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Aromatic hydrocarbon

Index Aromatic hydrocarbon

An aromatic hydrocarbon or arene (or sometimes aryl hydrocarbon) is a hydrocarbon with sigma bonds and delocalized pi electrons between carbon atoms forming a circle. [1]

100 relations: Acid, Aliphatic compound, Alkoxy group, Alkyne, Alkyne trimerisation, Aniline, Arene substitution pattern, Aromaticity, Aromatization, Aryl, Arylene, Asphaltene, Aspirin, August Kekulé, Benzene, Benzoic acid, Bergman cyclization, Biphenyl, Bond order, Carbon dioxide, Carbon–carbon bond, Carbon–nitrogen bond, Carbon–oxygen bond, Carcinogen, Coal, Comet, Coupling reaction, Cresol, Cycloaddition, Cyclohexane, Cyclooctadecanonaene, Cyclopentadienone, Cyclotetradecaheptaene, Dearomatization reaction, Decalin, Diels–Alder reaction, Durene, Electrophilic aromatic substitution, Electrophilic substitution, Enol, Enyne, Ethylbenzene, Excimer, Furan, Graphene, Hückel's rule, Heteroatom, Hexafluorobenzene, Hydrocarbon, Hydrodealkylation, ..., Hydrogenation, Hydroxy group, Interstellar medium, Isomer, Journal of Chemical Education, Journal of the Chemical Society, Mesitylene, Meteorite, Methyl group, Methyl iodide, Mutagen, Naphthalene, Nitrobenzene, Nitrogen, Nucleophilic aromatic substitution, Oil, Organic synthesis, Oxygen, PAH world hypothesis, Paracetamol, Phenol, Pi bond, Picric acid, Polycyclic aromatic hydrocarbon, Pyridine, Pyrone, Quinone, Radical-nucleophilic aromatic substitution, Raney nickel, Resonance (chemistry), Resorcinol, Rhodium-platinum oxide, Robert Robinson (organic chemist), Salicylic acid, Selenium, Sigma bond, Simple aromatic ring, Sodium hydroxide, Substituent, Sulfur, Tar, Teratology, Three-center two-electron bond, Toluene, Wagner-Jauregg reaction, Wulff–Dötz reaction, Xylene, Xylenol, 1-Naphthol, 2-Phenylhexane. Expand index (50 more) »

Acid

An acid is a molecule or ion capable of donating a hydron (proton or hydrogen ion H+), or, alternatively, capable of forming a covalent bond with an electron pair (a Lewis acid).

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Aliphatic compound

In organic chemistry, hydrocarbons (compounds composed of carbon and hydrogen) are divided into two classes: aromatic compounds and aliphatic compounds (G. aleiphar, fat, oil) also known as non-aromatic compounds.

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Alkoxy group

In chemistry, the alkoxy group is an alkyl (carbon and hydrogen chain) group singularly bonded to oxygen; thus R–O.

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Alkyne

In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond.

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Alkyne trimerisation

An alkyne trimerisation reaction is a 2+2+2 cyclization reaction in which three molecules of alkyne react to form an arene.

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Aniline

Aniline is an organic compound with the formula C6H5NH2.

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Arene substitution pattern

Arene substitution patterns are part of organic chemistry IUPAC nomenclature and pinpoint the position of substituents other than hydrogen in relation to each other on an aromatic hydrocarbon.

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Aromaticity

In organic chemistry, the term aromaticity is used to describe a cyclic (ring-shaped), planar (flat) molecule with a ring of resonance bonds that exhibits more stability than other geometric or connective arrangements with the same set of atoms.

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Aromatization

Aromatization is a chemical reaction in which an aromatic system is formed.

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Aryl

In the context of organic molecules, aryl is any functional group or substituent derived from an aromatic ring, usually an aromatic hydrocarbon, such as phenyl and naphthyl.

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Arylene

An arylene or arenediyl is a substituent of an organic compound that is derived from an aromatic hydrocarbon (arene) that has had a hydrogen atom removed from two ring carbon atoms, such as phenylene.

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Asphaltene

Asphaltenes are molecular substances that are found in crude oil, along with resins, aromatic hydrocarbons, and saturates (i.e. saturated hydrocarbons such as alkanes).

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Aspirin

Aspirin, also known as acetylsalicylic acid (ASA), is a medication used to treat pain, fever, or inflammation.

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August Kekulé

Friedrich August Kekulé, later Friedrich August Kekule von Stradonitz (7 September 1829 – 13 July 1896), was a German organic chemist.

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Benzene

Benzene is an important organic chemical compound with the chemical formula C6H6.

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Benzoic acid

Benzoic acid, C7H6O2 (or C6H5COOH), is a colorless crystalline solid and a simple aromatic carboxylic acid.

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Bergman cyclization

The Bergman cyclization or Bergman reaction or Bergman cycloaromatization is an organic reaction and more specifically a rearrangement reaction taking place when an enediyne is heated in presence of a suitable hydrogen donor (Scheme 1).

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Biphenyl

Biphenyl (or diphenyl or phenylbenzene or 1,1′-biphenyl or lemonene) is an organic compound that forms colorless crystals.

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Bond order

Bond order is the number of chemical bonds between a pair of atoms.

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Carbon dioxide

Carbon dioxide (chemical formula) is a colorless gas with a density about 60% higher than that of dry air.

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Carbon–carbon bond

A carbon–carbon bond is a covalent bond between two carbon atoms.

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Carbon–nitrogen bond

A carbon–nitrogen bond is a covalent bond between carbon and nitrogen and is one of the most abundant bonds in organic chemistry and biochemistry.

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Carbon–oxygen bond

A carbon–oxygen bond is a polar covalent bond between carbon and oxygen.

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Carcinogen

A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis, the formation of cancer.

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Coal

Coal is a combustible black or brownish-black sedimentary rock usually occurring in rock strata in layers or veins called coal beds or coal seams.

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Comet

A comet is an icy small Solar System body that, when passing close to the Sun, warms and begins to release gases, a process called outgassing.

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Coupling reaction

A coupling reaction in organic chemistry is a general term for a variety of reactions where two hydrocarbon fragments are coupled with the aid of a metal catalyst.

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Cresol

Cresols (also hydroxytoluene) are organic compounds which are methylphenols.

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Cycloaddition

A cycloaddition is a pericyclic chemical reaction, in which "two or more unsaturated molecules (or parts of the same molecule) combine with the formation of a cyclic adduct in which there is a net reduction of the bond multiplicity." The resulting reaction is a cyclization reaction.

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Cyclohexane

Cyclohexane is a cycloalkane with the molecular formula C6H12 (the alkyl is abbreviated Cy).

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Cyclooctadecanonaene

Cyclooctadecanonaene or annulene is a planar annulene with chemical formula.

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Cyclopentadienone

Cyclopentadienone is an organic compound with molecular formula C5H4O.

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Cyclotetradecaheptaene

Cyclotetradecaheptaene is a nonplanar aromatic annulene with molecular formula C14H14.

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Dearomatization reaction

A dearomatization reaction is an organic reaction which involves arenes as reactants and in which the reaction products have permanently lost their aromaticity.

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Decalin

Decalin (decahydronaphthalene, also known as bicyclodecane), a bicyclic organic compound, is an industrial solvent.

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Diels–Alder reaction

The Diels–Alder reaction is an organic chemical reaction (specifically, a cycloaddition) between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene derivative.

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Durene

Durene, or 1,2,4,5-tetramethylbenzene, is an organic compound with the formula C6H2(CH3)4.

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Electrophilic aromatic substitution

Electrophilic aromatic substitution is an organic reaction in which an atom that is attached to an aromatic system (usually hydrogen) is replaced by an electrophile.

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Electrophilic substitution

Electrophilic substitution reactions are chemical reactions in which an electrophile displaces a functional group in a compound, which is typically, but not always, a hydrogen atom.

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Enol

Enols, or more formally, alkenols, are a type of reactive structure or intermediate in organic chemistry that is represented as an alkene (olefin) with a hydroxyl group attached to one end of the alkene double bond.

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Enyne

An enyne is a functional group in organic chemistry consisting of a conjugated alkyne and alkene group.

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Ethylbenzene

Ethylbenzene is an organic compound with the formula C6H5CH2CH3.

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Excimer

An excimer (originally short for excited dimer) is a short-lived dimeric or heterodimeric molecule formed from two species, at least one of which has completely filled valence shell by electrons (for example, noble gases).

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Furan

Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen.

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Graphene

Graphene is a semi-metal with a small overlap between the valence and the conduction bands (zero bandgap material).

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Hückel's rule

In organic chemistry, Hückel's rule estimates whether a planar ring molecule will have aromatic properties.

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Heteroatom

In chemistry, a heteroatom (from Ancient Greek heteros, "different", + atomos, "uncut") is any atom that is not carbon or hydrogen.

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Hexafluorobenzene

Hexafluorobenzene, HFB,, or perfluorobenzene is an organic, aromatic compound.

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Hydrocarbon

In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon.

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Hydrodealkylation

Hydrodealkylation is a chemical reaction that often involves reacting an aromatic hydrocarbon, such as toluene, in the presence of hydrogen gas to form a simpler aromatic hydrocarbon devoid of functional groups.

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Hydrogenation

Hydrogenation – to treat with hydrogen – is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum.

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Hydroxy group

A hydroxy or hydroxyl group is the entity with the formula OH.

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Interstellar medium

In astronomy, the interstellar medium (ISM) is the matter and radiation that exists in the space between the star systems in a galaxy.

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Isomer

An isomer (from Greek ἰσομερής, isomerès; isos.

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Journal of Chemical Education

The Journal of Chemical Education is a monthly peer-reviewed academic journal available in both print and electronic versions.

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Journal of the Chemical Society

The Journal of the Chemical Society was a scientific journal established by the Chemical Society in 1849 as the Quarterly Journal of the Chemical Society.

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Mesitylene

Mesitylene or 1,3,5-trimethylbenzene is a derivative of benzene with three methyl substituents positioned symmetrically around the ring.

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Meteorite

A meteorite is a solid piece of debris from an object, such as a comet, asteroid, or meteoroid, that originates in outer space and survives its passage through the atmosphere to reach the surface of a planet or moon.

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Methyl group

A methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms — CH3.

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Methyl iodide

Methyl iodide, also called iodomethane, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I.

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Mutagen

In genetics, a mutagen is a physical or chemical agent that changes the genetic material, usually DNA, of an organism and thus increases the frequency of mutations above the natural background level.

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Naphthalene

Naphthalene is an organic compound with formula.

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Nitrobenzene

Nitrobenzene is an organic compound with the chemical formula C6H5NO2.

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Nitrogen

Nitrogen is a chemical element with symbol N and atomic number 7.

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Nucleophilic aromatic substitution

Aromatic nucleophilic substitution A nucleophilic aromatic substitution is a substitution reaction in organic chemistry in which the nucleophile displaces a good leaving group, such as a halide, on an aromatic ring.

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Oil

An oil is any nonpolar chemical substance that is a viscous liquid at ambient temperatures and is both hydrophobic (does not mix with water, literally "water fearing") and lipophilic (mixes with other oils, literally "fat loving").

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Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds.

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Oxygen

Oxygen is a chemical element with symbol O and atomic number 8.

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PAH world hypothesis

The PAH world hypothesis is a speculative hypothesis that proposes that polycyclic aromatic hydrocarbons (PAH), known to be abundant in the universe, including in comets, and, as well, assumed to be abundant in the primordial soup of the early Earth, played a major role in the origin of life by mediating the synthesis of RNA molecules, leading into the RNA world.

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Paracetamol

--> Acetanilide was the first aniline derivative serendipitously found to possess analgesic as well as antipyretic properties, and was quickly introduced into medical practice under the name of Antifebrin by A. Cahn and P. Hepp in 1886. But its unacceptable toxic effects, the most alarming being cyanosis due to methemoglobinemia, prompted the search for less toxic aniline derivatives. Harmon Northrop Morse had already synthesised paracetamol at Johns Hopkins University via the reduction of ''p''-nitrophenol with tin in glacial acetic acid in 1877, but it was not until 1887 that clinical pharmacologist Joseph von Mering tried paracetamol on humans. In 1893, von Mering published a paper reporting on the clinical results of paracetamol with phenacetin, another aniline derivative. Von Mering claimed that, unlike phenacetin, paracetamol had a slight tendency to produce methemoglobinemia. Paracetamol was then quickly discarded in favor of phenacetin. The sales of phenacetin established Bayer as a leading pharmaceutical company. Overshadowed in part by aspirin, introduced into medicine by Heinrich Dreser in 1899, phenacetin was popular for many decades, particularly in widely advertised over-the-counter "headache mixtures", usually containing phenacetin, an aminopyrine derivative of aspirin, caffeine, and sometimes a barbiturate. Paracetamol is the active metabolite of phenacetin and acetanilide, both once popular as analgesics and antipyretics in their own right. However, unlike phenacetin, acetanilide and their combinations, paracetamol is not considered carcinogenic at therapeutic doses. Von Mering's claims remained essentially unchallenged for half a century, until two teams of researchers from the United States analyzed the metabolism of acetanilide and paracetamol. In 1947 David Lester and Leon Greenberg found strong evidence that paracetamol was a major metabolite of acetanilide in human blood, and in a subsequent study they reported that large doses of paracetamol given to albino rats did not cause methemoglobinemia. In three papers published in the September 1948 issue of the Journal of Pharmacology and Experimental Therapeutics, Bernard Brodie, Julius Axelrod and Frederick Flinn confirmed using more specific methods that paracetamol was the major metabolite of acetanilide in human blood, and established that it was just as efficacious an analgesic as its precursor. They also suggested that methemoglobinemia is produced in humans mainly by another metabolite, phenylhydroxylamine. A follow-up paper by Brodie and Axelrod in 1949 established that phenacetin was also metabolised to paracetamol. This led to a "rediscovery" of paracetamol. It has been suggested that contamination of paracetamol with 4-aminophenol, the substance von Mering synthesised it from, may be the cause for his spurious findings. Paracetamol was first marketed in the United States in 1950 under the name Triagesic, a combination of paracetamol, aspirin, and caffeine. Reports in 1951 of three users stricken with the blood disease agranulocytosis led to its removal from the marketplace, and it took several years until it became clear that the disease was unconnected. Paracetamol was marketed in 1953 by Sterling-Winthrop Co. as Panadol, available only by prescription, and promoted as preferable to aspirin since it was safe for children and people with ulcers. In 1955, paracetamol was marketed as Children's Tylenol Elixir by McNeil Laboratories. In 1956, 500 mg tablets of paracetamol went on sale in the United Kingdom under the trade name Panadol, produced by Frederick Stearns & Co, a subsidiary of Sterling Drug Inc. In 1963, paracetamol was added to the British Pharmacopoeia, and has gained popularity since then as an analgesic agent with few side-effects and little interaction with other pharmaceutical agents. Concerns about paracetamol's safety delayed its widespread acceptance until the 1970s, but in the 1980s paracetamol sales exceeded those of aspirin in many countries, including the United Kingdom. This was accompanied by the commercial demise of phenacetin, blamed as the cause of analgesic nephropathy and hematological toxicity. In 1988 Sterling Winthrop was acquired by Eastman Kodak which sold the over the counter drug rights to SmithKline Beecham in 1994. Available without a prescription since 1959, it has since become a common household drug. Patents on paracetamol have long expired, and generic versions of the drug are widely available.

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Phenol

Phenol, also known as phenolic acid, is an aromatic organic compound with the molecular formula C6H5OH.

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Pi bond

In chemistry, pi bonds (π bonds) are covalent chemical bonds where two lobes of an orbital on one atom overlap two lobes of an orbital on another atom.

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Picric acid

Picric acid is an organic compound with the formula (O2N)3C6H2OH.

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Polycyclic aromatic hydrocarbon

Polycyclic aromatic hydrocarbons (PAHs, also polyaromatic hydrocarbons or polynuclear aromatic hydrocarbons) are hydrocarbons—organic compounds containing only carbon and hydrogen—that are composed of multiple aromatic rings (organic rings in which the electrons are delocalized).

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Pyridine

Pyridine is a basic heterocyclic organic compound with the chemical formula C5H5N.

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Pyrone

Pyrones or pyranones are a class of cyclic chemical compounds.

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Quinone

The quinones are a class of organic compounds that are formally "derived from aromatic compounds by conversion of an even number of –CH.

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Radical-nucleophilic aromatic substitution

Radical-nucleophilic aromatic substitution or SRN1 in organic chemistry is a type of substitution reaction in which a certain substituent on an aromatic compound is replaced by a nucleophile through an intermediary free radical species: The substituent X is a halide and nucleophiles can be sodium amide, an alkoxide or a carbon nucleophile such as an enolate.

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Raney nickel

Raney nickel, also called spongy nickel, is a fine-grained solid composed mostly of nickel derived from a nickel-aluminium alloy.

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Resonance (chemistry)

In chemistry, resonance or mesomerism is a way of describing delocalized electrons within certain molecules or polyatomic ions where the bonding cannot be expressed by one single Lewis structure.

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Resorcinol

Resorcinol (or resorcin) is a benzenediol (''m''-dihydroxybenzene).

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Rhodium-platinum oxide

Rhodium-platinum oxide (Rh–Pt oxide), or Nishimura's catalyst, is an inorganic compound used as a hydrogenation catalyst.

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Robert Robinson (organic chemist)

Sir Robert Robinson (13 September 1886 – 8 February 1975) was a British organic chemist and Nobel laureate recognised in 1947 for his research on plant dyestuffs (anthocyanins) and alkaloids.

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Salicylic acid

Salicylic acid (from Latin salix, willow tree) is a lipophilic monohydroxybenzoic acid, a type of phenolic acid, and a beta hydroxy acid (BHA).

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Selenium

Selenium is a chemical element with symbol Se and atomic number 34.

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Sigma bond

In chemistry, sigma bonds (σ bonds) are the strongest type of covalent chemical bond.

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Simple aromatic ring

Simple aromatic rings, also known as simple arenes or simple aromatics, are aromatic organic compounds that consist only of a conjugated planar ring system.

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Sodium hydroxide

Sodium hydroxide, also known as lye, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions. Sodium hydroxide is a highly caustic base and alkali that decomposes proteins at ordinary ambient temperatures and may cause severe chemical burns. It is highly soluble in water, and readily absorbs moisture and carbon dioxide from the air. It forms a series of hydrates NaOH·n. The monohydrate NaOH· crystallizes from water solutions between 12.3 and 61.8 °C. The commercially available "sodium hydroxide" is often this monohydrate, and published data may refer to it instead of the anhydrous compound. As one of the simplest hydroxides, it is frequently utilized alongside neutral water and acidic hydrochloric acid to demonstrate the pH scale to chemistry students. Sodium hydroxide is used in many industries: in the manufacture of pulp and paper, textiles, drinking water, soaps and detergents, and as a drain cleaner. Worldwide production in 2004 was approximately 60 million tonnes, while demand was 51 million tonnes.

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Substituent

In organic chemistry and biochemistry, a substituent is an atom or group of atoms which replaces one or more hydrogen atoms on the parent chain of a hydrocarbon, becoming a moiety of the resultant new molecule.

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Sulfur

Sulfur or sulphur is a chemical element with symbol S and atomic number 16.

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Tar

Tar is a dark brown or black viscous liquid of hydrocarbons and free carbon, obtained from a wide variety of organic materials through destructive distillation.

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Teratology

Teratology is the study of abnormalities of physiological development.

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Three-center two-electron bond

A three-center two-electron bond is an electron-deficient chemical bond where three atoms share two electrons.

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Toluene

Toluene, also known as toluol, is an aromatic hydrocarbon.

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Wagner-Jauregg reaction

The Wagner-Jauregg reaction is a classic organic reaction in organic chemistry, named after Theodor Wagner-Jauregg, describing the double Diels–Alder reaction of 2 equivalents of maleic anhydride with a 1,1-diarylethylene.

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Wulff–Dötz reaction

The Wulff–Dötz reaction (also known as the Dötz reaction or the benzannulation reaction of the Fischer carbene complexes) is the chemical reaction of an aromatic or vinylic alkoxy pentacarbonyl chromium carbene complex with an alkyne and carbon monoxide to give a Cr(CO)3-coordinated substituted phenol.

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Xylene

Xylene (from Greek ξύλο, xylo, "wood"), xylol or dimethylbenzene is any one of three isomers of dimethylbenzene, or a combination thereof.

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Xylenol

Xylenols are organic compounds with the formula (CH3)2C6H3OH.

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1-Naphthol

1-Naphthol, or α-naphthol, is a fluorescent organic compound with the formula C10H7OH.

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2-Phenylhexane

2-Phenylhexane is an aromatic hydrocarbon.

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Arene, Arene compound, Arenes, Aromatic hydrocarbons, Aryl hydrocarbon, Homologues of benzene, Hydrocarbons, aromatic, Monocyclic aromatic hydrocarbon.

References

[1] https://en.wikipedia.org/wiki/Aromatic_hydrocarbon

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