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Metal carbonyl

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3092: 3083: 3067: 3420: 31: 273: 307: 643: 2346: 1292: 3362: 663: 42: 3614: 615:, such as CO-stretching vibrations, are often fast compared to intramolecular processes, whereas NMR transitions occur at lower frequencies and thus sample structures on a time scale that, it turns out, is comparable to the rate of intramolecular ligand exchange processes. NMR data provide information on "time-averaged structures", whereas IR is an instant "snapshot". Illustrative of the differing time scales, investigation of 592: 2911: 321: 291: 3563: 535:) CO ligands appear at even lower energies. In addition to symmetrical bridging modes, CO can be found to bridge asymmetrically or through donation from a metal d orbital to the π* orbital of CO. The increased π-bonding due to back-donation from multiple metal centers results in further weakening of the C–O bond. 3132:
are metal carbonyl complexes that are being developed as potential drugs to release CO. At low concentrations, CO functions as a vasodilatory and an anti-inflammatory agent. CO-RMs have been conceived as a pharmacological strategic approach to carry and deliver controlled amounts of CO to tissues and
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orbitals projecting from the carbon atom of the CO. The latter kind of binding requires that the metal have d-electrons, and that the metal be in a relatively low oxidation state (0 or +1) which makes the back-donation of electron density favorable. As electrons from the metal fill the π-antibonding
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Finze, Maik; Bernhardt, Eduard; Willner, Helge; Lehmann, Christian W.; Aubke, Friedhelm (2005-05-10). "Homoleptic, σ-Bonded Octahedral Superelectrophilic Metal Carbonyl Cations of Iron(II), Ruthenium(II), and Osmium(II). Part 2: Syntheses and Characterizations of [M(CO)6][BF4]2 (M =
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of the complexes, any inherent toxicity of the metal is generally made much more severe due to ease of exposure. Exposure occurs by inhalation, or for liquid metal carbonyls by ingestion or due to the good fat solubility by skin resorption. Most clinical experience were gained from toxicological
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Chronic exposure by inhalation of low concentrations of nickel tetracarbonyl can cause neurological symptoms such as insomnia, headaches, dizziness and memory loss. Nickel tetracarbonyl is considered carcinogenic, but it can take 20 to 30 years from the start of exposure to the clinical
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Ellis, John E.; Chi, Kai Ming (1990). "Highly reduced organometallics. 28. Synthesis, isolation, and characterization of [K(cryptand 2.2.2)]2[Hf(CO)6], the first substance to contain hafnium in a negative oxidation state. Structural characterization of [K(cryptand
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The synthesis of ionic carbonyl complexes is possible by oxidation or reduction of the neutral complexes. Anionic metal carbonylates can be obtained for example by reduction of dinuclear complexes with sodium. A familiar example is the sodium salt of iron tetracarbonylate
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The synthesis of metal carbonyls is a widely studied subject of organometallic research. Since the work of Mond and then Hieber, many procedures have been developed for the preparation of mononuclear metal carbonyls as well as homo- and heterometallic carbonyl clusters.
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in a greenish-yellowish color; when heated in a glass tube it formed a nickel mirror. The gas could be condensed to a colorless, water-clear liquid with a boiling point of 43 Â°C. Thus, Mond and his coworker had discovered the first pure, homoleptic metal carbonyl,
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compared with free carbon monoxide, while the metal–carbon bond is strengthened. Because of the multiple bond character of the M–CO linkage, the distance between the metal and carbon atom is relatively short, often less than 1.8 Ă…, about 0.2 Ă… shorter than a
3672:. The presence of isolobal analog fragments does not mean that the desired structures can be synthesized. In his Nobel Prize lecture Hoffmann emphasized that the isolobal analogy is a useful but simple model, and in some cases does not lead to success. 5311:
Sillner, H.; Bodenbinder, M.; Brochler, R.; Hwang, G.; Rettig, S. J.; Trotter, J.; von Ahsen, B.; Westphal, U.; Jonas, V.; Thiel, W.; Aubke, F. (2001). "Superelectrophilic Tetrakis(carbonyl)palladium(II)- and platinum(II) Undecafluorodiantimonate(V),
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displays CO bands at 2082, 2019 and 1829 cm. The number of IR-observable vibrational modes for some metal carbonyls are shown in the table. Exhaustive tabulations are available. These rules apply to metal carbonyls in solution or the gas phase.
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The nomenclature of the metal carbonyls depends on the charge of the complex, the number and type of central atoms, and the number and type of ligands and their binding modes. They occur as neutral complexes, as positively-charged metal carbonyl
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and H. O. Jones were able to determine the structure of diiron nonacarbonyl, which is produced from iron pentacarbonyl by the action of sunlight. After Mond, who died in 1909, the chemistry of metal carbonyls fell for several years in oblivion.
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occur. In addition to pathological alterations of the lung, such as by metalation of the alveoli, damages are observed in the brain, liver, kidneys, adrenal glands, and spleen. A metal carbonyl poisoning often necessitates a lengthy recovery.
700:) at the bottom of this section, the hexacarbonyls show decreasing π-backbonding as one increases (makes more positive) the charge on the metal. π-Basic ligands increase π-electron density at the metal, and improved backbonding reduces ν 5644:
Finze, M.; Bernhardt, E.; Willner, H.; Lehmann, C. W.; Aubke, F. (2005). "Homoleptic, σ-Bonded Octahedral Superelectrophilic Metal Carbonyl Cations of Iron(II), Ruthenium(II), and Osmium(II). Part 2: Syntheses and Characterizations of
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For the rational design of new complexes the concept of the isolobal analogy has been found useful. Roald Hoffmann was awarded the Nobel Prize in chemistry for the development of the concept. This describes metal carbonyl fragments of
2015:. Although CO is considered generally as a ligand for low-valent metal ions, the tetravalent iron complex (16-valence electron complex) quantitatively binds CO to give the diamagnetic Fe(IV)-carbonyl (18-valence electron complex). 1435:
already at 80 Â°C and atmospheric pressure, finely divided iron reacts at temperatures between 150 and 200 Â°C and a carbon monoxide pressure of 50–200 bar. Other metal carbonyls are prepared by less direct methods.
498: 2472:. The parent compounds for many of these mixed ligand complexes are the binary carbonyls, those species of the formula , many of which are commercially available. The formulae of many metal carbonyls can be inferred from the 634:
bands, far more than expected for a single compound. This complexity reflects the presence of isomers with and without bridging CO ligands. The C NMR spectrum of the same substance exhibits only a single signal at a
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Jin, Jiaye; Yang, Tao; Xin, Ke; Wang, Guanjun; Jin, Xiaoyang; Zhou, Mingfei; Frenking, Gernot (2018-04-25). "Octacarbonyl Anion Complexes of Group Three Transition Metals (TM = Sc, Y, La) and the 18-Electron Rule".
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to the metal oxides. It is discussed whether in the reducing hydrothermal environments of the prebiotic prehistory such complexes were formed and could have been available as catalysts for the synthesis of critical
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provides information about the structure and composition of the complexes. Spectra for metal polycarbonyls are often easily interpretable, because the dominant fragmentation process is the loss of carbonyl ligands
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range for terminally bound ligands is 150 to 220 ppm. Bridging ligands resonate between 230 and 280 ppm. The C signals shift toward higher fields with an increasing atomic number of the central metal.
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H. J. Buttery; G. Keeling; S. F. A. Kettle; I. Paul; P. J. Stamper (1969). "Correlation between crystal structure and carbonyl-bond stretching vibrations of methyl benzene transition metal tricarbonyls".
5320:: Syntheses, Physical and Spectroscopic Properties, Their Crystal, Molecular, and Extended Structures, and Density Functional Theory Calculations: An Experimental, Computational, and Comparative Study". 6013:
Clark, George R.; Marsden, Karen; Roper, Warren R.; Wright, L. James (1980). "Carbonyl, Thiocarbonyl, Selenocarbonyl, and Tellurocarbonyl Complexes Derived from a Dichlorocarbene Complex of Osmium".
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Butcher, C. P. G.; Dyson, P. J.; Johnson, B. F. G.; Khimyak, T.; McIndoe, J. S. (2003). "Fragmentation of Transition Metal Carbonyl Cluster Anions: Structural Insights from Mass Spectrometry".
3049:, followed by hydrogenation of the resulting hydroxyaldehyde. The "oxo aldehydes" resulting from hydroformylation are used for large-scale synthesis of fatty alcohols, which are precursors to 4808:
Cody, G. D.; Boctor, N. Z.; Filley, T. R.; Hazen, R. M.; Scott, J. H.; Sharma, A.; Yoder, H. S. Jr. (2000). "Primordial Carbonylated Iron–Sulfur Compounds and the Synthesis of Pyruvate".
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Resonance structures of a metal carbonyl. From left to right, the contributions of the right-hand-side canonical forms increase as the back-bonding power of M to CO increases.
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Braga, Dario; Grepioni, Fabrizia; Orpen, A. Guy (1993). "Nickel carbonyl [Ni(CO)4] and iron carbonyl [Fe(CO)5]: molecular structures in the solid state".
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played in the years following 1928 a decisive role in the development of metal carbonyl chemistry. He systematically investigated and discovered, among other things, the
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Sargent, A. L.; Hall, M. B. (1989). "Linear Semibridging Carbonyls. 2. Heterobimetallic Complexes Containing a Coordinatively Unsaturated Late Transition Metal Center".
3492:, which is produced by a similar procedure as nickel tetracarbonyl. Mond recognized the economic potential of this class of compounds, which he commercially used in the 3163:, are numerous. In contrast to metal carbonyls, however, homoleptic metal nitrosyls are rare. NO is a stronger π-acceptor than CO. Well known nitrosyl carbonyls include 374:
bond. The M-CO and MC-O distance are sensitive to other ligands on the metal. Illustrative of these effects are the following data for Mo-C and C-O distances in Mo(CO)
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Londergan, C. H.; Kubiak, C. P. (2003). "Electron Transfer and Dynamic Infrared-Band Coalescence: It Looks like Dynamic NMR spectroscopy, but a Billion Times Faster".
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and are observed. The number of observable IR transitions (but not their energies) can thus be predicted. For example, the CO ligands of octahedral complexes, such as
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metals, oxides, and salts. As part of their experiments the group treated nickel with carbon monoxide. They found that the resulting gas colored the gas flame of a
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band is observed in the IR spectra of the octahedral metal hexacarbonyls. Spectra for complexes of lower symmetry are more complex. For example, the IR spectrum of
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solvents are ideal for high resolution. For measurements on solid samples of metal carbonyls, the number of bands can increase owing in part to site symmetry.
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is usually shifted by 100–200 cm to lower energy compared to the signatures of terminal CO, which are in the region 1800 cm. Bands for face-capping (
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of the parent complex can be determined, as well as information about structural rearrangements involving loss of carbonyl ligands under ESI-MS conditions.
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Brathwaite, Antonio D.; Maner, Jonathon A.; Duncan, Michael A. (2013). "Testing the Limits of the 18-Electron Rule: The Gas-Phase Carbonyls of Sc and Y".
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is higher than that for free carbon monoxide. In nonclassical CO complexes, the C-O distance is shorter than free CO (113.7 pm). The structure of , with d
7007: 393: 185:-CO complexes, both the carbon and oxygen are bonded to the metal. More commonly only carbon is bonded, in which case the hapticity is not mentioned. 5365:
Malischewski, Moritz; Seppelt, Konrad; Sutter, JĂśrg; Munz, Dominik; Meyer, Karsten (2018). "A Ferrocene-Based Dicationic Iron(IV) Carbonyl Complex".
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Metal–metal bonds are cleaved by halogens. Depending on the electron-counting scheme used, this can be regarded as an oxidation of the metal atoms:
166:, and their homologs, build neutral mononuclear complexes. Polynuclear metal carbonyls are formed from metals with odd atomic numbers and contain a 7183: 6857: 6511: 4515: 3231: 2942:, a highly pure metal powder, is prepared by thermal decomposition of iron pentacarbonyl. Carbonyl iron is used inter alia for the preparation of 7201: 7037: 563:
in vacuum, although this process is often accompanied by degradation. Metal carbonyls are soluble in nonpolar and polar organic solvents such as
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The carbonyl ligand engages in a wide range of bonding modes in metal carbonyl dimers and clusters. In the most common bridging mode, denoted
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and their derivatives. In these reactions, for example, nickel tetracarbonyl or cobalt carbonyls act as catalysts. Reppe also discovered the
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Metal carbonyls are used in several industrial processes. Perhaps the earliest application was the extraction and purification of nickel via
547:, a uniquely stable 17-electron metal carbonyl, is a blue-black solid. Dimetallic and polymetallic carbonyls tend to be more deeply colored. 3091: 2027:
of carbon monoxide by other ligands, the oxidation or reduction reactions of the metal center, and reactions at the carbon monoxide ligand.
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identified by infrared spectroscopy. Four infrared stretching frequencies were found for the terminal and bridging carbon monoxide ligands.
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is the most common technique for characterizing the neutral metal carbonyls. Neutral metal carbonyls can be converted to charged species by
7239: 2506:(M = Ca, Sr, Ba). The compounds were characterized in cryogenic matrices by vibrational spectroscopy and in gas phase by mass spectrometry. 2454: 8178: 3456:, investigated in the 1890s with Carl Langer and Friedrich Quincke various processes for the recovery of chlorine which was lost in the 7865: 7093: 688:
band for the metal carbonyls correlates with the strength of the carbon–oxygen bond, and inversely correlated with the strength of the
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Jost, A.; Rees, B.; Yelon, W. B. (1975-11-01). "Electronic structure of chromium hexacarbonyl at 78 K. I. Neutron diffraction study".
7164: 6888: 6182:"MĂŠmoires sur quelques rĂŠactions donnant lieu Ă  la production de l'oxychlorure de carbone, et sur nouveau composĂŠ volatil de platine" 2281:, followed by the release of carbon dioxide and the formation of metal hydrides or carbonylmetalates. A well-studied example of this 7626: 2003:
The use of strong acids succeeded in preparing gold carbonyl cations such as , which is used as a catalyst for the carbonylation of
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Wu, Xuan; Zhao, Lili; Jin, Jiaye; Pan, Sudip; Li, Wei; Jin, Xiaoyang; Wang, Guanjun; Zhou, Mingfei; Frenking, Gernot (2018-08-31).
4686:"Human Carboxyhemoglobin at 2.2 Ă… Resolution: Structure and Solvent Comparisons of R-State, R2-State and T-State Hemoglobins" 3850:
Schut, D. A.; Tyler, D. R.; Weakley, T. J. R. (1996). "The Crystal Structure of Tris(4-methylpyridine) Tricarbonylmolybdenum(0)".
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and financed more research on related compounds. Heinrich Hirtz and his colleague M. Dalton Cowap synthesized metal carbonyls of
1280: 608: 3687:, led to growth of the area. Metal carbonyl compounds were discovered in the active sites of three naturally occurring enzymes. 2055:, are effective ligands that afford synthetically useful derivatives. Substitution of 18-electron complexes generally follows a 8171: 7701: 7471: 7029: 3636:– or CH– fragments in organic chemistry. In example dimanganese decacarbonyl is formed in terms of the isolobal analogy of two 3567: 2512:
with 4 valence electrons are expected to form heptacarbonyls; while these are extremely rare, substituted derivatives of Ti(CO)
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between the metal and the carbon. The π-basicity of the metal center depends on a lot of factors; in the isoelectronic series (
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enzymes contain CO bound to iron. It is thought that the CO stabilizes low oxidation states, which facilitates the binding of
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Iron pentacarbonyl exhibits only a single C NMR signal owing to rapid exchange of the axial and equatorial CO ligands by
6837: 6708: 6415: 6254: 6129: 6104: 6076: 5997: 5855: 5785: 5425: 5264: 5157: 5076: 4911: 4590: 4565: 4499: 4252: 4227: 4200: 4144: 4040: 4007: 3894: 3834: 3782: 3754: 3578:, an industrial chemist and later board member of BASF, discovered a number of homogeneous catalytic processes, such as the 3430:
The synthesis of the first true heteroleptic metal carbonyl complex was performed by Paul SchĂźtzenberger in 1868 by passing
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Most mononuclear carbonyl complexes are colorless or pale yellow, volatile liquids or solids that are flammable and toxic.
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is a sensitive probe for the presence of bridging carbonyl ligands. For compounds with doubly bridging CO ligands, denoted
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Tard, C; Pickett, C. J. (2009). "Structural and Functional Analogues of the Active Sites of the -, -, and -Hydrogenases".
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are known but uncommon. The rarity of such complexes is partly attributable to the fact that the obvious source material,
7838: 7670: 7420: 7364: 7286: 6880: 6832: 6432: 3714: 3129: 2865: 2500: 7808: 2699:. In fact the cobalt derivative of this octacarbonyl is the only stable member, but all three tetramers are well known: 2522:
with 5 valence electrons, again are subject to steric effects that prevent the formation of M–M bonded species such as V
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Metal carbonyls are important precursors for the synthesis of other organometallic complexes. Common reactions are the
1637:. In the presence of carbon monoxide, cobalt salts are quantitatively converted to the tetracarbonylcobalt(−1) anion: 8454: 7196: 7105: 6962: 6761: 5914:
Hayton, T. W.; Legzdins, P.; Sharp, W. B. (2002). "Coordination and Organometallic Chemistry of Metal−NO Complexes".
5182: 3478: 199:, the CO ligand bridges a pair of metals. This bonding mode is observed in the commonly available metal carbonyls: Co 4482:
Adams R. D., Barnard T. S., Cortopassi J. E., Wu W., Li Z. (1998). "Platinum-ruthenium carbonyl cluster complexes".
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Tolman, C. A. (1977). "Steric effects of Phosphorus Ligands in Organometallic Chemistry and Homogeneous Catalysis".
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Metal carbonyls are toxic by skin contact, inhalation or ingestion, in part because of their ability to carbonylate
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Boczkowski, J.; Poderoso, J. J.; Motterlini, R. (2006). "CO–Metal Interaction: Vital Signaling from a Lethal Gas".
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also form extensive families of complexes that are related to the metal carbonyls. Typical isocyanide ligands are
6867: 6640: 6628: 6599: 6594: 6497: 3272:, an unstable molecule that forms stable complexes whose behavior closely parallels that of the metal carbonyls. 2308: 231:. In certain higher nuclearity clusters, CO bridges between three or even four metals. These ligands are denoted 2345: 7933: 6943: 6847: 6801: 6684: 6604: 6558: 4641:
Ricks, A.M.; Reed, Z.E.; Duncan, M.A. (2011). "Infrared spectroscopy of mass-selected metal carbonyl cations".
3198:, is unstable. Thus, the synthesis of thiocarbonyl complexes requires indirect routes, such as the reaction of 2159:
The rate of substitution in 18-electron complexes is sometimes catalysed by catalytic amounts of oxidants, via
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Petz, W. (2008). "40 Years of Transition-Metal Thiocarbonyl Chemistry and the Related CSe and CTe Compounds".
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and benzene derivatives with metal carbonyls as catalysts. BASF built in the 1960s a production facility for
3551:, the first known route to metal carbonyl hydrides and synthetic pathways leading to metal carbonyls such as 3301:
due to their use in industry. Nickel tetracarbonyl is considered as one of the strongest inhalation poisons.
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Ohst, H. H.; Kochi, J. K. (1986). "Electron-Transfer Catalysis of Ligand Substitution in Triiron Clusters".
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Xu, Q.; Imamura, Y.; Fujiwara, M.; Souma, Y. (1997). "A New Gold Catalyst: Formation of Gold(I) Carbonyl, (
1235:(ESI), instrumentation for which is often widely available. For example, treatment of a metal carbonyl with 7599: 7135: 6957: 6671: 3696: 3453: 1452:
in the presence of high pressure of carbon monoxide. A variety of reducing agents are employed, including
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Li, P.; Curtis, M. D. (1989). "A New Coordination Mode for Carbon Monoxide. Synthesis and Structure of Cp
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of 204 ppm. This simplicity indicates that the isomers quickly (on the NMR timescale) interconvert.
611:. These two techniques provide structural information on two very different time scales. Infrared-active 6320: 3117:
as well as rhodium and iridium carbonyl catalysts, respectively. Related carbonylation reactions afford
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Most metal carbonyl complexes contain a mixture of ligands. Examples include the historically important
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Cotton, F. Albert (1968). "Proposed nomenclature for olefin-metal and other organometallic complexes".
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in Sewage Gas by using Cryotrapping Gas Chromatography Inductively Coupled Plasma Mass Spectrometry".
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by the Reppe process, which was only superseded in 1996 by more modern methods based on the catalytic
1347:. Traces of the carbonyls of iron, nickel, and tungsten were found in the gaseous emanations from the 7784: 4980: 3313: 3265: 1572: 1375: 1166:
of ligand exchange processes can be determined by the temperature dependence of the line broadening.
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Der Unfallmann: Begutachtung der Folgen von Arbeitsunfällen, privaten Unfällen und Berufskrankheiten
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Mass Spectrometry of Inorganic, Coordination and Organometallic Compounds: Tools – Techniques – Tips
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started in 1924 the industrial production of iron pentacarbonyl by a process which was developed by
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Lubbe, Stephanie C. C.; Vermeeren, Pascal; Fonseca Guerra, CĂŠlia; Bickelhaupt, F. Matthias (2020).
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also are involved in bioprocessing of CO. Carbon monoxide containing complexes are invoked for the
1269:. By adjusting the cone voltage or temperature, the degree of fragmentation can be controlled. The 720: 96: 8163: 8004: 7736: 7694: 6907: 5805: 5473:"Observation of alkaline earth complexes M(CO)8 (M = Ca, Sr, or Ba) that mimic transition metals" 3705: 2902:= 112.9 pm, illustrates this effect. These complexes are usually cationic, sometimes dicationic. 2628: 2565: 2551: 2120: 1232: 666:
The number of infrared-active vibrational modes of several prototypical metal carbonyl complexes.
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Roland, E.; Vahrenkamp, H. (1985). "Zwei neue Metallcarbonyle: Darstellung und Struktur von RuCo
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Elliot. Band; E. L. Muetterties (1978). "Mechanistic features of metal cluster rearrangements".
7889: 7547: 7002: 6814: 3552: 3345: 3285: 3154: 2867:(M = Ca, Sr, Ba), characterized in gas phase by mass spectrometry and vibrational spectroscopy. 2849: 2664: 2604: 2278: 2063: 2012: 1719: 1469: 1240: 1228: 762:
mode (antisymmetric stretch of the apical carbonyl ligands) is IR-allowed. Thus, only a single
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Herrmann, W. A. (1988). "100 Jahre Metallcarbonyle. Eine Zufallsentdeckung macht Geschichte".
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can be prepared according to the following equations by reaction of finely divided metal with
7858: 7577: 7494: 7464: 7452: 6842: 6307: 5688:"The Nature of Nonclassical Carbonyl Ligands Explained by Kohn–Sham Molecular Orbital Theory" 3538: 3534: 3309: 3254: 2987: 2744: 2558: 2323: 2307:
Hydride reagents also attack CO ligands, especially in cationic metal complexes, to give the
2282: 2113: 2024: 1887: 1796:). On further heating, the products decompose eventually into the metal and carbon monoxide. 1576: 1445: 728: 671: 616: 604: 600: 583:. Some salts of cationic and anionic metal carbonyls are soluble in water or lower alcohols. 544: 507: 173:
Carbon monoxide has distinct binding modes in metal carbonyls. They differ in terms of their
151: 99:, metal carbonyls serve as precursors for the preparation of other organometallic complexes. 72: 1980:
can be prepared from the carbonyl halides under carbon monoxide pressure by reaction with a
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Motterlini Roberto, Otterbein Leo (2010). "The therapeutic potential of carbon monoxide".
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Hieber, W.; Fuchs, H. (1941). "Über Metallcarbonyle. XXXVIII. Über Rheniumpentacarbonyl".
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is formed as a reaction product. In the reduction of metal chlorides with carbon monoxide
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Tielens, A. G.; Wooden, D. H.; Allamandola, L. J.; Bregman, J.; Witteborn, F. C. (1996).
4605: 3555:. Hieber, who was since 1934 the Director of the Institute of Inorganic Chemistry at the 3509: 3485: 2932: 2754:
unlike the majority of the other 18 VE transition metal carbonyls is sensitive to oxygen.
2675: 2105: 1785: 1507:, as the reducing agent leads to the oxidative coupling of the alkyl radical to form the 1371: 1224: 770: 576: 6351: 6158: 6040:
D. Lentz (1994). "Fluorinated Isocyanides - More than Ligands with Unusual Properties".
5488: 5045: 4821: 4794: 4742: 4724: 4654: 3419: 147:), but more commonly metal carbonyls are heteroleptic and contain a mixture of ligands. 30: 8267: 7539: 7188: 6934: 6539: 6294: 6244: 5896: 5828: 5806:"Organo Transition Metal Compounds as Intermediates in Homogeneous Catalytic Reactions" 5712: 5687: 5398: 5220: 4727:"The Infrared Spectrum of the Galactic Center and the Composition of Interstellar Dust" 4509: 4124: 3867: 3591: 3579: 3489: 3372:
Initial experiments on the reaction of carbon monoxide with metals were carried out by
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Also the cyclization of acetylene to cyclooctatetraene uses metal carbonyl catalysts:
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Braye, E. H.; HĂźbel, W.; Rausch, M. D.; Wallace, T. M. (1966). H. F. Holtzlaw (ed.).
5072: 5032: 4944: 4907: 4884: 4833: 4756: 4707: 4666: 4623: 4586: 4561: 4495: 4464: 4429: 4421: 4385: 4314: 4248: 4223: 4217: 4196: 4140: 4073: 4036: 4003: 3890: 3830: 3778: 3750: 3373: 3365: 3250: 2544: 2531: 2215: 2160: 1868: 1634: 1508: 1500: 1477: 1465: 1324: 1296: 1276: 1174: 1163: 1144: 642: 314: 284: 107: 68: 5402: 3871: 3525:. The iron pentacarbonyl was used for the production of high-purity iron, so-called 3384:. As demonstrated later, the compound was not a carbonyl, but the potassium salt of 2832:
as monoanions resemble neutral group 10 metal carbonyl. is the best studied member.
245:-CO. Less common are bonding modes in which both C and O bond to the metal, such as 170:. Complexes with different metals but only one type of ligand are called isoleptic. 150:
Mononuclear metal carbonyls contain only one metal atom as the central atom. Except
8284: 8262: 8246: 8238: 7653: 7391: 6455: 6355: 6340:
Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences
6218: 6162: 6049: 6022: 5985: 5958: 5923: 5880: 5832: 5820: 5748: 5707: 5699: 5660: 5610: 5583: 5538: 5492: 5450: 5374: 5337: 5329: 5293: 5252: 5229: 5145: 5103: 5049: 4991: 4936: 4876: 4825: 4746: 4697: 4683: 4658: 4615: 4538: 4487: 4456: 4413: 4377: 4348: 4306: 4278: 4171: 4162: 4132: 4065: 4028: 3973: 3919: 3859: 3807: 3684: 3118: 3102: 3058: 2963: 2757: 2473: 2367: 1872: 1766: 1352: 612: 493:{\displaystyle {\ce {M^{-}-C{\equiv }O+<->M=C=O<->M+{\equiv }C-O^{-}}}} 167: 76: 57: 5801: 4829: 4370:
Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry
4245:
Symmetry and Spectroscopy: Introduction to Vibrational and Electronic Spectroscopy
3077:. The example below is for the synthesis of acrylic acid and acrylic acid esters: 2007:. The cationic platinum carbonyl complex can be prepared by working in so-called 603:, important analytical techniques for the characterization of metal carbonyls are 8366: 8324: 8300: 8254: 8230: 8217: 7404: 7348: 7344: 7307: 7298: 6240: 5574: 4776:"IR Spectroscopic Evidence of Metal Carbonyl Clusters in the Jiange H5 Chondrite" 4190: 3680: 3281: 3114: 2882: 2876: 2870: 2829: 2820: 2814: 2808: 2802: 2785: 2688: 2617: 2581: 2540: 2519: 2509: 2451: 2359: 1432: 1403: 1316: 1300: 715:
The number of vibrational modes of a metal carbonyl complex can be determined by
336:". The M–C bonding has three components, giving rise to a partial triple bond. A 132: 80: 61: 5135: 4555: 4127:(2005). "4. Carbonyls, Phosphine Complexes, and Ligand Substitution Reactions". 1283:
can provide vibrational informations for ionic carbonyl complexes in gas phase.
8408: 8272: 8222: 7331: 7321: 6952: 6236: 5643: 5310: 5149: 4940: 4491: 4032: 3661: 3522: 3457: 3435: 3106: 3035: 2571:. Group 6 elements (as well as group 7) are also well known for exhibiting the 2259: 2180: 2172: 2036: 1761:
from the chloride salts. Carbon monoxide is also suitable for the reduction of
1750: 1715: 1148: 724: 689: 636: 333: 325: 131:. The carbon monoxide ligand may be bound terminally to a single metal atom or 41: 5962: 5753: 5736: 4702: 4685: 4662: 4381: 4353: 4336: 3477:). The unusual high volatility of the metal compound nickel tetracarbonyl led 2199:
For iron pentacarbonyl, one obtains the tetracarbonylferrate with loss of CO:
1291: 8443: 8418: 6661: 6566: 6145:
Trout, W. E. Jr. (1937). "The Metal Carbonyls. I. History; II. Preparation".
5737:"Iron and Calcium Bioavailability of Fortified Foods and Dietary Supplements" 5622: 5550: 5506: 5386: 5256: 5233: 5107: 5053: 4995: 4670: 4468: 4425: 4389: 4318: 4267: 3676: 3544: 3526: 3465: 3401: 2995: 2975: 2939: 2366:. For example, they resist attack by alkylating agents, mild acids, and mild 2335: 2274: 2270: 1348: 568: 5824: 5497: 5472: 5284:= 1, 2), in Sulfuric Acid and Its Application to Carbonylation of Olefins". 2986:, hydrogen gas, and carbon monoxide react together with a catalyst (such as 1633:
In the aqueous phase, nickel or cobalt salts can be reduced, for example by
7263: 7217: 6467: 6360: 6335: 6053: 5989: 5935: 5892: 5762: 5721: 5703: 5672: 5630: 5558: 5542: 5514: 5394: 5378: 5351: 4948: 4888: 4837: 4760: 4627: 4619: 4433: 4136: 4095:. Upper Saddle River, NJ: Pearson Prentice Hall. pp. 109–119, 534–538. 4077: 4069: 3603: 3575: 3493: 3385: 3203: 3054: 2928: 2848:
are also well known. Many metal carbonyl anions can be protonated to give
2371: 2363: 2218:
can insert into the metal–metal bonds of some polynuclear metal carbonyls:
1344: 1340: 1334:
In the oxygen-rich atmosphere of the Earth, metal carbonyls are subject to
716: 84: 4711: 3586:
react with carbon monoxide and water to form products such as unsaturated
3380:
he prepared a substance having the empirical formula KCO, which he called
1784:
of mononuclear carbonyls generates di- and polymetallic carbonyls such as
8423: 8356: 6726: 6489: 6375: 6222: 5066: 4282: 3513: 3449: 3423: 3337: 3289: 3110: 3042: 2979: 2885:
as dications also resemble neutral group 6 derivatives (M = Fe, Ru, Os).
2641:. The heavier two members are unstable, tending to decarbonylate to give 2578:(the labilization of CO in the cis position) in organometallic synthesis. 2247: 1781: 1504: 1359: 361: 311: 128: 6026: 5454: 4542: 4460: 4310: 4175: 3977: 3923: 3811: 3533:. Not until 1927 did A. Job and A. Cassal succeed in the preparation of 3361: 2691:
with 9 valence electrons and are expected to form tetracarbonyl dimers M
1468:. Illustrative is the formation of chromium hexacarbonyl from anhydrous 360:
arises from overlap of filled d-orbitals on the metal with a pair of π*-
27:
Coordination complexes of transition metals with carbon monoxide ligands
5685: 3863: 3628:
as parts of octahedral building blocks in analogy to the tetrahedral CH
3501: 3246: 2572: 2331: 2040: 1981: 1973: 1777: 1659: 1560: 1270: 1262: 559:) forms deep green crystals. The crystalline metal carbonyls often are 337: 295: 281: 136: 103: 6459: 6166: 5927: 5664: 5614: 5587: 5333: 5297: 5279: 5177:(3rd ed.). Sausalito, CA: University Science Books. p. 190. 4417: 681:, occurs at 2143 cm for carbon monoxide gas. The energies of the 662: 8428: 8403: 8387: 8361: 6120:
Mehrtens, G.; Reichenbach, M.; HĂśffler, D.; Mollowitz, G. G. (1998).
5144:. Vol. 8. Hoboken, NJ: John Wiley & Sons. pp. 178–181. 4880: 3607: 3595: 3505: 3377: 3050: 2999: 2879:
as monocations resemble neutral group 6 derivative (M = Mn, Tc, Re).
2841: 2796: 2492: 2008: 1969: 1852: 1584: 1564: 1335: 1328: 1320: 1308: 353: 349: 345: 277: 174: 6206: 5884: 5572:
Ellis, J. E. (2003). "Metal Carbonyl Anions: from to and Beyond".
5125:. Vol. 1: Transition-Metal Compounds. New York: Academic Press. 4297:
2.2.2)]2[M(CO)6].cntdot.pyridine (M = Ti, Zr, and Hf)".
2119:
Substitution in 17-electron complexes, which are rare, proceeds via
1143:. To improve the sensitivity of this technique, complexes are often 7396: 4751: 4726: 3997: 3889:(2nd ed.). New York: Oxford University Press. pp. 79–82. 3645: 3613: 3431: 3341: 3325: 3160: 2991: 2943: 2845: 2788: 2047:(CN), nitrogen donors, and even ethers, especially chelating ones. 1754: 1556: 1461: 1457: 1363: 1327:
clouds were detected. Iron carbonyl clusters were also observed in
1266: 1236: 1155:
NMR spectroscopy can be used for experimental determination of the
693: 155: 8193: 5975: 5734: 4684:
VĂĄsquez, G. B.; Ji, X.; Fronticelli, C.; Gilliland, G. L. (1998).
3559:
published in four decades 249 papers on metal carbonyl chemistry.
3481:
to the statement that Mond had "given wings to the heavy metals".
260: 8351: 8346: 8340: 7326: 5870: 3599: 3530: 3333: 2947: 2792: 2488: 2266: 2044: 1977: 1864: 1860: 1762: 1694: 1588: 1568: 1473: 1449: 591: 572: 564: 357: 299: 4376:(11). International Union of Crystallography (IUCr): 2649–2658. 3777:(in German) (102nd ed.). Berlin: de Gruyter. p. 1780. 2910: 1390: 8197: 5067:
Miessler, Gary L.; Paul J. Fischer; Donald Arthur Tarr (2013).
4773: 4556:
Riedel, E.; Alsfasser, R.; Janiak, C.; KlapĂśtke, T. M. (2007).
4023:
McFarlane, W.; Wilkinson, G. (1966). "Triiron Dodecacarbonyl".
3665: 3583: 3497: 3461: 3317: 3073:
Another important reaction catalyzed by metal carbonyls is the
2983: 2974:
Metal carbonyls are used in a number of industrially important
2837: 2496: 2176: 2048: 2004: 1867:
are often generated by abstraction of CO from solvents such as
1856: 1580: 1543: 1511: 1453: 340:
arises from overlap of the nonbonding (or weakly anti-bonding)
163: 124: 111: 92: 64: 5012:
Huheey, J.; Keiter, E.; Keiter, R. (1995). "Metallcarbonyle".
5011: 4242: 3884: 2039:
by donor ligands. The range of ligands is large, and includes
332:
Carbon monoxide bonds to transition metals using "synergistic
6405:
Chemicals from Synthesis Gas: Catalytic Reactions of CO and H
6269: 6246:
Eureka and Euphorias: The Oxford Book of Scientific Anecdotes
6069:
Rechtsmedizin. Befunderhebung - Rekonstruktion – Begutachtung
5364: 5030:
Mittasch, A. (1928). "Über Eisencarbonyl und Carbonyleisen".
4528: 4055: 3329: 3321: 2955: 2052: 1824:) provides higher-nuclear osmium carbonyl clusters such as Os 1258: 670:
An important technique for characterizing metal carbonyls is
371: 310:
The lowest unoccupied molecular orbital (LUMO) of CO is a π*
6272:"Note on a Volatile Compound of Cobalt with Carbon Monoxide" 4926: 4402: 3336:. After some time, severe pulmonary symptoms such as cough, 3113:
is produced from methanol, carbon monoxide, and water using
6380:
From Coello to Inorganic Chemistry: A Lifetime of Reactions
5848:
Organotransition Metal Chemistry: From Bonding to Catalysis
4580: 3587: 3562: 3541:, the first synthesis of other homoleptic metal carbonyls. 3518: 3141:
Many ligands are known to form homoleptic and mixed ligand
2811:
as monoanions resemble again neutral group 6 derivatives: .
2035:
The substitution of CO ligands can be induced thermally or
1714:
Some metal carbonyls are prepared using CO directly as the
697: 320: 290: 159: 7438: 6433:"Building Bridges between Inorganic and Organic Chemistry" 5247:
Pike, R. D. (2001). "Disodium Tetracarbonylferrate(−II)".
4337:"Crystal and Molecular Structure of Vanadium Hexacarbonyl" 4090: 4002:(102nd ed.). Berlin: de Gruyter. pp. 1780–1822. 3617:
Isolobal fragments with tetrahedral or octahedral geometry
1945: 1134: 5172: 3909: 3039: 2817:
as monoanions resemble neutral group 8 derivatives: , , .
1816:
The thermal decomposition of triosmium dodecacarbonyl (Os
712:
fragment to order ligands by their π-donating abilities.
646:
The Berry pseudorotation mechanism for iron pentacarbonyl
5197: 5173:
Girolami, G.S.; Rauchfuss, T.B.; Angelici, R.J. (1999).
4334: 2479: 2362:, metal carbonyls are relatively unreactive toward many 6336:"The Physical and Chemical Properties of Iron Carbonyl" 6012: 5778:
Stealth-Kampfflugzeuge: Täuschen und Tarnen in der Luft
5440: 4486:. Inorganic Syntheses. Vol. 32. pp. 280–284. 4335:
Bellard, S.; Rubinson, K. A.; Sheldrick, G. M. (1979).
2894:
Nonclassical describes those carbonyl complexes where ν
2326:
add with metal carbonyls to acylmetal carbonyl anions.
1913:
leads selectively to mixed-metal carbonyls such as RuCo
5978:
Chlorothiocarbonyl-bis(triphenylphosphine) iridium(I)
4027:. Inorganic Syntheses. Vol. 8. pp. 181–183. 3280:
The toxicity of metal carbonyls is due to toxicity of
2760:
with 10 valence electrons form tetracarbonyls such as
1599:+ 4 Na + 6 CO + 2 diglyme → Na(diglyme) 1439: 6445: 5600: 4807: 4129:
The Organometallic Chemistry of the Transition Metals
3034:
Butyraldehyde is converted on an industrial scale to
1315:
In the investigation of the infrared spectrum of the
396: 5850:. New York: University Science Books. p. 1160. 4904:
Bioorganometallics: Biomolecules, Labeling, Medicine
3710:
Pages displaying wikidata descriptions as a fallback
3701:
Pages displaying wikidata descriptions as a fallback
2823:
as dianaions resemble neutral group 10 derivatives:
8060: 7926: 7754: 7728: 7680: 7486: 7445: 7430: 5913: 5091: 3936: 2805:
as dianions resemble neutral group 6 derivatives: .
2584:with 7 valence electrons form pentacarbonyl dimers 135:to two or more metal atoms. These complexes may be 45:
Sample of iron pentacarbonyl, an air-stable liquid.
6179: 6042:Angewandte Chemie International Edition in English 5976:Hill, A. F. & Wilton-Ely, J. D. E. T. (2002). 5095:Zeitschrift fĂźr anorganische und allgemeine Chemie 4446: 4412:(12). American Chemical Society (ACS): 4206–4214. 4305:(16). American Chemical Society (ACS): 6022–6025. 4022: 3124: 2914:Spheres of nickel manufactured by the Mond process 2889: 2855: 2183:to give carbonylmetalate (or carbonylate) anions: 492: 6204: 4455:(4). American Chemical Society (ACS): 1481–1483. 3849: 3744: 2779: 8441: 5418:Inorganic and Organometallic Reaction Mechanisms 4108: 3998:Holleman, A. F.; Wiberg, E.; Wiberg, N. (2007). 3566:Kaiser Wilhelm Institute for Coal Research (now 3376:in 1834. By passing carbon monoxide over molten 3057:, especially if the reaction proceeds with high 2246:The CO ligand is often susceptible to attack by 627:) by means of infrared spectroscopy provides 13 6097:Encyclopaedia of Occupational Health and Safety 6094: 4972: 4640: 4123: 3053:. The hydroformylation is a reaction with high 2378:, for example, forms ferrous carbonyl halides: 1718:. In this way, Hieber and Fuchs first prepared 719:. Only vibrational modes that transform as the 154:, only metals with even atomic number, such as 117: 6402: 5775: 5527: 5249:Encyclopedia of Reagents for Organic Synthesis 5175:Synthesis and Technique in Inorganic Chemistry 5016:(2nd ed.). Berlin / New York: de Gruyter. 4774:Xu, Y.; Xiao, X.; Sun, S.; Ouyang, Z. (1996). 3772: 586: 8179: 7233: 6505: 6485:metal carbonyls at Louisiana State University 6211:Journal of the Chemical Society, Transactions 5845: 5735:Fairweather-Tait, S. J.; Teucher, B. (2002). 5415: 4851:Feldmann, J. (1999). "Determination of Ni(CO) 4367: 4215: 4188: 2663:. The two other principal iron carbonyls are 2620:with 8 valence electrons form pentacarbonyls 1772: 1391:Direct reaction of metal with carbon monoxide 7247: 6430: 6090: 6088: 5571: 5470: 5029: 4581:Henderson, W.; McIndoe, J. S. (2005-04-01). 4514:: CS1 maint: multiple names: authors list ( 4104: 4102: 3824: 2543:with 6 valence electrons form hexacarbonyls 2241: 6235: 5246: 5120: 5025: 5023: 3827:Transition Metal Carbonyl Cluster Chemistry 3145:that are analogous to the metal carbonyls. 2826:, , . Condensed derivatives are also known. 2799:, form the 20-electron monoanions , , and . 2285:is the conversion of iron pentacarbonyl to 2112:and 155 kJ/mol (37 kcal/mol) for 1323:, monoxide vibrations of iron carbonyls in 1139:Metal carbonyls are often characterized by 538: 71:and as catalysts or catalyst precursors in 8186: 8172: 7240: 7226: 6519: 6512: 6498: 6374: 6333: 6270:Mond, L.; Hirtz, H.; Cowap, M. D. (1908). 6205:Mond, L.; Langer, C.; Quincke, F. (1890). 4901: 3773:Holleman, Arnold F.; Wiberg, Nils (2007). 3438:, where dicarbonyldichloroplatinum (Pt(CO) 2108:is 105 kJ/mol (25 kcal/mol) for 6359: 6085: 6066: 5800: 5752: 5711: 5496: 5341: 5007: 5005: 4750: 4701: 4352: 4243:Harris, D. C.; Bertolucci, M. D. (1980). 4099: 3885:Spessard, G. O.; Miessler, G. L. (2010). 3675:The economic benefits of metal-catalysed 3185: 1444:Some metal carbonyls are prepared by the 6187:Bulletin de la SociĂŠtĂŠ Chimique de Paris 6039: 6015:Journal of the American Chemical Society 5948: 5443:Journal of the American Chemical Society 5322:Journal of the American Chemical Society 5020: 4850: 4844: 4299:Journal of the American Chemical Society 4295: 3966:Journal of the American Chemical Society 3912:Journal of the American Chemical Society 3800:Journal of the American Chemical Society 3699: â€“ carbon dioxide bonding to metals 3612: 3561: 3418: 3360: 2909: 1290: 1243:that is amenable to analysis by ESI-MS: 661: 641: 590: 386:: 2.06 vs 1.90 and 1.11 vs 1.18 Ă…. 344:electron pair on carbon with a blend of 319: 305: 289: 276:The highest occupied molecular orbital ( 271: 267: 40: 29: 5531:Angewandte Chemie International Edition 5367:Angewandte Chemie International Edition 4330: 4328: 3878: 3768: 3766: 3740: 3738: 3736: 3734: 3732: 3730: 3241: 2059:, involving 16-electron intermediates. 1965:), which is used in organic synthesis. 1946:Metal carbonyl cations and carbonylates 1476:with aluminum as a reducing agent, and 1286: 1281:infrared photodissociation spectroscopy 1135:Nuclear magnetic resonance spectroscopy 674:. The C–O vibration, typically denoted 14: 8442: 7273: 5002: 4968: 4966: 4964: 4962: 4960: 4958: 4159: 4153: 3993: 3991: 3989: 3987: 3903: 3797: 3568:Max Planck Institute for Coal Research 139:, containing only CO ligands, such as 8167: 8049: 7221: 6493: 6424: 6207:"Action of Carbon Monoxide on Nickel" 6144: 5466: 5464: 4475: 4192:Chemical Applications of Group Theory 4091:Miessler, G. L.; Tarr, D. A. (2011). 4049: 3825:Dyson, P. J.; McIndoe, J. S. (2000). 3159:Metal nitrosyls, compounds featuring 3148: 2918: 2480:Charge-neutral binary metal carbonyls 2353: 6410:. Vol. 2. Kluwer. p. 106. 5166: 4325: 4195:(3rd ed.). Wiley Interscience. 3763: 3727: 3136: 2994:. Illustrative is the production of 2499:can all form octacarbonyl complexes 1757:is formed, as in the preparation of 1431:Nickel tetracarbonyl is formed with 1169: 4955: 4869:Journal of Environmental Monitoring 4219:Molecular Symmetry and Group Theory 3984: 3715:Alkaline earth octacarbonyl complex 3708: â€“ class of chemical compounds 3130:Carbon monoxide-releasing molecules 1968:The cationic hexacarbonyl salts of 1440:Reduction of metal salts and oxides 657: 521:-CO, the bond stretching frequency 37:: an iron atom with five CO ligands 24: 5984:. Vol. 33. pp. 244–245. 5461: 4574: 3829:. Amsterdam: Gordon & Breach. 2370:. Most metal carbonyls do undergo 2344: 2256:potassium bis(trimethylsilyl)amide 2123:with a 19-electron intermediates. 2030: 1897: 1464:, as well as metal alkyls such as 25: 8476: 6478: 6124:. Berlin / Heidelberg: Springer. 4643:Journal of Molecular Spectroscopy 4131:(4th ed.). pp. 87–124. 4000:Lehrbuch der Anorganischen Chemie 3930: 3775:Lehrbuch der Anorganischen Chemie 1499:The use of metal alkyls, such as 8383:Graphite intercalation compounds 6334:Dewar, J.; Jones, H. O. (1905). 3284:, the metal, and because of the 3090: 3081: 3065: 2277:attacks the CO ligand to give a 1257:Some metal carbonyls react with 595:Isomers of dicobalt octacarbonyl 259: 110:, which prevents the binding of 67:. Metal carbonyls are useful in 6439: 6396: 6368: 6327: 6286: 6263: 6229: 6198: 6173: 6138: 6113: 6060: 6033: 6006: 5969: 5942: 5907: 5864: 5839: 5794: 5769: 5728: 5679: 5637: 5594: 5565: 5521: 5434: 5409: 5358: 5304: 5273: 5240: 5191: 5129: 5114: 5085: 5060: 4920: 4895: 4801: 4767: 4718: 4677: 4634: 4599: 4549: 4522: 4440: 4396: 4361: 4289: 4261: 4236: 4209: 4182: 4117: 4084: 4016: 3178:, which are analogues of Ni(CO) 3125:CO-releasing molecules (CO-RMs) 2905: 2890:Nonclassical carbonyl complexes 2856:Cationic binary metal carbonyls 2287:hydridoiron tetracarbonyl anion 365:orbital of CO, they weaken the 127:or as negatively charged metal 5951:Coordination Chemistry Reviews 5692:Chemistry – A European Journal 5343:11858/00-001M-0000-0024-1DEC-5 5071:. Prentice Hall. p. 696. 4929:Trends in Biochemical Sciences 3843: 3818: 3791: 2780:Anionic binary metal carbonyls 2530:, which is unknown. The 17-VE 2334:of these anions, such as with 1875:. Typical is the synthesis of 453: 431: 181:, and their bridging mode. In 13: 1: 6147:Journal of Chemical Education 5873:Nature Reviews Drug Discovery 4830:10.1126/science.289.5483.1337 4608:Chemistry: A European Journal 4058:Chemistry: A European Journal 3720: 3484:The following year, Mond and 3275: 3200:disodium tetracarbonylferrate 2349:Synthesis of Fischer carbenes 1368:carbon monoxide dehydrogenase 328:in transition metal carbonyls 6403:Sheldon, R. A., ed. (1983). 6099:. International Labour Org. 5286:Journal of Organic Chemistry 3697:Metal carbon dioxide complex 3454:Imperial Chemical Industries 3400:) and the potassium salt of 2969: 2958:-absorbing materials in the 2426: 2358:Despite being in low formal 2166: 2062:Substitution proceeds via a 2018: 1381: 118:Nomenclature and terminology 7: 6431:Hoffmann, R. (1981-12-08). 6249:. Oxford University Press. 6180:SchĂźtzenberger, P. (1868). 4783:Lunar and Planetary Science 4558:Moderne Anorganische Chemie 4247:. Oxford University Press. 3690: 3557:Technical University Munich 2171:Metal carbonyls react with 1231:, which enables the use of 804:average M-CO distance (pm) 706:Tolman electronic parameter 587:Analytical characterization 302:orbitals of carbon monoxide 294:Energy level scheme of the 10: 8481: 8051: 5813:Pure and Applied Chemistry 5150:10.1002/9780470132395.ch46 4941:10.1016/j.tibs.2006.09.001 4492:10.1002/9780470132630.ch44 4033:10.1002/9780470132395.ch47 3745:Elschenbroich, C. (2006). 3356: 3152: 2836:Large anionic clusters of 1851:Mixed ligand carbonyls of 1773:Photolysis and thermolysis 1680:+ 6 OH + 4 CO → 1571:salts may be reduced with 807:average C-O distance (pm) 8396: 8375: 8333: 8205: 7275: 7256: 7176: 7086: 6927: 6900: 6786: 6754: 6582: 6551: 6527: 6382:. Springer. p. 101. 5963:10.1016/j.ccr.2007.12.011 5754:10.1301/00296640260385801 4731:The Astrophysical Journal 4703:10.1107/S0907444997012250 4663:10.1016/j.jms.2011.03.006 4585:. John Wiley & Sons. 4382:10.1107/s0567740875008394 4354:10.1107/S0567740879003332 4109:Braterman, P. S. (1975). 3488:independently discovered 3452:, one of the founders of 3434:and carbon monoxide over 3353:manifestation of cancer. 3314:carbon monoxide poisoning 3238:have been characterized. 2242:Nucleophilic attack at CO 1941:+ 4 KCl + 11 CO 1894:in boiling DMF solution. 1749:If metal oxides are used 1573:lithium aluminium hydride 1522:+ 6 CO + 2 Al(C 1488:+ Al + 6 CO → Cr(CO) 324:Diagram showing synergic 8455:Organometallic chemistry 6095:Stellman, J. M. (1998). 5257:10.1002/047084289X.rd465 5234:10.1002/cber.19851180330 5123:Organometallic Syntheses 5108:10.1002/zaac.19412480304 5054:10.1002/ange.19280413002 4996:10.1002/ciuz.19880220402 4902:Jaouen, G., ed. (2006). 4690:Acta Crystallographica D 3887:Organometallic Chemistry 3670:dimanganese decacarbonyl 3264:CNC). A special case is 2873:form and in gas phase. 2269:, respectively. In the " 1905:of salts such as KCo(CO) 1903:Salt metathesis reaction 1759:osmium carbonyl chloride 1303:at the apical position, 721:electric dipole operator 539:Physical characteristics 356:on the metal. A pair of 97:organometallic chemistry 91:is used to produce pure 6241:"132: Metal Takes Wing" 5825:10.1351/pac197850080677 5776:Richardson, D. (2002). 5498:10.1126/science.aau0839 4906:. Weinheim: Wiley-VCH. 3749:. Weinheim: Wiley-VCH. 3706:Metal phosphine complex 3668:, these can combine to 3598:and its derivatives to 3594:and tetramerization of 2954:, in the production of 2850:metal carbonyl hydrides 1583:as a reducing agent in 1420:Fe + 5 CO → Fe(CO) 1410:Ni + 4 CO → Ni(CO) 1233:electrospray ionization 1141:C NMR spectroscopy 609:C NMR spectroscopy 8195:Inorganic compounds of 6521:Coordination complexes 6361:10.1098/rspa.1905.0063 6054:10.1002/anie.199413151 5990:10.1002/0471224502.ch4 5846:Hartwig, John (2010). 5704:10.1002/chem.202003768 5543:10.1002/anie.201802590 5416:Jim D. Atwood (1997). 5379:10.1002/anie.201809464 4976:Chemie in unserer Zeit 4620:10.1002/chem.200390116 4341:Acta Crystallographica 4216:Carter, R. L. (1997). 4189:Cotton, F. A. (1990). 4137:10.1002/0471718769.ch4 4111:Metal Carbonyl Spectra 4070:10.1002/chem.200305028 3648:to the methyl radical 3618: 3582:, in which olefins or 3571: 3553:dirhenium decacarbonyl 3427: 3369: 3346:gastrointestinal tract 3186:Thiocarbonyl complexes 3155:Metal nitrosyl complex 2915: 2537:is however well known. 2350: 2324:Organolithium reagents 2300:Na + NaOH → Na + NaHCO 2279:metallacarboxylic acid 2258:convert CO ligands to 2121:associative mechanisms 2064:dissociative mechanism 2057:dissociative mechanism 2013:antimony pentafluoride 1720:dirhenium decacarbonyl 1470:chromium(III) chloride 1312: 667: 647: 596: 549:Triiron dodecacarbonyl 494: 329: 317: 303: 287: 54:coordination complexes 46: 38: 5420:(2 ed.). Wiley. 3616: 3565: 3539:tungsten hexacarbonyl 3535:chromium hexacarbonyl 3422: 3364: 3344:, or problems in the 3310:non-specific symptoms 3190:Complexes containing 2988:dicobalt octacarbonyl 2938:By a similar process 2913: 2348: 2283:nucleophilic addition 2114:chromium hexacarbonyl 1888:iridium(III) chloride 1886:from the reaction of 1577:Vanadium hexacarbonyl 1341:biochemical compounds 1295:A heme unit of human 1294: 1239:generates an anionic 672:infrared spectroscopy 665: 645: 617:dicobalt octacarbonyl 605:infrared spectroscopy 601:X-ray crystallography 594: 545:Vanadium hexacarbonyl 508:Infrared spectroscopy 495: 323: 309: 293: 275: 268:Structure and bonding 152:vanadium hexacarbonyl 73:homogeneous catalysis 44: 33: 6223:10.1039/CT8905700749 5957:(15–17): 1689–1733. 5780:. ZĂźrich: Dietikon. 5138:Diiron Enneacarbonyl 5121:King, R. B. (1965). 4283:10.1039/DF9694700048 4271:Discuss. Faraday Soc 3660:. In analogy to how 3644:fragments, that are 3549:Hieber base reaction 3471:nickel tetracarbonyl 3306:nickel tetracarbonyl 3295:nickel tetracarbonyl 3242:Isocyanide complexes 2925:nickel tetracarbonyl 2252:trimethylamine oxide 2110:nickel tetracarbonyl 1396:Nickel tetracarbonyl 1329:Jiange H5 chondrites 1287:Occurrence in nature 1263:isocyanato complexes 652:Berry pseudorotation 581:carbon tetrachloride 394: 141:nickel tetracarbonyl 89:nickel tetracarbonyl 6352:1905RSPSA..76..558D 6159:1937JChEd..14..453T 6071:. Springer-Verlag. 6027:10.1021/ja00523a070 5982:Inorganic Syntheses 5698:(67): 15690–15699. 5652:Inorganic Chemistry 5649:(M = Fe, Ru, Os)". 5603:Inorganic Chemistry 5489:2018Sci...361..912W 5455:10.1021/ja00271a019 5373:(44): 14597–14601. 5142:Inorganic Syntheses 5069:Inorganic Chemistry 5046:1928AngCh..41..827M 5014:Anorganische Chemie 4822:2000Sci...289.1337C 4816:(5483): 1337–1340. 4795:1996LPI....27.1457X 4743:1996ApJ...461..210T 4655:2011JMoSp.266...63R 4543:10.1021/cr60316a003 4484:Inorganic Syntheses 4461:10.1021/om00028a082 4406:Inorganic Chemistry 4311:10.1021/ja00172a017 4176:10.1021/cr60307a002 4093:Inorganic Chemistry 4025:Inorganic Syntheses 3978:10.1021/ja00203a040 3924:10.1021/ja00187a005 3812:10.1021/ja01024a059 3510:diiron nonacarbonyl 3486:Marcellin Berthelot 2952:dietary supplements 2933:carbonyl metallurgy 2106:dissociation energy 1786:diiron nonacarbonyl 1372:acetyl-CoA synthase 1225:Electron ionization 577:glacial acetic acid 8450:Carbonyl complexes 8397:Oxides and related 6295:Chemical Abstracts 6067:Madea, B. (2003). 5221:Chemische Berichte 3864:10.1007/BF01673678 3852:J Chem Crystallogr 3619: 3592:cyclotrimerization 3580:hydrocarboxylation 3574:Also in the 1930s 3572: 3490:iron pentacarbonyl 3428: 3370: 3299:iron pentacarbonyl 3196:carbon monosulfide 3149:Nitrosyl complexes 3075:hydrocarboxylation 3047:aldol condensation 2978:reactions. In the 2960:stealth technology 2919:Metallurgical uses 2916: 2767:. Curiously Pd(CO) 2376:Iron pentacarbonyl 2354:With electrophiles 2351: 1892:triphenylphosphine 1769:is the byproduct. 1400:iron pentacarbonyl 1313: 801:C NMR shift (ppm) 723:will have nonzero 668: 648: 597: 517:-CO or often just 490: 382:(4-methylpyridine) 367:carbon–oxygen bond 330: 318: 304: 288: 47: 39: 35:Iron pentacarbonyl 8460:Transition metals 8437: 8436: 8161: 8160: 8155: 8154: 7215: 7214: 6460:10.1021/cr800542q 6435:. Nobelprize.org. 6417:978-90-277-1489-3 6315:Missing or empty 6256:978-0-19-280403-7 6167:10.1021/ed014p453 6131:978-3-540-63538-3 6106:978-91-630-5495-2 6078:978-3-540-43885-4 6048:(13): 1315–1331. 5999:978-0-471-20825-9 5928:10.1021/cr000074t 5857:978-1-938787-15-7 5787:978-3-7276-7096-1 5741:Nutrition Reviews 5665:10.1021/ic0482483 5659:(12): 4206–4214. 5615:10.1021/ic402729g 5588:10.1021/om030105l 5582:(17): 3322–3338. 5537:(21): 6236–6241. 5483:(6405): 912–916. 5449:(11): 2897–2908. 5427:978-0-471-18897-1 5334:10.1021/ja002360s 5298:10.1021/jo9620122 5266:978-0-471-93623-7 5159:978-0-470-13239-5 5078:978-0-321-81105-9 5033:Angewandte Chemie 4913:978-3-527-30990-0 4592:978-0-470-85015-2 4567:978-3-11-019060-1 4501:978-0-470-13263-0 4418:10.1021/ic0482483 4254:978-0-19-855152-2 4229:978-0-471-14955-2 4202:978-0-471-51094-9 4146:978-0-471-71876-5 4113:. Academic Press. 4064:(24): 5962–5969. 4042:978-0-470-13239-5 4009:978-3-11-017770-1 3972:(21): 8279–8280. 3896:978-0-19-533099-1 3836:978-90-5699-289-7 3806:(22): 6230–6232. 3784:978-3-11-017770-1 3756:978-3-527-29390-2 3529:, and iron oxide 3374:Justus von Liebig 3366:Justus von Liebig 3258:-butyl isocyanide 3251:methyl isocyanide 3137:Related compounds 3038:, a precursor to 2758:Group 10 elements 2309:formyl derivative 2175:such as metallic 2161:electron transfer 1962:Collman's reagent 1869:dimethylformamide 1734:+ 17 CO → Re 1635:sodium dithionite 1587:solvents such as 1579:is prepared with 1501:triethylaluminium 1480:as the catalyst: 1478:aluminum chloride 1466:triethylaluminium 1427:(100 bar, 175 °C) 1325:interstellar dust 1297:carboxyhemoglobin 1277:Mass spectrometry 1175:Mass spectrometry 1170:Mass spectrometry 1164:activation energy 1147:with CO. Typical 1132: 1131: 1103:2044, 2070, 2074 1015: 1014: 613:vibrational modes 482: 473: 459: 452: 444: 436: 424: 415: 401: 108:carboxyhemoglobin 69:organic synthesis 58:transition metals 16:(Redirected from 8472: 8200:and related ions 8188: 8181: 8174: 8165: 8164: 7631: 7260: 7259: 7242: 7235: 7228: 7219: 7218: 6514: 6507: 6500: 6491: 6490: 6472: 6471: 6454:(6): 2245–2274. 6448:Chemical Reviews 6443: 6437: 6436: 6428: 6422: 6421: 6400: 6394: 6393: 6389:978-030-646774-5 6372: 6366: 6365: 6363: 6346:(513): 558–577. 6331: 6325: 6324: 6318: 6313: 6311: 6303: 6290: 6284: 6283: 6267: 6261: 6260: 6233: 6227: 6226: 6202: 6196: 6195: 6177: 6171: 6170: 6142: 6136: 6135: 6117: 6111: 6110: 6092: 6083: 6082: 6064: 6058: 6057: 6037: 6031: 6030: 6021:(3): 1206–1207. 6010: 6004: 6003: 5973: 5967: 5966: 5946: 5940: 5939: 5916:Chemical Reviews 5911: 5905: 5904: 5868: 5862: 5861: 5843: 5837: 5836: 5810: 5798: 5792: 5791: 5773: 5767: 5766: 5756: 5732: 5726: 5725: 5715: 5683: 5677: 5676: 5641: 5635: 5634: 5609:(2): 1166–1169. 5598: 5592: 5591: 5569: 5563: 5562: 5525: 5519: 5518: 5500: 5468: 5459: 5458: 5438: 5432: 5431: 5413: 5407: 5406: 5362: 5356: 5355: 5345: 5308: 5302: 5301: 5292:(6): 1594–1598. 5277: 5271: 5270: 5244: 5238: 5237: 5228:(3): 1133–1142. 5195: 5189: 5188: 5170: 5164: 5163: 5133: 5127: 5126: 5118: 5112: 5111: 5089: 5083: 5082: 5064: 5058: 5057: 5027: 5018: 5017: 5009: 5000: 4999: 4984: 4970: 4953: 4952: 4924: 4918: 4917: 4899: 4893: 4892: 4881:10.1039/A807277I 4848: 4842: 4841: 4805: 4799: 4798: 4780: 4771: 4765: 4764: 4754: 4722: 4716: 4715: 4705: 4681: 4675: 4674: 4638: 4632: 4631: 4603: 4597: 4596: 4578: 4572: 4571: 4553: 4547: 4546: 4526: 4520: 4519: 4513: 4505: 4479: 4473: 4472: 4444: 4438: 4437: 4400: 4394: 4393: 4365: 4359: 4358: 4356: 4332: 4323: 4322: 4293: 4287: 4286: 4265: 4259: 4258: 4240: 4234: 4233: 4213: 4207: 4206: 4186: 4180: 4179: 4163:Chemical Reviews 4157: 4151: 4150: 4121: 4115: 4114: 4106: 4097: 4096: 4088: 4082: 4081: 4053: 4047: 4046: 4020: 4014: 4013: 3995: 3982: 3981: 3934: 3928: 3927: 3918:(5): 1563–1569. 3907: 3901: 3900: 3882: 3876: 3875: 3847: 3841: 3840: 3822: 3816: 3815: 3795: 3789: 3788: 3770: 3761: 3760: 3742: 3711: 3702: 3685:hydroformylation 3664:combine to form 3659: 3658: 3657: 3382:Kohlenoxidkalium 3226:CS + 2 NaCl 3119:acetic anhydride 3107:Cativa processes 3094: 3085: 3069: 3059:regioselectivity 2964:thermal spraying 2883:Group 8 elements 2877:Group 7 elements 2871:Group 3 elements 2862:Group 2 elements 2830:Group 9 elements 2821:Group 8 elements 2815:Group 7 elements 2809:Group 5 elements 2803:Group 4 elements 2786:Group 3 elements 2689:Group 9 elements 2618:Group 8 elements 2582:Group 7 elements 2541:Group 6 elements 2520:Group 5 elements 2510:Group 4 elements 2486:Group 2 elements 2474:18-electron rule 2368:oxidizing agents 2360:oxidation states 2340:Fischer carbenes 2273:base reaction", 1873:2-methoxyethanol 1767:carbonyl sulfide 1722:from the oxide: 1705: 1703: 1702: 1691: 1690: 1689: 1679: 1677: 1676: 1668: 1667: 1656: 1654: 1653: 1650: 1647: 1621: 1619: 1618: 1615: 1612: 1426: 1416: 1353:treatment plants 1265:with release of 1219: 1218: 1217: 1204: 1203: 1202: 1017: 1016: 941: 940: 939: 917: 916: 915: 864: 863: 862: 837: 836: 835: 788: 787: 658:Infrared spectra 499: 497: 496: 491: 489: 488: 487: 480: 478: 471: 470: 465: 464: 457: 450: 449: 442: 441: 434: 430: 429: 422: 420: 413: 412: 407: 406: 399: 334:pi* back-bonding 263: 168:metal–metal bond 77:hydroformylation 21: 18:Carbonyl complex 8480: 8479: 8475: 8474: 8473: 8471: 8470: 8469: 8465:Carbon monoxide 8440: 8439: 8438: 8433: 8414:Metal carbonyls 8392: 8371: 8329: 8320: 8316: 8308: 8304: 8296: 8288: 8280: 8276: 8258: 8250: 8242: 8234: 8226: 8201: 8192: 8162: 8157: 8156: 8064: 8008: 7953: 7949: 7941: 7937: 7932: 7930: 7925: 7923: 7919: 7914: 7912: 7904: 7899: 7897: 7893: 7885: 7881: 7877: 7873: 7869: 7864: 7862: 7842: 7804: 7796: 7792: 7788: 7783: 7781: 7777: 7772: 7770: 7766: 7758: 7753: 7751: 7747: 7742: 7740: 7732: 7727: 7725: 7721: 7713: 7709: 7705: 7700: 7698: 7684: 7674: 7657: 7632: 7629: 7622: 7614: 7610: 7605: 7603: 7598: 7596: 7592: 7587: 7585: 7581: 7574: 7563: 7555: 7551: 7543: 7532: 7527: 7525: 7521: 7513: 7509: 7505: 7500: 7498: 7490: 7485: 7483: 7479: 7475: 7470: 7468: 7460: 7456: 7451: 7449: 7444: 7442: 7434: 7424: 7408: 7403: 7400: 7376: 7372: 7368: 7352: 7347: 7343: 7340: 7320: 7318: 7313: 7311: 7302: 7294: 7290: 7267: 7252: 7246: 7216: 7211: 7192: 7172: 7159: 7151: 7147: 7139: 7131: 7127: 7123: 7114: 7101: 7097: 7082: 7078: 7070: 7062: 7054: 7045: 7041: 7033: 7025: 7011: 6998: 6990: 6986: 6978: 6974: 6966: 6947: 6938: 6923: 6919: 6911: 6896: 6884: 6875: 6871: 6828: 6805: 6797: 6782: 6777: 6769: 6765: 6750: 6746: 6742: 6734: 6730: 6717: 6704: 6700: 6692: 6688: 6675: 6657: 6653: 6644: 6636: 6632: 6624: 6620: 6612: 6608: 6578: 6574: 6570: 6562: 6547: 6543: 6523: 6518: 6481: 6476: 6475: 6444: 6440: 6429: 6425: 6418: 6408: 6401: 6397: 6390: 6373: 6369: 6332: 6328: 6316: 6314: 6305: 6304: 6292: 6291: 6287: 6268: 6264: 6257: 6234: 6230: 6203: 6199: 6178: 6174: 6143: 6139: 6132: 6118: 6114: 6107: 6093: 6086: 6079: 6065: 6061: 6038: 6034: 6011: 6007: 6000: 5974: 5970: 5947: 5943: 5912: 5908: 5885:10.1038/nrd3228 5869: 5865: 5858: 5844: 5840: 5808: 5799: 5795: 5788: 5774: 5770: 5747:(11): 360–367. 5733: 5729: 5684: 5680: 5648: 5642: 5638: 5599: 5595: 5575:Organometallics 5570: 5566: 5526: 5522: 5469: 5462: 5439: 5435: 5428: 5414: 5410: 5363: 5359: 5319: 5315: 5309: 5305: 5278: 5274: 5267: 5245: 5241: 5217: 5213: 5209: 5205: 5201: 5196: 5192: 5185: 5171: 5167: 5160: 5134: 5130: 5119: 5115: 5090: 5086: 5079: 5065: 5061: 5040:(30): 827–833. 5028: 5021: 5010: 5003: 4978: 4971: 4956: 4935:(11): 614–621. 4925: 4921: 4914: 4900: 4896: 4866: 4862: 4858: 4854: 4849: 4845: 4806: 4802: 4778: 4772: 4768: 4723: 4719: 4682: 4678: 4639: 4635: 4604: 4600: 4593: 4579: 4575: 4568: 4554: 4550: 4527: 4523: 4507: 4506: 4502: 4480: 4476: 4449:Organometallics 4445: 4441: 4401: 4397: 4366: 4362: 4333: 4326: 4294: 4290: 4266: 4262: 4255: 4241: 4237: 4230: 4214: 4210: 4203: 4187: 4183: 4158: 4154: 4147: 4125:Crabtree, R. H. 4122: 4118: 4107: 4100: 4089: 4085: 4054: 4050: 4043: 4021: 4017: 4010: 3996: 3985: 3963: 3952: 3948: 3944: 3940: 3935: 3931: 3908: 3904: 3897: 3883: 3879: 3848: 3844: 3837: 3823: 3819: 3796: 3792: 3785: 3771: 3764: 3757: 3747:Organometallics 3743: 3728: 3723: 3709: 3700: 3693: 3681:Reppe chemistry 3662:methyl radicals 3656: 3653: 3652: 3651: 3649: 3643: 3635: 3631: 3627: 3476: 3445: 3441: 3415: 3411: 3407: 3399: 3395: 3391: 3359: 3293:poisoning with 3282:carbon monoxide 3278: 3269: 3263: 3244: 3225: 3221: 3217: 3213: 3188: 3181: 3177: 3173: 3168: 3157: 3151: 3139: 3127: 3115:hydrogen iodide 3029: 3025: 3021: 3017: 3013: 3009: 2972: 2921: 2908: 2901: 2897: 2892: 2858: 2782: 2775:are not stable. 2774: 2770: 2765: 2752: 2748: 2741: 2737: 2730: 2726: 2719: 2715: 2708: 2704: 2698: 2694: 2683: 2679: 2672: 2668: 2661: 2657: 2650: 2646: 2639: 2632: 2625: 2612: 2608: 2602: 2598: 2593: 2589: 2569: 2562: 2555: 2548: 2535: 2529: 2525: 2515: 2504: 2482: 2470: 2466: 2462: 2458: 2452:antiknock agent 2448: 2444: 2440: 2436: 2429: 2421: 2417: 2413: 2409: 2397: 2393: 2389: 2385: 2356: 2318: 2303: 2296: 2263: 2250:. For example, 2244: 2237: 2233: 2229: 2225: 2210: 2206: 2194: 2190: 2173:reducing agents 2169: 2154: 2147: 2138: 2132: 2099: 2092: 2082: 2075: 2037:photochemically 2033: 2031:CO substitution 2021: 1997: 1991: 1958: 1954: 1948: 1940: 1936: 1932: 1928: 1920: 1916: 1912: 1908: 1900: 1898:Salt metathesis 1884: 1880: 1847: 1843: 1839: 1835: 1831: 1827: 1823: 1819: 1811: 1807: 1803: 1795: 1791: 1775: 1745: 1741: 1737: 1733: 1729: 1709: 1701: 1698: 1697: 1696: 1693: 1688: 1685: 1684: 1683: 1681: 1675: 1672: 1671: 1670: 1666: 1663: 1662: 1661: 1658: 1651: 1648: 1645: 1644: 1642: 1629: 1625: 1616: 1613: 1610: 1609: 1607: 1602: 1598: 1551: 1547: 1541: 1537: 1533: 1529: 1525: 1521: 1495: 1491: 1487: 1442: 1433:carbon monoxide 1424: 1423: 1414: 1413: 1404:carbon monoxide 1393: 1384: 1378:and signaling. 1317:Galactic Center 1301:carbonyl ligand 1289: 1252: 1216: 1210: 1209: 1208: 1206: 1201: 1196: 1195: 1194: 1192: 1172: 1137: 1120: 1116: 1100: 1096: 1080: 1076: 1067: 1060: 1051: 1044: 1035: 1028: 1001: 984: 964: 955: 938: 935: 934: 933: 931: 914: 911: 910: 909: 907: 890: 870:(paramagnetic) 861: 858: 857: 856: 854: 834: 831: 830: 829: 827: 797: 778: 774: 768: 761: 755:, but only the 754: 747: 740: 734:, transform as 732: 725:direct products 711: 708:uses the Ni(CO) 703: 687: 680: 660: 633: 626: 622: 589: 558: 554: 541: 534: 527: 516: 505: 504: 503: 500: 483: 479: 474: 466: 460: 456: 445: 437: 425: 421: 416: 408: 402: 398: 397: 395: 392: 391: 385: 381: 377: 270: 251: 244: 237: 230: 226: 222: 218: 214: 210: 206: 202: 194: 146: 120: 81:Reppe chemistry 62:carbon monoxide 50:Metal carbonyls 28: 23: 22: 15: 12: 11: 5: 8478: 8468: 8467: 8462: 8457: 8452: 8435: 8434: 8432: 8431: 8426: 8421: 8416: 8411: 8406: 8400: 8398: 8394: 8393: 8391: 8390: 8385: 8379: 8377: 8376:Nanostructures 8373: 8372: 8370: 8369: 8364: 8359: 8354: 8349: 8344: 8337: 8335: 8331: 8330: 8328: 8327: 8322: 8318: 8314: 8310: 8306: 8302: 8298: 8294: 8290: 8286: 8282: 8278: 8274: 8270: 8265: 8260: 8256: 8252: 8248: 8244: 8240: 8236: 8232: 8228: 8224: 8220: 8215: 8209: 8207: 8203: 8202: 8191: 8190: 8183: 8176: 8168: 8159: 8158: 8153: 8152: 8149: 8146: 8143: 8140: 8137: 8134: 8131: 8128: 8125: 8122: 8119: 8116: 8113: 8110: 8106: 8105: 8102: 8099: 8096: 8093: 8090: 8087: 8084: 8081: 8078: 8075: 8072: 8069: 8066: 8062: 8058: 8054: 8053: 8050: 8047: 8046: 8043: 8040: 8037: 8034: 8031: 8028: 8025: 8022: 8019: 8016: 8013: 8010: 8006: 8002: 7999: 7996: 7993: 7990: 7987: 7983: 7982: 7979: 7976: 7973: 7970: 7967: 7964: 7961: 7958: 7955: 7951: 7947: 7943: 7939: 7935: 7928: 7921: 7917: 7910: 7906: 7902: 7895: 7891: 7887: 7883: 7879: 7875: 7871: 7867: 7860: 7856: 7853: 7850: 7847: 7844: 7840: 7836: 7832: 7831: 7828: 7825: 7822: 7819: 7816: 7813: 7810: 7806: 7802: 7798: 7794: 7790: 7786: 7779: 7775: 7768: 7764: 7760: 7756: 7749: 7745: 7738: 7734: 7730: 7723: 7719: 7715: 7711: 7707: 7703: 7696: 7692: 7689: 7686: 7682: 7678: 7676: 7672: 7668: 7664: 7663: 7660: 7655: 7651: 7646: 7643: 7640: 7637: 7634: 7628: 7624: 7620: 7616: 7612: 7608: 7601: 7594: 7590: 7583: 7579: 7575: 7573: 7572: 7565: 7561: 7557: 7553: 7549: 7545: 7541: 7536: 7534: 7530: 7523: 7519: 7515: 7511: 7507: 7503: 7496: 7492: 7488: 7481: 7477: 7473: 7466: 7462: 7458: 7454: 7447: 7440: 7436: 7432: 7428: 7426: 7422: 7418: 7414: 7413: 7410: 7406: 7398: 7394: 7389: 7384: 7381: 7378: 7374: 7370: 7366: 7362: 7358: 7357: 7354: 7350: 7338: 7334: 7329: 7324: 7316: 7309: 7305: 7300: 7296: 7292: 7288: 7284: 7280: 7279: 7276: 7274: 7272: 7270: 7265: 7258: 7257: 7254: 7253: 7249:Metal carbonyl 7245: 7244: 7237: 7230: 7222: 7213: 7212: 7210: 7209: 7204: 7199: 7194: 7190: 7186: 7180: 7178: 7177:Halide donors: 7174: 7173: 7171: 7170: 7162: 7157: 7153: 7149: 7145: 7141: 7137: 7133: 7129: 7125: 7121: 7117: 7112: 7108: 7103: 7099: 7095: 7090: 7088: 7084: 7083: 7081: 7080: 7076: 7072: 7068: 7064: 7060: 7056: 7052: 7048: 7043: 7039: 7035: 7031: 7027: 7023: 7019: 7014: 7009: 7005: 7000: 6996: 6992: 6988: 6984: 6980: 6976: 6972: 6968: 6964: 6960: 6955: 6950: 6945: 6941: 6936: 6931: 6929: 6925: 6924: 6922: 6921: 6917: 6913: 6909: 6904: 6902: 6898: 6897: 6895: 6894: 6886: 6882: 6878: 6873: 6869: 6865: 6860: 6855: 6850: 6845: 6840: 6835: 6830: 6826: 6822: 6817: 6812: 6807: 6803: 6799: 6795: 6790: 6788: 6784: 6783: 6781: 6780: 6775: 6771: 6767: 6763: 6758: 6756: 6752: 6751: 6749: 6748: 6744: 6740: 6736: 6732: 6728: 6724: 6719: 6715: 6711: 6706: 6702: 6698: 6694: 6690: 6686: 6682: 6677: 6673: 6669: 6664: 6659: 6655: 6651: 6647: 6642: 6638: 6634: 6630: 6626: 6622: 6618: 6614: 6610: 6606: 6602: 6597: 6592: 6586: 6584: 6580: 6579: 6577: 6576: 6572: 6568: 6564: 6560: 6555: 6553: 6549: 6548: 6546: 6545: 6541: 6537: 6531: 6529: 6525: 6524: 6517: 6516: 6509: 6502: 6494: 6488: 6487: 6480: 6479:External links 6477: 6474: 6473: 6438: 6423: 6416: 6406: 6395: 6388: 6367: 6326: 6285: 6262: 6255: 6228: 6197: 6172: 6137: 6130: 6112: 6105: 6084: 6077: 6059: 6032: 6005: 5998: 5968: 5941: 5922:(4): 935–992. 5906: 5863: 5856: 5838: 5819:(8): 677–690. 5793: 5786: 5768: 5727: 5678: 5646: 5636: 5593: 5564: 5520: 5460: 5433: 5426: 5408: 5357: 5328:(4): 588–602. 5317: 5313: 5303: 5272: 5265: 5239: 5215: 5211: 5207: 5203: 5199: 5190: 5183: 5165: 5158: 5128: 5113: 5102:(3): 256–268. 5084: 5077: 5059: 5019: 5001: 4990:(4): 113–122. 4954: 4919: 4912: 4894: 4864: 4860: 4856: 4852: 4843: 4800: 4766: 4752:10.1086/177049 4737:(1): 210–222. 4717: 4696:(3): 355–366. 4676: 4633: 4614:(4): 944–950. 4598: 4591: 4573: 4566: 4560:. de Gruyter. 4548: 4537:(6): 639–658. 4521: 4500: 4474: 4439: 4404:Fe, Ru, Os)". 4395: 4360: 4347:(2): 271–274. 4324: 4288: 4260: 4253: 4235: 4228: 4208: 4201: 4181: 4170:(3): 313–348. 4152: 4145: 4116: 4098: 4083: 4048: 4041: 4015: 4008: 3983: 3961: 3950: 3946: 3942: 3938: 3929: 3902: 3895: 3877: 3858:(3): 235–237. 3842: 3835: 3817: 3790: 3783: 3762: 3755: 3725: 3724: 3722: 3719: 3718: 3717: 3712: 3703: 3692: 3689: 3677:carbonylations 3654: 3641: 3633: 3629: 3623: 3523:Alwin Mittasch 3474: 3458:Solvay process 3446:) was formed. 3443: 3439: 3436:platinum black 3413: 3409: 3405: 3397: 3393: 3389: 3358: 3355: 3304:Inhalation of 3277: 3274: 3267: 3261: 3243: 3240: 3228: 3227: 3223: 3219: 3215: 3211: 3187: 3184: 3179: 3175: 3171: 3166: 3153:Main article: 3150: 3147: 3138: 3135: 3126: 3123: 3096: 3095: 3087: 3086: 3071: 3070: 3036:2-ethylhexanol 3032: 3031: 3027: 3023: 3019: 3015: 3011: 3007: 2971: 2968: 2920: 2917: 2907: 2904: 2899: 2895: 2891: 2888: 2887: 2886: 2880: 2874: 2868: 2857: 2854: 2834: 2833: 2827: 2818: 2812: 2806: 2800: 2781: 2778: 2777: 2776: 2772: 2768: 2763: 2755: 2750: 2746: 2739: 2735: 2728: 2724: 2717: 2713: 2706: 2702: 2696: 2692: 2686: 2681: 2677: 2670: 2666: 2659: 2655: 2648: 2644: 2637: 2630: 2623: 2615: 2610: 2606: 2600: 2596: 2591: 2587: 2579: 2567: 2560: 2553: 2546: 2538: 2533: 2527: 2523: 2517: 2513: 2507: 2502: 2481: 2478: 2468: 2464: 2460: 2456: 2446: 2442: 2438: 2434: 2428: 2425: 2424: 2423: 2419: 2415: 2411: 2407: 2400: 2399: 2395: 2391: 2387: 2383: 2355: 2352: 2336:Meerwein salts 2321: 2320: 2316: 2305: 2304: 2301: 2298: 2294: 2261: 2243: 2240: 2239: 2238: 2235: 2231: 2227: 2223: 2213: 2212: 2208: 2204: 2197: 2196: 2192: 2188: 2181:sodium amalgam 2168: 2165: 2157: 2156: 2149: 2143: 2140: 2134: 2128: 2102: 2101: 2094: 2087: 2084: 2077: 2071: 2032: 2029: 2020: 2017: 2001: 2000: 1995: 1989: 1956: 1952: 1947: 1944: 1943: 1942: 1938: 1934: 1930: 1926: 1925:4 KCo(CO) 1918: 1914: 1910: 1906: 1899: 1896: 1882: 1878: 1845: 1841: 1837: 1833: 1829: 1825: 1821: 1817: 1814: 1813: 1809: 1805: 1801: 1793: 1789: 1774: 1771: 1751:carbon dioxide 1747: 1746: 1743: 1739: 1735: 1731: 1727: 1716:reducing agent 1712: 1711: 1707: 1699: 1686: 1673: 1664: 1631: 1630: 1627: 1623: 1604: 1600: 1596: 1554: 1553: 1549: 1545: 1539: 1535: 1531: 1527: 1523: 1519: 1497: 1496: 1493: 1489: 1485: 1441: 1438: 1429: 1428: 1421: 1418: 1417:(1 bar, 55 °C) 1411: 1392: 1389: 1383: 1380: 1376:toxicity of CO 1366:. The enzymes 1299:, showing the 1288: 1285: 1279:combined with 1255: 1254: 1248: 1241:metallaformate 1229:derivatization 1222: 1221: 1211: 1197: 1171: 1168: 1149:chemical shift 1136: 1133: 1130: 1129: 1126: 1124: 1121: 1118: 1114: 1110: 1109: 1107: 1104: 1101: 1098: 1094: 1090: 1089: 1087: 1084: 1081: 1078: 1074: 1070: 1069: 1065: 1058: 1053: 1049: 1042: 1037: 1033: 1026: 1021: 1013: 1012: 1009: 1006: 1004: 1002: 999: 995: 994: 992: 990: 988: 985: 982: 978: 977: 974: 971: 968: 965: 962: 958: 957: 953: 950: 947: 945: 942: 936: 928: 927: 925: 923: 921: 918: 912: 904: 903: 900: 897: 894: 891: 888: 884: 883: 881: 878: 871: 868: 865: 859: 851: 850: 847: 844: 841: 838: 832: 824: 823: 821: 819: 816: 813: 809: 808: 805: 802: 799: 795: 792: 776: 772: 766: 759: 752: 745: 738: 730: 709: 701: 685: 678: 659: 656: 637:chemical shift 631: 624: 620: 588: 585: 556: 552: 540: 537: 532: 525: 514: 501: 486: 477: 469: 463: 455: 448: 440: 433: 428: 419: 411: 405: 390: 389: 388: 383: 379: 375: 338:sigma (σ) bond 269: 266: 265: 264: 249: 242: 235: 228: 224: 220: 216: 212: 208: 204: 200: 192: 144: 119: 116: 26: 9: 6: 4: 3: 2: 8477: 8466: 8463: 8461: 8458: 8456: 8453: 8451: 8448: 8447: 8445: 8430: 8427: 8425: 8422: 8420: 8419:Carbonic acid 8417: 8415: 8412: 8410: 8407: 8405: 8402: 8401: 8399: 8395: 8389: 8386: 8384: 8381: 8380: 8378: 8374: 8368: 8367:Thiofulminate 8365: 8363: 8360: 8358: 8355: 8353: 8350: 8348: 8345: 8342: 8339: 8338: 8336: 8332: 8326: 8323: 8321: 8311: 8309: 8299: 8297: 8291: 8289: 8283: 8281: 8271: 8269: 8266: 8264: 8261: 8259: 8253: 8251: 8245: 8243: 8237: 8235: 8229: 8227: 8221: 8219: 8216: 8214: 8211: 8210: 8208: 8204: 8199: 8196: 8189: 8184: 8182: 8177: 8175: 8170: 8169: 8166: 8150: 8147: 8144: 8141: 8138: 8135: 8132: 8129: 8126: 8123: 8120: 8117: 8114: 8111: 8108: 8107: 8103: 8100: 8097: 8094: 8091: 8088: 8085: 8082: 8079: 8076: 8073: 8070: 8067: 8065: 8059: 8056: 8055: 8048: 8044: 8041: 8038: 8035: 8032: 8029: 8026: 8023: 8020: 8017: 8014: 8011: 8009: 8003: 8000: 7997: 7994: 7991: 7988: 7985: 7984: 7980: 7977: 7974: 7971: 7968: 7965: 7962: 7959: 7956: 7954: 7944: 7942: 7931: 7924: 7913: 7907: 7905: 7898: 7888: 7886: 7863: 7857: 7854: 7851: 7848: 7845: 7843: 7837: 7834: 7833: 7829: 7826: 7823: 7820: 7817: 7814: 7811: 7809: 7807: 7805: 7799: 7797: 7782: 7771: 7761: 7759: 7752: 7741: 7735: 7733: 7726: 7716: 7714: 7699: 7693: 7690: 7687: 7685: 7679: 7677: 7675: 7669: 7666: 7665: 7661: 7659: 7652: 7650: 7647: 7644: 7641: 7638: 7635: 7633: 7625: 7623: 7617: 7615: 7604: 7597: 7586: 7576: 7571: 7570: 7566: 7564: 7558: 7556: 7546: 7544: 7538: 7537: 7535: 7533: 7526: 7516: 7514: 7499: 7493: 7491: 7484: 7469: 7463: 7461: 7450: 7443: 7437: 7435: 7429: 7427: 7425: 7419: 7416: 7415: 7411: 7409: 7402: 7395: 7393: 7390: 7388: 7385: 7382: 7379: 7377: 7363: 7360: 7359: 7355: 7353: 7346: 7342: 7335: 7333: 7330: 7328: 7325: 7323: 7319: 7312: 7306: 7304: 7297: 7295: 7285: 7282: 7281: 7277: 7271: 7269: 7262: 7261: 7255: 7250: 7243: 7238: 7236: 7231: 7229: 7224: 7223: 7220: 7208: 7205: 7203: 7200: 7198: 7195: 7193: 7187: 7185: 7182: 7181: 7179: 7175: 7169: 7168: 7163: 7161: 7154: 7152: 7142: 7140: 7134: 7132: 7118: 7116: 7109: 7107: 7104: 7102: 7092: 7091: 7089: 7085: 7079: 7073: 7071: 7065: 7063: 7057: 7055: 7049: 7047: 7036: 7034: 7028: 7026: 7020: 7018: 7015: 7013: 7006: 7004: 7001: 6999: 6993: 6991: 6981: 6979: 6969: 6967: 6961: 6959: 6956: 6954: 6951: 6949: 6942: 6940: 6933: 6932: 6930: 6926: 6920: 6914: 6912: 6906: 6905: 6903: 6899: 6893: 6891: 6887: 6885: 6879: 6877: 6866: 6864: 6861: 6859: 6856: 6854: 6851: 6849: 6846: 6844: 6841: 6839: 6836: 6834: 6831: 6829: 6823: 6821: 6818: 6816: 6813: 6811: 6808: 6806: 6800: 6798: 6792: 6791: 6789: 6785: 6779: 6772: 6770: 6760: 6759: 6757: 6753: 6747: 6737: 6735: 6725: 6723: 6720: 6718: 6712: 6710: 6707: 6705: 6695: 6693: 6683: 6681: 6678: 6676: 6670: 6668: 6665: 6663: 6660: 6658: 6648: 6646: 6639: 6637: 6627: 6625: 6615: 6613: 6603: 6601: 6598: 6596: 6593: 6591: 6588: 6587: 6585: 6581: 6575: 6565: 6563: 6557: 6556: 6554: 6550: 6544: 6538: 6536: 6533: 6532: 6530: 6526: 6522: 6515: 6510: 6508: 6503: 6501: 6496: 6495: 6492: 6486: 6483: 6482: 6469: 6465: 6461: 6457: 6453: 6449: 6442: 6434: 6427: 6419: 6413: 6409: 6399: 6391: 6385: 6381: 6377: 6371: 6362: 6357: 6353: 6349: 6345: 6341: 6337: 6330: 6322: 6309: 6302:: 3315. 1908. 6301: 6297: 6296: 6289: 6281: 6277: 6276:Chemical News 6273: 6266: 6258: 6252: 6248: 6247: 6242: 6238: 6232: 6224: 6220: 6216: 6212: 6208: 6201: 6193: 6189: 6188: 6183: 6176: 6168: 6164: 6160: 6156: 6152: 6148: 6141: 6133: 6127: 6123: 6116: 6108: 6102: 6098: 6091: 6089: 6080: 6074: 6070: 6063: 6055: 6051: 6047: 6043: 6036: 6028: 6024: 6020: 6016: 6009: 6001: 5995: 5991: 5987: 5983: 5979: 5972: 5964: 5960: 5956: 5952: 5945: 5937: 5933: 5929: 5925: 5921: 5917: 5910: 5902: 5898: 5894: 5890: 5886: 5882: 5879:(9): 728–43. 5878: 5874: 5867: 5859: 5853: 5849: 5842: 5834: 5830: 5826: 5822: 5818: 5814: 5807: 5803: 5797: 5789: 5783: 5779: 5772: 5764: 5760: 5755: 5750: 5746: 5742: 5738: 5731: 5723: 5719: 5714: 5709: 5705: 5701: 5697: 5693: 5689: 5682: 5674: 5670: 5666: 5662: 5658: 5654: 5653: 5640: 5632: 5628: 5624: 5620: 5616: 5612: 5608: 5604: 5597: 5589: 5585: 5581: 5577: 5576: 5568: 5560: 5556: 5552: 5548: 5544: 5540: 5536: 5532: 5524: 5516: 5512: 5508: 5504: 5499: 5494: 5490: 5486: 5482: 5478: 5474: 5467: 5465: 5456: 5452: 5448: 5444: 5437: 5429: 5423: 5419: 5412: 5404: 5400: 5396: 5392: 5388: 5384: 5380: 5376: 5372: 5368: 5361: 5353: 5349: 5344: 5339: 5335: 5331: 5327: 5323: 5307: 5299: 5295: 5291: 5287: 5283: 5276: 5268: 5262: 5258: 5254: 5250: 5243: 5235: 5231: 5227: 5223: 5222: 5194: 5186: 5184:0-935702-48-2 5180: 5176: 5169: 5161: 5155: 5151: 5147: 5143: 5139: 5132: 5124: 5117: 5109: 5105: 5101: 5097: 5096: 5088: 5080: 5074: 5070: 5063: 5055: 5051: 5047: 5043: 5039: 5035: 5034: 5026: 5024: 5015: 5008: 5006: 4997: 4993: 4989: 4985: 4982: 4977: 4969: 4967: 4965: 4963: 4961: 4959: 4950: 4946: 4942: 4938: 4934: 4930: 4923: 4915: 4909: 4905: 4898: 4890: 4886: 4882: 4878: 4874: 4870: 4847: 4839: 4835: 4831: 4827: 4823: 4819: 4815: 4811: 4804: 4796: 4792: 4789:: 1457–1458. 4788: 4784: 4777: 4770: 4762: 4758: 4753: 4748: 4744: 4740: 4736: 4732: 4728: 4721: 4713: 4709: 4704: 4699: 4695: 4691: 4687: 4680: 4672: 4668: 4664: 4660: 4656: 4652: 4648: 4644: 4637: 4629: 4625: 4621: 4617: 4613: 4609: 4602: 4594: 4588: 4584: 4577: 4569: 4563: 4559: 4552: 4544: 4540: 4536: 4532: 4525: 4517: 4511: 4503: 4497: 4493: 4489: 4485: 4478: 4470: 4466: 4462: 4458: 4454: 4450: 4443: 4435: 4431: 4427: 4423: 4419: 4415: 4411: 4407: 4399: 4391: 4387: 4383: 4379: 4375: 4371: 4364: 4355: 4350: 4346: 4342: 4338: 4331: 4329: 4320: 4316: 4312: 4308: 4304: 4300: 4292: 4284: 4280: 4276: 4272: 4264: 4256: 4250: 4246: 4239: 4231: 4225: 4221: 4220: 4212: 4204: 4198: 4194: 4193: 4185: 4177: 4173: 4169: 4165: 4164: 4156: 4148: 4142: 4138: 4134: 4130: 4126: 4120: 4112: 4105: 4103: 4094: 4087: 4079: 4075: 4071: 4067: 4063: 4059: 4052: 4044: 4038: 4034: 4030: 4026: 4019: 4011: 4005: 4001: 3994: 3992: 3990: 3988: 3979: 3975: 3971: 3967: 3960: 3956: 3933: 3925: 3921: 3917: 3913: 3906: 3898: 3892: 3888: 3881: 3873: 3869: 3865: 3861: 3857: 3853: 3846: 3838: 3832: 3828: 3821: 3813: 3809: 3805: 3801: 3794: 3786: 3780: 3776: 3769: 3767: 3758: 3752: 3748: 3741: 3739: 3737: 3735: 3733: 3731: 3726: 3716: 3713: 3707: 3704: 3698: 3695: 3694: 3688: 3686: 3682: 3678: 3673: 3671: 3667: 3663: 3647: 3639: 3626: 3615: 3611: 3609: 3605: 3601: 3597: 3593: 3589: 3585: 3581: 3577: 3569: 3564: 3560: 3558: 3554: 3550: 3546: 3545:Walter Hieber 3542: 3540: 3536: 3532: 3528: 3527:carbonyl iron 3524: 3520: 3515: 3511: 3507: 3503: 3499: 3495: 3491: 3487: 3482: 3480: 3472: 3467: 3463: 3459: 3455: 3451: 3447: 3437: 3433: 3425: 3421: 3417: 3403: 3402:acetylenediol 3387: 3383: 3379: 3375: 3367: 3363: 3354: 3350: 3347: 3343: 3339: 3335: 3331: 3327: 3323: 3319: 3315: 3312:similar to a 3311: 3308:causes acute 3307: 3302: 3300: 3296: 3291: 3287: 3283: 3273: 3271: 3259: 3257: 3252: 3248: 3239: 3237: 3233: 3230:Complexes of 3209: 3208: 3207: 3205: 3201: 3197: 3193: 3183: 3169: 3162: 3156: 3146: 3144: 3134: 3131: 3122: 3120: 3116: 3112: 3108: 3104: 3099: 3093: 3089: 3088: 3084: 3080: 3079: 3078: 3076: 3068: 3064: 3063: 3062: 3060: 3056: 3052: 3048: 3044: 3041: 3037: 3005: 3004: 3003: 3001: 2997: 2996:butyraldehyde 2993: 2989: 2985: 2981: 2977: 2976:carbonylation 2967: 2965: 2961: 2957: 2953: 2949: 2945: 2941: 2940:carbonyl iron 2936: 2934: 2930: 2926: 2912: 2903: 2884: 2881: 2878: 2875: 2872: 2869: 2866: 2863: 2860: 2859: 2853: 2851: 2847: 2843: 2839: 2831: 2828: 2825: 2822: 2819: 2816: 2813: 2810: 2807: 2804: 2801: 2798: 2795:, as well as 2794: 2790: 2787: 2784: 2783: 2766: 2759: 2756: 2753: 2742: 2731: 2720: 2709: 2690: 2687: 2684: 2673: 2662: 2651: 2640: 2633: 2626: 2619: 2616: 2613: 2594: 2583: 2580: 2577: 2575: 2570: 2563: 2556: 2549: 2542: 2539: 2536: 2521: 2518: 2511: 2508: 2505: 2498: 2494: 2490: 2487: 2484: 2483: 2477: 2475: 2471: 2453: 2449: 2405: 2404: 2403: 2381: 2380: 2379: 2377: 2373: 2369: 2365: 2364:electrophiles 2361: 2347: 2343: 2341: 2337: 2333: 2329: 2325: 2314: 2313: 2312: 2310: 2299: 2292: 2291: 2290: 2288: 2284: 2280: 2276: 2275:hydroxide ion 2272: 2268: 2264: 2257: 2253: 2249: 2221: 2220: 2219: 2217: 2202: 2201: 2200: 2195:+ 2 Na → 2 Na 2186: 2185: 2184: 2182: 2178: 2174: 2164: 2162: 2152: 2146: 2141: 2137: 2131: 2126: 2125: 2124: 2122: 2117: 2115: 2111: 2107: 2097: 2090: 2085: 2080: 2074: 2069: 2068: 2067: 2065: 2060: 2058: 2054: 2051:, especially 2050: 2046: 2042: 2038: 2028: 2026: 2016: 2014: 2010: 2006: 1998: 1987: 1986: 1985: 1983: 1979: 1975: 1971: 1966: 1964: 1963: 1933:→ 2 RuCo 1924: 1923: 1922: 1904: 1895: 1893: 1889: 1885: 1874: 1870: 1866: 1862: 1858: 1854: 1849: 1799: 1798: 1797: 1787: 1783: 1779: 1770: 1768: 1764: 1760: 1756: 1752: 1725: 1724: 1723: 1721: 1717: 1704: 1678: 1640: 1639: 1638: 1636: 1605: 1603:+ 3 NaCl 1594: 1593: 1592: 1590: 1586: 1582: 1578: 1574: 1570: 1566: 1562: 1558: 1552: 1538:+ 2 AlCl 1517: 1516: 1515: 1513: 1510: 1506: 1502: 1483: 1482: 1481: 1479: 1475: 1471: 1467: 1463: 1459: 1455: 1451: 1450:metal halides 1447: 1437: 1434: 1419: 1409: 1408: 1407: 1405: 1401: 1397: 1388: 1379: 1377: 1373: 1369: 1365: 1361: 1356: 1354: 1351:of municipal 1350: 1349:sewage sludge 1346: 1342: 1337: 1332: 1330: 1326: 1322: 1318: 1310: 1306: 1302: 1298: 1293: 1284: 1282: 1278: 1274: 1272: 1268: 1264: 1260: 1253:M(CO) + RO → 1251: 1246: 1245: 1244: 1242: 1238: 1234: 1230: 1226: 1214: 1200: 1191: 1190: 1189: 1188: = 28). 1187: 1186: 1182: 1176: 1167: 1165: 1160: 1158: 1153: 1150: 1146: 1142: 1127: 1125: 1122: 1112: 1111: 1108: 1105: 1102: 1092: 1091: 1088: 1085: 1082: 1072: 1071: 1064: 1057: 1054: 1048: 1041: 1038: 1032: 1025: 1022: 1019: 1018: 1010: 1007: 1005: 1003: 997: 996: 993: 991: 989: 986: 980: 979: 975: 972: 969: 966: 960: 959: 951: 948: 946: 943: 930: 929: 926: 924: 922: 919: 906: 905: 901: 898: 895: 892: 886: 885: 882: 879: 876: 872: 869: 866: 853: 852: 848: 845: 842: 839: 826: 825: 822: 820: 817: 814: 811: 810: 806: 803: 800: 793: 790: 789: 786: 784: 779: 765: 758: 751: 744: 737: 733: 726: 722: 718: 713: 707: 699: 695: 691: 690:π-backbonding 684: 677: 673: 664: 655: 653: 644: 640: 638: 630: 618: 614: 610: 606: 602: 593: 584: 582: 578: 574: 570: 569:diethyl ether 566: 562: 550: 546: 536: 531: 524: 520: 513: 509: 484: 475: 467: 461: 446: 438: 426: 417: 409: 403: 387: 373: 368: 363: 359: 355: 351: 347: 343: 342:sp-hybridized 339: 335: 327: 326:π backbonding 322: 316: 313: 308: 301: 297: 292: 286: 283: 280:) of CO is a 279: 274: 262: 258: 257: 256: 254: 248: 241: 234: 198: 191: 186: 184: 180: 176: 171: 169: 165: 161: 157: 153: 148: 142: 138: 134: 130: 126: 115: 113: 109: 105: 100: 98: 94: 90: 86: 82: 78: 74: 70: 66: 63: 59: 55: 51: 43: 36: 32: 19: 8424:Bicarbonates 8413: 7568: 7248: 7166: 6889: 6666: 6451: 6447: 6441: 6426: 6404: 6398: 6379: 6370: 6343: 6339: 6329: 6317:|title= 6308:cite journal 6299: 6293: 6288: 6279: 6275: 6265: 6245: 6231: 6214: 6210: 6200: 6191: 6185: 6175: 6150: 6146: 6140: 6121: 6115: 6096: 6068: 6062: 6045: 6041: 6035: 6018: 6014: 6008: 5977: 5971: 5954: 5950: 5944: 5919: 5915: 5909: 5876: 5872: 5866: 5847: 5841: 5816: 5812: 5796: 5777: 5771: 5744: 5740: 5730: 5695: 5691: 5681: 5656: 5650: 5639: 5606: 5602: 5596: 5579: 5573: 5567: 5534: 5530: 5523: 5480: 5476: 5446: 5442: 5436: 5417: 5411: 5370: 5366: 5360: 5325: 5321: 5306: 5289: 5285: 5281: 5275: 5248: 5242: 5225: 5219: 5193: 5174: 5168: 5137: 5131: 5122: 5116: 5099: 5093: 5087: 5068: 5062: 5037: 5031: 5013: 4987: 4974: 4932: 4928: 4922: 4903: 4897: 4875:(1): 33–37. 4872: 4868: 4846: 4813: 4809: 4803: 4786: 4782: 4769: 4734: 4730: 4720: 4693: 4689: 4679: 4649:(2): 63–74. 4646: 4642: 4636: 4611: 4607: 4601: 4582: 4576: 4557: 4551: 4534: 4530: 4524: 4483: 4477: 4452: 4448: 4442: 4409: 4405: 4398: 4373: 4369: 4363: 4344: 4340: 4302: 4298: 4291: 4274: 4270: 4263: 4244: 4238: 4218: 4211: 4191: 4184: 4167: 4161: 4155: 4128: 4119: 4110: 4092: 4086: 4061: 4057: 4051: 4024: 4018: 3999: 3969: 3965: 3958: 3954: 3932: 3915: 3911: 3905: 3886: 3880: 3855: 3851: 3845: 3826: 3820: 3803: 3799: 3793: 3774: 3746: 3674: 3637: 3624: 3620: 3604:acrylic acid 3576:Walter Reppe 3573: 3543: 3494:Mond process 3483: 3448: 3429: 3426:, circa 1909 3386:benzenehexol 3381: 3371: 3351: 3303: 3279: 3255: 3245: 3229: 3204:thiophosgene 3189: 3158: 3140: 3128: 3100: 3097: 3072: 3055:atom economy 3043:plasticizers 3033: 2973: 2937: 2929:Mond process 2922: 2906:Applications 2893: 2835: 2573: 2433:IrCl(CO)(P(C 2430: 2401: 2372:halogenation 2357: 2327: 2322: 2315:+ H → Re(CO) 2306: 2248:nucleophiles 2245: 2234:Co−Hg−Co(CO) 2214: 2198: 2170: 2158: 2150: 2144: 2135: 2129: 2118: 2103: 2095: 2088: 2078: 2072: 2061: 2034: 2025:substitution 2022: 2002: 1967: 1960: 1949: 1901: 1877:IrCl(CO)(PPh 1850: 1815: 1776: 1748: 1713: 1632: 1555: 1498: 1443: 1430: 1394: 1385: 1357: 1345:pyruvic acid 1333: 1314: 1304: 1275: 1256: 1249: 1223: 1212: 1198: 1184: 1180: 1173: 1161: 1157:fluxionality 1154: 1138: 1062: 1055: 1046: 1039: 1030: 1023: 763: 756: 749: 742: 735: 717:group theory 714: 682: 675: 669: 649: 628: 598: 542: 529: 522: 518: 511: 506: 358:pi (π) bonds 331: 252: 246: 239: 232: 196: 189: 187: 182: 178: 172: 149: 129:carbonylates 121: 101: 85:Mond process 49: 48: 8357:Thiocyanate 8334:Carbon ions 6237:Gratzer, W. 6217:: 749–753. 6153:(10): 453. 4979: [ 4863:, and W(CO) 3610:oxidation. 3514:James Dewar 3450:Ludwig Mond 3424:Ludwig Mond 3338:tachycardia 3290:instability 3247:Isocyanides 3111:acetic acid 2980:oxo process 2297:+ NaOH → Na 2230:+ Hg → (CO) 2207:+ 2 Na → Na 2133:+ L → M(CO) 2093:+ L → M(CO) 1782:thermolysis 1742:+ 7 CO 1505:diethylzinc 1360:hydrogenase 1123:2045, 2075 1086:1846, 1862 1083:2060, 2084 987:2038, 2002 967:2022, 2000 599:Apart from 362:antibonding 312:antibonding 8444:Categories 8429:Carbonates 8388:Fullerides 7627:(Cu(CO)Cl) 6838:amino acid 6755:Si donors: 6376:Basolo, F. 6282:: 165–166. 6194:: 188–192. 3721:References 3679:, such as 3512:. In 1906 3502:molybdenum 3316:, such as 3286:volatility 3276:Toxicology 3170:and Fe(NO) 3161:NO ligands 3051:detergents 2990:) to give 2931:(see also 2771:and Pt(CO) 2516:are known. 2418:→ 2 Mn(CO) 2338:, affords 2332:Alkylation 2041:phosphines 2009:superacids 1982:Lewis acid 1974:technetium 1871:(DMF) and 1778:Photolysis 1706:+ 3 H 1606:+ H → H → 1561:molybdenum 1271:molar mass 873:200, 193 ( 561:sublimable 378:and Mo(CO) 354:p-orbitals 195:or simply 177:, denoted 137:homoleptic 104:hemoglobin 75:, such as 8362:Fulminate 8206:Compounds 7607:HC(Co(CO) 7322:(HC=CH)CO 7315:(C=C)(CO) 7251:complexes 7087:S donors: 6928:O donors: 6901:P donors: 6863:porphyrin 6810:imidazole 6787:N donors: 6583:C donors: 6552:B donors: 6528:H donors: 5901:205477130 5802:Wilke, G. 5623:0020-1669 5551:1433-7851 5507:0036-8075 5387:1433-7851 4671:0022-2852 4531:Chem. Rev 4510:cite book 4469:0276-7333 4426:0020-1669 4390:0567-7408 4319:0002-7863 4222:. Wiley. 3608:propylene 3596:acetylene 3506:ruthenium 3378:potassium 3334:dizziness 3143:complexes 3018:+ CO → CH 3000:propylene 2992:aldehydes 2970:Catalysis 2962:, and in 2944:inductors 2842:palladium 2797:lanthanum 2493:strontium 2427:Compounds 2167:Reduction 2148:L → M(CO) 2019:Reactions 1970:manganese 1853:ruthenium 1692:+ 3  1585:chelating 1565:manganese 1542:+ 3  1446:reduction 1382:Synthesis 1336:oxidation 1321:Milky Way 1309:histidine 1020:Carbonyl 791:Compound 485:− 476:− 468:≡ 454:⟷ 432:⟷ 418:≡ 410:− 404:− 175:hapticity 83:. In the 8409:Nitrides 8341:Carbides 6468:19438209 6378:(2002). 6239:(2002). 5936:11942784 5893:20811383 5804:(1978). 5763:12462518 5722:33045113 5673:15934749 5631:24380416 5559:29578636 5515:30166489 5403:52145802 5395:30176109 5352:11456571 4949:16996273 4889:11529076 4859:, Mo(CO) 4855:, Fe(CO) 4838:10958777 4761:11539170 4628:12584710 4434:15934749 4078:14679508 3872:98463160 3691:See also 3646:isolobal 3432:chlorine 3342:cyanosis 3326:headache 3222:→ Fe(CO) 3165:CoNO(CO) 3133:organs. 3103:Monsanto 2948:pigments 2846:platinum 2789:scandium 2450:and the 2390:→ Fe(CO) 2011:such as 1840:up to Os 1800:2 Fe(CO) 1765:, where 1763:sulfides 1755:phosgene 1557:Tungsten 1462:hydrogen 1458:aluminum 1364:hydrogen 1343:such as 1311:residue. 1267:nitrogen 1261:to give 1237:alkoxide 1145:enriched 783:polarity 694:titanium 238:-CO and 223:, and Co 156:chromium 133:bridging 106:to give 8352:Cyanate 8347:Cyanide 8052:  7569:more... 6701:& C 6348:Bibcode 6155:Bibcode 5833:4596194 5713:7756819 5485:Bibcode 5477:Science 5042:Bibcode 4818:Bibcode 4810:Science 4791:Bibcode 4739:Bibcode 4712:9761903 4651:Bibcode 3964:-CO)". 3600:benzene 3584:alkynes 3531:pigment 3473:(Ni(CO) 3357:History 3101:In the 2927:by the 2793:yttrium 2489:calcium 2467:)Mn(CO) 2216:Mercury 2076:→ M(CO) 2049:Alkenes 2045:cyanide 2005:alkenes 1999:+ CO → 1978:rhenium 1865:iridium 1861:rhodium 1655:⁠ 1643:⁠ 1626:+ V(CO) 1622: H 1620:⁠ 1608:⁠ 1589:diglyme 1569:rhodium 1534:→ W(CO) 1474:benzene 1319:of the 1307:to the 952:112 (BF 573:acetone 565:benzene 143:(Ni(CO) 125:cations 65:ligands 8404:Oxides 8198:carbon 8061:La(CO) 8005:Sg(CO) 7927:Os(CO) 7909:Os(CO) 7901:Re(CO) 7839:Ba(CO) 7801:Pd(CO) 7755:Ru(CO) 7737:Ru(CO) 7729:Tc(CO) 7710:Mo(CO) 7695:Mo(CO) 7671:Sr(CO) 7619:Ni(CO) 7600:Co(CO) 7560:Fe(CO) 7540:Fe(CO) 7529:Mn(CO) 7510:Cr(CO) 7495:Cr(CO) 7457:Ti(CO) 7446:Ti(CO) 7439:Ti(CO) 7431:Sc(CO) 7421:Ca(CO) 7405:(ClCO) 7345:H(CO)F 6609:=CH-CH 6466:  6414:  6386:  6253:  6128:  6103:  6075:  5996:  5934:  5899:  5891:  5854:  5831:  5784:  5761:  5720:  5710:  5671:  5629:  5621:  5557:  5549:  5513:  5505:  5424:  5401:  5393:  5385:  5350:  5263:  5206:und Ru 5181:  5156:  5075:  4947:  4910:  4887:  4836:  4759:  4710:  4669:  4626:  4589:  4564:  4498:  4467:  4432:  4424:  4388:  4317:  4277:: 48. 4251:  4226:  4199:  4143:  4076:  4039:  4006:  3893:  3870:  3833:  3781:  3753:  3666:ethane 3640:Mn(CO) 3508:, and 3498:cobalt 3479:Kelvin 3466:burner 3462:nickel 3368:(1860) 3340:, and 3332:, and 3318:nausea 3218:+ CSCl 3214:Fe(CO) 2984:alkene 2844:, and 2838:nickel 2762:Ni(CO) 2732:, and 2652:, and 2636:Os(CO) 2629:Ru(CO) 2622:Fe(CO) 2603:, and 2576:effect 2566:Sg(CO) 2564:, and 2552:Mo(CO) 2545:Cr(CO) 2497:barium 2495:, and 2382:Fe(CO) 2293:Fe(CO) 2271:Hieber 2203:Fe(CO) 2177:sodium 2155:L + CO 2053:dienes 1988:Mn(CO) 1955:Fe(CO) 1863:, and 1857:osmium 1682:Co(CO) 1657:  1581:sodium 1567:, and 1512:alkane 1492:+ AlCl 1454:copper 1425:  1415:  998:Ni(CO) 981:Ru(CO) 961:Fe(CO) 956:salt) 932:Fe(CO) 908:Mn(CO) 887:Cr(CO) 877:salt) 828:Ti(CO) 748:, and 729:Cr(CO) 704:. The 579:, and 370:metal– 352:, and 164:nickel 112:oxygen 93:nickel 7859:W(CO) 7681:Y(CO) 7487:V(CO) 7480:V(CO) 7465:V(CO) 7349:(FCO) 7308:C(CO) 6600:HC(O) 6595:RC(O) 5897:S2CID 5829:S2CID 5809:(PDF) 5399:S2CID 4983:] 4779:(PDF) 3868:S2CID 3632:–, CH 3622:M(CO) 3588:acids 3330:fever 3322:cough 3202:with 3045:, by 3010:CH=CH 2998:from 2982:, an 2956:radar 2950:, as 2864:form 2559:W(CO) 2532:V(CO) 2501:M(CO) 2142:M(CO) 2127:M(CO) 2086:M(CO) 2070:M(CO) 1992:Cl + 1909:with 1641:Co + 1509:dimer 1305:trans 1259:azide 1207:M(CO) 1193:M(CO) 1128:1819 1106:1886 1068:(cm) 1052:(cm) 1036:(cm) 944:2204 920:2100 893:2000 867:1859 855:V(CO) 840:1748 815:2143 798:(cm) 372:alkyl 95:. In 60:with 8343:, , 7950:(CO) 7938:(CO) 7920:(CO) 7894:(CO) 7882:(CO) 7793:(CO) 7778:(CO) 7767:(CO) 7748:(CO) 7722:(CO) 7649:SeCO 7593:(CO) 7582:(CO) 7552:(CO) 7522:(CO) 7373:(CO) 7365:Mg(O 7291:(CO) 7003:acac 6975:/HCO 6858:bipy 6617:C(CH 6464:PMID 6412:ISBN 6384:ISBN 6321:help 6251:ISBN 6126:ISBN 6101:ISBN 6073:ISBN 5994:ISBN 5932:PMID 5889:PMID 5852:ISBN 5782:ISBN 5759:PMID 5718:PMID 5669:PMID 5627:PMID 5619:ISSN 5555:PMID 5547:ISSN 5511:PMID 5503:ISSN 5422:ISBN 5391:PMID 5383:ISSN 5348:PMID 5316:and 5261:ISBN 5214:(CO) 5202:(CO) 5179:ISBN 5154:ISBN 5073:ISBN 4945:PMID 4908:ISBN 4885:PMID 4834:PMID 4757:PMID 4708:PMID 4667:ISSN 4624:PMID 4587:ISBN 4562:ISBN 4516:link 4496:ISBN 4465:ISSN 4430:PMID 4422:ISSN 4386:ISSN 4315:ISSN 4249:ISBN 4224:ISBN 4197:ISBN 4141:ISBN 4074:PMID 4037:ISBN 4004:ISBN 3891:ISBN 3831:ISBN 3779:ISBN 3751:ISBN 3683:and 3537:and 3519:BASF 3297:and 3288:and 3253:and 3234:and 3174:(CO) 3105:and 2791:and 2749:(CO) 2738:(CO) 2727:(CO) 2716:(CO) 2705:(CO) 2695:(CO) 2680:(CO) 2674:and 2669:(CO) 2658:(CO) 2647:(CO) 2634:and 2609:(CO) 2599:(CO) 2595:, Tc 2590:(CO) 2526:(CO) 2414:+ Cl 2410:(CO) 2398:+ CO 2265:and 2254:and 2226:(CO) 2211:+ CO 2191:(CO) 2104:The 2083:+ CO 1994:AlCl 1976:and 1937:(CO) 1917:(CO) 1890:and 1844:(CO) 1836:(CO) 1832:, Os 1828:(CO) 1820:(CO) 1812:+ CO 1808:(CO) 1804:→ Fe 1792:(CO) 1738:(CO) 1503:and 1484:CrCl 1398:and 1370:and 1358:The 1220:+ CO 1162:The 1117:(CO) 1097:(CO) 1077:(CO) 1011:113 1008:181 976:112 973:180 970:209 949:191 902:114 899:191 896:212 880:113 849:116 846:204 843:245 818:181 781:Low- 775:(CO) 698:iron 623:(CO) 607:and 555:(CO) 298:and 278:HOMO 227:(CO) 219:(CO) 215:, Fe 211:(CO) 207:, Fe 203:(CO) 160:iron 79:and 52:are 8325:SiC 8293:CSe 8263:COS 8151:No 8148:Md 8145:Fm 8142:Es 8139:Cf 8136:Bk 8133:Cm 8130:Am 8127:Pu 8124:Np 8118:Pa 8115:Th 8112:Ac 8109:** 8104:Yb 8101:Tm 8098:Er 8095:Ho 8092:Dy 8089:Tb 8086:Gd 8083:Eu 8080:Sm 8077:Pm 8074:Nd 8071:Pr 8068:Ce 8045:Og 8042:Ts 8039:Lv 8036:Mc 8033:Fl 8030:Nh 8027:Cn 8024:Rg 8021:Ds 8018:Mt 8015:Hs 8012:Bh 8001:Db 7998:Rf 7995:Lr 7992:** 7989:Ra 7986:Fr 7981:Rn 7978:At 7975:Po 7972:Bi 7969:Pb 7966:Tl 7963:Hg 7960:Au 7957:Pt 7855:Ta 7852:Hf 7849:Lu 7835:Cs 7830:Xe 7824:Te 7821:Sb 7818:Sn 7815:In 7812:Cd 7691:Nb 7688:Zr 7667:Rb 7662:Kr 7645:As 7642:Ge 7639:Ga 7636:Zn 7412:Ar 7392:SCO 7387:PCO 7383:Si 7380:Al 7361:Na 7356:Ne 7332:OCO 7327:NCO 7303:BCO 7283:Li 7278:He 7098:NCS 7075:OPR 7051:OSR 7030:ClO 7017:ONO 6995:RCO 6872:Si) 6868:(Me 6853:RCN 6820:RNO 6768:4−n 6766:SiR 6722:≡CR 6714:=CR 6709:RNC 6633:=CH 6456:doi 6452:109 6356:doi 6219:doi 6163:doi 6050:doi 6023:doi 6019:102 5986:doi 5959:doi 5955:252 5924:doi 5920:102 5881:doi 5821:doi 5749:doi 5708:PMC 5700:doi 5661:doi 5611:doi 5584:doi 5539:doi 5493:doi 5481:361 5451:doi 5447:108 5375:doi 5338:hdl 5330:doi 5326:123 5294:doi 5253:doi 5230:doi 5226:118 5218:". 5146:doi 5104:doi 5100:248 5050:doi 4992:doi 4937:doi 4877:doi 4826:doi 4814:289 4747:doi 4735:461 4698:doi 4659:doi 4647:266 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Index

Carbonyl complex

Iron pentacarbonyl

coordination complexes
transition metals
carbon monoxide
ligands
organic synthesis
homogeneous catalysis
hydroformylation
Reppe chemistry
Mond process
nickel tetracarbonyl
nickel
organometallic chemistry
hemoglobin
carboxyhemoglobin
oxygen
cations
carbonylates
bridging
homoleptic
nickel tetracarbonyl
vanadium hexacarbonyl
chromium
iron
nickel
metal–metal bond
hapticity

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