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Rothemund Reaction
The Rothemund reaction is a condensation/oxidation process that converts four pyrroles and four aldehydes into a porphyrin. It is based on work by Paul Rothemund, who first reported it in 1936. The method underpin more modern synthesis such as those described by Adler and Longo and by Lindsey. The Rothemund reactions is common in university teaching labs. Method The reaction employs an organic acidic medium such as acetic acid or propionic acid as typical reaction solvents. Alternatively ''p''-toluenesulfonic acid or various Lewis acids can be used with chlorinated solvents. The aldehyde and pyrrole are heated in this medium to afford modest yields of the meso tetrasubstituted porphyrins CC4H2Nsub>4H2. The reaction entails both condensation of the aldehydes with the 2,5-positions of the pyrrole but also oxidative dehydrogenatioin of the porphyrinogen CC4H2NHsub>4. Reaction history The Nobel Prize-winning multi-step syntheses of Hemin and Chlorophyll by Hans Fischer. inspir ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
H2TPPsyn
H, or h, is the eighth letter in the Latin alphabet, used in the modern English alphabet, the alphabets of other western European languages and others worldwide. Its name in English is ''aitch'' (pronounced , plural ''aitches''), or regionally ''haitch'' ."H" ''Oxford English Dictionary,'' 2nd edition (1989); ''Merriam-Webster's Third New International Dictionary of the English Language, Unabridged'' (1993); "aitch" or "haitch", op. cit. History The original Semitic letter Heth most likely represented the voiceless pharyngeal fricative (). The form of the letter probably stood for a fence or posts. The Greek Eta 'Η' in archaic Greek alphabets, before coming to represent a long vowel, , still represented a similar sound, the voiceless glottal fricative . In this context, the letter eta is also known as Heta to underline this fact. Thus, in the Old Italic alphabets, the letter Heta of the Euboean alphabet was adopted with its original sound value . While Etruscan and La ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Formaldehyde
Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section Forms below), hence it is stored as an aqueous solution (formalin), which is also used to store animal specimens. It is the simplest of the aldehydes (). The common name of this substance comes from its similarity and relation to formic acid. Formaldehyde is an important precursor to many other materials and chemical compounds. In 1996, the installed capacity for the production of formaldehyde was estimated at 8.7 million tons per year. It is mainly used in the production of industrial resins, e.g., for particle board and coatings. Forms Formaldehyde is more complicated than many simple carbon compounds in that it adopts several diverse forms. These compounds can often be used interchangeably and can be interconverted. *Molecular formald ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organochloride
An organochloride, organochlorine compound, chlorocarbon, or chlorinated hydrocarbon is an organic compound containing at least one covalent bond, covalently bonded atom of chlorine. The chloroalkane class (alkanes with one or more hydrogens substituted by chlorine) provides common examples. The wide structural variety and divergent chemical properties of organochlorides lead to a broad range of names, applications, and properties. Organochlorine compounds have wide use in many applications, though some are of profound environmental concern, with 2,3,7,8-Tetrachlorodibenzodioxin, TCDD being one of the most notorious. Physical and chemical properties Chlorination reaction, Chlorination modifies the physical properties of hydrocarbons in several ways. These compounds are typically denser than water due to the higher atomic weight of chlorine versus hydrogen. Aliphatic organochlorides are often alkylating agents as chlorine can act as a leaving group, which can result in cellular dam ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Trifluoroacetic Acid
Trifluoroacetic acid (TFA) is an organofluorine compound with the chemical formula CF3CO2H. It is a structural analogue of acetic acid with all three of the acetyl group's hydrogen atoms replaced by fluorine atoms and is a colorless liquid with a vinegar-like odor. TFA is a stronger acid than acetic acid, having an acid ionisation constant, ''K''a, that is approximately 34,000 times higher, as the highly electronegative fluorine atoms and consequent electron-withdrawing nature of the trifluoromethyl group weakens the oxygen-hydrogen bond (allowing for greater acidity) and stabilises the anionic conjugate base. TFA is widely used in organic chemistry for various purposes. Synthesis TFA is prepared industrially by the electrofluorination of acetyl chloride or acetic anhydride, followed by hydrolysis of the resulting trifluoroacetyl fluoride: : + 4 → + 3 + : + → + Where desired, this compound may be dried by addition of trifluoroacetic anhydride. An older route to ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organic Acid
An organic acid is an organic compound with acidic properties. The most common organic acids are the carboxylic acids, whose acidity is associated with their carboxyl group –COOH. Sulfonic acids, containing the group –SO2OH, are relatively stronger acids. Alcohols, with –OH, can act as acids but they are usually very weak. The relative stability of the conjugate base of the acid determines its acidity. Other groups can lsoconfer acidity, usually weakly: the thiol group –SH, the enol group, and the phenol group. In biological systems, organic compounds containing these groups are generally referred to as organic acids. A few common examples include: * lactic acid * acetic acid * formic acid * citric acid * oxalic acid * uric acid * malic acid * tartaric acid Characteristics In general, organic acids are weak acids and do not dissociate completely in water, whereas the strong mineral acids do. Lower molecular mass organic acids such as formic and lactic ac ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Boron Trifluoride
Boron trifluoride is the inorganic compound with the formula BF3. This pungent, colourless, and toxic gas forms white fumes in moist air. It is a useful Lewis acid and a versatile building block for other boron compounds. Structure and bonding The geometry of a molecule of BF3 is trigonal planar. Its D3h symmetry conforms with the prediction of VSEPR theory. The molecule has no dipole moment by virtue of its high symmetry. The molecule is isoelectronic with the carbonate anion, . BF3 is commonly referred to as " electron deficient," a description that is reinforced by its exothermic reactivity toward Lewis bases. In the boron trihalides, BX3, the length of the B–X bonds (1.30 Å) is shorter than would be expected for single bonds, and this shortness may indicate stronger B–X π-bonding in the fluoride. A facile explanation invokes the symmetry-allowed overlap of a p orbital on the boron atom with the in-phase combination of the three similarly oriented p orbitals ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Lewis Acids And Bases
A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any species that has a filled orbital containing an electron pair which is not involved in bonding but may form a dative bond with a Lewis acid to form a Lewis adduct. For example, NH3 is a Lewis base, because it can donate its lone pair of electrons. Trimethylborane (Me3B) is a Lewis acid as it is capable of accepting a lone pair. In a Lewis adduct, the Lewis acid and base share an electron pair furnished by the Lewis base, forming a dative bond. In the context of a specific chemical reaction between NH3 and Me3B, a lone pair from NH3 will form a dative bond with the empty orbital of Me3B to form an adduct NH3•BMe3. The terminology refers to the contributions of Gilbert N. Lewis. From p. 142: "We are inclined to think of substances as pos ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Yield (chemistry)
In chemistry, yield, also referred to as reaction yield, is a measure of the quantity of Mole (unit), moles of a Product (chemistry), product formed in relation to the reactant consumed, obtained in a chemical reaction, usually expressed as a percentage. Yield is one of the primary factors that scientists must consider in organic synthesis, organic and inorganic chemical synthesis processes. In chemical reaction engineering, "yield", "Conversion (chemistry), conversion" and "selectivity" are terms used to describe ratios of how much of a reactant was consumed (conversion), how much desired product was formed (yield) in relation to the undesired product (selectivity), represented as X, Y, and S. Definitions In chemical reaction engineering, "yield", "Conversion (chemistry), conversion" and "selectivity" are terms used to describe ratios of how much of a reactant has reacted—conversion, how much of a desired product was formed—yield, and how much desired product was formed ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Catalysis
Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quickly, very small amounts of catalyst often suffice; mixing, surface area, and temperature are important factors in reaction rate. Catalysts generally react with one or more reactants to form intermediates that subsequently give the final reaction product, in the process of regenerating the catalyst. Catalysis may be classified as either homogeneous, whose components are dispersed in the same phase (usually gaseous or liquid) as the reactant, or heterogeneous, whose components are not in the same phase. Enzymes and other biocatalysts are often considered as a third category. Catalysis is ubiquitous in chemical industry of all kinds. Estimates are that 90% of all commercially produced chemical products involve catalysts at some s ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Pyridine
Pyridine is a basic heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid with a distinctive, unpleasant fish-like smell. Pyridine is colorless, but older or impure samples can appear yellow, due to the formation of extended, unsaturated polymeric chains, which show significant electrical conductivity. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Historically, pyridine was produced from coal tar. As of 2016, it is synthesized on the scale of about 20,000 tons per year worldwide. Properties Physical properties The molecular electric dipole moment is 2.2 debyes. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Pyrex
Pyrex (trademarked as ''PYREX'' and ''pyrex'') is a brand introduced by Corning Inc. in 1915 for a line of clear, low-thermal-expansion borosilicate glass used for laboratory glassware and kitchenware. It was later expanded to include kitchenware products made of soda-lime glass and other materials. In 1998, the kitchenware division of Corning Inc. responsible for the development of Pyrex spun off from its parent company as Corning Consumer Products Company, subsequently renamed Corelle Brands (and would later merge with Instant Brands). Corning Inc. no longer manufactures or markets consumer products, only industrial ones. Both trademarks, PYREX (all uppercase) and pyrex (all lowercase, introduced in 1975), were used interchangeably in the marketing of kitchenware products made of both borosilicate and soda lime glass, in addition to related accessories, for several decades. The latter trademark is now used for kitchenware sold in the United States, South America, and Asia. I ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Porphine
Porphine or porphin is an organic chemical compound with formula . The molecule, which is flat, consists of four pyrrole-like rings joined by four methine (= C H−) groups to form a larger macrocycle ring, which makes it the simplest of the tetrapyrroles. It is classified as an aromatic and heterocyclic compound. Porphine is only of theoretical interest. It has been detected in GC-MS of certain fractions of ''Piper betle''. Porphine derivatives: porphyrins Substituted derivatives of porphine are called porphyrins. Many porphyrins are found in nature with the dominant example being protoporphyrin IX. Many synthetic porphyrins are also known, including octaethylporphyrin and tetraphenylporphyrin. File:PPIXtransH.png, Derivatives of protoporphyrin IX are common in nature, the precursor to hemes. File:H2octaethylporphyrin.png , Octaethylporphyrin (H2OEP) is a synthetic analogue of protoporphyrin IX. Unlike the natural porphyrin ligands, OEP2− is highly symmetrical. File ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
