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Asmic
Anisyl sulfanyl methyl isocyanide (Asmic) is an organic compound with the formula . The molecule contains an ''ortho-''methoxy-phenyl sulfide group to which is attached the isocyanide. Asmic is used as a reagent for the synthesis of tri-substituted isocyanides. The compound is a colorless although samples can appear off-white. Preparation and reactions Asmic is prepared by dehydration of the corresponding formamide by POCl3. Asmic can be deprotonated at the methylene adjacent to the isocyanide. The anionic form of Asmic, which is stable at low temperatures, can be alkylated with a variety of electrophiles. Two sequential deprotonation-alkylation reactions and a subsequent sulfur-lithium exchange reaction allow the synthesis of tri-substituted isocyanides. The ''ortho-''methoxy-phenyl sulfide group is thought to facilitate deprotonation by chelating to metalated bases allowing for the base to achieve optimal trajectory during the deprotonation. Asmic can be used to prepare o ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organic Compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-containing compounds such as alkanes (e.g. methane ) and its derivatives are universally considered organic, but many others are sometimes considered inorganic, such as certain compounds of carbon with nitrogen and oxygen (e.g. cyanide ion , hydrogen cyanide , chloroformic acid , carbon dioxide , and carbonate ion ). Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, and even ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Thioether
In organic chemistry, a sulfide (British English sulphide) or thioether is an organosulfur functional group with the connectivity as shown on right. Like many other sulfur-containing compounds, Volatile organic compound, volatile sulfides have foul odors. A sulfide is similar to an ether except that it contains a sulfur atom in place of the oxygen. The grouping of oxygen and sulfur in the periodic table suggests that the chemical properties of ethers and sulfides are somewhat similar, though the extent to which this is true in practice varies depending on the application. Nomenclature Sulfides are sometimes called thioethers, especially in the old literature. The two organic substituents are indicated by the prefixes. (CH3)2S is called dimethylsulfide. Some sulfides are named by modifying the common name for the corresponding ether. For example, C6H5SCH3 is methyl phenyl sulfide, but is more commonly called thioanisole, since its structure is related to that for anisole, C6H5OCH ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Isocyanide
An isocyanide (also called isonitrile or carbylamine) is an organic compound with the functional group –. It is the isomer of the related nitrile (–C≡N), hence the prefix is ''isocyano''.IUPAC Goldboo''isocyanides''/ref> The organic fragment is connected to the isocyanide group through the nitrogen atom, not via the carbon. They are used as building blocks for the synthesis of other compounds. Properties Structure and bonding The C-N distance in isocyanides is 115.8 pm in methyl isocyanide. The C-N-C angles are near 180°. Akin to carbon monoxide, isocyanides are described by two Resonance (chemistry), resonance structures, one with a triple bond between the nitrogen and the carbon and one with a double bond between. The π lone pair of the nitrogen stabilizes the structure and is responsible of the linearity of isocyanides, although the reactivity of isocyanides reflects some carbene character, at least in a formal sense. Thus, both resonance structures are useful repres ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Dehydration Reaction
In chemistry, a dehydration reaction is a chemical reaction that involves the loss of an H2O from the reacting molecule(s) or ion(s). This reaction results in the release of the H2O as water. When the reaction involves the coupling of two molecules into a single molecule it is referred to as a condensation reaction. Dehydration reactions are common processes in the manufacture of chemical compounds as well as naturally occurring within living organisms. The reverse of a dehydration reaction is called a hydration reaction. The reverse of a condensation reaction yielding water is called hydrolysis. Condensation reactions occurring in living organisms Condensation dehydration reactions are fundamental to the existence of life as this type of reaction produces proteins from amino acids, DNA and RNA from nucleotides, fats from fatty acids, and polysaccharides (eg. cellulose, starch, sugar, lactose) from monosaccharides (eg. glucose and fructose). The formation of the pyrophosphat ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Formamide
Formamide is an amide derived from formic acid. It is a colorless liquid which is miscible with water and has an ammonia-like odor. It is chemical feedstock for the manufacture of sulfa drugs and other pharmaceuticals, herbicides and pesticides, and in the manufacture of hydrocyanic acid. It has been used as a softener for paper and fiber. It is a solvent for many ionic compounds. It has also been used as a solvent for resins and plasticizers. Some astrobiologists suggest that it may be an alternative to water as the main solvent in other forms of life. Formamides are compounds of the type RR′NCHO. One important formamide is dimethylformamide, (CH3)2NCHO. Production Historical production In the past, formamide was produced by treating formic acid with ammonia, which produces ammonium formate, which in turn yields formamide upon heating: : HCOOH + NH3 → : → HCONH2 + H2O Formamide is also generated by aminolysis of ethyl formate: :HCOOCH2CH3 + NH3 → HCONH2 + CH3 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Phosphoryl Chloride
Phosphoryl chloride (commonly called phosphorus oxychloride) is a colourless liquid with the formula . It hydrolyses in moist air releasing phosphoric acid and fumes of hydrogen chloride. It is manufactured industrially on a large scale from phosphorus trichloride and oxygen or phosphorus pentoxide. It is mainly used to make phosphate esters. Structure Like phosphate, is tetrahedral in shape. It features three P−Cl bonds and one strong P–O bond, with an estimated bond dissociation energy of 533.5 kJ/mol. Unlike in the case of , the Schomaker-Stevenson rule predicts appropriate bond length for the P–O bond only if the P–O bond is treated as a double bond, P=O. More modern treatments explain the tight P–O bond as a combination of lone pair transfer from the phosphorus to the oxygen atom and a dative ''π'' back-bond that produces an effective + −configuration. Phosphoryl chloride exists as neutral molecules in the solid, liquid and gas states. This is u ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Carbanion
In organic chemistry, a carbanion is an anion with a lone pair attached to a tervalent carbon atom. This gives the carbon atom a negative charge. Formally, a carbanion is the conjugate base of a carbon acid: : where B stands for the base (chemistry), base. The carbanions formed from deprotonation of alkanes (at an Orbital hybridisation#sp3, sp3 carbon), alkenes (at an Orbital hybridisation#sp2, sp2 carbon), arenes (at an sp2 carbon), and alkynes (at an Orbital hybridisation#sp, sp carbon) are known as alkyl, alkenyl (Vinyl group, vinyl), aryl, and alkynyl (acetylide) anions, respectively. Carbanions have a concentration of electron density at the negatively charged carbon, which, in most cases, reacts efficiently with a variety of electrophiles of varying strengths, including carbonyl groups, Imine, imines/Iminium, iminium salts, halogenating reagents (e.g., N-Bromosuccinimide, ''N''-bromosuccinimide and Iodine, diiodine), and Brønsted–Lowry acid–base theory, proton donors. A ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Alkylation
Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting alkylation. Alkyl groups can also be removed in a process known as dealkylation. Alkylating agents are often classified according to their nucleophilic or electrophilic character. In oil refining contexts, alkylation refers to a particular alkylation of isobutane with alkene, olefins. For upgrading of petroleum, alkylation produces a premium blending stock for gasoline. In medicine, alkylation of DNA is used in chemotherapy to damage the DNA of cancer cells. Alkylation is accomplished with the class of drugs called alkylating antineoplastic agents. Nucleophilic alkylating agents Nucleophilic alkylating agents deliver the equivalent of an alkyl anion (carbanion). The formal "alkyl anion" attacks an electrophile, forming a new covalent bond ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Deprotonation
Deprotonation (or dehydronation) is the removal (transfer) of a proton (or hydron, or hydrogen cation), (H+) from a Brønsted–Lowry acid in an acid–base reaction.Henry Jakubowski, Biochemistry Online Chapter 2A3, https://employees.csbsju.edu/hjakubowski/classes/ch331/protstructure/PS_2A3_AA_Charges.html, accessed 12/2/2020 The species formed is the conjugate base of that acid. The complementary process, when a proton is added (transferred) to a Brønsted–Lowry base, is protonation (or hydronation). The species formed is the conjugate acid of that base. A species that can either accept or donate a proton is referred to as amphiprotic. An example is the H2O (water) molecule, which can gain a proton to form the hydronium ion, H3O+, or lose a proton, leaving the hydroxide ion, OH−. The relative ability of a molecule to give up a proton is measured by its p''K''a value. A low p''K''a value indicates that the compound is acidic and will easily give up its proton to a base ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
TosMIC
TosMIC (toluenesulfonylmethyl isocyanide) is an organic compound with the formula CH3C6H4SO2CH2NC. The molecule contains both sulfonyl and isocyanide groups. It is a colourless solid that, unlike many isocyanides, is odorless. It is prepared by dehydration of the related formamide derivative. It is used to convert ketones to nitriles ( Van Leusen reaction) and in the preparation of oxazoles. and imidazole Imidazole (ImH) is an organic compound with the formula . It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. It can be classified as a heterocycle, specifically as a diazole. Many natural products, ...s. The versatility of TosMIC in organic synthesis has been documented. It is a fairly strong carbon acid, with an estimated p''K''a of 14 (compared to 29 for methyl tolyl sulfone), the isocyano group acting as an electron acceptor of strength comparable to an ester group. References Further reading * {{cite book , doi=10.1002/04 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Thioethers
In organic chemistry, a sulfide (British English sulphide) or thioether is an organosulfur functional group with the connectivity as shown on right. Like many other sulfur-containing compounds, volatile sulfides have foul odors. A sulfide is similar to an ether except that it contains a sulfur atom in place of the oxygen. The grouping of oxygen and sulfur in the periodic table suggests that the chemical properties of ethers and sulfides are somewhat similar, though the extent to which this is true in practice varies depending on the application. Nomenclature Sulfides are sometimes called thioethers, especially in the old literature. The two organic substituents are indicated by the prefixes. (CH3)2S is called dimethylsulfide. Some sulfides are named by modifying the common name for the corresponding ether. For example, C6H5SCH3 is methyl phenyl sulfide, but is more commonly called thioanisole, since its structure is related to that for anisole, C6H5OCH3. The modern systemati ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
