127 relations: Acetamide, Acetic acid, Acid, Acid dissociation constant, Acid–base reaction, Activation energy, Acyl chloride, Acyl group, Addition reaction, Alcohol, Aldehyde, Alkali, Alkene, Aluminium chloride, Amide reduction, Amidicity, Amidogen, Amine, Amino radical, Aminolysis, Ammonia, Aniline, Aramid, Base (chemistry), Beckmann rearrangement, Benzenesulfonyl chloride, Biochemistry, Biomolecular structure, Bischler–Napieralski reaction, Brønsted–Lowry acid–base theory, Bromine, Carbon, Carbonium ion, Carbonyl group, Carboxamide, Carboximidate, Carboxylic acid, Catalysis, Chemische Berichte, Conjugate acid, Delocalized electron, Dimethylacetamide, Dimethylamine, Dimethylformamide, Double bond, Electron, Electrophile, Enzyme, Ester, Formamide, ..., Functional group, Grignard reaction, Hair, HATU, Hemiaminal, Hofmann rearrangement, Homologation reaction, Homonym, Hydrogen, Hydrogen bond, Hydrolysis, Hydroxy group, Hydroxybenzotriazole, Hydroxylamine, Imine, In silico, Infrared spectroscopy, Ion, Isocyanate, Isopeptide bond, Ketone, Kevlar, Lactam, Lewis acids and bases, List of organic reactions, Lithium aluminium hydride, Lumière–Barbier method, Lysergic acid diethylamide, Metal amides, Molecular orbital, Nitrile, Nitrogen, Nuclear magnetic resonance spectroscopy, Nucleophilic aromatic substitution, Nylon, Organic acid anhydride, Organic compound, Organic reaction, Organic Reactions, Oxygen, Paracetamol, Passerini reaction, Penicillin, Peptide bond, Peptide synthesis, Phosphoramide, Phosphorus pentoxide, Phosphoryl chloride, Photochemistry, Pi bond, Polyamide, Protease, Protein, PyBOP, Pyridine, Quinuclidone, Radical (chemistry), Reaction mechanism, Resonance (chemistry), Ritter reaction, Rudolf Leuckart (chemist), Ruthenium, Schmidt reaction, Schotten–Baumann reaction, Secondary (chemistry), Sodium hydroxide, Solubility, Spider silk, Sulfonamide, Thionyl chloride, Trifluoroacetic anhydride, Tris(2,2,2-trifluoroethyl) borate, Twaron, Ugi reaction, Vilsmeier–Haack reaction, Water, Willgerodt rearrangement. Expand index (77 more) » « Shrink index
Acetamide (systematic name: ethanamide) is an organic compound with the formula CH3CONH2.
Acetic acid, systematically named ethanoic acid, is a colourless liquid organic compound with the chemical formula CH3COOH (also written as CH3CO2H or C2H4O2).
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).
An acid dissociation constant, Ka, (also known as acidity constant, or acid-ionization constant) is a quantitative measure of the strength of an acid in solution.
An acid–base reaction is a chemical reaction that occurs between an acid and a base, which can be used to determine pH.
In chemistry and physics, activation energy is the energy which must be available to a chemical or nuclear system with potential reactants to result in: a chemical reaction, nuclear reaction, or other various other physical phenomena.
In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group -COCl. Their formula is usually written RCOCl, where R is a side chain.
An acyl group is a moiety derived by the removal of one or more hydroxyl groups from an oxoacid, including inorganic acids.
An addition reaction, in organic chemistry, is in its simplest terms an organic reaction where two or more molecules combine to form the larger one (the adduct).
In chemistry, an alcohol is any organic compound in which the hydroxyl functional group (–OH) is bound to a carbon.
An aldehyde or alkanal is an organic compound containing a functional group with the structure −CHO, consisting of a carbonyl center (a carbon double-bonded to oxygen) with the carbon atom also bonded to hydrogen and to an R group, which is any generic alkyl or side chain.
In chemistry, an alkali (from Arabic: al-qaly “ashes of the saltwort”) is a basic, ionic salt of an alkali metal or alkaline earth metal chemical element.
In organic chemistry, an alkene is an unsaturated hydrocarbon that contains at least one carbon–carbon double bond.
Aluminium chloride (AlCl3) is the main compound of aluminium and chlorine.
Amide reduction is a reaction in organic synthesis where an amide is reduced to either an amine or an aldehyde functional group.
The amidicity scale is a computational method for calculating the strength of an amide bond in an organic compound on a linear scale.
In chemistry, amidogen is a radical compound of nitrogen and hydrogen with the formula NH2.
In organic chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair.
The amino radical,, also known as the aminyl radical or azanyl radical, is the neutral form of the amide ion.
Aminolysis is any chemical reaction in which a molecule is split into two parts by reacting with a molecule of ammonia or an amine.
Ammonia is a compound of nitrogen and hydrogen with the formula NH3.
Aniline is an organic compound with the formula C6H5NH2.
Aramid fibers are a class of heat-resistant and strong synthetic fibers.
In chemistry, bases are substances that, in aqueous solution, release hydroxide (OH−) ions, are slippery to the touch, can taste bitter if an alkali, change the color of indicators (e.g., turn red litmus paper blue), react with acids to form salts, promote certain chemical reactions (base catalysis), accept protons from any proton donor, and/or contain completely or partially displaceable OH− ions.
The Beckmann rearrangement, named after the German chemist Ernst Otto Beckmann (1853–1923), is an acid-catalyzed rearrangement of an oxime to substituted amide.
Benzenesulfonyl chloride is an organosulfur compound with the formula C6H5SO2Cl.
Biochemistry, sometimes called biological chemistry, is the study of chemical processes within and relating to living organisms.
Biomolecular structure is the intricate folded, three-dimensional shape that is formed by a molecule of protein, DNA, or RNA, and that is important to its function.
The Bischler–Napieralski reaction is an intramolecular electrophilic aromatic substitution reaction that allows for the cyclization of β-arylethylamides or β-arylethylcarbamates.
The Brønsted–Lowry theory is an acid–base reaction theory which was proposed independently by Johannes Nicolaus Brønsted and Thomas Martin Lowry in 1923.
Bromine is a chemical element with symbol Br and atomic number 35.
Carbon (from carbo "coal") is a chemical element with symbol C and atomic number 6.
In chemistry, carbonium ion is any cation that has a pentavalent carbon atom, The name carbonium may also be used for the simplest member of the class, properly called methanium, where the five valences are filled with hydrogen atoms.
In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C.
In organic chemistry carboxamides (or amino carbonyls) are functional groups with the general structure R-CO-NR'R′′ with R, R', and R′′ as organic substituents, or hydrogen.
Carboximidates (or more general imidates) are organic compounds, which can be thought of as esters formed between a carboximidic acid (R-C(.
A carboxylic acid is an organic compound that contains a carboxyl group (C(.
Catalysis is the increase in the rate of a chemical reaction due to the participation of an additional substance called a catalysthttp://goldbook.iupac.org/C00876.html, which is not consumed in the catalyzed reaction and can continue to act repeatedly.
Chemische Berichte (usually abbreviated as Ber. or Chem. Ber.) was a German-language scientific journal of all disciplines of chemistry founded in 1868.
A conjugate acid, within the Brønsted–Lowry acid–base theory, is a species formed by the reception of a proton (H+) by a base—in other words, it is a base with a hydrogen ion added to it.
In chemistry, delocalized electrons are electrons in a molecule, ion or solid metal that are not associated with a single atom or a covalent bond.
Dimethylacetamide (DMAc or DMA) is the organic compound with the formula CH3C(O)N(CH3)2.
Dimethylamine is an organic compound with the formula (CH3)2NH.
Dimethylformamide is an organic compound with the formula (CH3)2NC(O)H.
A double bond in chemistry is a chemical bond between two chemical elements involving four bonding electrons instead of the usual two.
The electron is a subatomic particle, symbol or, whose electric charge is negative one elementary charge.
In organic chemistry, an electrophile is a reagent attracted to electrons.
Enzymes are macromolecular biological catalysts.
In chemistry, an ester is a chemical compound derived from an acid (organic or inorganic) in which at least one –OH (hydroxyl) group is replaced by an –O–alkyl (alkoxy) group.
Formamide, also known as methanamide, is an amide derived from formic acid.
In organic chemistry, functional groups are specific substituents or moieties within molecules that are responsible for the characteristic chemical reactions of those molecules.
The Grignard reaction (pronounced) is an organometallic chemical reaction in which alkyl, vinyl, or aryl-magnesium halides (Grignard reagents) add to a carbonyl group in an aldehyde or ketone.
Hair is a protein filament that grows from follicles found in the dermis.
HATU (1--1H-1,2,3-triazolopyridinium 3-oxid hexafluorophosphate, Hexafluorophosphate Azabenzotriazole Tetramethyl Uronium) is a reagent used in peptide coupling chemistry to generate an active ester from a carboxylic acid.
A hemiaminal (also carbinolamine) is a functional group or type of chemical compound that has a hydroxyl group and an amine attached to the same carbon atom: -C(OH)(NR2)-.
The Hofmann rearrangement is the organic reaction of a primary amide to a primary amine with one fewer carbon atom.
A homologation reaction, also known as homologization, is any chemical reaction that converts the reactant into the next member of the homologous series.
In linguistics, homonyms, broadly defined, are words which sound alike or are spelled alike, but have different meanings.
Hydrogen is a chemical element with symbol H and atomic number 1.
A hydrogen bond is a partially electrostatic attraction between a hydrogen (H) which is bound to a more electronegative atom such as nitrogen (N), oxygen (O), or fluorine (F), and another adjacent atom bearing a lone pair of electrons.
Hydrolysis is a term used for both an electro-chemical process and a biological one.
A hydroxy or hydroxyl group is the entity with the formula OH.
Hydroxybenzotriazole (abbreviated HOBt) is an organic compound that is a derivative of benzotriazole.
Hydroxylamine is an inorganic compound with the formula NH2OH.
An imine is a functional group or chemical compound containing a carbon–nitrogen double bond.
In silico (literally cod Latin for "in silicon", alluding to the mass use of silicon for semiconductor computer chips) is an expression used to mean "performed on computer or via computer simulation." The phrase was coined in 1989 as an allusion to the Latin phrases in vivo, in vitro, and in situ, which are commonly used in biology (see also systems biology) and refer to experiments done in living organisms, outside living organisms, and where they are found in nature, respectively.
Infrared spectroscopy (IR spectroscopy or vibrational spectroscopy) involves the interaction of infrared radiation with matter.
An ion is an atom or molecule that has a non-zero net electrical charge (its total number of electrons is not equal to its total number of protons).
Isocyanate is the functional group with the formula R–N.
An isopeptide bond is an amide bond that is not present on the main chain of a protein.
In chemistry, a ketone (alkanone) is an organic compound with the structure RC(.
Kevlar is a heat-resistant and strong synthetic fiber, related to other aramids such as Nomex and Technora.
A lactam is a cyclic amide.
A Lewis acid 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.
Well-known reactions and reagents in organic chemistry include.
Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula LiAlH4.
The Lumière–Barbier method is a method of acetylating aromatic amines in aqueous solutions.
Lysergic acid diethylamide (LSD), also known as acid, is a psychedelic drug known for its psychological effects, which may include altered awareness of one's surroundings, perceptions, and feelings as well as sensations and images that seem real though they are not.
Metal amides are a class of coordination compounds composed of a metal center with amide ligands of the form NR2.
In chemistry, a molecular orbital (MO) is a mathematical function describing the wave-like behavior of an electron in a molecule.
A nitrile is any organic compound that has a −C≡N functional group.
Nitrogen is a chemical element with symbol N and atomic number 7.
Nuclear magnetic resonance spectroscopy, most commonly known as NMR spectroscopy or magnetic resonance spectroscopy (MRS), is a spectroscopic technique to observe local magnetic fields around atomic nuclei.
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.
Nylon is a generic designation for a family of synthetic polymers, based on aliphatic or semi-aromatic polyamides.
An organic acid anhydride is an acid anhydride that is an organic compound.
In chemistry, an organic compound is generally any chemical compound that contains carbon.
Organic reactions are chemical reactions involving organic compounds.
Organic Reactions is a secondary reference which synthesizes the organic chemistry literature around particular chemical transformations.
Oxygen is a chemical element with symbol O and atomic number 8.
--> 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.
The Passerini reaction is a chemical reaction involving an isocyanide, an aldehyde (or ketone), and a carboxylic acid to form a α-acyloxy amide.
Penicillin (PCN or pen) is a group of antibiotics which include penicillin G (intravenous use), penicillin V (use by mouth), procaine penicillin, and benzathine penicillin (intramuscular use).
A peptide bond is a covalent chemical bond linking two consecutive amino acid monomers along a peptide or protein chain.
In organic chemistry, peptide synthesis is the production of peptides, compounds where multiple amino acids are linked via amide bonds, also known as peptide bonds.
Phosphoramide is a chemical compound with the molecular formula P(.
Phosphorus pentoxide is a chemical compound with molecular formula P4O10 (with its common name derived from its empirical formula, P2O5).
Phosphoryl chloride (commonly called phosphorus oxychloride) is a colourless liquid with the formula 3.
Photochemistry is the branch of chemistry concerned with the chemical effects of light.
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.
A polyamide is a macromolecule with repeating units linked by amide bonds.
A protease (also called a peptidase or proteinase) is an enzyme that performs proteolysis: protein catabolism by hydrolysis of peptide bonds.
Proteins are large biomolecules, or macromolecules, consisting of one or more long chains of amino acid residues.
PyBOP (benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate) is a peptide coupling reagent used in solid phase peptide synthesis.
Pyridine is a basic heterocyclic organic compound with the chemical formula C5H5N.
Quinuclidones are a class of bicyclic organic compounds with chemical formula C7H11NO with two structural isomers for the base skeleton 3-quinuclidone and 2-quinuclidone.
In chemistry, a radical (more precisely, a free radical) is an atom, molecule, or ion that has an unpaired valence electron.
In chemistry, a reaction mechanism is the step by step sequence of elementary reactions by which overall chemical change occurs.
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.
The Ritter reaction is a chemical reaction that transforms a nitrile into an N-alkyl amide using various electrophilic alkylating reagents.
Carl Louis Rudolf Alexander Leuckart (June 23, 1854 – July 24, 1889) was a German chemist who discovered the Leuckart reaction and Leuckart thiophenol reaction.
Ruthenium is a chemical element with symbol Ru and atomic number 44.
The Schmidt reaction is an organic reaction in which an azide reacts with a carbonyl group to give an amine or amide, with expulsion of nitrogen.
The Schotten–Baumann reaction is a method to synthesise amides from amines and acid chlorides: Sometimes the name for this reaction is also used to indicate the reaction between an acid chloride and an alcohol to form an ester.
Secondary is a term used in organic chemistry to classify various types of compounds (e. g. alcohols, alkyl halides, amines) or reactive intermediates (e. g. alkyl radicals, carbocations).
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.
Solubility is the property of a solid, liquid or gaseous chemical substance called solute to dissolve in a solid, liquid or gaseous solvent.
Spider silk is a protein fibre spun by spiders.
In chemistry, the sulfonamide functional group (also spelled sulphonamide) is -S(.
Thionyl chloride is an inorganic compound with the chemical formula SOCl2.
Trifluoroacetic anhydride (TFAA) is the acid anhydride of trifluoroacetic acid.
Tris(2,2,2-trifluoroethyl) borate, also commonly referred to as the Sheppard amidation reagent, is a chemical compound with the formula B(OCH2CF3)3.
Twaron (a brand name of Teijin Aramid) is a para-aramid.
The Ugi reaction is a multi-component reaction in organic chemistry involving a ketone or aldehyde, an amine, an isocyanide and a carboxylic acid to form a bis-amide.
The Vilsmeier–Haack reaction (also called the Vilsmeier reaction) is the chemical reaction of a substituted amide (1) with phosphorus oxychloride and an electron-rich arene (3) to produce an aryl aldehyde or ketone (5).
Water is a transparent, tasteless, odorless, and nearly colorless chemical substance that is the main constituent of Earth's streams, lakes, and oceans, and the fluids of most living organisms.
The Willgerodt rearrangement or Willgerodt reaction is an organic reaction converting an aryl alkyl ketone to the corresponding amide by reaction with ammonium polysulfide, named after Conrad Willgerodt.