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Vinylogous
In organic chemistry, vinylogy is the transmission of electronic effects through a conjugated organic bonding system. The concept was introduced in 1926 by Ludwig Claisen to explain the acidic properties of formylacetone and related ketoaldehydes. Formylacetone, technically , only exists in the ionized form or . Its adjectival form, vinylogous, is used to describe functional groups in which the standard moieties of the group are separated by a carbon–carbon double bond. For example, a carboxylic acid is defined as a carbonyl group () directly attached to a hydroxyl group (): O=C–OH. A vinylogous carboxylic acid has a vinyl unit (, vinylene) between the two groups that define the acid: O=C–C=C–OH. The usual resonance of a carboxylate can propagate through the alkene of a vinylogous carboxylate. Likewise, 3-dimethylaminoacrolein is the vinylogous-amide analog of dimethylformamide. Due to the transmission of electronic information through conjugation, ''vinylogous'' ...
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Conjugate Addition
Nucleophilic conjugate addition is a type of organic reaction. Ordinary nucleophilic additions or 1,2-nucleophilic additions deal mostly with additions to carbonyl compounds. Simple alkene compounds do not show 1,2 reactivity due to lack of polarity, unless the alkene is activated with special substituents. With α,β-unsaturated carbonyl compounds such as cyclohexenone it can be deduced from resonance structures that the β position is an electrophilic site which can react with a nucleophile. The negative charge in these structures is stored as an alkoxide anion. Such a nucleophilic addition is called a nucleophilic conjugate addition or 1,4-nucleophilic addition. The most important active alkenes are the aforementioned conjugated carbonyls and acrylonitriles. Reaction mechanism Conjugate addition is the vinylogous counterpart of direct nucleophilic addition. A nucleophile reacts with a α,β-unsaturated carbonyl compound in the β position. The negative charge carried by t ...
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Conjugation (organic Chemistry)
In physical organic chemistry, a conjugated system is a system of connected p-orbitals with delocalized electrons in a molecule, which in general lowers the overall energy of the molecule and increases stability. It is conventionally represented as having alternating single and multiple bonds. Lone pairs, radicals or carbenium ions may be part of the system, which may be cyclic, acyclic, linear or mixed. The term "conjugated" was coined in 1899 by the German chemist Johannes Thiele. Conjugation is the overlap of one p-orbital with another across an adjacent σ bond (in transition metals, d-orbitals can be involved). A conjugated system has a region of overlapping p-orbitals, bridging the interjacent locations that simple diagrams illustrate as not having a π bond. They allow a delocalization of π electrons across all the adjacent aligned p-orbitals. The π electrons do not belong to a single bond or atom, but rather to a group of atoms. Molecules containing conjug ...
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Vinyl Group
In organic chemistry, a vinyl group (abbr. Vi; IUPAC name: ethenyl group) is a functional group with the formula . It is the ethylene (IUPAC name: ethene) molecule () with one fewer hydrogen atom. The name is also used for any compound containing that group, namely where R is any other group of atoms. An industrially important example is vinyl chloride, precursor to PVC, a plastic commonly known as ''vinyl''. Vinyl is one of the alkenyl functional groups. On a carbon skeleton, sp2-hybridized carbons or positions are often called vinylic. Allyls, acrylates and styrenics contain vinyl groups. (A styrenic crosslinker with two vinyl groups is called '' divinyl benzene''.) Vinyl polymers Vinyl groups can polymerize with the aid of a radical initiator or a catalyst, forming vinyl polymers. Vinyl polymers contain no vinyl groups. Instead they are saturated. The following table gives some examples of vinyl polymers. Synthesis and reactivity Vinyl derivatives are alke ...
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Acidic
An acid is a molecule or ion capable of either donating a proton (i.e. hydrogen cation, H+), known as a Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis acid. The first category of acids are the proton donors, or Brønsted–Lowry acids. In the special case of aqueous solutions, proton donors form the hydronium ion H3O+ and are known as Arrhenius acids. Brønsted and Lowry generalized the Arrhenius theory to include non-aqueous solvents. A Brønsted–Lowry or Arrhenius acid usually contains a hydrogen atom bonded to a chemical structure that is still energetically favorable after loss of H+. Aqueous Arrhenius acids have characteristic properties that provide a practical description of an acid. Acids form aqueous solutions with a sour taste, can turn blue litmus red, and react with bases and certain metals (like calcium) to form salts. The word ''acid'' is derived from the Latin , meaning 'sour'. An aqueous solution of an ...
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Formic Acid
Formic acid (), systematically named methanoic acid, is the simplest carboxylic acid. It has the chemical formula HCOOH and structure . This acid is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Esters, salts, and the anion derived from formic acid are called formates. Industrially, formic acid is produced from methanol. Natural occurrence Formic acid, which has a pungent, penetrating odor, is found naturally in insects, weeds, fruits and vegetables, and forest emissions. It appears in most ants and in stingless bees of the genus '' Oxytrigona''. Wood ants from the genus ''Formica'' can spray formic acid on their prey or to defend the nest. The puss moth caterpillar (''Cerura vinula'') will spray it as well when threatened by predators. It is also found in the trichomes of stinging nettle (''Urtica dioica''). Apart from that, this acid is incorporated in many fruits such as pineapple (0.21 mg per 100 g), apple (2 mg per ...
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Parent Structure
In chemistry, a parent structure is the structure of an unadorned ion or molecule from which derivatives can be visualized. Parent structures underpin systematic nomenclature and facilitate classification. Fundamental parent structures have one or no functional groups and often have various types of symmetry. Benzene () is a chemical itself consisting of a hexagonal ring of carbon atoms with a hydrogen atom attached to each, and is the parent of many derivatives that have substituent atoms or groups replacing one or more of the hydrogens. Some parents are rare or nonexistent themselves, as in the case of porphine, though many simple and complex derivatives are known. File:Benzene circle.png, Benzene is the parent. File:Toluene-vec.svg, Toluene is a derivative of benzene. File:Porphyrin.svg, Porphine is the parent of porphyrins. File:PPIXtransH.png, Protoporphyrin IX is a natural derivative of the parent porphine. File:H2octaethylporphyrin.png, Octaethylporphyrin is a ...
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Heuristic
A heuristic or heuristic technique (''problem solving'', '' mental shortcut'', ''rule of thumb'') is any approach to problem solving that employs a pragmatic method that is not fully optimized, perfected, or rationalized, but is nevertheless "good enough" as an approximation or attribute substitution. Where finding an optimal solution is impossible or impractical, heuristic methods can be used to speed up the process of finding a satisfactory solution. Heuristics can be mental shortcuts that ease the cognitive load of making a decision. Context Gigerenzer & Gaissmaier (2011) state that sub-sets of ''strategy'' include heuristics, regression analysis, and Bayesian inference. Heuristics are strategies based on rules to generate optimal decisions, like the anchoring effect and utility maximization problem. These strategies depend on using readily accessible, though loosely applicable, information to control problem solving in human beings, machines and abstract i ...
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Brønsted–Lowry Acid–base Theory
The Brønsted–Lowry theory (also called proton theory of acids and bases) is an acid–base reaction theory which was developed independently in 1923 by physical chemists Johannes Nicolaus Brønsted (in Denmark) and Thomas Martin Lowry (in the United Kingdom). The basic concept of this theory is that when an acid and a base react with each other, the acid forms its conjugate base, and the base forms its conjugate acid by exchange of a proton (the hydrogen cation, or H+). This theory generalises the Arrhenius theory. Definitions of acids and bases In the Arrhenius theory, acids are defined as substances that dissociate in aqueous solutions to give H+ ( hydrogen cations or protons), while bases are defined as substances that dissociate in aqueous solutions to give OH− (hydroxide ions). In 1923, physical chemists Johannes Nicolaus Brønsted in Denmark and Thomas Martin Lowry in England both independently proposed the theory named after them. In the Brønsted–Lowry ...
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Phenylene
In organic chemistry, the phenylene group () is based on a di-substituted benzene ring ( arylene). For example, poly(''p''-phenylene) is a polymer built up from ''para''-phenylene repeating units.p. C-9, Section 11.6, Handbook of Chemistry and Physics, 62nd Edition, 1981-1982, CRC Press The phenylene group has three structural isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is a compound that contains the same number and type of atoms, but with a different connectivity (i.e. arrangement of bonds) between them. The ...s, based on which hydrogens are substituted: ''para''-phenylene, ''meta''-phenylene, and ''ortho''-phenylene. References Arenediyl groups {{Aromatic-stub ...
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Enols
In organic chemistry, enols are a type of functional group or intermediate in organic chemistry containing a group with the formula (R = many substituents). The term ''enol'' is an abbreviation of ''alkenol'', a portmanteau deriving from "-ene"/"alkene" and the "-ol". Many kinds of enols are known. Keto–enol tautomerism refers to a chemical equilibrium between a "keto" form (a carbonyl, named for the common ketone case) and an enol. The interconversion of the two forms involves the transfer of an alpha hydrogen atom and the reorganisation of bonding electrons. The keto and enol forms are tautomers of each other. Enolization Organic esters, ketones, and aldehydes with an α-hydrogen ( bond adjacent to the carbonyl group) often form enols. The reaction involves migration of a proton () from carbon to oxygen: : In the case of ketones, the conversion is called a keto-enol tautomerism, although this name is often more generally applied to all such tautomerizations. Usually th ...
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Vitamin C
Vitamin C (also known as ascorbic acid and ascorbate) is a water-soluble vitamin found in citrus and other fruits, berries and vegetables. It is also a generic prescription medication and in some countries is sold as a non-prescription dietary supplement. As a therapy, it is used to prevent and treat scurvy, a disease caused by vitamin C deficiency. Vitamin C is an essential nutrient involved in the repair of tissue, the formation of collagen, and the enzymatic production of certain neurotransmitters. It is required for the functioning of several enzymes and is important for immune system function. It also functions as an antioxidant. Vitamin C may be taken by mouth or by intramuscular, subcutaneous or intravenous injection. Various health claims exist on the basis that moderate vitamin C deficiency increases disease risk, such as for the common cold, cancer or COVID-19. There are also claims of benefits from vitamin C supplementation in excess of the recommended d ...
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