamond
110:cyanide
80:halides
70:methane
66:alkanes
35:Methane
3477:Tholin
3298:Pyrene
2743:Silane
2713:Ketene
2215:Oxygen
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1042:, and
1008:lipids
962:sugars
930:, and
891:, and
811:, and
794:(COOH)
723:Ni(CO)
624:anion
616:anion
559:oxides
490:alloys
289:) and
144:, and
108:(e.g.
106:oxygen
90:(e.g.
68:(e.g.
3463:(PAH)
3051:atoms
2986:atoms
2926:atoms
2924:Eight
2854:atoms
2852:Seven
2760:atoms
2654:atoms
2524:atoms
2512:Water
2442:Ozone
2384:(HNC)
2378:(HCN)
1780:S2CID
1720:15945
1614:S2CID
1588:arXiv
1304:IUPAC
1065:Most
928:metal
841:(COO)
780:CO(NH
494:steel
395:salts
214:into
212:water
169:atoms
52:as a
2984:Nine
2652:Five
2562:HCCN
2522:Four
2482:SiNC
1895:PMID
1877:ISSN
1818:PMID
1772:PMID
1764:ISSN
1725:PMID
1541:2024
1511:PMID
1460:ISSN
1388:2024
1291:2016
1256:OCLC
1246:ISBN
1188:and
1169:and
1125:The
1110:The
1089:and
1073:and
1030:and
1010:and
990:are
968:and
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885:CHCl
864:and
789:nor
777:urea
679:COCl
667:CClF
664:and
610:BrCN
602:(CN)
540:and
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416:The
400:and
391:urea
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1867:doi
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1095:DNA
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