Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and sometimes broadened to include metalloids like boron, silicon, and selenium, as well. Aside from bonds to organyl fragments or molecules, bonds to 'inorganic' carbon, like carbon monoxide, cyanide, or carbide, are generally considered to be organometallic as well. Some related compounds such as transition metal hydrides and metal phosphine complexes are often included in discussions of organometallic compounds, though strictly speaking, they are not necessarily organometallic. The related but distinct term "metalorganic compound" refers to metal-containing compounds lacking direct metal-carbon bonds but which contain organic ligands. Metal β-diketonates, alkoxides, dialkylamides, and metal phosphine complexes are representative members of this class. The field of organometallic chemistry combines aspects of traditional inorganic and organic chemistry.
Tin is a chemical element with the symbol Sn and atomic number 50. Tin is a silvery-coloured metal.
Chloroethane, commonly known as ethyl chloride, is a chemical compound with chemical formula CH3CH2Cl, once widely used in producing tetraethyllead, a gasoline additive. It is a colorless, flammable gas or refrigerated liquid with a faintly sweet odor.
In organic chemistry, an acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.
Allyl chloride is the organic compound with the formula CH2=CHCH2Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a chlorinated derivative of propylene. It is an alkylating agent, which makes it both useful and hazardous to handle.
Tin(IV) chloride, also known as tin tetrachloride or stannic chloride, is an inorganic compound with the formula SnCl4. It is a colorless hygroscopic liquid, which fumes on contact with air. It is used as a precursor to other tin compounds. It was first discovered by Andreas Libavius (1550–1616) and was known as spiritus fumans libavii.
In chemistry, quaternary ammonium cations, also known as quats, are positively-charged polyatomic ions of the structure [NR4]+, where R is an alkyl group, an aryl group or organyl group. Unlike the ammonium ion and the primary, secondary, or tertiary ammonium cations, the quaternary ammonium cations are permanently charged, independent of the pH of their solution. Quaternary ammonium salts or quaternary ammonium compounds are salts of quaternary ammonium cations. Polyquats are a variety of engineered polymer forms which provide multiple quat molecules within a larger molecule.
Phosphorus trichloride is an inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is toxic and reacts readily with water to release hydrogen chloride.
Organotin chemistry is the scientific study of the synthesis and properties of organotin compounds or stannanes, which are organometallic compounds containing tin carbon bonds. 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.
Tributyltin oxide (TBTO) is an organotin compound chiefly used as a biocide (fungicide and molluscicide), especially a wood preservative. Its chemical formula is [(C4H9)3Sn]2O. It is a colorless viscous liquid. It is poorly soluble in water (20 ppm) but highly soluble in organic solvents. It is a potent skin irritant.
Tetrabutyltin is the organotin compound with the molecular formula Sn(CH2CH2CH2CH3)4 or SnBu4, where Bu is butyl −CH2CH2CH2CH3. Sometimes abbreviated TTBT, it is a colorless, lipophilic oil.
Tributyltin (TBT) is an umbrella term for a class of organotin compounds which contain the (C4H9)3Sn group, with a prominent example being tributyltin oxide. For 40 years TBT was used as a biocide in anti-fouling paint, commonly known as bottom paint, applied to the hulls of oceangoing vessels. Bottom paint improves ship performance and durability as it reduces the rate of biofouling, the growth of organisms on the ship's hull. The TBT slowly leaches out into the marine environment where it is highly toxic toward nontarget organisms. TBT toxicity can lead to biomagnification or bioaccumulation within such nontarget organisms like invertebrates, vertebrates, and a variety of mammals. TBT is also an obesogen. After it led to collapse of local populations of organisms, TBT was banned.
Thiophosgene is a red liquid with the formula CSCl2. It is a molecule with trigonal planar geometry. There are two reactive C–Cl bonds that allow it to be used in diverse organic syntheses.
Tetramethyltin is an organometallic compound with the formula (CH3)4Sn. This liquid, one of the simplest organotin compounds, is useful for transition-metal mediated conversion of acid chlorides to methyl ketones and aryl halides to aryl methyl ketones. It is volatile and toxic, so care should be taken when using it in the laboratory.
Triphenyltin compounds are organotin compounds with the general formula (C6H5)3SnX. They contain the triphenyltin group, (C6H5)3Sn, or Ph3Sn, which consists of an atom of tin bonded to three phenyl groups. Examples of triphenyltins include:
Tin poisoning refers to the toxic effects of tin and its compounds. Cases of poisoning from tin metal, its oxides, and its salts are "almost unknown"; on the other hand, certain organotin compounds are almost as toxic as cyanide.
In chemistry, redistribution usually refers to the exchange of anionic ligands bonded to metal and metalloid centers. The conversion does not involve redox, in contrast to disproportionation reactions. Some useful redistribution reactions are conducted at higher temperatures; upon cooling the mixture, the product mixture is kinetically frozen and the individual products can be separated. In cases where redistribution is rapid at mild temperatures, the reaction is less useful synthetically but still important mechanistically.
Calcium cyanide is the inorganic compound with the formula Ca(CN)2. It is the calcium salt derived from hydrocyanic acid. It is a white solid, although the pure material is rarely encountered. It hydrolyses readily (even in moist air) to release hydrogen cyanide and is very toxic.
Dibutyltin dilaurate is an organotin compound with the formula (CH310CO2)2Sn( 3CH3)2. It is a colorless viscous and oily liquid. It is used as a catalyst.
Stannoxane is a functional group in organotin chemistry with the connectivity SnIV−O−SnIV. Aside from the oxide group, usually 3 or 4 other substituents are attached to tin. In aqueous or aquatic environments, most organotin compounds contain this group.
