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Phosphinous Acids
Phosphinous acids are usually organophosphorus compounds with the formula R2POH. They are pyramidal in structure. Phosphorus is in the oxidation state III. Most phosphinous acids rapidly convert to the corresponding phosphine oxide, which are tetrahedral and are assigned oxidation state V. Synthesis Only one example is known, bis(trifluoromethyl)phosphinous acid, (CF3)2POH. It is prepared in several steps from phosphorus trichloride (Et = ethyl): :PCl3 + 2 Et2NH → PCl2NEt2 + Et2NH2Cl :2 P(NEt2)3 + PCl2NEt2 + 2 CF3Br → P(CF3)2NEt2 + 2 BrClP(NEt2)3 :P(CF3)2NEt2 + H2O → P(CF3)2OH + HNEt2 Reactions With the lone exception of the bis(trifluoromethyl) derivative, the dominant reaction of phosphinous acids is tautomerization: :PR2OH → OPR2H Even the pentafluorophenyl compound P(C6F5)2OH is unstable with respect to the phosphine oxide. Although phosphinous acids are rare, their P-bonded coordination complexes are well established, e.g. Mo(CO)5P(OH)3 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organophosphorus Compound
Organophosphorus compounds are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective insecticides, although some are extremely toxic to humans, including sarin and VX nerve agents. Organophosphorus chemistry is the corresponding science of the properties and reactivity of organophosphorus compounds. Phosphorus, like nitrogen, is in group 15 of the periodic table, and thus phosphorus compounds and nitrogen compounds have many similar properties. The definition of organophosphorus compounds is variable, which can lead to confusion. In industrial and environmental chemistry, an organophosphorus compound need contain only an organic substituent, but need not have a direct phosphorus-carbon (P-C) bond. Thus a large proportion of pesticides (e.g., malathion), are often included in this class of compounds. Phosphorus can adopt ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Phosphorus Trichloride
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. History Phosphorus trichloride was first prepared in 1808 by the French chemists Joseph Louis Gay-Lussac and Louis Jacques Thénard by heating calomel (Hg2Cl2) with phosphorus. Later during the same year, the English chemist Humphry Davy produced phosphorus trichloride by burning phosphorus in chlorine gas. Preparation World production exceeds one-third of a million tonnes. Phosphorus trichloride is prepared industrially by the reaction of chlorine with white phosphorus, using phosphorus trichloride as the solvent. In this continuous process PCl3 is removed as it is formed in order to avoid the formation of PCl5. :P4 + 6 Cl2 → 4 PCl3 Structure and spectroscopy It has a trig ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ethyl Group
In organic chemistry, an ethyl group (abbr. Et) is an alkyl substituent with the formula , derived from ethane (). ''Ethyl'' is used in the International Union of Pure and Applied Chemistry's nomenclature of organic chemistry for a saturated two-carbon moiety in a molecule, while the prefix "''eth-''" is used to indicate the presence of two carbon atoms in the molecule. Ethylation Ethylation is the formation of a compound by introduction of the ethyl group. The most widely practiced example of this reaction is the ethylation of benzene with ethylene to yield ethylbenzene, a precursor to styrene, which is a precursor to polystyrene. Approximately 24.7 million tons of ethylbenzene were produced in 1999. :: Many ethyl-containing compounds are generated by electrophilic ethylation, i.e. treatment of nucleophiles with sources of Et+. Triethyloxonium tetrafluoroborate t3OF4 is such a reagent. For good nucleophiles, less electrophilic reagents are employed, such as ethyl h ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tautomerization
Tautomers () are structural isomers (constitutional isomers) of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the relocation of a hydrogen atom within the compound. The phenomenon of tautomerization is called tautomerism, also called desmotropism. Tautomerism is for example relevant to the behavior of amino acids and nucleic acids, two of the fundamental building blocks of life. Care should be taken not to confuse tautomers with depictions of "contributing structures" in chemical resonance. Tautomers are distinct chemical species that can be distinguished by their differing atomic connectivities, molecular geometries, and physicochemical and spectroscopic properties, whereas resonance forms are merely alternative Lewis structure (valence bond theory) depictions of a single chemical species, whose true structure is best described as the "average" of the idealized, hypothe ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Phosphine Oxide
Phosphine oxides are phosphorus compounds with the formula OPX3. When X = alkyl or aryl, these are organophosphine oxides. Triphenylphosphine oxide is an example. An inorganic phosphine oxide is phosphoryl chloride (POCl3). Structure and bonding Tertiary phosphine oxides Tertiary phosphine oxides are the most commonly encountered phosphine oxides. With the formula R3PO, they are tetrahedral compounds. They are usually prepared by oxidation of tertiary phosphines. The P-O bond is short and polar. According to molecular orbital theory, the short P–O bond is attributed to the donation of the lone pair electrons from oxygen p-orbitals to the antibonding phosphorus-carbon bonds. The nature of the P–O bond was once hotly debated. Some discussions invoked a role for phosphorus-centered d-orbitals in bonding, but this analysis is not supported by computational analyses. In terms of simple Lewis structure, the bond is more accurately represented as a dative bond, as is currently us ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Coordination Complex
A coordination complex consists of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of bound molecules or ions, that are in turn known as ''ligands'' or complexing agents. Many metal-containing compounds, especially those that include transition metals (elements like titanium that belong to the Periodic Table's d-block), are coordination complexes. Nomenclature and terminology Coordination complexes are so pervasive that their structures and reactions are described in many ways, sometimes confusingly. The atom within a ligand that is bonded to the central metal atom or ion is called the donor atom. In a typical complex, a metal ion is bonded to several donor atoms, which can be the same or different. A polydentate (multiple bonded) ligand is a molecule or ion that bonds to the central atom through several of the ligand's atoms; ligands with 2, 3, 4 or even 6 bonds to the central atom are common. These compl ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Diethylphosphite
Diethylphosphite is the organophosphorus compound with the formula (C2H5O)2P(O)H. It is a popular reagent for generating other organophosphorus compounds, exploiting the high reactivity of the P-H bond. Diethylphosphite is a colorless liquid. The molecule is tetrahedral. Synthesis and properties The compound was probably prepared in the 1850s by combining phosphorus trichloride and ethanol, but intentional preparations came later. It arises as follows: :PCl3 + 3 C2H5OH → (C2H5O)2P(O)H + 2 HCl + C2H5Cl Many derivatives can be prepared similarly. Despite being named as a phosphite it exists overwhelmingly in its phosphonate form, , a property it shares with its parent acid phosphorous acid; despite this many of its reactions are difficult to rationalise without assuming the existence of the following tautomerism equilibrium between phosphorus(V) and phosphorus(III) forms: :(C2H5O)2PV(O)H ⇌ (C2H5O)2PIII(OH) Reactions Alkoxide exchange Diethylphosphite undergoes transesterific ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Phosphorous Acid
Phosphorous acid (or phosphonic acid (singular)) is the compound described by the formula H3PO3. This acid is diprotic (readily ionizes two protons), not triprotic as might be suggested by this formula. Phosphorous acid is an intermediate in the preparation of other phosphorus compounds. Organic derivatives of phosphorous acid, compounds with the formula RPO3H2, are called phosphonic acids. Nomenclature and tautomerism H3PO3 is more clearly described with the structural formula HPO(OH)2. In the solid state, has tetrahedral geometry about the central phosphorus atom, with a P–H bond of 132 pm, one P=O double bond of 148 pm and two longer P–O(H) single bonds of 154 pm. This species exists in equilibrium with an extremely minor tautomer . IUPAC recommends that the latter be called phosphorous acid, whereas the dihydroxy form is called phosphonic acid.. Only the reduced phosphorus compounds are spelled with an "ous" ending. Other important oxyacids of pho ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Diphenylphosphine Oxide
Diphenylphosphine oxide is an organophosphorus compound with the formula (C6H5)2P(O)H. It is a white solid that soluble in polar organic solvents. Synthesis Diphenylphosphine oxide can be prepared by the reaction of phosphonic esters, such as diethylphosphite, with Grignard reagents followed by acid workup: :(C2H5O)2P(O)H + 3C6H5MgBr → (C6H5)2P(O)MgBr + C2H5OMgBr :(C6H5)2P(O)MgBr + HCl → (C6H5)2P(O)H + MgBrCl Alternatively, it may be prepared by the partial hydrolysis of chlorodiphenylphosphine or diphenylphosphine. Reactions Diphenylphosphine oxide exists in equilibrium with its minor tautomer diphenylphosphinous acid, ((C6H5)2POH: : Diphenylphosphine oxide is used in Buchwald-Hartwig coupling reactions to introduce diphenylphosphino substituents. Thionyl chloride converts diphenylphosphine oxide to chlorodiphenylphosphine. Organophosphinous acids are deoxygenated with DIBAH. The resulting secondary phosphines are precursors to phosphine ligand A metal-phos ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hypophosphorous Acid
Hypophosphorous acid (HPA), or phosphinic acid, is a phosphorus oxyacid and a powerful reducing agent with molecular formula H3PO2. It is a colorless low-melting compound, which is soluble in water, dioxane and alcohols. The formula for this acid is generally written H3PO2, but a more descriptive presentation is HOP(O)H2, which highlights its monoprotic character. Salts derived from this acid are called hypophosphites. HOP(O)H2 exists in equilibrium with the minor tautomer HP(OH)2. Sometimes the minor tautomer is called hypophosphorous acid and the major tautomer is called phosphinic acid. Preparation and availability Hypophosphorous acid was first prepared in 1816 by the French chemist Pierre Louis Dulong (1785–1838). The acid is prepared industrially via a two step process: Firstly, elemental white phosphorus reacts with alkali and alkaline earth hydroxides to give an aqueous solution of hypophosphites: :P4 + 4 OH− + 4 H2O → 4 + 2 H2 Any phosph ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Functional Groups
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The reactivity of a functional group can be modified by other functional groups nearby. Functional group interconversion can be used in retrosynthetic analysis to plan organic synthesis. A functional group is a group of atoms in a molecule with distinctive chemical properties, regardless of the other atoms in the molecule. The atoms in a functional group are linked to each other and to the rest of the molecule by covalent bonds. For repeating units of polymers, functional groups attach to their nonpolar core of carbon atoms and thus add chemical character to carbon chains. Functi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
