Tetramesityldiiron

Last updated
Tetramesityldiiron
Fe2mes4.png
Names
Other names
dimesityliron
Identifiers
3D model (JSmol)
PubChem CID
  • (monomer):InChI=1S/2C9H11.Fe/c2*1-7-4-8(2)6-9(3)5-7;/h2*4-5H,1-3H3;/q2*-1;+2
    Key: JEIASHLOEHTPQS-UHFFFAOYSA-N
  • (monomer):c1(C)cc(C)cc(C)c1[Fe]c2c(C)cc(C)cc2(C)
Properties
C36H44Fe2
Appearancered solid
Density 1.19 g/cm3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tetramesityldiiron is an organoiron compound with the formula Fe2(C6H2(CH3)3)4. It is a red, air-sensitive solid that is used as a precursor to other iron complexes. It adopts a centrosymmetric structure. [1] The complex is a Lewis acid, forming monomeric adducts, e.g. Fe(C6H2(CH3)3)2 pyridine 2. The complex is prepared by treating ferrous halides with the Grignard reagent formed from mesityl bromide: [2] [3]

2 FeCl2 + 4 BrMgC6H2(CH3)3 → Fe2(C6H2(CH3)3)4 + 2 MgBrCl

Related Research Articles

Mesitylene or 1,3,5-trimethylbenzene is a derivative of benzene with three methyl substituents positioned symmetrically around the ring. The other two isomeric trimethylbenzenes are 1,2,4-trimethylbenzene (pseudocumene) and 1,2,3-trimethylbenzene (hemimellitene). All three compounds have the formula C6H3(CH3)3, which is commonly abbreviated C6H3Me3. Mesitylene is a colorless liquid with sweet aromatic odor. It is a component of coal tar, which is its traditional source. It is a precursor to diverse fine chemicals. The mesityl group (Mes) is a substituent with the formula C6H2Me3 and is found in various other compounds.

Iron(III) chloride Inorganic compound

Iron(III) chloride is the inorganic compound with the formula FeCl3. Also called ferric chloride, it is a common compound of iron in the +3 oxidation state. The anhydrous compound is a crystalline solid with a melting point of 307.6 °C. The color depends on the viewing angle: by reflected light the crystals appear dark green, but by transmitted light they appear purple-red.

Iron(II) chloride Chemical compound

Iron(II) chloride, also known as ferrous chloride, is the chemical compound of formula FeCl2. It is a paramagnetic solid with a high melting point. The compound is white, but typical samples are often off-white. FeCl2 crystallizes from water as the greenish tetrahydrate, which is the form that is most commonly encountered in commerce and the laboratory. There is also a dihydrate. The compound is highly soluble in water, giving pale green solutions.

Organotin chemistry Branch of organic chemistry

Organotin compounds or stannanes are chemical compounds based on tin with hydrocarbon substituents. Organotin chemistry is part of the wider field of organometallic chemistry. The first organotin compound was diethyltin diiodide, discovered by Edward Frankland in 1849. The area grew rapidly in the 1900s, especially after the discovery of the Grignard reagents, which are useful for producing Sn–C bonds. The area remains rich with many applications in industry and continuing activity in the research laboratory.

Grignard reagent Organometallic compounds used in organic synthesis

A Grignard reagent or Grignard compound is a chemical compound with the generic formula R−Mg−X, where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride Cl−Mg−CH3 and phenylmagnesium bromide (C6H5)−Mg−Br. They are a subclass of the organomagnesium compounds.

Iron(II) bromide Chemical compound

Iron(II) bromide is an inorganic compound with the chemical formula FeBr2. The anhydrous compound is a yellow or brownish-colored paramagnetic solid. Several hydrates of FeBr2 are also known, all being pale colored solids. It is a common precursor to other iron compounds in research laboratory, but no applications exist for this compound.

Group 2 organometallic chemistry

Group 2 organometallic chemistry refers to the chemistry of compounds containing carbon bonded to any group 2 element. By far the most common group 2 organometallic compounds are the magnesium-containing Grignard reagents which are widely used in organic chemistry. Other organmetallic group 2 compounds are rare and are typically limited to academic interests.

Organonickel chemistry

Organonickel chemistry is a branch of organometallic chemistry that deals with organic compounds featuring nickel-carbon bonds. They are used as a catalyst, as a building block in organic chemistry and in chemical vapor deposition. Organonickel compounds are also short-lived intermediates in organic reactions. The first organonickel compound was nickel tetracarbonyl Ni(CO)4, reported in 1890 and quickly applied in the Mond process for nickel purification. Organonickel complexes are prominent in numerous industrial processes including carbonylations, hydrocyanation, and the Shell higher olefin process.

Sodium tetraphenylborate Chemical compound

Sodium tetraphenylborate is the organic compound with the formula NaB(C6H5)4. It is a salt, wherein the anion consists of four phenyl rings bonded to boron. This white crystalline solid is used to prepare other tetraphenylborate salts, which are often highly soluble in organic solvents. The compound is used in inorganic and organometallic chemistry as a precipitating agent for potassium, ammonium, rubidium, and cesium ions, and some organic nitrogen compounds.

Organogallium chemistry

Organogallium chemistry is the chemistry of organometallic compounds containing a carbon to gallium (Ga) chemical bond. Despite their high toxicity, organogallium compounds have some use in organic synthesis. The compound trimethylgallium is of some relevance to MOCVD as a precursor to gallium arsenide via its reaction with arsine at 700 °C:

Organoiron chemistry is the chemistry of iron compounds containing a carbon-to-iron chemical bond. Organoiron compounds are relevant in organic synthesis as reagents such as iron pentacarbonyl, diiron nonacarbonyl and disodium tetracarbonylferrate. While iron adopts oxidation states from Fe(−II) through to Fe(VII), Fe(IV) is the highest established oxidation state for organoiron species. Although iron is generally less active in many catalytic applications, it is less expensive and "greener" than other metals. Organoiron compounds feature a wide range of ligands that support the Fe-C bond; as with other organometals, these supporting ligands prominently include phosphines, carbon monoxide, and cyclopentadienyl, but hard ligands such as amines are employed as well.

Organovanadium chemistry is the chemistry of organometallic compounds containing a carbon (C) to vanadium (V) chemical bond. Organovanadium compounds find only minor use as reagents in organic synthesis but are significant for polymer chemistry as catalysts.

Organosilver chemistry

Organosilver chemistry in chemistry of compounds containing a carbon to silver chemical bond. The theme is less developed than organocopper chemistry.

Organorhenium chemistry describes the compounds with Re−C bonds. Because rhenium is a rare element, relatively few applications exist, but the area has been a rich source of concepts and a few useful catalysts.

Metal bis(trimethylsilyl)amides

Metal bis(trimethylsilyl)amides are coordination complexes composed of a cationic metal with anionic bis(trimethylsilyl)amide ligands and are part of a broader category of metal amides.

Metal-phosphine complex

A metal-phosphine complex is a In coordination complex containing one or more phosphine ligands. Almost always, the phosphine is an organophosphine of the type R3P (R = alkyl, aryl). Metal phosphine complexes are useful in homogeneous catalysis. Prominent examples of metal phosphine complexes include Wilkinson's catalyst (Rh(PPh3)3Cl), Grubbs' catalyst, and tetrakis(triphenylphosphine)palladium(0).

Cyclopentadienyliron dicarbonyl dimer Chemical compound

Cyclopentadienyliron dicarbonyl dimer is an organometallic compound with the formula [(η5-C5H5)Fe(CO)2]2, often abbreviated to Cp2Fe2(CO)4, [CpFe(CO)2]2 or even Fp2, with the colloquial name "fip dimer". It is a dark reddish-purple crystalline solid, which is readily soluble in moderately polar organic solvents such as chloroform and pyridine, but less soluble in carbon tetrachloride and carbon disulfide. Cp2Fe2(CO)4 is insoluble in but stable toward water. Cp2Fe2(CO)4 is reasonably stable to storage under air and serves as a convenient starting material for accessing other Fp (CpFe(CO)2) derivatives (described below).

Iron(II) hydride, systematically named iron dihydride and poly(dihydridoiron) is solid inorganic compound with the chemical formula (FeH
2
)
n
. ). It is kinetically unstable at ambient temperature, and as such, little is known about its bulk properties. However, it is known as a black, amorphous powder, which was synthesised for the first time in 2014.

Transition metal isocyanide complexes

Transition metal isocyanide complexes are coordination compounds containing isocyanide ligands. Because isocyanide are relatively basic, but also good pi-acceptors, a wide range of complexes are known. Some isocyanide complexes are used in medical imaging.

Transition metal porphyrin complexes

Transition metal porphyrin complexes are a family of coordination complexes of the conjugate base of porphyrins. Iron porphyrin complexes occur widely in Nature, which has stimulated extensive studies on related synthetic complexes. The metal-porphyrin interaction is a strong one such that metalloporphyrins are thermally robust. They are catalysts and exhibit rich optical properties, although these complexes remain mainly of academic interest.

References

  1. Müller, Hardy; Seidel, Wolfgang; Görls, Helmar (1993). "Chemistry of dimesityliron. VI. The structure of tetramesityldiiron". Journal of Organometallic Chemistry. 445: 133–6. doi:10.1016/0022-328X(93)80198-K.
  2. Klose, Alain; Solari, Euro; Floriani, Carlo; Chiesi-Villa, Angiola; Rizzoli, Corrado; Re, Nazzareno (1994). "Magnetic Properties Diagnostic for the Existence of Iron(II)-Iron(II) Bonds in Dinuclear Complexes Which Derive from Stepwise Insertion Reactions on Unsupported Iron-Aryl Bonds". J. Am. Chem. Soc. 116 (20): 9123–9135. doi:10.1021/ja00099a030.
  3. Martinez, Gabriel Espinosa; Killion, Jack A.; Jackson, Bailey J.; Fout, Alison R. (2018). Dimesityliron(II) Dimer and Dimesityldipyridineiron(II) (Mes = mesityl = C6H2-2,4,6-Me3) Crowded σ- and π-Bonded Metal Aryl Complexes. Inorganic Syntheses. Vol. 36. pp. 50–55. doi:10.1002/9781119477822.ch4. S2CID   104749729.