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Acetyl Cyanide
Acetyl cyanide is the organic compound with the formula CH3C(O)CN. It is an acyl cyanide. Acetyl cyanide is a colorless liquid. Structure Its structure was determined through the use of electron diffraction intensities and rotational spectroscopy. Reactions Two main types of reactions can occur with acetyl cyanide as a reactant; aldol condensation and enolate substitution. Aldol condensation can occur when acetyl cyanide reacts with (Z)-but-2-enal to form (2E,4E)-hexa-2,4-dienoyl cyanide: The photochemical and thermal reactions of acetyl cyanide have been extensively studied. For example, formyl cyanide does not undergo unimolecular decomposition to HCN and CO spontaneously. However, acetyl cyanide, also a member of this family, breaks down through this unimolecular decomposition at 470 °C. This reaction occurs through decarbonylation. This division of the molecule to a ketone and hydrogen cyanide were noted to be under competitive circumstances. This caused a study o ...
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Royal Society Of Chemistry
The Royal Society of Chemistry (RSC) is a learned society (professional association) in the United Kingdom with the goal of "advancing the chemistry, chemical sciences". It was formed in 1980 from the amalgamation of the Chemical Society, the Royal Institute of Chemistry, the Faraday Society, and the Society for Analytical Chemistry with a new Royal Charter and the dual role of learned society and professional body. At its inception, the Society had a combined membership of 34,000 in the UK and a further 8,000 abroad. The headquarters of the Society are at Burlington House, Piccadilly, London. It also has offices in Thomas Graham House in Cambridge (named after Thomas Graham (chemist), Thomas Graham, the first president of the Chemical Society) where ''RSC Publishing'' is based. The Society has offices in the United States, on the campuses of The University of Pennsylvania and Drexel University, at the University City Science Center in Philadelphia, Pennsylvania, in both Beijing a ...
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Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. 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, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Living t ...
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Acyl Cyanide
In organic chemistry, an acyl cyanide is a functional group with the formula and structure . It consists of an acyl group () attached to cyanide (). Examples include acetyl cyanide, formyl cyanide, and oxalyl dicyanide. Acyl cyanides are reagents in organic synthesis. Synthesis Classically acyl cyanides are produced by the salt metathesis reaction of acyl chlorides with sodium cyanide: :\ce + \ce \longrightarrow + \ce Alternatively, they can be produced by dehydration of acyl aldoximes: :\ce\ce \longrightarrow + \ce Acetyl cyanide is also prepared by hydrocyanation of ketene: :\ce + \ce \longrightarrow \ce Reactions They are mild acylating agents. With aqueous base, acyl cyanides break down to cyanide and the carboxylate: : + \ce \longrightarrow \ce + \ce + \ce With azides, acyl cyanides undergo the click reaction to give acyl tetrazole Tetrazoles are a class of synthetic organic heterocyclic compound, consisting of a 5-member ring of four nitrogen atom ...
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Electron Diffraction
Electron diffraction refers to the bending of electron beams around atomic structures. This behaviour, typical for waves, is applicable to electrons due to the wave–particle duality stating that electrons behave as both particles and waves. Since the diffracted beams interfere, they generate diffraction patterns widely used for analysis of the objects which caused the diffraction. Therefore, electron diffraction can also refer to derived experimental techniques used for material characterization. This technique is similar to X-ray and neutron diffraction. Electron diffraction is most frequently used in solid state physics and chemistry to study crystalline, quasi-crystalline and amorphous materials using electron microscopes. In these instruments, electrons are accelerated by an electrostatic potential in order to gain energy and shorten their wavelength. With the wavelength sufficiently short, the atomic structure acts as a diffraction grating generating diffraction patte ...
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Aldol Condensation Of Acetyl Cyanide
In organic chemistry, an aldol describes a structural motif consisting of a 3-hydroxy ketone or 3-hydroxyaldehyde. Aldols are usually the product of aldol addition. When used alone, the term "aldol" may refer to 3-hydroxybutanal. Stereochemistry Despite having only two functional groups, many aldols can have complicated structures arising from the relative positions of the OH group and the substituent between it and the carbonyl. Controlling reactions in order to favor the formation of one of these isomers is of great interest in the area of asymmetric synthesis. Reactions The chemistry of aldols is dominated by one reaction, dehydration: :RC(O)CH2CH(OH)R' → RC(O)CH=CHR' + H2O Hydroxypivaldehyde Hydroxypivaldehyde is the organic compound with the formula HOCH2(CH3)2CCHO. A colorless liquid, it is produced by condensation of formaldehyde and isobutyraldehyde: :CH2O + (CH3)2CHCHO → HOCH2(CH3)2CCHO The compound is a rare example of a ... is a rare example of a relati ...
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Formyl Cyanide
Formyl cyanide is a simple organic compound with the formula HCOCN and structure . It is simultaneously a nitrile () and an aldehyde (). Formyl cyanide is the simplest member of the acyl cyanide family. It is known to occur in space in the Sgr B2 molecular cloud. Production Formyl cyanide was first made by heating methoxyacetonitrile at 600 °C. Formyl cyanide can also be made by heating cinnamyloxyacetonitrile or allyloxyacetonitrile. In molecular clouds, formation of formyl cyanide is speculated to result from formaldehyde and the cyanide radical: :CH2O + CN^\bullet -> HCOCN + H^\bullet In Earth's atmosphere, the pollutant acrylonitrile reacts with hydroxyl radical forming formyl cyanide, hydroperoxyl and formaldehyde: :CH2=CHCN + OH^\bullet + 3/2 O2 -> HO2 + HCOCN + CH2O Reactions Formyl cyanide reacts with water to form formic acid and hydrogen cyanide Hydrogen cyanide, sometimes called prussic acid, is a chemical compound with the formula HCN and structure . ...
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Ketene
In organic chemistry, a ketene is an organic compound of the form , where R and R' are two arbitrary monovalent chemical groups (or two separate substitution sites in the same molecule). The name may also refer to the specific compound ethenone , the simplest ketene. Although they are highly useful, most ketenes are unstable. When used as reagents in a chemical procedure, they are typically generated when needed, and consumed as soon as (or while) they are produced. History Ketenes were first studied as a class by Hermann Staudinger before 1905. Ketenes were systematically investigated by Hermann Staudinger in 1905 in the form of diphenylketene (conversion of \alpha-chlorodiphenyl acetyl chloride with zinc). Staudinger was inspired by the first examples of reactive organic intermediates and stable radicals discovered by Moses Gomberg in 1900 (compounds with triphenylmethyl group). Properties Ketenes are highly electrophilic at the carbon atom bonded with the heteroatom, ...
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Hydrogen Cyanide
Hydrogen cyanide, sometimes called prussic acid, is a chemical compound with the formula HCN and structure . It is a colorless, extremely poisonous, and flammable liquid that boils slightly above room temperature, at . HCN is produced on an industrial scale and is a highly valued precursor to many chemical compounds ranging from polymers to pharmaceuticals. Large-scale applications are for the production of potassium cyanide and adiponitrile, used in mining and plastics, respectively. It is more toxic than solid cyanide compounds due to its volatile nature. Structure and general properties Hydrogen cyanide is a linear molecule, with a triple bond between carbon and nitrogen. The tautomer of HCN is HNC, hydrogen isocyanide. Hydrogen cyanide is weakly acidic with a p''K''a of 9.2. It partially ionizes in water solution to give the cyanide anion, CN−. A solution of hydrogen cyanide in water, represented as HCN, is called ''hydrocyanic acid''. The salts of the cyanide ani ...
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Acyl Cyanide Synthesis
In chemistry, an acyl group is a moiety derived by the removal of one or more hydroxyl groups from an oxoacid, including inorganic acids. It contains a double-bonded oxygen atom and an alkyl group (). In organic chemistry, the acyl group (IUPAC name: alkanoyl) is usually derived from a carboxylic acid, in which case it has the formula , where R represents an alkyl group that is linked to the carbon atom of the group by a single bond. Although the term is almost always applied to organic compounds, acyl groups can in principle be derived from other types of acids such as sulfonic acids and phosphonic acids. In the most common arrangement, acyl groups are attached to a larger molecular fragment, in which case the carbon and oxygen atoms are linked by a double bond. Compounds Well-known acyl compounds are the acyl chlorides, such as acetyl chloride (CH3COCl) and benzoyl chloride (C6H5COCl). These compounds, which are treated as sources of acylium cations, are good reagents for attac ...
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Acyl Cyanides
In chemistry, an acyl group is a moiety derived by the removal of one or more hydroxyl groups from an oxoacid, including inorganic acids. It contains a double-bonded oxygen atom and an alkyl group (). In organic chemistry, the acyl group (IUPAC name: alkanoyl) is usually derived from a carboxylic acid, in which case it has the formula , where R represents an alkyl group that is linked to the carbon atom of the group by a single bond. Although the term is almost always applied to organic compounds, acyl groups can in principle be derived from other types of acids such as sulfonic acids and phosphonic acids. In the most common arrangement, acyl groups are attached to a larger molecular fragment, in which case the carbon and oxygen atoms are linked by a double bond. Compounds Well-known acyl compounds are the acyl chlorides, such as acetyl chloride (CH3COCl) and benzoyl chloride (C6H5COCl). These compounds, which are treated as sources of acylium cations, are good reagents for attac ...
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