445:
408:
480:
461:
430:
495:
370:
147:
2029:
587:
2188:
1892:
22:
2235:
1795:
355:
340:
389:
4097:
1473:
4121:
4737:
4588:
4656:
4493:
4133:
4109:
1730:
540:). However, if any of the ligands form a direct metal-carbon (M-C) bond, then the complex is considered to be organometallic. Although the IUPAC has not formally defined the term, some chemists use the term "metalorganic" to describe any coordination compound containing an organic ligand regardless of the presence of a direct M-C bond.
559:) may vary with the nature of the anionic moiety, the metal ion, and possibly the medium. In the absence of direct structural evidence for a carbon–metal bond, such compounds are not considered to be organometallic. For instance, lithium enolates often contain only Li-O bonds and are not organometallic, while zinc enolates (
1503:(e.g., margarine production) rely on heterogeneous catalysts, for the production of fine chemicals such hydrogenations rely on soluble (homogenous) organometallic complexes or involve organometallic intermediates. Organometallic complexes allow these hydrogenations to be effected asymmetrically.
444:
678:
identifies three classes of ligands, X,L, and Z; which are based on the electron donating interactions of the ligand. Many organometallic compounds do not follow the 18e rule. The metal atoms in organometallic compounds are frequently described by their
460:
1630:. Sigma-bond metathesis is typically used with early transition-metal complexes that are in their highest oxidation state. Using transition-metals that are in their highest oxidation state prevents other reactions from occurring, such as
407:
479:
2038:
2036:
2034:
2032:
429:
650:. The 18e rule has two representative electron counting models, ionic and neutral (also known as covalent) ligand models, respectively. The hapticity of a metal-ligand complex, can influence the electron count.
133:
Organometallic compounds are widely used both stoichiometrically in research and industrial chemical reactions, as well as in the role of catalysts to increase the rates of such reactions (e.g., as in uses of
714:
is a common technique used to obtain information on the electronic structure of organometallic compounds. It is also used monitor the progress of organometallic reactions, as well as determine their
2240:
2238:
1816:
1814:
1812:
1810:
1808:
1806:
1804:
1802:
1800:
1798:
369:
161:
Organometallic compounds are distinguished by the prefix "organo-" (e.g., organopalladium compounds), and include all compounds which contain a bond between a metal atom and a carbon atom of an
1740:
Natural and contaminant organometallic compounds are found in the environment. Some that are remnants of human use, such as organolead and organomercury compounds, are toxicity hazards.
2055:
Nelson, Ryan C.; Miller, Jeffrey T. (2012). "An introduction to X-ray absorption spectroscopy and its in situ application to organometallic compounds and homogeneous catalysts".
702:
is a particularly important technique that can locate the positions of atoms within a solid compound, providing a detailed description of its structure. Other techniques like
3084:
1642:. Neither sigma-bond metathesis or olefin metathesis change the oxidation state of the metal. Many other methods are used to form new carbon-carbon bonds, including
494:
873:
114:
are often included in discussions of organometallic compounds, though strictly speaking, they are not necessarily organometallic. The related but distinct term "
122:, dialkylamides, and metal phosphine complexes are representative members of this class. The field of organometallic chemistry combines aspects of traditional
339:
354:
2496:
Magano, Javier; Dunetz, Joshua R. (9 March 2011). "Large-Scale
Applications of Transition Metal-Catalyzed Couplings for the Synthesis of Pharmaceuticals".
2300:
2209:
1839:
2829:
375:
670:
ligand bond equally and contribute one electron to the iron center. Ligands that bind non-contiguous atoms are denoted the Greek letter kappa, κ.
4171:
3192:
1944:
2022:
473:
required by several crucial enzymatic reactions that take place in the human body. It is a rare example of a metal (cobalt) alkyl in biology.
388:
3293:
1753:
727:
595:
3298:
1430:, examples of which are highly basic and highly reducing, are useful stoichiometrically but also catalyze many polymerization reactions.
1760:
roxarsone is a controversial animal feed additive. In 2006, approximately one million kilograms of it were produced in the U.S alone.
2874:
698:
A wide variety of physical techniques are used to determine the structure, composition, and properties of organometallic compounds.
2917:
118:" refers to metal-containing compounds lacking direct metal-carbon bonds but which contain organic ligands. Metal β-diketonates,
3276:
707:
2115:[About the effect between platinum chloride and alcohol, and about the new substances that are created in the process].
3320:
2813:
2775:
2756:
2737:
2708:
2689:
2670:
2651:
2398:"Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners"
1998:
1928:
1883:
1748:
additive but has fallen into disuse because of lead's toxicity. Its replacements are other organometallic compounds, such as
3332:
3271:
4164:
3185:
2932:
812:
and synthetic material containing a metal-carbon bond.) The abundant and diverse products from coal and petroleum led to
675:
3024:
2317:
2226:
488:
is a red-orange liquid prepared directly from the union of finely divided iron and carbon monoxide gas under pressure.
438:
has a linear coordination. It is a volatile pyrophoric liquid that is used in the preparation of semiconducting films.
4869:
1484:-derived polymers rely on organometallic catalysts. The world's polyethylene and polypropylene are produced via both
3059:
3054:
3019:
1539:
869:
758:
711:
4137:
3069:
3064:
3049:
1596:
590:
a single crystal of a Mn(II) complex, 4Br2. Its bright green color originates from spin-forbidden d-d transitions
398:
4149:
326:
bond. This complex, along with other biologically relevant complexes are often discussed within the subfield of
4157:
4016:
3178:
3074:
2952:
2259:"Development of Group IV Molecular Catalysts for High Temperature Ethylene-α-Olefin Copolymerization Reactions"
741:. Air-free handling of organometallic compounds typically requires the use of laboratory apparatuses such as a
737:
Due to their high reactivity towards oxygen and moisture, organometallic compounds often must be handled using
534:
3459:
3213:
2867:
2842:
1493:
723:
691:. Chemical bonding and reactivity in organometallic compounds is often discussed from the perspective of the
1782:
500:
654:(η, lowercase Greek eta), describes the number of contiguous ligands coordinated to a metal. For example,
3736:
3223:
3125:
1777:
1705:
Organometallic complexes are commonly used in small-scale fine chemical synthesis as well, especially in
1699:
1679:
1037:
710:
are also frequently used to obtain information on the structure and bonding of organometallic compounds.
327:
138:), where target molecules include polymers, pharmaceuticals, and many other types of practical products.
1698:
processes, analogous to those listed above. Additionally, organometallic intermediates are assumed for
974:
4726:
4721:
4716:
4711:
4706:
4701:
4696:
4691:
4686:
4681:
4676:
4671:
4661:
4604:
4498:
4419:
4414:
4271:
4113:
3662:
3633:
3613:
3566:
3130:
1714:
1326:
1281:
1277:
1055:
2567:
1433:
Almost all processes involving carbon monoxide rely on catalysts, notable examples being described as
4762:
4464:
4434:
4424:
4404:
4392:
4360:
4325:
4293:
4261:
4256:
4216:
3251:
2942:
2113:"Von der Wirkung zwischen Platinchlorid und Alkohol, und von den dabei entstehenden neuen Substanzen"
1955:
1562:
1399:
1317:
1293:
1285:
1269:
1248:
1220:
1187:
1183:
1166:
882:
766:
111:
2096:
4807:
4802:
4797:
4792:
4787:
4782:
4777:
4772:
4767:
4752:
4742:
4593:
4568:
4563:
4548:
4533:
4513:
4508:
4459:
4387:
4370:
4320:
4315:
4310:
4305:
4281:
4241:
4231:
4195:
4006:
3922:
3014:
2978:
2860:
1643:
1616:
1586:
1558:
1427:
1387:
1378:
1366:
1354:
1338:
1334:
1313:
1256:
1216:
1212:
1208:
1204:
1131:
1110:
1092:
1078:
1061:
1043:
947:
921:
719:
647:
107:
2599:"Total tin and organotin speciation in historic layers of antifouling paint on leisure boat hulls"
4757:
4747:
4558:
4543:
4528:
4518:
4503:
4444:
4429:
4409:
4399:
4380:
4375:
4365:
4355:
4298:
4266:
3944:
3855:
3818:
3702:
3628:
3449:
3432:
3375:
1710:
1706:
1695:
1485:
1395:
1391:
1374:
1350:
1342:
1301:
1289:
1273:
1265:
1252:
1244:
1200:
1162:
954:
831:
Recognition of organometallic chemistry as a distinct subfield culminated in the Nobel Prizes to
659:
470:
1911:
Rodríguez-Reyes, J.C.F.; Silva-Quiñones, D. (2018). "Metalorganic
Functionalization in Vacuum".
800:'s organomagnesium compounds. (Although not always acknowledged as an organometallic compound,
4666:
4581:
4523:
4486:
4481:
4469:
4449:
4439:
4345:
4340:
4335:
4276:
4251:
4236:
4226:
3862:
3850:
3741:
3606:
3380:
3246:
3159:
3044:
2091:
1757:
1687:
1438:
1419:
1346:
1330:
1305:
1297:
1236:
1232:
1228:
1179:
1170:
1142:
599:
594:
Most organometallic compounds are solids at room temperature, however some are liquids such as
178:
575:. For highly electropositive elements, such as lithium and sodium, the carbon ligand exhibits
205:
are considered to form organometallic compounds. Examples of organometallic compounds include
4474:
4286:
4221:
4211:
4011:
3908:
3893:
3823:
3746:
3578:
3528:
3437:
3362:
3261:
3079:
1675:
1658:
Organometallic complexes are commonly used in catalysis. Major industrial processes include
1623:
1571:
1411:
805:
703:
548:
544:
135:
4553:
4538:
4350:
4330:
4001:
3956:
3731:
3551:
3481:
3238:
3218:
3034:
2897:
2124:
1718:
1543:
1370:
1358:
1240:
1224:
1103:
809:
790:
603:
560:
234:
2804:
Shriver, Duward; Weller, Mark; Overton, Tina; Armstrong, Fraser; Rourke, Jonathan (2014).
2701:
Basic
Organometallic Chemistry: Concepts, Syntheses, and Applications of Transition Metals
1453:. The bulk of the synthetic alcohols, at least those larger than ethanol, are produced by
8:
4454:
4024:
3978:
3903:
3876:
3774:
3756:
3709:
3647:
3543:
3523:
3392:
3387:
3288:
3154:
2973:
2947:
2902:
1761:
1581:
1507:
1476:
A constrained geometry organotitanium complex is a precatalyst for olefin polymerization.
1309:
817:
738:
514:
273:
123:
106:, are generally considered to be organometallic as well. Some related compounds such as
2128:
146:
4101:
4067:
3929:
3898:
3779:
3721:
3419:
3402:
3397:
3352:
3315:
3305:
3266:
2968:
2922:
2786:
2727:
2473:
2446:
2422:
2397:
2016:
1920:
1765:
1683:
1647:
1631:
1567:
1519:
1068:
1064:
852:
836:
832:
731:
692:
688:
485:
413:
297:
170:
4120:
4082:
4047:
4030:
3968:
3886:
3881:
3809:
3794:
3764:
3685:
3652:
3623:
3618:
3593:
3583:
3503:
3491:
3370:
3283:
3149:
3120:
3110:
3039:
2809:
2792:
2771:
2752:
2733:
2714:
2704:
2685:
2666:
2647:
2620:
2513:
2478:
2427:
2313:
2280:
2222:
2004:
1994:
1924:
1879:
1671:
1635:
1622:
The synthesis of many organic molecules are facilitated by organometallic complexes.
1591:
1523:
1489:
1125:
1072:
856:
813:
715:
699:
635:
615:
552:
518:
466:
174:
127:
79:
51:
1849:
1437:. The production of acetic acid from methanol and carbon monoxide is catalyzed via
4125:
4042:
3697:
3556:
3533:
3486:
3427:
3115:
3009:
2912:
2907:
2610:
2579:
2546:
2505:
2468:
2458:
2417:
2409:
2342:
2305:
2270:
2214:
2175:
2132:
2064:
1916:
1853:
1844:
1691:
1511:
1450:
1442:
1383:
1322:
1261:
1196:
1175:
1158:
997:
970:
901:
848:
821:
774:
680:
639:
242:
218:
63:
21:
2360:
804:, a mixed-valence iron-cyanide complex, was first prepared in 1706 by paint maker
642:
is helpful in predicting the stabilities of organometallic complexes, for example
4179:
3983:
3939:
3934:
3828:
3804:
3638:
3601:
3454:
3444:
3327:
2988:
2983:
2846:
2615:
2598:
2597:
Lagerström, Maria; Strand, Jakob; Eklund, Britta; Ytreberg, Erik (January 2017).
2537:
2333:
Waterman, Rory (23 December 2013). "σ-Bond
Metathesis: A 30-Year Retrospective".
2275:
2258:
1663:
1611:
1606:
1601:
1576:
1515:
1423:
1138:
1134:
1121:
1026:
950:
915:
886:
797:
770:
684:
607:
586:
417:
394:
308:
293:
91:
3867:
3845:
3840:
3835:
3790:
3786:
3769:
3726:
3657:
3518:
3513:
3498:
3310:
3228:
3105:
3004:
2927:
2378:
1741:
1667:
1458:
1446:
1081:
1012:
978:
964:
643:
610:(reactive towards oxygen and moisture), and thus they must be handled under an
508:
451:
348:
is an archetypal organoiron complex. It is an air-stable, sublimable compound.
285:
250:
206:
95:
75:
25:
2796:
2583:
2463:
1499:
Most processes involving hydrogen rely on metal-based catalysts. Whereas bulk
4863:
4826:
4072:
3961:
3917:
3642:
3476:
3471:
3464:
3342:
3100:
2718:
2309:
2218:
2136:
2008:
1848:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
1659:
1500:
1454:
1434:
1415:
1362:
1191:
1117:
1095:
1085:
1004:
982:
943:
for the treatment of syphilis, an early arsenic based organometallic compound
801:
782:
619:
579:
character, but free carbon-based anions are extremely rare, an example being
246:
230:
226:
162:
115:
55:
2180:
2163:
1857:
687:. These concepts can be used to help predict their reactivity and preferred
3949:
3799:
3714:
3690:
3680:
3672:
3573:
3508:
3407:
3256:
2852:
2624:
2517:
2482:
2431:
2284:
1466:
1113:
1051:
1047:
1008:
993:
960:
936:
925:
844:
746:
435:
420:
281:
166:
157:, which, like several other organometallic compounds, is pyrophoric in air.
1988:
454:, a type of organocopper complex frequently employed in organic synthesis.
3347:
3029:
1030:
989:
911:
905:
840:
786:
778:
363:
is a structural analogue of ferrocene, but is highly reactive toward air.
360:
312:
261:
154:
32:
3170:
1410:
Organometallic compounds find wide use in commercial reactions, both as
529:
such as oxygen or nitrogen are considered coordination compounds (e.g.,
3973:
2068:
1627:
623:
526:
257:
182:
83:
2551:
2532:
2509:
2413:
2346:
1472:
571:
The metal-carbon bond in organometallic compounds is generally highly
563:) contain both Zn-O and Zn-C bonds, and are organometallic in nature.
4035:
3337:
3202:
3141:
2937:
2840:
web listing of US chemists who specialize in organometallic chemistry
1749:
1733:
1535:
1099:
1019:
940:
929:
671:
655:
651:
611:
576:
379:
345:
269:
238:
222:
31:, an organometallic compound. Four lithium atoms (in purple) form a
2112:
225:. Boron-containing organometallic compounds are often the result of
4057:
2396:
Jana, Ranjan; Pathak, Tejas P.; Sigman, Matthew S. (9 March 2011).
2257:
Klosin, Jerzy; Fontaine, Philip P.; Figueroa, Ruth (21 July 2015).
1745:
1462:
890:
742:
572:
202:
186:
119:
2839:
2082:
1036:, the first biomolecule found to contain a metal-carbon bond, see
39:
groups attached to the faces (carbon is black, hydrogen is white).
4077:
2834:
1639:
1527:
876:
762:
580:
556:
522:
450:
Lithium diphenylcuprate bis(diethyl etherate) is an example of a
210:
198:
194:
103:
99:
87:
718:. The dynamics of organometallic compounds can be studied using
86:
like boron, silicon, and selenium, as well. Aside from bonds to
4181:
2447:"Recent Developments in the Suzuki-Miyaura Reaction: 2010–2014"
1531:
1481:
894:
530:
525:. Complexes where the organic ligands bind the metal through a
323:
319:
214:
71:
59:
2596:
1554:
Organometallic compounds undergo several important reactions:
2803:
2162:
Dragutan, V.; Dragutan, I.; Balaban, A. T. (1 January 2006).
2042:
1910:
662:
giving a hapticity of 5, where all five carbon atoms of the C
190:
67:
36:
1729:
509:
Distinction from coordination compounds with organic ligands
423:. It is used in the industrial production of some alcohols.
378:
is used in the commercial production of many aldehyde-based
4052:
3085:
Arene complexes of univalent gallium, indium, and thallium
1768:
but have since been banned due to environmental concerns.
90:
fragments or molecules, bonds to 'inorganic' carbon, like
4062:
2642:
Clayden, Jonathan; Greeves, Nick; Warren, Stuart (2012).
1993:(6 ed.). Hoboken, New Jersey. pp. 43, 44, 205.
1694:. Organometallic intermediates are also invoked in many
1154:
Subspecialty areas of organometallic chemistry include:
2298:
2206:
2161:
1457:
of hydroformylation-derived aldehydes. Similarly, the
757:
Early developments in organometallic chemistry include
638:
is useful for organizing organometallic chemistry. The
2256:
2143:
1526:. These volatile compounds are decomposed along with
503:
is used to image the heart muscle in nuclear medicine.
2663:
1990:
The organometallic chemistry of the transition metals
245:. Other examples of organometallic compounds include
2641:
1736:
is an organoarsenic compound used as an animal feed.
1626:
is a synthetic method for forming new carbon-carbon
862:
761:'s synthesis of methyl arsenic compounds related to
241:
are examples of organometallic compounds containing
2207:W. Bertleff; M. Roeper; X. Sava. "Carbonylation".
2445:Maluenda, Irene; Navarro, Oscar (24 April 2015).
1717:for producing aryl amines from aryl halides, and
4861:
2395:
1873:
1145:for palladium catalyzed cross coupling reactions
376:Tris(triphenylphosphine)rhodium carbonyl hydride
307:A naturally occurring organometallic complex is
2766:Lippard, Stephen J.; Berg, Jeremy Mark (1994).
2444:
1538:and related hydrides on a heated substrate via
2301:Ullmann's Encyclopedia of Industrial Chemistry
2210:Ullmann's Encyclopedia of Industrial Chemistry
547:has a negative charge that is shared between (
16:Study of organic compounds containing metal(s)
4165:
3186:
2868:
2679:
2194:
1449:. Most synthetic aldehydes are produced via
2882:
2830:MIT OpenCourseWare: Organometallic Chemistry
2749:Homogeneous Catalysis: Understanding the Art
2530:
2495:
2054:
1754:methylcyclopentadienyl manganese tricarbonyl
1638:is used to synthesize various carbon-carbon
728:electron paramagnetic resonance spectroscopy
596:methylcyclopentadienyl manganese tricarbonyl
2765:
1898:
1549:
855:shared the Nobel Prize for metal-catalyzed
566:
141:
4172:
4158:
3193:
3179:
2969:Oxidative addition / reductive elimination
2875:
2861:
2698:
2021:: CS1 maint: location missing publisher (
1480:Almost all industrial processes involving
1405:
1088:for creation of the Woodward-Hoffman Rules
629:
4184:with other elements in the periodic table
3200:
2835:Rob Toreki's Organometallic HyperTextbook
2751:. Springer Science & Business Media.
2614:
2550:
2472:
2462:
2421:
2274:
2179:
2095:
1724:
828:, and alkenes as feedstocks and ligands.
165:. In addition to the traditional metals (
2918:Polyhedral skeletal electron pair theory
2660:
2533:"The Rise and Fall of Tetraethyllead. 2"
2524:
2332:
2291:
2149:
1986:
1869:
1867:
1865:
1820:
1728:
1634:. In addition to sigma-bond metathesis,
1471:
614:. Some organometallic compounds such as
585:
145:
20:
2784:
2746:
2725:
2565:
2244:
2200:
1492:catalysis and homogeneously, e.g., via
708:nuclear magnetic resonance spectroscopy
334:Representative Organometallic Compounds
4862:
4201:
4153:
3174:
2856:
2110:
1982:
1980:
1978:
1976:
1913:Encyclopedia of Interfacial Chemistry
1862:
1542:(MOVPE) process in the production of
543:The status of compounds in which the
416:is an organometallic compound with a
82:, and sometimes broadened to include
4843:Academic research, no widespread use
4108:
3025:Transition metal fullerene complexes
2768:Principles of Bioinorganic Chemistry
2729:Organometallic Reagents in Synthesis
2297:
2081:
1835:
1833:
1831:
1829:
1709:that form carbon-carbon bonds, e.g.
606:. Many organometallic compounds are
4132:
2747:Leeuwen, Piet W. N. M. van (2005).
722:. Other notable techniques include
676:covalent bond classification method
13:
3060:Transition metal carbyne complexes
3055:Transition metal carbene complexes
3020:Transition metal indenyl complexes
1973:
1921:10.1016/B978-0-12-409547-2.13135-X
1845:Compendium of Chemical Terminology
14:
4881:
3070:Transition metal alkyne complexes
3065:Transition metal alkene complexes
2823:
2703:. Hyderabad: Universities Press.
2680:Elschenbroich, Christoph (2016).
1826:
863:Organometallic chemistry timeline
551:) a carbon atom and an atom more
4735:
4654:
4586:
4491:
4191:
4131:
4119:
4107:
4096:
4095:
3075:Transition-metal allyl complexes
2699:Gupta, B. D; Elias, A J (2013).
2365:The Organometallic HyperTextBook
1540:metalorganic vapor phase epitaxy
870:Louis Claude Cadet de Gassicourt
712:Ultraviolet-visible spectroscopy
634:As in other areas of chemistry,
493:
478:
459:
443:
428:
406:
387:
368:
353:
338:
155:(magnesium bis-cyclopentadienyl)
3050:Transition metal acyl complexes
2590:
2572:Chemical & Engineering News
2568:"Arsenic In Chicken Production"
2566:Hileman, Bette (9 April 2007).
2559:
2489:
2438:
2389:
2371:
2353:
2326:
2250:
2164:"2005 Nobel Prize in Chemistry"
2155:
2104:
2075:
1597:carbon-hydrogen bond activation
399:transition metal alkene complex
189:, semimetals, and the elements
2048:
1937:
1904:
1494:constrained geometry catalysts
963:invents lithium cuprates, see
674:κ2-acetate is an example. The
150:A steel bottle containing MgCp
1:
3460:Interface and colloid science
3214:Glossary of chemical formulae
2263:Accounts of Chemical Research
2117:Annalen der Physik und Chemie
1954:. 24 May 2016. Archived from
1788:
724:X-ray absorption spectroscopy
2770:. University Science Books.
2661:Crabtree, Robert H. (2009).
2616:10.1016/j.envpol.2016.11.001
2383:Organometallic HyperTextBook
2276:10.1021/acs.accounts.5b00065
1987:Crabtree, Robert H. (2014).
1783:Metal carbon dioxide complex
1653:
1461:is used in the oxidation of
1106:for asymmetric hydrogenation
1029:determines the structure of
824:catalysis which employ CO, H
521:between a metal and organic
7:
3737:Bioorganometallic chemistry
3224:List of inorganic compounds
3126:Shell higher olefin process
2933:Dewar–Chatt–Duncanson model
2785:Pearson, Anthony J (1985).
2732:. Oxford University Press.
1778:Bioorganometallic chemistry
1771:
1038:bioorganometallic chemistry
328:bioorganometallic chemistry
10:
4886:
3663:Dynamic covalent chemistry
3634:Enantioselective synthesis
3614:Physical organic chemistry
3567:Organolanthanide chemistry
3015:Cyclopentadienyl complexes
2979:β-hydride elimination
2953:Metal–ligand multiple bond
2635:
1744:was prepared for use as a
1715:Buchwald-Hartwig amination
1327:organolanthanide chemistry
1282:organotechnetium chemistry
1278:organomolybdenum chemistry
752:
4818:
4732:
4651:
4203:
4199:
4189:
4091:
3994:
3755:
3671:
3592:
3542:
3418:
3361:
3252:Electroanalytical methods
3237:
3209:
3139:
3093:
3080:Transition metal carbides
2997:
2961:
2890:
2788:Metallo-organic chemistry
2726:Jenkins, Paul R. (1992).
2684:. John Wiley & Sons.
2665:. John Wiley & Sons.
2584:10.1021/cen-v085n015.p034
2464:10.3390/molecules20057528
1945:"Triethylaluminium – SDS"
1874:C. Elschenbroich (2006).
1764:were once widely used in
1563:dissociative substitution
1428:organoaluminium compounds
1400:organoneptunium chemistry
1318:organotellurium chemistry
1294:organopalladium chemistry
1286:organoruthenium chemistry
1270:organozirconium chemistry
1249:organogermanium chemistry
1221:organomanganese chemistry
1188:organoaluminium chemistry
1184:organomagnesium chemistry
1167:organoberyllium chemistry
883:William Christopher Zeise
771:platinum-ethylene complex
767:William Christopher Zeise
112:metal phosphine complexes
108:transition metal hydrides
4870:Organometallic chemistry
4007:Nobel Prize in Chemistry
3923:Supramolecular chemistry
3562:Organometallic chemistry
2884:Organometallic chemistry
2310:10.1002/14356007.a13_487
2219:10.1002/14356007.a05_217
2137:10.1002/andp.18310970402
1850:organometallic compounds
1707:cross-coupling reactions
1644:beta-hydride elimination
1617:nucleophilic abstraction
1550:Organometallic reactions
1439:metal carbonyl complexes
1388:organoactinide chemistry
1379:organopolonium chemistry
1367:organothallium chemistry
1355:organoplatinum chemistry
1339:organotungsten chemistry
1335:organotantalum chemistry
1314:organoantimony chemistry
1257:organoselenium chemistry
1217:organochromium chemistry
1213:organovanadium chemistry
1209:organotitanium chemistry
1205:organoscandium chemistry
1149:
1027:Dorothy Crawfoot Hodgkin
1011:prize for his work with
996:develop metal-catalyzed
720:dynamic NMR spectroscopy
660:cyclopentadienyl ligands
567:Structure and properties
142:Organometallic compounds
54:containing at least one
48:organometallic compounds
44:Organometallic chemistry
3945:Combinatorial chemistry
3856:Food physical chemistry
3819:Environmental chemistry
3703:Bioorthogonal chemistry
3629:Retrosynthetic analysis
3450:Chemical thermodynamics
3433:Spectroelectrochemistry
3376:Computational chemistry
3045:Half sandwich compounds
2603:Environmental Pollution
2379:"Sigma Bond Metathesis"
2304:. Weinheim: Wiley-VCH.
2213:. Weinheim: Wiley-VCH.
2181:10.1595/147106706X94140
1899:Lippard & Berg 1994
1858:10.1351/goldbook.O04328
1711:Suzuki-Miyaura coupling
1700:Fischer–Tropsch process
1696:heterogeneous catalysis
1416:stoichiometric reagents
1406:Industrial applications
1396:organouranium chemistry
1392:organothorium chemistry
1375:organobismuth chemistry
1363:organomercury chemistry
1351:organoiridium chemistry
1343:organorhenium chemistry
1302:organocadmium chemistry
1290:organorhodium chemistry
1274:organoniobium chemistry
1266:organoyttrium chemistry
1253:organoarsenic chemistry
1245:organogallium chemistry
1201:organocalcium chemistry
1192:organosilicon chemistry
1163:organolithium chemistry
1000:and acetylene chemistry
630:Concepts and techniques
4838:Many uses in chemistry
4833:Core organic chemistry
4017:of element discoveries
3863:Agricultural chemistry
3851:Carbohydrate chemistry
3742:Bioinorganic chemistry
3607:Alkane stereochemistry
3552:Coordination chemistry
3381:Mathematical chemistry
3247:Instrumental chemistry
3160:Bioinorganic chemistry
2845:11 August 2010 at the
2168:Platinum Metals Review
2084:Platinum Metals Review
1758:organoarsenic compound
1737:
1725:Environmental concerns
1688:methanol carbonylation
1680:alkene oligomerization
1477:
1347:organoosmium chemistry
1331:organocerium chemistry
1306:organoindium chemistry
1298:organosilver chemistry
1237:organocopper chemistry
1233:organonickel chemistry
1229:organocobalt chemistry
1180:organosodium chemistry
1171:organoborane chemistry
1056:Ziegler–Natta catalyst
591:
179:post transition metals
158:
40:
4012:Timeline of chemistry
3909:Post-mortem chemistry
3894:Clandestine chemistry
3824:Atmospheric chemistry
3747:Biophysical chemistry
3579:Solid-state chemistry
3529:Equilibrium chemistry
3438:Photoelectrochemistry
3131:Ziegler–Natta process
3035:Metal tetranorbornyls
2531:Seyferth, D. (2003).
2111:Zeise, W. C. (1831).
1732:
1676:alkene polymerization
1624:Sigma-bond metathesis
1587:β-hydride elimination
1572:reductive elimination
1544:light-emitting diodes
1475:
874:organoarenic compound
806:Johann Jacob Diesbach
704:infrared spectroscopy
626:on contact with air.
589:
486:Iron(0) pentacarbonyl
149:
136:homogeneous catalysis
116:metalorganic compound
24:
4002:History of chemistry
3957:Chemical engineering
3732:Bioorganic chemistry
3482:Structural chemistry
3219:List of biomolecules
3140:Related branches of
2898:Crystal field theory
1915:. pp. 761–768.
1719:Sonogashira coupling
1412:homogenous catalysts
1371:organolead chemistry
1359:organogold chemistry
1241:organozinc chemistry
1225:organoiron chemistry
1104:Karl Barry Sharpless
810:coordination polymer
604:nickel tetracarbonyl
561:Reformatsky reagents
501:Technetium sestamibi
318:), which contains a
235:Tetracarbonyl nickel
4025:The central science
3979:Ceramic engineering
3904:Forensic toxicology
3877:Chemistry education
3775:Radiation chemistry
3757:Interdisciplinarity
3710:Medicinal chemistry
3648:Fullerene chemistry
3524:Microwave chemistry
3393:Molecular mechanics
3388:Molecular modelling
3155:Inorganic chemistry
2974:Migratory insertion
2948:Agostic interaction
2903:Ligand field theory
2806:Inorganic Chemistry
2609:(Pt B): 1333–1341.
2361:"Olefin Metathesis"
2129:1831AnP....97..497Z
2057:Catal. Sci. Technol
2043:Shriver et al. 2014
1766:anti-fouling paints
1762:Organotin compounds
1648:insertion reactions
1582:migratory insertion
1310:organotin chemistry
1124:on metal-catalyzed
739:air-free techniques
397:is an example of a
274:tributyltin hydride
171:alkali earth metals
4068:Chemical substance
3930:Chemical synthesis
3899:Forensic chemistry
3780:Actinide chemistry
3722:Clinical chemistry
3403:Molecular geometry
3398:Molecular dynamics
3353:Elemental analysis
3306:Separation process
3040:Sandwich compounds
2998:Types of compounds
2923:Isolobal principle
2195:Elschenbroich 2016
2069:10.1039/C2CY00343K
1961:on 25 January 2022
1738:
1684:hydrocarboxylation
1632:oxidative addition
1568:oxidative addition
1520:trimethylaluminium
1510:are produced from
1478:
1073:sandwich compounds
1069:Ernst Otto Fischer
1065:Geoffrey Wilkinson
988:1930's and 1940's
853:Richard R. Schrock
837:Geoffrey Wilkinson
759:Louis Claude Cadet
732:elemental analysis
693:isolobal principle
592:
555:than carbon (e.g.
519:coordination bonds
414:Trimethylaluminium
298:trimethylaluminium
296:compounds such as
284:compounds such as
272:compounds such as
260:compounds such as
249:compounds such as
159:
52:chemical compounds
41:
4857:
4856:
4813:
4812:
4147:
4146:
4083:Quantum mechanics
4048:Chemical compound
4031:Chemical reaction
3969:Materials science
3887:General chemistry
3882:Amateur chemistry
3810:Photogeochemistry
3795:Stellar chemistry
3765:Nuclear chemistry
3686:Molecular biology
3653:Polymer chemistry
3624:Organic synthesis
3619:Organic reactions
3584:Ceramic chemistry
3574:Cluster chemistry
3504:Chemical kinetics
3492:Molecular physics
3371:Quantum chemistry
3284:Mass spectrometry
3168:
3167:
3150:Organic chemistry
3121:Olefin metathesis
3111:Grignard reaction
3010:Grignard reagents
2815:978-1-4292-9906-0
2808:. W. H. Freeman.
2777:978-0-935702-73-6
2758:978-1-4020-3176-2
2739:978-0-19-855666-4
2710:978-81-7371-709-3
2691:978-3-527-80514-3
2672:978-0-470-25762-3
2653:978-0-19-927029-3
2644:Organic Chemistry
2552:10.1021/om030621b
2545:(25): 5154–5178.
2510:10.1021/cr100346g
2414:10.1021/cr100327p
2347:10.1021/om400760k
2341:(24): 7249–7263.
2000:978-1-118-78824-0
1930:978-0-12-809894-3
1885:978-3-527-29390-2
1672:olefin metathesis
1636:olefin metathesis
1592:electron transfer
1524:trimethylantimony
1384:Period 7 elements
1323:Period 6 elements
1262:Period 5 elements
1197:Period 4 elements
1176:Period 3 elements
1159:Period 2 elements
1126:alkene metathesis
857:olefin metathesis
700:X-ray diffraction
636:electron counting
616:triethylaluminium
467:Adenosylcobalamin
243:transition metals
219:Grignard reagents
175:transition metals
128:organic chemistry
80:transition metals
4877:
4849:
4844:
4839:
4834:
4739:
4738:
4658:
4657:
4590:
4589:
4495:
4494:
4192:
4174:
4167:
4160:
4151:
4150:
4135:
4134:
4123:
4111:
4110:
4099:
4098:
4043:Chemical element
3698:Chemical biology
3557:Magnetochemistry
3534:Mechanochemistry
3487:Chemical physics
3428:Electrochemistry
3333:Characterization
3195:
3188:
3181:
3172:
3171:
3116:Monsanto process
2913:d electron count
2908:18-electron rule
2877:
2870:
2863:
2854:
2853:
2819:
2800:
2781:
2762:
2743:
2722:
2695:
2676:
2657:
2629:
2628:
2618:
2594:
2588:
2587:
2563:
2557:
2556:
2554:
2528:
2522:
2521:
2504:(3): 2177–2250.
2498:Chemical Reviews
2493:
2487:
2486:
2476:
2466:
2457:(5): 7528–7557.
2442:
2436:
2435:
2425:
2408:(3): 1417–1492.
2402:Chemical Reviews
2393:
2387:
2386:
2375:
2369:
2368:
2357:
2351:
2350:
2330:
2324:
2323:
2295:
2289:
2288:
2278:
2269:(7): 2004–2016.
2254:
2248:
2242:
2233:
2232:
2204:
2198:
2192:
2186:
2185:
2183:
2159:
2153:
2147:
2141:
2140:
2108:
2102:
2101:
2099:
2079:
2073:
2072:
2052:
2046:
2040:
2027:
2026:
2020:
2012:
1984:
1971:
1970:
1968:
1966:
1960:
1949:
1941:
1935:
1934:
1908:
1902:
1896:
1890:
1889:
1871:
1860:
1837:
1824:
1818:
1692:hydroformylation
1512:trimethylgallium
1451:hydroformylation
1443:Monsanto process
1418:. For instance,
1007:was awarded the
998:hydroformylation
971:Eugene G. Rochow
902:Edward Frankland
849:Robert H. Grubbs
822:hydroformylation
789:'s discovery of
777:'s discovery of
775:Edward Frankland
681:d electron count
640:18-electron rule
612:inert atmosphere
602:liquids such as
497:
482:
463:
447:
432:
410:
391:
372:
357:
342:
221:, which contain
209:, which contain
64:organic molecule
46:is the study of
4885:
4884:
4880:
4879:
4878:
4876:
4875:
4874:
4860:
4859:
4858:
4853:
4852:
4847:
4842:
4837:
4832:
4814:
4736:
4655:
4587:
4492:
4185:
4178:
4148:
4143:
4087:
3990:
3984:Polymer science
3940:Click chemistry
3935:Green chemistry
3829:Ocean chemistry
3805:Biogeochemistry
3751:
3667:
3639:Total synthesis
3602:Stereochemistry
3588:
3538:
3455:Surface science
3445:Thermochemistry
3414:
3357:
3328:Crystallography
3233:
3205:
3199:
3169:
3164:
3135:
3089:
3005:Gilman reagents
2993:
2989:Carbometalation
2984:Transmetalation
2957:
2886:
2881:
2847:Wayback Machine
2826:
2816:
2778:
2759:
2740:
2711:
2692:
2682:Organometallics
2673:
2654:
2638:
2633:
2632:
2595:
2591:
2564:
2560:
2538:Organometallics
2529:
2525:
2494:
2490:
2443:
2439:
2394:
2390:
2377:
2376:
2372:
2359:
2358:
2354:
2335:Organometallics
2331:
2327:
2320:
2296:
2292:
2255:
2251:
2243:
2236:
2229:
2205:
2201:
2193:
2189:
2160:
2156:
2148:
2144:
2109:
2105:
2097:10.1.1.693.9965
2080:
2076:
2053:
2049:
2041:
2030:
2014:
2013:
2001:
1985:
1974:
1964:
1962:
1958:
1947:
1943:
1942:
1938:
1931:
1909:
1905:
1897:
1893:
1886:
1876:Organometallics
1872:
1863:
1838:
1827:
1819:
1796:
1791:
1774:
1727:
1664:hydrosilylation
1656:
1612:cyclometalation
1607:hydrometalation
1602:carbometalation
1577:transmetalation
1552:
1516:trimethylindium
1486:heterogeneously
1424:organomagnesium
1408:
1152:
1139:Ei-ichi Negishi
1135:Richard F. Heck
1122:Richard Schrock
1034:
951:Victor Grignard
916:nickel carbonyl
865:
827:
818:Fischer–Tropsch
798:Victor Grignard
794:
755:
685:oxidation state
669:
665:
644:metal carbonyls
632:
569:
553:electronegative
545:canonical anion
538:
511:
504:
498:
489:
483:
474:
464:
455:
448:
439:
433:
424:
411:
402:
392:
383:
373:
364:
358:
349:
343:
316:
309:methylcobalamin
303:
294:organoaluminium
291:
279:
267:
207:Gilman reagents
153:
144:
96:metal carbonyls
92:carbon monoxide
17:
12:
11:
5:
4883:
4873:
4872:
4855:
4854:
4851:
4850:
4845:
4840:
4835:
4830:
4827:Chemical bonds
4823:
4822:
4820:
4816:
4815:
4811:
4810:
4805:
4800:
4795:
4790:
4785:
4780:
4775:
4770:
4765:
4760:
4755:
4750:
4745:
4740:
4733:
4730:
4729:
4724:
4719:
4714:
4709:
4704:
4699:
4694:
4689:
4684:
4679:
4674:
4669:
4664:
4659:
4652:
4649:
4648:
4644:
4643:
4640:
4637:
4634:
4631:
4628:
4625:
4622:
4619:
4616:
4613:
4610:
4607:
4602:
4599:
4596:
4591:
4584:
4579:
4575:
4574:
4571:
4566:
4561:
4556:
4551:
4546:
4541:
4536:
4531:
4526:
4521:
4516:
4511:
4506:
4501:
4496:
4489:
4484:
4478:
4477:
4472:
4467:
4462:
4457:
4452:
4447:
4442:
4437:
4432:
4427:
4422:
4417:
4412:
4407:
4402:
4397:
4395:
4390:
4384:
4383:
4378:
4373:
4368:
4363:
4358:
4353:
4348:
4343:
4338:
4333:
4328:
4323:
4318:
4313:
4308:
4303:
4301:
4296:
4290:
4289:
4284:
4279:
4274:
4269:
4264:
4259:
4254:
4248:
4247:
4244:
4239:
4234:
4229:
4224:
4219:
4214:
4208:
4207:
4204:
4202:
4200:
4198:
4190:
4187:
4186:
4177:
4176:
4169:
4162:
4154:
4145:
4144:
4142:
4141:
4129:
4117:
4105:
4092:
4089:
4088:
4086:
4085:
4080:
4075:
4070:
4065:
4060:
4055:
4050:
4045:
4040:
4039:
4038:
4028:
4021:
4020:
4019:
4009:
4004:
3998:
3996:
3992:
3991:
3989:
3988:
3987:
3986:
3981:
3976:
3966:
3965:
3964:
3954:
3953:
3952:
3947:
3942:
3937:
3927:
3926:
3925:
3914:
3913:
3912:
3911:
3906:
3896:
3891:
3890:
3889:
3884:
3873:
3872:
3871:
3870:
3868:Soil chemistry
3860:
3859:
3858:
3853:
3846:Food chemistry
3843:
3841:Carbochemistry
3838:
3836:Clay chemistry
3833:
3832:
3831:
3826:
3815:
3814:
3813:
3812:
3807:
3797:
3791:Astrochemistry
3787:Cosmochemistry
3784:
3783:
3782:
3777:
3772:
3770:Radiochemistry
3761:
3759:
3753:
3752:
3750:
3749:
3744:
3739:
3734:
3729:
3727:Neurochemistry
3724:
3719:
3718:
3717:
3707:
3706:
3705:
3695:
3694:
3693:
3688:
3677:
3675:
3669:
3668:
3666:
3665:
3660:
3658:Petrochemistry
3655:
3650:
3645:
3636:
3631:
3626:
3621:
3616:
3611:
3610:
3609:
3598:
3596:
3590:
3589:
3587:
3586:
3581:
3576:
3571:
3570:
3569:
3559:
3554:
3548:
3546:
3540:
3539:
3537:
3536:
3531:
3526:
3521:
3519:Spin chemistry
3516:
3514:Photochemistry
3511:
3506:
3501:
3499:Femtochemistry
3496:
3495:
3494:
3484:
3479:
3474:
3469:
3468:
3467:
3457:
3452:
3447:
3442:
3441:
3440:
3435:
3424:
3422:
3416:
3415:
3413:
3412:
3411:
3410:
3400:
3395:
3390:
3385:
3384:
3383:
3373:
3367:
3365:
3359:
3358:
3356:
3355:
3350:
3345:
3340:
3335:
3330:
3325:
3324:
3323:
3318:
3311:Chromatography
3308:
3303:
3302:
3301:
3296:
3291:
3281:
3280:
3279:
3274:
3269:
3264:
3254:
3249:
3243:
3241:
3235:
3234:
3232:
3231:
3229:Periodic table
3226:
3221:
3216:
3210:
3207:
3206:
3198:
3197:
3190:
3183:
3175:
3166:
3165:
3163:
3162:
3157:
3152:
3146:
3144:
3137:
3136:
3134:
3133:
3128:
3123:
3118:
3113:
3108:
3106:Cativa process
3103:
3097:
3095:
3091:
3090:
3088:
3087:
3082:
3077:
3072:
3067:
3062:
3057:
3052:
3047:
3042:
3037:
3032:
3027:
3022:
3017:
3012:
3007:
3001:
2999:
2995:
2994:
2992:
2991:
2986:
2981:
2976:
2971:
2965:
2963:
2959:
2958:
2956:
2955:
2950:
2945:
2940:
2935:
2930:
2925:
2920:
2915:
2910:
2905:
2900:
2894:
2892:
2888:
2887:
2880:
2879:
2872:
2865:
2857:
2851:
2850:
2837:
2832:
2825:
2824:External links
2822:
2821:
2820:
2814:
2801:
2782:
2776:
2763:
2757:
2744:
2738:
2723:
2709:
2696:
2690:
2677:
2671:
2658:
2652:
2646:. OUP Oxford.
2637:
2634:
2631:
2630:
2589:
2558:
2523:
2488:
2437:
2388:
2370:
2352:
2325:
2319:978-3527306732
2318:
2290:
2249:
2234:
2228:978-3527306732
2227:
2199:
2187:
2154:
2142:
2123:(4): 497–541.
2103:
2074:
2063:(3): 461–470.
2047:
2028:
1999:
1972:
1936:
1929:
1903:
1891:
1884:
1861:
1825:
1793:
1792:
1790:
1787:
1786:
1785:
1780:
1773:
1770:
1742:Tetraethyllead
1726:
1723:
1668:hydrocyanation
1655:
1652:
1620:
1619:
1614:
1609:
1604:
1599:
1594:
1589:
1584:
1579:
1574:
1565:
1551:
1548:
1508:semiconductors
1501:hydrogenations
1459:Wacker process
1447:Cativa process
1435:carbonylations
1407:
1404:
1403:
1402:
1381:
1320:
1259:
1194:
1173:
1151:
1148:
1147:
1146:
1128:
1107:
1089:
1082:Roald Hoffmann
1075:
1058:
1040:
1032:
1023:
1016:
1013:metal carbonyl
1001:
986:
981:for preparing
979:direct process
975:Richard Müller
967:
965:Gilman reagent
957:
944:
933:
922:John Ulric Nef
918:
908:
898:
879:
864:
861:
825:
792:
754:
751:
667:
663:
648:metal hydrides
631:
628:
568:
565:
536:
510:
507:
506:
505:
499:
492:
490:
484:
477:
475:
465:
458:
456:
452:Gilman reagent
449:
442:
440:
434:
427:
425:
412:
405:
403:
393:
386:
384:
374:
367:
365:
359:
352:
350:
344:
337:
335:
314:
301:
289:
286:triethylborane
277:
265:
151:
143:
140:
76:alkaline earth
15:
9:
6:
4:
3:
2:
4882:
4871:
4868:
4867:
4865:
4846:
4841:
4836:
4831:
4828:
4825:
4824:
4821:
4817:
4809:
4806:
4804:
4801:
4799:
4796:
4794:
4791:
4789:
4786:
4784:
4781:
4779:
4776:
4774:
4771:
4769:
4766:
4764:
4761:
4759:
4756:
4754:
4751:
4749:
4746:
4744:
4741:
4734:
4731:
4728:
4725:
4723:
4720:
4718:
4715:
4713:
4710:
4708:
4705:
4703:
4700:
4698:
4695:
4693:
4690:
4688:
4685:
4683:
4680:
4678:
4675:
4673:
4670:
4668:
4665:
4663:
4660:
4653:
4650:
4646:
4645:
4641:
4638:
4635:
4632:
4629:
4626:
4623:
4620:
4617:
4614:
4611:
4608:
4606:
4603:
4600:
4597:
4595:
4592:
4585:
4583:
4580:
4577:
4576:
4572:
4570:
4567:
4565:
4562:
4560:
4557:
4555:
4552:
4550:
4547:
4545:
4542:
4540:
4537:
4535:
4532:
4530:
4527:
4525:
4522:
4520:
4517:
4515:
4512:
4510:
4507:
4505:
4502:
4500:
4497:
4490:
4488:
4485:
4483:
4480:
4479:
4476:
4473:
4471:
4468:
4466:
4463:
4461:
4458:
4456:
4453:
4451:
4448:
4446:
4443:
4441:
4438:
4436:
4433:
4431:
4428:
4426:
4423:
4421:
4418:
4416:
4413:
4411:
4408:
4406:
4403:
4401:
4398:
4396:
4394:
4391:
4389:
4386:
4385:
4382:
4379:
4377:
4374:
4372:
4369:
4367:
4364:
4362:
4359:
4357:
4354:
4352:
4349:
4347:
4344:
4342:
4339:
4337:
4334:
4332:
4329:
4327:
4324:
4322:
4319:
4317:
4314:
4312:
4309:
4307:
4304:
4302:
4300:
4297:
4295:
4292:
4291:
4288:
4285:
4283:
4280:
4278:
4275:
4273:
4270:
4268:
4265:
4263:
4260:
4258:
4255:
4253:
4250:
4249:
4245:
4243:
4240:
4238:
4235:
4233:
4230:
4228:
4225:
4223:
4220:
4218:
4215:
4213:
4210:
4209:
4205:
4197:
4194:
4193:
4188:
4183:
4180:Compounds of
4175:
4170:
4168:
4163:
4161:
4156:
4155:
4152:
4140:
4139:
4130:
4128:
4127:
4122:
4118:
4116:
4115:
4106:
4104:
4103:
4094:
4093:
4090:
4084:
4081:
4079:
4076:
4074:
4073:Chemical bond
4071:
4069:
4066:
4064:
4061:
4059:
4056:
4054:
4051:
4049:
4046:
4044:
4041:
4037:
4034:
4033:
4032:
4029:
4026:
4022:
4018:
4015:
4014:
4013:
4010:
4008:
4005:
4003:
4000:
3999:
3997:
3993:
3985:
3982:
3980:
3977:
3975:
3972:
3971:
3970:
3967:
3963:
3962:Stoichiometry
3960:
3959:
3958:
3955:
3951:
3948:
3946:
3943:
3941:
3938:
3936:
3933:
3932:
3931:
3928:
3924:
3921:
3920:
3919:
3918:Nanochemistry
3916:
3915:
3910:
3907:
3905:
3902:
3901:
3900:
3897:
3895:
3892:
3888:
3885:
3883:
3880:
3879:
3878:
3875:
3874:
3869:
3866:
3865:
3864:
3861:
3857:
3854:
3852:
3849:
3848:
3847:
3844:
3842:
3839:
3837:
3834:
3830:
3827:
3825:
3822:
3821:
3820:
3817:
3816:
3811:
3808:
3806:
3803:
3802:
3801:
3798:
3796:
3792:
3788:
3785:
3781:
3778:
3776:
3773:
3771:
3768:
3767:
3766:
3763:
3762:
3760:
3758:
3754:
3748:
3745:
3743:
3740:
3738:
3735:
3733:
3730:
3728:
3725:
3723:
3720:
3716:
3713:
3712:
3711:
3708:
3704:
3701:
3700:
3699:
3696:
3692:
3689:
3687:
3684:
3683:
3682:
3679:
3678:
3676:
3674:
3670:
3664:
3661:
3659:
3656:
3654:
3651:
3649:
3646:
3644:
3643:Semisynthesis
3640:
3637:
3635:
3632:
3630:
3627:
3625:
3622:
3620:
3617:
3615:
3612:
3608:
3605:
3604:
3603:
3600:
3599:
3597:
3595:
3591:
3585:
3582:
3580:
3577:
3575:
3572:
3568:
3565:
3564:
3563:
3560:
3558:
3555:
3553:
3550:
3549:
3547:
3545:
3541:
3535:
3532:
3530:
3527:
3525:
3522:
3520:
3517:
3515:
3512:
3510:
3507:
3505:
3502:
3500:
3497:
3493:
3490:
3489:
3488:
3485:
3483:
3480:
3478:
3477:Sonochemistry
3475:
3473:
3472:Cryochemistry
3470:
3466:
3465:Micromeritics
3463:
3462:
3461:
3458:
3456:
3453:
3451:
3448:
3446:
3443:
3439:
3436:
3434:
3431:
3430:
3429:
3426:
3425:
3423:
3421:
3417:
3409:
3406:
3405:
3404:
3401:
3399:
3396:
3394:
3391:
3389:
3386:
3382:
3379:
3378:
3377:
3374:
3372:
3369:
3368:
3366:
3364:
3360:
3354:
3351:
3349:
3346:
3344:
3343:Wet chemistry
3341:
3339:
3336:
3334:
3331:
3329:
3326:
3322:
3319:
3317:
3314:
3313:
3312:
3309:
3307:
3304:
3300:
3297:
3295:
3292:
3290:
3287:
3286:
3285:
3282:
3278:
3275:
3273:
3270:
3268:
3265:
3263:
3260:
3259:
3258:
3255:
3253:
3250:
3248:
3245:
3244:
3242:
3240:
3236:
3230:
3227:
3225:
3222:
3220:
3217:
3215:
3212:
3211:
3208:
3204:
3196:
3191:
3189:
3184:
3182:
3177:
3176:
3173:
3161:
3158:
3156:
3153:
3151:
3148:
3147:
3145:
3143:
3138:
3132:
3129:
3127:
3124:
3122:
3119:
3117:
3114:
3112:
3109:
3107:
3104:
3102:
3101:Carbonylation
3099:
3098:
3096:
3092:
3086:
3083:
3081:
3078:
3076:
3073:
3071:
3068:
3066:
3063:
3061:
3058:
3056:
3053:
3051:
3048:
3046:
3043:
3041:
3038:
3036:
3033:
3031:
3028:
3026:
3023:
3021:
3018:
3016:
3013:
3011:
3008:
3006:
3003:
3002:
3000:
2996:
2990:
2987:
2985:
2982:
2980:
2977:
2975:
2972:
2970:
2967:
2966:
2964:
2960:
2954:
2951:
2949:
2946:
2944:
2941:
2939:
2936:
2934:
2931:
2929:
2928:π backbonding
2926:
2924:
2921:
2919:
2916:
2914:
2911:
2909:
2906:
2904:
2901:
2899:
2896:
2895:
2893:
2889:
2885:
2878:
2873:
2871:
2866:
2864:
2859:
2858:
2855:
2848:
2844:
2841:
2838:
2836:
2833:
2831:
2828:
2827:
2817:
2811:
2807:
2802:
2798:
2794:
2790:
2789:
2783:
2779:
2773:
2769:
2764:
2760:
2754:
2750:
2745:
2741:
2735:
2731:
2730:
2724:
2720:
2716:
2712:
2706:
2702:
2697:
2693:
2687:
2683:
2678:
2674:
2668:
2664:
2659:
2655:
2649:
2645:
2640:
2639:
2626:
2622:
2617:
2612:
2608:
2604:
2600:
2593:
2585:
2581:
2578:(15): 34–35.
2577:
2573:
2569:
2562:
2553:
2548:
2544:
2540:
2539:
2534:
2527:
2519:
2515:
2511:
2507:
2503:
2499:
2492:
2484:
2480:
2475:
2470:
2465:
2460:
2456:
2452:
2448:
2441:
2433:
2429:
2424:
2419:
2415:
2411:
2407:
2403:
2399:
2392:
2384:
2380:
2374:
2366:
2362:
2356:
2348:
2344:
2340:
2336:
2329:
2321:
2315:
2311:
2307:
2303:
2302:
2294:
2286:
2282:
2277:
2272:
2268:
2264:
2260:
2253:
2246:
2241:
2239:
2230:
2224:
2220:
2216:
2212:
2211:
2203:
2196:
2191:
2182:
2177:
2173:
2169:
2165:
2158:
2152:, p. 98.
2151:
2150:Crabtree 2009
2146:
2138:
2134:
2130:
2126:
2122:
2119:(in German).
2118:
2114:
2107:
2098:
2093:
2089:
2085:
2078:
2070:
2066:
2062:
2058:
2051:
2044:
2039:
2037:
2035:
2033:
2024:
2018:
2010:
2006:
2002:
1996:
1992:
1991:
1983:
1981:
1979:
1977:
1957:
1953:
1946:
1940:
1932:
1926:
1922:
1918:
1914:
1907:
1900:
1895:
1887:
1881:
1877:
1870:
1868:
1866:
1859:
1855:
1851:
1847:
1846:
1841:
1836:
1834:
1832:
1830:
1822:
1821:Crabtree 2009
1817:
1815:
1813:
1811:
1809:
1807:
1805:
1803:
1801:
1799:
1794:
1784:
1781:
1779:
1776:
1775:
1769:
1767:
1763:
1759:
1755:
1751:
1747:
1743:
1735:
1731:
1722:
1720:
1716:
1712:
1708:
1703:
1701:
1697:
1693:
1689:
1685:
1681:
1677:
1673:
1669:
1665:
1661:
1660:hydrogenation
1651:
1649:
1645:
1641:
1637:
1633:
1629:
1625:
1618:
1615:
1613:
1610:
1608:
1605:
1603:
1600:
1598:
1595:
1593:
1590:
1588:
1585:
1583:
1580:
1578:
1575:
1573:
1569:
1566:
1564:
1560:
1557:
1556:
1555:
1547:
1545:
1541:
1537:
1533:
1529:
1525:
1521:
1517:
1513:
1509:
1504:
1502:
1497:
1495:
1491:
1490:Ziegler–Natta
1487:
1483:
1474:
1470:
1468:
1464:
1460:
1456:
1455:hydrogenation
1452:
1448:
1444:
1440:
1436:
1431:
1429:
1425:
1421:
1420:organolithium
1417:
1413:
1401:
1397:
1393:
1389:
1385:
1382:
1380:
1376:
1372:
1368:
1364:
1360:
1356:
1352:
1348:
1344:
1340:
1336:
1332:
1328:
1324:
1321:
1319:
1315:
1311:
1307:
1303:
1299:
1295:
1291:
1287:
1283:
1279:
1275:
1271:
1267:
1263:
1260:
1258:
1254:
1250:
1246:
1242:
1238:
1234:
1230:
1226:
1222:
1218:
1214:
1210:
1206:
1202:
1198:
1195:
1193:
1189:
1185:
1181:
1177:
1174:
1172:
1168:
1164:
1160:
1157:
1156:
1155:
1144:
1140:
1136:
1133:
1129:
1127:
1123:
1119:
1118:Robert Grubbs
1115:
1112:
1108:
1105:
1101:
1097:
1096:W. S. Knowles
1094:
1090:
1087:
1086:Kenichi Fukui
1083:
1080:
1076:
1074:
1070:
1066:
1063:
1059:
1057:
1053:
1049:
1045:
1041:
1039:
1035:
1028:
1024:
1022:is discovered
1021:
1017:
1014:
1010:
1006:
1005:Walter Hieber
1002:
999:
995:
991:
987:
984:
983:organosilicon
980:
977:discover the
976:
972:
968:
966:
962:
958:
956:
955:Paul Sabatier
952:
949:
945:
942:
938:
934:
931:
928:using sodium
927:
923:
919:
917:
913:
909:
907:
903:
899:
896:
892:
888:
884:
880:
878:
875:
872:isolates the
871:
867:
866:
860:
858:
854:
850:
846:
842:
838:
834:
833:Ernst Fischer
829:
823:
819:
815:
814:Ziegler–Natta
811:
808:as the first
807:
803:
802:Prussian blue
799:
795:
788:
784:
780:
776:
772:
768:
764:
760:
750:
748:
744:
740:
735:
733:
729:
725:
721:
717:
713:
709:
705:
701:
696:
694:
690:
686:
682:
677:
673:
661:
657:
653:
649:
645:
641:
637:
627:
625:
621:
617:
613:
609:
608:air sensitive
605:
601:
597:
588:
584:
582:
578:
574:
564:
562:
558:
554:
550:
546:
541:
539:
532:
528:
524:
520:
516:
502:
496:
491:
487:
481:
476:
472:
468:
462:
457:
453:
446:
441:
437:
431:
426:
422:
419:
415:
409:
404:
400:
396:
390:
385:
381:
377:
371:
366:
362:
356:
351:
347:
341:
336:
333:
332:
331:
329:
325:
321:
317:
310:
305:
299:
295:
287:
283:
275:
271:
263:
259:
255:
254:-butyllithium
253:
248:
247:organolithium
244:
240:
236:
232:
231:carboboration
228:
227:hydroboration
224:
220:
216:
212:
208:
204:
200:
196:
192:
188:
184:
180:
176:
172:
168:
167:alkali metals
164:
163:organyl group
156:
148:
139:
137:
131:
129:
125:
121:
117:
113:
109:
105:
101:
97:
93:
89:
85:
81:
77:
73:
69:
65:
61:
57:
56:chemical bond
53:
49:
45:
38:
34:
30:
29:-Butyllithium
28:
23:
19:
4848:Bond unknown
4136:
4124:
4112:
4100:
3950:Biosynthesis
3800:Geochemistry
3715:Pharmacology
3691:Cell biology
3681:Biochemistry
3561:
3509:Spectroscopy
3408:VSEPR theory
3257:Spectroscopy
3201:Branches of
3094:Applications
3030:Metallocenes
2883:
2805:
2787:
2767:
2748:
2728:
2700:
2681:
2662:
2643:
2606:
2602:
2592:
2575:
2571:
2561:
2542:
2536:
2526:
2501:
2497:
2491:
2454:
2450:
2440:
2405:
2401:
2391:
2382:
2373:
2364:
2355:
2338:
2334:
2328:
2299:
2293:
2266:
2262:
2252:
2245:Leeuwen 2005
2208:
2202:
2190:
2174:(1): 35–37.
2171:
2167:
2157:
2145:
2120:
2116:
2106:
2090:(2): 76–83.
2087:
2083:
2077:
2060:
2056:
2050:
1989:
1963:. Retrieved
1956:the original
1951:
1939:
1912:
1906:
1894:
1875:
1843:
1739:
1704:
1657:
1621:
1553:
1505:
1498:
1479:
1467:acetaldehyde
1432:
1409:
1153:
1143:Akira Suzuki
1114:Yves Chauvin
1052:Giulio Natta
1048:Karl Ziegler
1009:Alfred Stock
994:Walter Reppe
961:Henry Gilman
937:Paul Ehrlich
926:alkynylation
889:; the first
887:Zeise's salt
845:Yves Chauvin
841:metallocenes
839:for work on
830:
783:dimethylzinc
756:
747:Schlenk line
736:
697:
658:, , has two
633:
593:
570:
542:
512:
436:Dimethylzinc
421:methyl group
395:Zeise's salt
306:
282:organoborane
251:
160:
132:
70:, including
47:
43:
42:
35:, with four
26:
18:
4138:WikiProject
3363:Theoretical
3348:Calorimetry
2943:spin states
2247:, p. .
2197:, p. .
2045:, p. .
1901:, p. .
1823:, p. .
1756:(MMT). The
1628:sigma bonds
1559:associative
1132:Nobel prize
1111:Nobel prize
1093:Nobel prize
1079:Nobel prize
1062:Nobel prize
1044:Nobel prize
990:Otto Roelen
948:Nobel Prize
939:introduces
912:Ludwig Mond
906:diethylzinc
843:. In 2005,
787:Ludwig Mond
577:carbanionic
549:delocalized
361:Cobaltocene
311:(a form of
262:diethylzinc
233:reactions.
183:lanthanides
62:atom of an
33:tetrahedron
3974:Metallurgy
3673:Biological
3239:Analytical
2891:Principles
2797:1200566627
1789:References
1015:chemistry.
930:acetylides
924:discovers
914:discovers
904:discovers
620:pyrophoric
598:, or even
527:heteroatom
380:fragrances
258:organozinc
256:(n-BuLi),
84:metalloids
58:between a
4829:to carbon
4036:Catalysis
3544:Inorganic
3338:Titration
3203:chemistry
3142:chemistry
2962:Reactions
2938:Hapticity
2791:. Wiley.
2719:903314566
2451:Molecules
2092:CiteSeerX
2017:cite book
2009:863383849
1965:3 January
1952:chemBlink
1750:ferrocene
1734:Roxarsone
1654:Catalysis
1536:phosphine
1100:R. Noyori
1031:vitamin B
1020:Ferrocene
985:compounds
941:Salvarsan
885:produces
672:Chelating
656:ferrocene
652:Hapticity
622:and will
515:complexes
346:Ferrocene
313:Vitamin B
270:organotin
239:ferrocene
223:magnesium
187:actinides
124:inorganic
120:alkoxides
4864:Category
4102:Category
4058:Molecule
3995:See also
3420:Physical
2843:Archived
2625:27836476
2518:21391570
2483:25919276
2432:21319862
2285:26151395
1772:See also
1746:gasoline
1640:pi bonds
1546:(LEDs).
1463:ethylene
891:platinum
779:diethyl-
743:glovebox
716:kinetics
689:geometry
600:volatile
573:covalent
557:enolates
535:Fe(acac)
517:feature
471:cofactor
418:bridging
292:B), and
203:selenium
4647:
4114:Commons
4078:Alchemy
3594:Organic
2636:Sources
2474:6272665
2423:3075866
2125:Bibcode
1878:. VCH.
1721:, etc.
1528:ammonia
1441:in the
1414:and as
897:complex
877:cacodyl
763:cacodyl
753:History
581:cyanide
523:ligands
211:lithium
199:arsenic
195:silicon
104:carbide
100:cyanide
88:organyl
4819:Legend
4182:carbon
4126:Portal
3272:UV-Vis
2812:
2795:
2774:
2755:
2736:
2717:
2707:
2688:
2669:
2650:
2623:
2516:
2481:
2471:
2430:
2420:
2316:
2283:
2225:
2094:
2007:
1997:
1927:
1882:
1690:, and
1532:arsine
1522:, and
1482:alkene
1426:, and
1120:, and
895:olefin
796:, and
791:Ni(CO)
730:, and
624:ignite
531:heme A
324:methyl
320:cobalt
280:SnH),
217:, and
215:copper
201:, and
177:, and
78:, and
72:alkali
66:and a
60:carbon
3299:MALDI
3267:Raman
1959:(PDF)
1948:(PDF)
1840:IUPAC
1506:Many
1150:Scope
1130:2010
1109:2005
1091:2001
1077:1981
1060:1973
1042:1963
1025:1956
1018:1951
1003:1951
969:1940
959:1930
946:1912
935:1909
920:1899
910:1890
900:1848
881:1827
868:1760
513:Many
469:is a
304:Al).
268:Zn),
191:boron
102:, or
68:metal
37:butyl
4053:Atom
3321:HPLC
2810:ISBN
2793:OCLC
2772:ISBN
2753:ISBN
2734:ISBN
2715:OCLC
2705:ISBN
2686:ISBN
2667:ISBN
2648:ISBN
2621:PMID
2514:PMID
2479:PMID
2428:PMID
2314:ISBN
2281:PMID
2223:ISBN
2023:link
2005:OCLC
1995:ISBN
1967:2021
1925:ISBN
1880:ISBN
1752:and
1646:and
1570:and
1561:and
1488:via
1445:and
1102:and
1084:and
1067:and
1050:and
1046:for
992:and
973:and
953:and
851:and
835:and
781:and
706:and
683:and
646:and
618:are
533:and
237:and
229:and
213:and
126:and
110:and
4793:CEs
4788:CCf
4783:CBk
4778:CCm
4773:CAm
4768:CPu
4763:CNp
4753:CPa
4748:CTh
4727:CYb
4722:CTm
4717:CEr
4712:CHo
4707:CDy
4702:CTb
4697:CGd
4692:CEu
4687:CSm
4682:CPm
4677:CNd
4672:CPr
4667:CCe
4662:CLa
4642:Og
4639:Ts
4636:Lv
4633:Mc
4630:Fl
4627:Nh
4624:Cn
4621:Rg
4618:Ds
4615:Mt
4612:Hs
4609:Bh
4605:CSg
4601:Db
4598:Rf
4582:CRa
4578:Fr
4573:Rn
4569:CAt
4564:CPo
4559:CBi
4554:CPb
4549:CTl
4544:CHg
4539:CAu
4534:CPt
4529:CIr
4524:COs
4519:CRe
4509:CTa
4504:CHf
4499:CLu
4487:CBa
4482:CCs
4475:CXe
4465:CTe
4460:CSb
4455:CSn
4450:CIn
4445:CCd
4440:CAg
4435:CPd
4430:CRh
4425:CRu
4420:CTc
4415:CMo
4410:CNb
4405:CZr
4393:CSr
4388:CRb
4381:CKr
4376:CBr
4371:CSe
4366:CAs
4361:CGe
4356:CGa
4351:CZn
4346:CCu
4341:CNi
4336:CCo
4331:CFe
4326:CMn
4321:CCr
4311:CTi
4306:CSc
4299:CCa
4287:CAr
4282:CCl
4267:CSi
4262:CAl
4257:CMg
4252:CNa
4246:Ne
4217:CBe
4212:CLi
4206:He
4063:Ion
3294:ICP
3277:NMR
2611:doi
2607:220
2580:doi
2547:doi
2506:doi
2502:111
2469:PMC
2459:doi
2418:PMC
2410:doi
2406:111
2343:doi
2306:doi
2271:doi
2215:doi
2176:doi
2133:doi
2065:doi
1917:doi
1854:doi
1852:".
1465:to
1398:,
1390:,
1215:,
1071:on
1054:on
769:'s
745:or
300:(Me
288:(Et
276:(Bu
264:(Et
181:),
98:),
4866::
4808:No
4803:Md
4798:Fm
4758:CU
4743:Ac
4594:Lr
4514:CW
4470:CI
4400:CY
4316:CV
4294:CK
4277:CS
4272:CP
4242:CF
4237:CO
4232:CN
4227:CC
4222:CB
4196:CH
3793:/
3789:/
3641:/
3316:GC
3289:EI
3262:IR
2713:.
2619:.
2605:.
2601:.
2576:85
2574:.
2570:.
2543:22
2541:.
2535:.
2512:.
2500:.
2477:.
2467:.
2455:20
2453:.
2449:.
2426:.
2416:.
2404:.
2400:.
2381:.
2363:.
2339:32
2337:.
2312:.
2279:.
2267:48
2265:.
2261:.
2237:^
2221:.
2172:50
2170:.
2166:.
2131:.
2121:97
2088:28
2086:.
2059:.
2031:^
2019:}}
2015:{{
2003:.
1975:^
1950:.
1923:.
1864:^
1842:,
1828:^
1797:^
1713:,
1702:.
1686:,
1682:,
1678:,
1674:,
1670:,
1666:,
1662:,
1650:.
1534:,
1530:,
1518:,
1514:,
1496:.
1469:.
1422:,
1394:,
1386::
1377:,
1373:,
1369:,
1365:,
1361:,
1357:,
1353:,
1349:,
1345:,
1341:,
1337:,
1333:,
1329:,
1325::
1316:,
1312:,
1308:,
1304:,
1300:,
1296:,
1292:,
1288:,
1284:,
1280:,
1276:,
1272:,
1268:,
1264::
1255:,
1251:,
1247:,
1243:,
1239:,
1235:,
1231:,
1227:,
1223:,
1219:,
1211:,
1207:,
1203:,
1199::
1190:,
1186:,
1182:,
1178::
1169:,
1165:,
1161::
1141:,
1137:,
1116:,
1098:,
1033:12
893:/
859:.
847:,
820:,
816:,
785:,
773:,
765:,
749:.
734:.
726:,
695:.
583:.
330:.
315:12
197:,
193:,
185:,
173:,
169:,
130:.
74:,
50:,
4173:e
4166:t
4159:v
4027:"
4023:"
3194:e
3187:t
3180:v
2876:e
2869:t
2862:v
2849:.
2818:.
2799:.
2780:.
2761:.
2742:.
2721:.
2694:.
2675:.
2656:.
2627:.
2613::
2586:.
2582::
2555:.
2549::
2520:.
2508::
2485:.
2461::
2434:.
2412::
2385:.
2367:.
2349:.
2345::
2322:.
2308::
2287:.
2273::
2231:.
2217::
2184:.
2178::
2139:.
2135::
2127::
2100:.
2071:.
2067::
2061:2
2025:)
2011:.
1969:.
1933:.
1919::
1888:.
1856::
932:.
826:2
793:4
668:5
666:H
664:5
537:3
401:.
382:.
322:-
302:3
290:3
278:3
266:2
252:n
152:2
94:(
27:n
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
