2288:
3517:
2270:
402:
3481:
20:
2279:
3505:
736:, 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.
3493:
393:. 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.
477:
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
476:
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
227:, 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.
843:
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,
731:
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
351:). 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.
717:) 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
907:
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
195:, 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 (
949:
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
2052:
443:
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
343:
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
764:
The relatively narrow definition of organic compounds as those containing C-H bonds excludes compounds that are (historically and practically) considered organic. Neither
1292:
792:
on organic nomenclature specifically mentions urea and oxalic acid as organic compounds. Other compounds lacking C-H bonds but traditionally considered organic include
3301:
3221:
3037:
2972:
2912:
2840:
2746:
2640:
2510:
2061:
1343:
1329:
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.
2045:
1676:
332:
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" (
2004:
1948:
2038:
160:), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as
1984:
1124:. Structures and a large diversity of physical and chemical properties are available for each substance, with reference to original literature.
1174:
53:; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-containing compounds such as
1649:
1624:
1120:
contains information on 9.8 million substances, covers the scientific literature from 1771 to the present, and is today accessible via
3424:
1271:
3324:
1238:
789:
1517:
3449:
1941:
534:
1339:
188:
on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive.
427:, showing features typical of organic compounds. Carbon atoms are in black, hydrogens gray, oxygens red, and nitrogen blue.
3374:
1814:
3409:
1776:
2605:
67:) and its derivatives are universally considered organic, but many others are sometimes considered inorganic, such as
3547:
3542:
1934:
1567:
1107:
1101:
1047:". They may be either compounds that are already found in plants/animals or those artificial compounds that do not
1561:
Jiang, C.; Srinivasan, S. G.; Caro, A.; Maloy, S. A. (2008). "Structural, elastic, and electronic properties of Fe
306:
are also excluded because they are simple substances composed of a single element and so not generally considered
3364:
3359:
3172:
2540:
2019:
1201:
920:
470:
46:
3404:
2830:
2600:
2560:
1543:
1206:
728:
2761:
2736:
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1149:
912:
723:
340:
466:
50:
3339:
3132:
2460:
2401:
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2214:
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758:
654:
2465:
2136:
3394:
3369:
3007:
2766:
2625:
2610:
2580:
2172:
1178:
1166:
219:) or other sources of energy. Most synthetically-produced organic compounds are ultimately derived from
2696:
2676:
2349:
2721:
1478:"VitalismâA Worldview Revisited: A Critique Of Vitalism And Its Implications For Integrative Medicine"
3455:
3439:
3064:
2435:
2406:
2287:
2111:
1847:
1685:
1586:
1403:
854:
801:
788:
are organic by this definition, yet they were two key compounds in the vitalism debate. However, the
707:
682:
645:
80:
72:
2359:
542:). Other compounds and materials that are considered 'inorganic' by most authorities include: metal
3399:
3379:
3192:
2882:
2716:
2370:
2234:
2209:
2177:
2096:
1646:"IUPAC Blue Book, Table 28(a) Carboxylic acids and related groups. Unsubstituted parent structures"
1326:
1133:
1048:
375:
363:
348:
235:
181:
2386:
1086:
of an organism is altered to express compounds not ordinarily produced by the organism. Many such
3497:
3419:
3389:
3334:
3211:
3187:
2932:
2686:
2620:
2485:
2445:
2329:
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1768:
1602:
1576:
1190:
1116:
1044:
845:
813:
740:
686:
283:
76:
2480:
431:
Although vitalism has been discredited, scientific nomenclature retains the distinction between
2391:
3444:
3027:
2927:
2897:
2815:
2555:
2440:
2396:
2344:
2151:
2146:
2078:
1999:
1958:
1883:
1865:
1806:
1760:
1752:
1713:
1499:
1448:
1244:
1234:
1226:
1196:
1170:
1140:
A great number of more specialized databases exist for diverse branches of organic chemistry.
902:
618:
585:
386:
307:
161:
113:
42:
2575:
1105:
database is the most comprehensive repository for data on organic compounds. The search tool
3521:
3509:
3329:
3259:
3234:
3182:
2615:
2490:
2455:
2376:
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2324:
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1994:
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1004:
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631:
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262:
249:
For historical reasons discussed below, a few types of carbon-containing compounds, such as
192:
177:
106:
1645:
1620:
3117:
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2791:
2630:
2570:
2550:
2470:
2354:
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2131:
2121:
2014:
1082:âare manufactured industrially using organisms such as bacteria and yeast. Typically, the
718:
564:
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530:
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303:
266:
258:
1851:
1689:
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1407:
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1436:
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270:
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173:
124:
893:
would be organic, though these compounds share many physical and chemical properties.
401:
3536:
3384:
3239:
3122:
3097:
3078:
3022:
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2244:
2126:
2106:
1974:
1708:
1671:
1159:
1087:
1032:
805:
520:
355:
354:
Vitalism survived for a short period after the formulation of modern ideas about the
231:
220:
2030:
1772:
1606:
1302:
3460:
3314:
3167:
3107:
3087:
3059:
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2850:
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2756:
2661:
2381:
2334:
2182:
2009:
1834:
Borysov, Stanislav S.; Geilhufe, R. Matthias; Balatsky, Alexander V. (2017-02-09).
1008:
984:
976:
969:
930:
Another distinction, based on the size of organic compounds, distinguishes between
793:
497:), as well as other metal and semimetal carbides (including "ionic" carbides, e.g,
344:
196:
1860:
3434:
3344:
3309:
3276:
3202:
3177:
3017:
2922:
2892:
2776:
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2411:
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1969:
1926:
1297:
972:
complicated molecules present in reasonable concentrations in living organisms.
962:
779:
448:
367:
238:
224:
19:
1798:
1415:
199:) that begins with the conversion of carbon dioxide and a hydrogen source like
180:
despite the fact it contains a carbon-hydrogen bond), are generally considered
3349:
3291:
3254:
3229:
3127:
2937:
2800:
1916:
1748:
1155:
1132:
contains 18.4 million entries on compounds and especially covers the field of
1020:
1000:
924:
908:
872:
863:
577:
543:
459:
406:
287:
164:. For historical reasons, a few classes of carbon-containing compounds (e.g.,
153:
1869:
1756:
1452:
1301:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
1248:
3281:
3146:
2982:
2786:
2666:
2520:
2495:
1836:"Organic materials database: An open-access online database for data mining"
1732:
1364:
1310:
958:
808:, which contains no C-H bonds, is considered a possible organic compound in
733:
701:
674:
486:
299:
254:
212:
165:
134:
1887:
1810:
1764:
1717:
1698:
1503:
3249:
3161:
2962:
2825:
2810:
2781:
2650:
2425:
2249:
2193:
2187:
2156:
2101:
2069:
1904:(Fourth, Revised and Enlarged Edition). Springer-Verlag Berlin Heidelberg
1043:
Compounds that are prepared by reaction of other compounds are known as "
954:
663:
610:
589:
581:
371:
329:
324:
295:
208:
90:
3414:
3244:
3197:
3156:
3112:
3054:
3049:
3012:
3002:
2997:
2952:
2947:
2887:
2820:
2711:
2706:
2656:
2535:
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1263:
1128:
1079:
1075:
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1055:
1028:
1016:
1012:
992:
980:
935:
817:
602:
291:
279:
250:
185:
169:
98:
68:
58:
23:
1598:
739:
Metal complexes with organic ligands but no carbon-metal bonds (e.g.,
3465:
3286:
3268:
2731:
2701:
2203:
1121:
1063:
1024:
988:
547:
478:
94:
54:
473:, as well as covalent bonds from carbon to oxygen and to nitrogen.
2500:
2430:
1581:
996:
950:
916:
498:
482:
400:
200:
18:
1670:
S. A. Benner; K. G. Devine; L. N. Matveeva; D. H. Powell (2000).
809:
765:
379:
157:
2034:
1930:
1083:
757:) are not considered organometallic; instead, they are called
465:
molecule presents some features typical of organic compounds:
191:
Although organic compounds make up only a small percentage of
310:.The word "organic" in this context does not mean "natural".
184:. Other than those just named, little consensus exists among
1900:
Ernö Pretsch, Philippe BĂŒhlmann, Martin
Badertscher (2009),
862:
would be considered by this rule to be "inorganic", whereas
1193: â Chemical compound without any carbon-hydrogen bonds
370:, a compound known to occur only in living organisms, from
1090:-engineered compounds did not previously exist in nature.
1921:
1731:
Korpi, Anne; JĂ€rnberg, Jill; Pasanen, Anna-Liisa (2009).
1391:
968:, and, in general, those natural products with large or
234:, frequently represented by the letter R, refers to any
1231:
1621:"IUPAC Blue Book, Urea and Its Derivatives Rule C-971"
1209: â Study of organic compounds containing metal(s)
1476:
Coulter, Ian; Snider, Pamela; Neil, Amy (June 2019).
1066:) are organic synthetic or semi-synthetic compounds.
721:. Nickel tetracarbonyl is typically classified as an
584:
derivatives not containing an organic residue (e.g.,
644:
solvent). Halides of carbon without hydrogen (e.g.,
3300:
3220:
3145:
3036:
2971:
2911:
2839:
2745:
2639:
2509:
2295:
2077:
2068:
704:are also considered inorganic by some authorities.
1797:Durland, Justin; Ahmadian-Moghadam, Hamid (2022),
1390:Naylor, R. L.; Martin, J. D.; Staley, R. (2023).
455:, but this neologism remains relatively obscure.
1805:, Treasure Island (FL): StatPearls Publishing,
1677:Proceedings of the National Academy of Sciences
1268:American Fuel & Petrochemical Manufacturers
2046:
1942:
533:, and graphite intercalation compounds, e.g.
362:. It first came under question in 1824, when
347:(organic compounds) or whether they did not (
8:
1902:Structure Determination of Organic Compounds
1325:are more frequently considered organic, and
812:soil. Terrestrially, it, and its anhydride,
609:, etc.), and heavier analogs thereof (e.g.,
172:), along with a few other exceptions (e.g.,
1482:Integrative Medicine: A Clinician's Journal
923:, which feature bonds between carbon and a
915:, which feature bonds between carbon and a
2074:
2053:
2039:
2031:
1949:
1935:
1927:
727:as it satisfies the broad definition that
33:) is among the simplest organic compounds.
1877:
1859:
1707:
1697:
1580:
1493:
1460:
975:Further compounds of prime importance in
1550:. Harvard University Press. p. 309.
1074:Many organic compoundsâtwo examples are
888:
884:
875:
866:
857:
848:
831:
827:
823:
784:
774:
770:
751:
747:
743:
713:
696:
692:
669:
657:
648:
636:
621:
592:
571:
567:
558:
537:
523:
514:
505:
501:
492:
423:
419:
415:
273:
241:whose open valence is on a carbon atom.
129:
118:
89:), and certain compounds of carbon with
85:
63:
29:
1672:"The missing organic molecules on Mars"
1218:
1733:"Microbial volatile organic compounds"
1274:from the original on 11 September 2021
336:) that only living organisms possess.
1548:A Source Book in Chemistry, 1400-1900
1365:"Life Force, Naturalism & Holism"
397:Modern classification and ambiguities
7:
1522:Routledge Encyclopedia of Philosophy
1233:. Thomson Brooks/Cole. p. 342.
37:Some chemical authorities define an
1518:"Vitalism: Physiological Chemistry"
903:Organic chemistry § compounds
761:(and might be considered organic).
16:Carbon-containing chemical compound
3425:Nexus for Exoplanet System Science
1298:Compendium of Chemical Terminology
816:, are associated with the mineral
14:
3325:Atomic and molecular astrophysics
2062:Molecules detected in outer space
439:compounds. The modern meaning of
3515:
3503:
3491:
3480:
3479:
2286:
2277:
2268:
1546:; Herbert S. Klickstein (1951).
3450:Polycyclic aromatic hydrocarbon
1817:from the original on 2023-07-09
1779:from the original on 2023-01-04
1652:from the original on 2021-06-28
1627:from the original on 2021-05-06
1437:"History of Clinical Chemistry"
1346:from the original on 2022-09-16
1229:; Slabaugh, Michael R. (2004).
481:that contain carbon, including
156:(form chains with other carbon
1737:Critical Reviews in Toxicology
1058:(a category that includes all
519:and "covalent" carbides, e.g.
1:
3375:Extraterrestrial liquid water
1435:Wilkinson, Ian (2002-06-10).
230:In chemical nomenclature, an
1861:10.1371/journal.pone.0171501
961:, certain nutrients such as
2606:Protonated hydrogen cyanide
451:as a modern alternative to
374:. A further experiment was
152:Due to carbon's ability to
3564:
1922:Organic Materials Database
1917:Organic Compounds Database
1568:Journal of Applied Physics
1565:C from first principles".
1416:10.1007/s00016-023-00297-z
1197:List of chemical compounds
1147:
921:organophosphorus compounds
900:
322:
290:) of pure carbon, such as
3474:
3365:Earliest known life forms
3360:Diffuse interstellar band
2831:Protonated cyanoacetylene
2601:Protonated carbon dioxide
2561:Hydromagnesium isocyanide
2266:
2020:List of organic compounds
1965:
1749:10.1080/10408440802291497
1202:List of organic compounds
282:are generally considered
3410:Ironâsulfur world theory
3405:Photodissociation region
3108:Methyl-cyano-diacetylene
1544:Henry Marshall Leicester
1207:Organometallic chemistry
913:organometallic compounds
729:organometallic chemistry
3485:Category:Astrochemistry
3075:, fullerene, buckyball)
2762:Cyanobutadiynyl radical
2737:Silicon-carbide cluster
2727:Protonated formaldehyde
1799:"Genetics, Mutagenesis"
1369:Encyclopedia Britannica
1311:10.1351/goldbook.O04329
1150:Structure determination
1144:Structure determination
759:metal-organic compounds
724:organometallic compound
640:is often classed as an
376:Wöhler's 1828 synthesis
3498:Outer space portal
3340:Circumstellar envelope
2305:Aluminium(I) hydroxide
2215:Phosphorus mononitride
2092:Aluminium monofluoride
2087:Aluminium monochloride
1699:10.1073/pnas.040539497
1575:(4): 043502â043502â8.
1396:Physics in Perspective
428:
34:
3395:Interplanetary medium
3370:Extraterrestrial life
3008:Octatetraynyl radical
2626:Tricarbon monosulfide
2173:Magnesium monohydride
1179:X-ray crystallography
471:carbonâhydrogen bonds
458:The organic compound
447:has been proposed by
404:
223:consisting mainly of
213:autotrophic organisms
22:
3522:Chemistry portal
3510:Astronomy portal
3456:RNA world hypothesis
3440:PAH world hypothesis
3133:Heptatrienyl radical
3065:Buckminsterfullerene
2953:Methylcyanoacetylene
2461:Silicon carbonitride
2436:Methylidynephosphane
2402:Magnesium isocyanide
2310:Aluminium isocyanide
2112:Carbon monophosphide
802:carbon tetrachloride
708:Nickel tetracarbonyl
700:), and other exotic
683:nickel tetracarbonyl
341:Jöns Jacob Berzelius
81:carbon tetrachloride
3400:Interstellar medium
3380:Forbidden mechanism
3193:Hydrogen isocyanide
2883:Hexatriynyl radical
2466:c-Silicon dicarbide
2371:Hydrogen isocyanide
2235:Silicon monosulfide
2210:Phosphorus monoxide
2178:Methylidyne radical
2137:Fluoromethylidynium
2097:Aluminium(II) oxide
1852:2017PLoSO..1271501B
1690:2000PNAS...97.2425B
1591:2008JAP...103d3502J
1408:2023PhP....25....1N
1340:"Organic Chemistry"
1327:fullerene chemistry
1175:UV/Vis Spectroscopy
1154:The main tools are
1134:medicinal chemistry
1039:Synthetic compounds
970:stereoisometrically
467:carbonâcarbon bonds
382:from the inorganic
349:inorganic compounds
286:. Different forms (
284:inorganic compounds
77:carbon-carbon bonds
3420:Molecules in stars
3390:Intergalactic dust
3335:Circumstellar dust
3277:Naphthalene cation
3212:Trihydrogen cation
3188:Hydrogen deuteride
3113:Methyltriacetylene
2948:Hexapentaenylidene
2767:E-Cyanomethanimine
2687:Cyclopropenylidene
2621:Tricarbon monoxide
2611:Silicon tricarbide
2581:Methylene amidogen
2571:Isothiocyanic acid
2486:Thioxoethenylidene
2446:Trihydrogen cation
2260:Titanium(II) oxide
2220:Potassium chloride
2199:Sulfur mononitride
2142:Helium hydride ion
2117:Carbon monosulfide
1227:Seager, Spencer L.
1191:Inorganic compound
1117:Beilstein database
814:mellitic anhydride
687:mellitic anhydride
429:
308:chemical compounds
207:and other organic
71:of carbon without
51:carbonâcarbon bond
35:
3548:Organic chemistry
3543:Organic compounds
3530:
3529:
3445:Pseudo-panspermia
3141:
3140:
3088:Cyanodecapentayne
3028:N-Methylformamide
3003:Methyldiacetylene
2928:Aminoacetonitrile
2898:Methyl isocyanate
2816:Methyl isocyanide
2697:Isocyanoacetylene
2677:Cyanoformaldehyde
2556:Hydrogen peroxide
2441:Potassium cyanide
2397:Magnesium cyanide
2350:Disilicon carbide
2345:Dicarbon monoxide
2152:Hydrogen fluoride
2147:Hydrogen chloride
2028:
2027:
2000:Organic synthesis
1995:Organic reactions
1990:Organic compounds
1980:Functional groups
1959:organic chemistry
1599:10.1063/1.2884529
1171:Mass spectrometry
1005:neurotransmitters
947:Natural compounds
942:Natural compounds
462:
409:
387:potassium cyanate
360:chemical elements
162:organic chemistry
114:chloroformic acid
43:chemical compound
3555:
3520:
3519:
3518:
3508:
3507:
3506:
3496:
3495:
3494:
3483:
3482:
3430:Organic compound
3330:Chemical formula
3235:Dihydroxyacetone
3183:Hydrogen cyanide
2868:Cyanodiacetylene
2722:Propadienylidene
2616:Thioformaldehyde
2491:Titanium dioxide
2456:Sodium hydroxide
2377:Hydrogen sulfide
2365:Hydrogen cyanide
2325:Carbonyl sulfide
2290:
2281:
2272:
2230:Silicon monoxide
2163:Hydroxyl radical
2075:
2055:
2048:
2041:
2032:
1975:Covalent bonding
1951:
1944:
1937:
1928:
1905:
1898:
1892:
1891:
1881:
1863:
1831:
1825:
1824:
1823:
1822:
1794:
1788:
1787:
1785:
1784:
1728:
1722:
1721:
1711:
1701:
1684:(6): 2425â2430.
1667:
1661:
1660:
1658:
1657:
1642:
1636:
1635:
1633:
1632:
1617:
1611:
1610:
1584:
1558:
1552:
1551:
1540:
1534:
1533:
1531:
1529:
1524:. March 10, 2024
1514:
1508:
1507:
1497:
1473:
1467:
1466:
1464:
1432:
1426:
1425:
1423:
1422:
1387:
1381:
1380:
1378:
1376:
1361:
1355:
1354:
1352:
1351:
1336:
1330:
1319:
1313:
1290:
1284:
1283:
1281:
1279:
1264:"Petrochemicals"
1259:
1253:
1252:
1223:
1163:NMR spectroscopy
891:
878:
869:
860:
851:
839:
787:
777:
755:
716:
699:
672:
660:
651:
639:
632:carbon disulfide
624:
616:
608:
595:
574:
563:, and arguably,
561:
540:
527:
517:
508:
496:
485:(which contains
460:
441:organic compound
426:
407:
391:ammonium sulfate
364:Friedrich Wöhler
304:carbon nanotubes
276:
263:oxides of carbon
259:carbonate esters
197:the carbon cycle
178:hydrogen cyanide
148:
147:
146:
143:
132:
122:
111:
107:hydrogen cyanide
104:
88:
66:
45:that contains a
39:organic compound
32:
3563:
3562:
3558:
3557:
3556:
3554:
3553:
3552:
3533:
3532:
3531:
3526:
3516:
3514:
3504:
3502:
3492:
3490:
3470:
3296:
3272:
3263:
3216:
3206:
3149:
3137:
3118:Propionaldehyde
3093:Ethylene glycol
3082:
3074:
3070:
3041:
3039:
3032:
2988:Cyanohexatriyne
2974:
2967:
2914:
2907:
2842:
2835:
2795:
2748:
2741:
2712:Methoxy radical
2642:
2635:
2631:Thiocyanic acid
2512:
2505:
2415:
2355:Ethynyl radical
2291:
2285:
2284:
2283:
2282:
2276:
2275:
2274:
2273:
2264:
2255:Sulfur monoxide
2240:Sodium chloride
2225:Silicon carbide
2132:Diatomic carbon
2122:Carbon monoxide
2064:
2059:
2029:
2024:
2015:Stereochemistry
1961:
1955:
1913:
1908:
1899:
1895:
1846:(2): e0171501.
1833:
1832:
1828:
1820:
1818:
1796:
1795:
1791:
1782:
1780:
1730:
1729:
1725:
1669:
1668:
1664:
1655:
1653:
1644:
1643:
1639:
1630:
1628:
1619:
1618:
1614:
1564:
1560:
1559:
1555:
1542:
1541:
1537:
1527:
1525:
1516:
1515:
1511:
1475:
1474:
1470:
1434:
1433:
1429:
1420:
1418:
1392:"Vital Physics"
1389:
1388:
1384:
1374:
1372:
1371:. July 20, 1998
1363:
1362:
1358:
1349:
1347:
1338:
1337:
1333:
1320:
1316:
1291:
1287:
1277:
1275:
1261:
1260:
1256:
1241:
1225:
1224:
1220:
1216:
1187:
1167:IR Spectroscopy
1152:
1146:
1096:
1072:
1049:occur naturally
1041:
966:
944:
932:small molecules
905:
899:
890:
886:
882:
877:
873:
868:
864:
859:
855:
850:
846:
837:
833:
829:
825:
821:
790:IUPAC Blue Book
786:
782:
776:
772:
768:
753:
749:
745:
741:
719:carbon monoxide
715:
711:
698:
694:
690:
679:metal carbonyls
671:
667:
659:
655:
650:
646:
638:
634:
623:
619:
614:
606:
594:
590:
573:
569:
565:
560:
556:
539:
535:
525:
521:
516:
512:
507:
503:
499:
494:
490:
425:
421:
417:
413:
399:
327:
321:
316:
275:
271:
247:
166:carbonate salts
144:
141:
140:
138:
131:
127:
120:
116:
109:
102:
87:
83:
73:carbon-hydrogen
65:
61:
47:carbonâhydrogen
31:
27:
17:
12:
11:
5:
3561:
3559:
3551:
3550:
3545:
3535:
3534:
3528:
3527:
3525:
3524:
3512:
3500:
3488:
3475:
3472:
3471:
3469:
3468:
3463:
3458:
3453:
3447:
3442:
3437:
3432:
3427:
3422:
3417:
3412:
3407:
3402:
3397:
3392:
3387:
3382:
3377:
3372:
3367:
3362:
3357:
3355:Cosmochemistry
3352:
3347:
3342:
3337:
3332:
3327:
3322:
3320:Astrochemistry
3317:
3312:
3306:
3304:
3298:
3297:
3295:
3294:
3289:
3284:
3279:
3274:
3270:
3266:
3261:
3257:
3252:
3247:
3242:
3237:
3232:
3226:
3224:
3218:
3217:
3215:
3214:
3209:
3204:
3200:
3195:
3190:
3185:
3180:
3175:
3173:Formyl radical
3170:
3165:
3159:
3153:
3151:
3143:
3142:
3139:
3138:
3136:
3135:
3130:
3125:
3120:
3115:
3110:
3105:
3103:Methyl acetate
3100:
3095:
3090:
3085:
3080:
3076:
3072:
3068:
3062:
3057:
3052:
3046:
3044:
3034:
3033:
3031:
3030:
3025:
3020:
3015:
3010:
3005:
3000:
2995:
2993:Dimethyl ether
2990:
2985:
2979:
2977:
2969:
2968:
2966:
2965:
2960:
2958:Methyl formate
2955:
2950:
2945:
2943:Glycolaldehyde
2940:
2935:
2930:
2925:
2919:
2917:
2909:
2908:
2906:
2905:
2900:
2895:
2890:
2885:
2880:
2878:Glycolonitrile
2875:
2873:Ethylene oxide
2870:
2865:
2864:
2863:
2853:
2847:
2845:
2837:
2836:
2834:
2833:
2828:
2823:
2818:
2813:
2808:
2803:
2798:
2793:
2789:
2784:
2779:
2774:
2772:Cyclopropenone
2769:
2764:
2759:
2753:
2751:
2743:
2742:
2740:
2739:
2734:
2729:
2724:
2719:
2714:
2709:
2704:
2699:
2694:
2689:
2684:
2679:
2674:
2672:Cyanoacetylene
2669:
2664:
2659:
2654:
2647:
2645:
2637:
2636:
2634:
2633:
2628:
2623:
2618:
2613:
2608:
2603:
2598:
2593:
2591:Methyl radical
2588:
2583:
2578:
2573:
2568:
2566:Isocyanic acid
2563:
2558:
2553:
2548:
2543:
2538:
2533:
2531:Isocyanic acid
2528:
2523:
2517:
2515:
2507:
2506:
2504:
2503:
2498:
2493:
2488:
2483:
2478:
2476:Sulfur dioxide
2473:
2468:
2463:
2458:
2453:
2451:Sodium cyanide
2448:
2443:
2438:
2433:
2428:
2423:
2418:
2413:
2409:
2404:
2399:
2394:
2389:
2384:
2379:
2374:
2368:
2362:
2360:Formyl radical
2357:
2352:
2347:
2342:
2337:
2332:
2327:
2322:
2320:Carbon dioxide
2317:
2312:
2307:
2301:
2299:
2293:
2292:
2267:
2265:
2263:
2262:
2257:
2252:
2247:
2242:
2237:
2232:
2227:
2222:
2217:
2212:
2207:
2201:
2196:
2191:
2185:
2180:
2175:
2170:
2168:Iron(II) oxide
2165:
2160:
2154:
2149:
2144:
2139:
2134:
2129:
2124:
2119:
2114:
2109:
2104:
2099:
2094:
2089:
2083:
2081:
2072:
2066:
2065:
2060:
2058:
2057:
2050:
2043:
2035:
2026:
2025:
2023:
2022:
2017:
2012:
2007:
2002:
1997:
1992:
1987:
1982:
1977:
1972:
1966:
1963:
1962:
1956:
1954:
1953:
1946:
1939:
1931:
1925:
1924:
1919:
1912:
1911:External links
1909:
1907:
1906:
1893:
1826:
1789:
1743:(2): 139â193.
1723:
1662:
1637:
1612:
1562:
1553:
1535:
1509:
1468:
1447:(4): 114â118.
1427:
1382:
1356:
1331:
1314:
1303:Organyl groups
1285:
1254:
1239:
1217:
1215:
1212:
1211:
1210:
1204:
1199:
1194:
1186:
1183:
1148:Main article:
1145:
1142:
1138:
1137:
1125:
1112:
1095:
1092:
1071:
1068:
1040:
1037:
964:
943:
940:
901:Main article:
898:
897:Classification
895:
835:
798:mesoxalic acid
398:
395:
339:In the 1810s,
323:Main article:
320:
317:
315:
312:
265:(for example,
246:
243:
221:petrochemicals
217:photosynthesis
174:carbon dioxide
125:carbon dioxide
15:
13:
10:
9:
6:
4:
3:
2:
3560:
3549:
3546:
3544:
3541:
3540:
3538:
3523:
3513:
3511:
3501:
3499:
3489:
3487:
3486:
3477:
3476:
3473:
3467:
3464:
3462:
3459:
3457:
3454:
3451:
3448:
3446:
3443:
3441:
3438:
3436:
3433:
3431:
3428:
3426:
3423:
3421:
3418:
3416:
3413:
3411:
3408:
3406:
3403:
3401:
3398:
3396:
3393:
3391:
3388:
3386:
3385:Homochirality
3383:
3381:
3378:
3376:
3373:
3371:
3368:
3366:
3363:
3361:
3358:
3356:
3353:
3351:
3348:
3346:
3343:
3341:
3338:
3336:
3333:
3331:
3328:
3326:
3323:
3321:
3318:
3316:
3313:
3311:
3308:
3307:
3305:
3303:
3299:
3293:
3290:
3288:
3285:
3283:
3280:
3278:
3275:
3273:
3267:
3265:
3258:
3256:
3253:
3251:
3248:
3246:
3243:
3241:
3240:Methoxyethane
3238:
3236:
3233:
3231:
3228:
3227:
3225:
3223:
3219:
3213:
3210:
3208:
3201:
3199:
3196:
3194:
3191:
3189:
3186:
3184:
3181:
3179:
3176:
3174:
3171:
3169:
3166:
3163:
3160:
3158:
3155:
3154:
3152:
3148:
3144:
3134:
3131:
3129:
3126:
3124:
3123:Butyronitrile
3121:
3119:
3116:
3114:
3111:
3109:
3106:
3104:
3101:
3099:
3098:Ethyl formate
3096:
3094:
3091:
3089:
3086:
3084:
3077:
3066:
3063:
3061:
3058:
3056:
3053:
3051:
3048:
3047:
3045:
3043:
3035:
3029:
3026:
3024:
3023:Propionitrile
3021:
3019:
3016:
3014:
3011:
3009:
3006:
3004:
3001:
2999:
2996:
2994:
2991:
2989:
2986:
2984:
2981:
2980:
2978:
2976:
2970:
2964:
2961:
2959:
2956:
2954:
2951:
2949:
2946:
2944:
2941:
2939:
2936:
2934:
2931:
2929:
2926:
2924:
2921:
2920:
2918:
2916:
2910:
2904:
2903:Vinyl alcohol
2901:
2899:
2896:
2894:
2891:
2889:
2886:
2884:
2881:
2879:
2876:
2874:
2871:
2869:
2866:
2862:
2861:Vinyl cyanide
2859:
2858:
2857:
2856:Acrylonitrile
2854:
2852:
2849:
2848:
2846:
2844:
2838:
2832:
2829:
2827:
2824:
2822:
2821:Pentynylidyne
2819:
2817:
2814:
2812:
2809:
2807:
2804:
2802:
2799:
2797:
2790:
2788:
2785:
2783:
2780:
2778:
2775:
2773:
2770:
2768:
2765:
2763:
2760:
2758:
2755:
2754:
2752:
2750:
2744:
2738:
2735:
2733:
2730:
2728:
2725:
2723:
2720:
2718:
2717:Methylenimine
2715:
2713:
2710:
2708:
2705:
2703:
2700:
2698:
2695:
2693:
2690:
2688:
2685:
2683:
2680:
2678:
2675:
2673:
2670:
2668:
2665:
2663:
2660:
2658:
2655:
2652:
2649:
2648:
2646:
2644:
2638:
2632:
2629:
2627:
2624:
2622:
2619:
2617:
2614:
2612:
2609:
2607:
2604:
2602:
2599:
2597:
2596:Propynylidyne
2594:
2592:
2589:
2587:
2586:Methyl cation
2584:
2582:
2579:
2577:
2574:
2572:
2569:
2567:
2564:
2562:
2559:
2557:
2554:
2552:
2549:
2547:
2546:Fulminic acid
2544:
2542:
2539:
2537:
2534:
2532:
2529:
2527:
2524:
2522:
2519:
2518:
2516:
2514:
2508:
2502:
2499:
2497:
2494:
2492:
2489:
2487:
2484:
2482:
2479:
2477:
2474:
2472:
2469:
2467:
2464:
2462:
2459:
2457:
2454:
2452:
2449:
2447:
2444:
2442:
2439:
2437:
2434:
2432:
2429:
2427:
2424:
2422:
2421:Nitrous oxide
2419:
2417:
2410:
2408:
2405:
2403:
2400:
2398:
2395:
2393:
2390:
2388:
2385:
2383:
2380:
2378:
2375:
2372:
2369:
2366:
2363:
2361:
2358:
2356:
2353:
2351:
2348:
2346:
2343:
2341:
2338:
2336:
2333:
2331:
2328:
2326:
2323:
2321:
2318:
2316:
2315:Amino radical
2313:
2311:
2308:
2306:
2303:
2302:
2300:
2298:
2294:
2289:
2280:
2271:
2261:
2258:
2256:
2253:
2251:
2248:
2246:
2245:Sodium iodide
2243:
2241:
2238:
2236:
2233:
2231:
2228:
2226:
2223:
2221:
2218:
2216:
2213:
2211:
2208:
2205:
2202:
2200:
2197:
2195:
2192:
2189:
2186:
2184:
2181:
2179:
2176:
2174:
2171:
2169:
2166:
2164:
2161:
2158:
2155:
2153:
2150:
2148:
2145:
2143:
2140:
2138:
2135:
2133:
2130:
2128:
2127:Cyano radical
2125:
2123:
2120:
2118:
2115:
2113:
2110:
2108:
2107:Carbon cation
2105:
2103:
2100:
2098:
2095:
2093:
2090:
2088:
2085:
2084:
2082:
2080:
2076:
2073:
2071:
2067:
2063:
2056:
2051:
2049:
2044:
2042:
2037:
2036:
2033:
2021:
2018:
2016:
2013:
2011:
2008:
2006:
2003:
2001:
1998:
1996:
1993:
1991:
1988:
1986:
1983:
1981:
1978:
1976:
1973:
1971:
1968:
1967:
1964:
1960:
1952:
1947:
1945:
1940:
1938:
1933:
1932:
1929:
1923:
1920:
1918:
1915:
1914:
1910:
1903:
1897:
1894:
1889:
1885:
1880:
1875:
1871:
1867:
1862:
1857:
1853:
1849:
1845:
1841:
1837:
1830:
1827:
1816:
1812:
1808:
1804:
1800:
1793:
1790:
1778:
1774:
1770:
1766:
1762:
1758:
1754:
1750:
1746:
1742:
1738:
1734:
1727:
1724:
1719:
1715:
1710:
1705:
1700:
1695:
1691:
1687:
1683:
1679:
1678:
1673:
1666:
1663:
1651:
1647:
1641:
1638:
1626:
1622:
1616:
1613:
1608:
1604:
1600:
1596:
1592:
1588:
1583:
1578:
1574:
1570:
1569:
1557:
1554:
1549:
1545:
1539:
1536:
1523:
1519:
1513:
1510:
1505:
1501:
1496:
1491:
1487:
1483:
1479:
1472:
1469:
1463:
1458:
1454:
1450:
1446:
1442:
1438:
1431:
1428:
1417:
1413:
1409:
1405:
1401:
1397:
1393:
1386:
1383:
1370:
1366:
1360:
1357:
1345:
1341:
1335:
1332:
1328:
1324:
1318:
1315:
1312:
1308:
1304:
1300:
1299:
1294:
1289:
1286:
1273:
1269:
1265:
1262:Smith, Cory.
1258:
1255:
1250:
1246:
1242:
1240:9780534399696
1236:
1232:
1228:
1222:
1219:
1213:
1208:
1205:
1203:
1200:
1198:
1195:
1192:
1189:
1188:
1184:
1182:
1180:
1176:
1172:
1168:
1164:
1161:
1157:
1151:
1143:
1141:
1135:
1131:
1130:
1126:
1123:
1119:
1118:
1113:
1110:
1109:
1104:
1103:
1098:
1097:
1093:
1091:
1089:
1088:biotechnology
1085:
1081:
1077:
1070:Biotechnology
1069:
1067:
1065:
1061:
1057:
1052:
1050:
1046:
1038:
1036:
1034:
1033:fats and oils
1030:
1026:
1022:
1018:
1014:
1010:
1009:nucleic acids
1006:
1002:
998:
994:
990:
986:
985:carbohydrates
982:
978:
973:
971:
967:
960:
956:
952:
948:
941:
939:
937:
933:
928:
926:
922:
918:
914:
910:
904:
896:
894:
892:
879:
870:
861:
852:
841:
819:
815:
811:
807:
806:Mellitic acid
803:
799:
795:
791:
781:
767:
762:
760:
756:
737:
735:
730:
726:
725:
720:
709:
705:
703:
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684:
680:
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665:
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652:
643:
633:
629:
625:
612:
604:
600:
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579:
575:
562:
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532:
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518:
509:
488:
484:
480:
474:
472:
468:
464:
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454:
450:
446:
442:
438:
434:
411:
403:
396:
394:
392:
388:
385:
381:
377:
373:
369:
365:
361:
357:
356:atomic theory
352:
350:
346:
342:
337:
335:
331:
326:
318:
313:
311:
309:
305:
301:
297:
293:
289:
285:
281:
277:
268:
264:
260:
256:
252:
244:
242:
240:
237:
233:
232:organyl group
228:
226:
222:
218:
215:using light (
214:
210:
206:
205:simple sugars
202:
198:
194:
193:Earth's crust
189:
187:
183:
179:
175:
171:
170:cyanide salts
167:
163:
159:
155:
150:
136:
126:
115:
108:
100:
96:
92:
82:
78:
74:
70:
60:
56:
52:
48:
44:
40:
25:
21:
3478:
3461:Spectroscopy
3429:
3315:Astrobiology
3168:Formaldehyde
3060:Benzonitrile
2851:Acetaldehyde
2806:Methanethiol
2757:Acetonitrile
2662:Carbodiimide
2541:Formaldehyde
2536:Cyanoethynyl
2387:Iron cyanide
2382:Hydroperoxyl
2183:Nitric oxide
2010:Spectroscopy
2005:Publications
1989:
1985:Nomenclature
1957:Concepts in
1901:
1896:
1843:
1839:
1829:
1819:, retrieved
1802:
1792:
1781:. Retrieved
1740:
1736:
1726:
1681:
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1665:
1654:. Retrieved
1640:
1629:. Retrieved
1615:
1572:
1566:
1556:
1547:
1538:
1526:. Retrieved
1521:
1512:
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1485:
1481:
1471:
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1440:
1430:
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1402:(1â2): 1â2.
1399:
1395:
1385:
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1368:
1359:
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1334:
1322:
1317:
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1288:
1276:. Retrieved
1267:
1257:
1230:
1221:
1153:
1139:
1127:
1115:
1106:
1100:
1073:
1053:
1042:
977:biochemistry
974:
945:
929:
906:
842:
794:benzenehexol
763:
738:
722:
706:
641:
475:
457:
452:
444:
440:
436:
432:
430:
366:synthesized
353:
338:
333:
328:
248:
229:
225:hydrocarbons
190:
151:
38:
36:
3435:Outer space
3345:Cosmic dust
3310:Abiogenesis
3222:Unconfirmed
3178:Heavy water
3018:Ethanethiol
2933:Cyanoallene
2923:Acetic acid
2893:Methylamine
2777:Diacetylene
2692:Formic acid
2682:Cyanomethyl
2340:Diazenylium
2330:CCP radical
2206:(molecular)
2190:(molecular)
2159:(molecular)
1970:Aromaticity
1323:derivatives
1278:18 December
1111:is offered.
1021:amino acids
1001:fatty acids
909:heteroatoms
780:oxalic acid
630:; although
580:of carbon,
550:of carbon (
463:-isoleucine
449:E. J. Corey
410:-isoleucine
368:oxalic acid
334:vis vitalis
257:(excluding
239:substituent
176:, and even
3537:Categories
3350:Cosmic ray
3292:Silylidyne
3255:Hemolithin
3230:Anthracene
3147:Deuterated
3128:Pyrimidine
2938:Ethanimine
2801:Ketenimine
2657:Butadiynyl
2481:Thioformyl
2335:Chloronium
1821:2023-01-04
1803:StatPearls
1783:2023-01-04
1656:2009-11-22
1631:2009-11-22
1421:2024-03-10
1350:2022-08-25
1321:Fullerene
1214:References
959:terpenoids
925:phosphorus
702:oxocarbons
675:carboranes
578:allotropes
544:carbonates
445:carbogenic
412:molecule,
300:fullerenes
288:allotropes
261:), simple
255:carbonates
245:Definition
236:monovalent
3282:Phosphine
3150:molecules
3083:fullerene
2983:Acetamide
2787:Formamide
2667:Cyanamide
2521:Acetylene
2496:Tricarbon
2407:Methylene
2392:Isoformyl
2297:Triatomic
2070:Molecules
1870:1932-6203
1757:1547-6898
1582:0711.1528
1528:March 10,
1453:1650-3414
1375:March 10,
1249:155910842
1160:carbon-13
1108:SciFinder
1094:Databases
1045:synthetic
963:vitamin B
955:alkaloids
834:·16H
734:cementite
546:, simple
487:cementite
437:inorganic
345:synthesis
209:molecules
182:inorganic
135:carbonate
3269:Linear C
3250:Graphene
3162:Ammonium
2963:Acrolein
2826:Propynal
2811:Methanol
2782:Ethylene
2651:Ammonium
2426:Nitroxyl
2250:Sulfanyl
2194:Imidogen
2188:Nitrogen
2157:Hydrogen
2102:Argonium
2079:Diatomic
1888:28182744
1840:PLOS ONE
1815:archived
1811:32809354
1777:Archived
1773:98688955
1765:19204852
1718:10706606
1650:Archived
1625:Archived
1607:94576016
1504:32549817
1344:Archived
1272:Archived
1185:See also
1060:plastics
1056:polymers
1029:vitamins
1017:peptides
1013:proteins
993:hormones
981:antigens
936:polymers
911:, e.g.,
664:phosgene
611:cyaphide
372:cyanogen
330:Vitalism
325:Vitalism
319:Vitalism
296:graphite
280:cyanides
251:carbides
186:chemists
154:catenate
91:nitrogen
3415:Kerogen
3302:Related
3245:Glycine
3198:Propyne
3157:Ammonia
3055:Benzene
3050:Acetone
3042:or more
3013:Propene
2998:Ethanol
2888:Propyne
2707:Methane
2576:Ketenyl
2526:Ammonia
1879:5300202
1848:Bibcode
1686:Bibcode
1587:Bibcode
1495:7217401
1462:6208063
1404:Bibcode
1129:PubChem
1080:insulin
1076:ethanol
1064:rubbers
1025:lectins
989:enzymes
953:, some
818:mellite
810:Martian
681:(e.g.,
642:organic
603:cyanate
582:cyanide
576:), the
453:organic
433:organic
314:History
292:diamond
99:cyanide
69:halides
59:methane
55:alkanes
24:Methane
3466:Tholin
3287:Pyrene
2732:Silane
2702:Ketene
2204:Oxygen
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1876:
1868:
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1156:proton
1122:Reaxys
1031:, and
997:lipids
951:sugars
919:, and
880:, and
800:, and
783:(COOH)
712:Ni(CO)
613:anion
605:anion
548:oxides
479:alloys
278:) and
133:, and
97:(e.g.
95:oxygen
79:(e.g.
57:(e.g.
3452:(PAH)
3040:atoms
2975:atoms
2915:atoms
2913:Eight
2843:atoms
2841:Seven
2749:atoms
2643:atoms
2513:atoms
2501:Water
2431:Ozone
2373:(HNC)
2367:(HCN)
1769:S2CID
1709:15945
1603:S2CID
1577:arXiv
1293:IUPAC
1054:Most
917:metal
830:(COO)
769:CO(NH
483:steel
384:salts
203:into
201:water
158:atoms
41:as a
2973:Nine
2641:Five
2551:HCCN
2511:Four
2471:SiNC
1884:PMID
1866:ISSN
1807:PMID
1761:PMID
1753:ISSN
1714:PMID
1530:2024
1500:PMID
1449:ISSN
1377:2024
1280:2016
1245:OCLC
1235:ISBN
1177:and
1158:and
1114:The
1099:The
1078:and
1062:and
1019:and
999:and
979:are
957:and
934:and
874:CHCl
853:and
778:nor
766:urea
668:COCl
656:CClF
653:and
599:BrCN
591:(CN)
529:and
510:and
435:and
405:The
389:and
380:urea
358:and
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1856:doi
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1102:CAS
1084:DNA
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628:COS
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