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Cross-conjugation
Cross-conjugation is a special type of conjugation in a molecule, when in a set of three pi bonds only two pi bonds interact with each other by conjugation, while the third one is excluded from interaction. Whereas a normal conjugated system such as a polyene typically has alternating single and double bonds along consecutive atoms, a cross-conjugated system has an alkene unit bonded to one of the middle atoms of another conjugated chain through a single bond. In classical terms, one of the double-bonds branches off rather than continuing consecutively: the main chain is conjugated, and part of that same main chain is conjugated with the side group, but all parts are not conjugated together as strongly. Examples of cross-conjugation can be found in molecules such as benzophenone, divinylketones, ''p''-quinones, dendralenes, radialenes, fullerene A fullerene is an allotrope of carbon whose molecule consists of carbon atoms connected by single and double bonds so as to form ...
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Dendralenes
A dendralene is a discrete acyclic cross-conjugated polyene. The simplest dendralene is buta-1,3-diene (1) or endralene followed by endralene (2), endralene (3) and endralene (4) and so forth. endralene (butadiene) is the only one not cross-conjugated. : The name ''dendralene'' is pulled together from the words dendrimer, linear and alkene. The higher dendralenes are of scientific interest because they open up a large array of new organic compounds from a relatively simple precursor especially by Diels-Alder chemistry. Their cyclic counterparts are aptly called radialenes. Synthesis Vinylbutadiene ( endralene) was first prepared in 1955 by pyrolysis of a triacetate: : This compound reacts with two equivalents of maleic anhydride in a tandem DA reaction: : With benzoquinone the reaction product was a linear polymer. Several syntheses of substituted endralenes have been reported, one via an allene, one via a Horner–Wadsworth–Emmons reaction, one via a cross-coupl ...
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Radialene
are alicyclic organic compounds containing n cross-conjugated exocyclic double bonds. The double bonds are commonly alkene groups but those with a carbonyl (C=O) group are also called radialenes. For some members the unsubstituted parent radialenes are elusive but many substituted derivatives are known. Radialenes are related to open-chain dendralenes and also to compounds like butadiene and benzene which also consist of a ring of sp2 hybridized carbon atoms. Radialenes are investigated in organic chemistry for their unusual properties and reactivity but have not ventured outside the laboratory. Reported uses are as experimental building blocks for novel organic conductors and ferromagnets. The first radialene called ''hexaethylidencyclohexane'' was synthesised in 1961. Conformation and adialenes are expected to have a planar molecular geometry with all carbon atoms in the same plane. This is verified experimentally in ''hexamethyl adialene'' and '. ' has a twist envelope ...
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Cross Conjugation Triene V
A cross is a geometrical figure consisting of two intersecting lines or bars, usually perpendicular to each other. The lines usually run vertically and horizontally. A cross of oblique lines, in the shape of the Latin letter X, is termed a saltire in heraldic terminology. The cross has been widely recognized as a symbol of Christianity from an early period.''Christianity: an introduction''
by Alister E. McGrath 2006 pages 321-323
However, the use of the cross as a religious symbol predates Christianity; in the ancient times it was a pagan religious symbol throughout Europe and western Asia. The effigy of a man hanging on a cross was set up in the fields to protect the crops. It often appeared in conjunction with the female-genital circle or oval, to signify the sacred marriage, as in Egyptian amule ...
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Conjugated System
In theoretical 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 conjugated sy ...
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Molecule
A molecule is a group of two or more atoms held together by attractive forces known as chemical bonds; depending on context, the term may or may not include ions which satisfy this criterion. In quantum physics, organic chemistry, and biochemistry, the distinction from ions is dropped and ''molecule'' is often used when referring to polyatomic ions. A molecule may be homonuclear, that is, it consists of atoms of one chemical element, e.g. two atoms in the oxygen molecule (O2); or it may be heteronuclear, a chemical compound composed of more than one element, e.g. water (molecule), water (two hydrogen atoms and one oxygen atom; H2O). In the kinetic theory of gases, the term ''molecule'' is often used for any gaseous particle regardless of its composition. This relaxes the requirement that a molecule contains two or more atoms, since the noble gases are individual atoms. Atoms and complexes connected by non-covalent interactions, such as hydrogen bonds or ionic bonds, are typic ...
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Pi Bond
In chemistry, pi bonds (π bonds) are covalent chemical bonds, in each of which two lobes of an orbital on one atom overlap with two lobes of an orbital on another atom, and in which this overlap occurs laterally. Each of these atomic orbitals has an electron density of zero at a shared nodal plane that passes through the two bonded nuclei. This plane also is a nodal plane for the molecular orbital of the pi bond. Pi bonds can form in double and triple bonds but do not form in single bonds in most cases. The Greek letter π in their name refers to p orbitals, since the orbital symmetry of the pi bond is the same as that of the p orbital when seen down the bond axis. One common form of this sort of bonding involves p orbitals themselves, though d orbitals also engage in pi bonding. This latter mode forms part of the basis for metal-metal multiple bonding. Pi bonds are usually weaker than sigma bonds. The C-C double bond, composed of one sigma and one pi bond, has a ...
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Polyene
In organic chemistry, polyenes are poly- unsaturated, organic compounds that contain at least three alternating double () and single () carbon–carbon bonds. These carbon–carbon double bonds interact in a process known as conjugation, resulting in some unusual optical properties. Related to polyenes are dienes, where there are only two alternating double and single bonds. The following polyenes are used as antibiotics for humans: amphotericin B, nystatin, candicidin, pimaricin, methyl partricin, and trichomycin. Optical properties Some polyenes are brightly colored, an otherwise rare property for a hydrocarbon. Normally alkenes absorb in the ultraviolet region of a spectrum, but the absorption energy state of polyenes with numerous conjugated double bonds can be lowered such that they enter the visible region of the spectrum, resulting in compounds which are coloured (because they contain a chromophore). Thus many natural dyes contain linear polyenes. Chemical and el ...
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Benzophenone
Benzophenone is the organic compound with the formula (C6H5)2CO, generally abbreviated Ph2CO. It is a white solid that is soluble in organic solvents. Benzophenone is a widely used building block in organic chemistry, being the parent diarylketone. Uses Benzophenone can be used as a photo initiator in UV(Ultra-violet)-curing applications such as inks, imaging, and clear coatings in the printing industry. Benzophenone prevents ultraviolet ( UV) light from damaging scents and colors in products such as perfumes and soaps. Benzophenone can also be added to plastic packaging as a UV blocker to prevent photo-degradation of the packaging polymers or its contents. Its use allows manufacturers to package the product in clear glass or plastic (such as a PETE water bottle). Without it, opaque or dark packaging would be required. In biological applications, benzophenones have been used extensively as photophysical probes to identify and map peptide–protein interactions. Benzophenone ...
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P-quinone
1,4-Benzoquinone, commonly known as ''para''-quinone, is a chemical compound with the formula C6H4O2. In a pure state, it forms bright-yellow crystals with a characteristic irritating odor, resembling that of chlorine, bleach, and hot plastic or formaldehyde. This six-membered ring compound is the oxidized derivative of 1,4-hydroquinone. The molecule is multifunctional: it exhibits properties of a ketone, being able to form oximes; an oxidant, forming the dihydroxy derivative; and an alkene, undergoing addition reactions, especially those typical for α,β-unsaturated ketones. 1,4-Benzoquinone is sensitive toward both strong mineral acids and alkali, which cause condensation and decomposition of the compound. Preparation 1,4-Benzoquinone is prepared industrially by oxidation of hydroquinone, which can be obtained by several routes. One route involves oxidation of diisopropylbenzene and the Hock rearrangement. The net reaction can be represented as follows: :C6H4(CHMe2)2 ...
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Fullerene
A fullerene is an allotrope of carbon whose molecule consists of carbon atoms connected by single and double bonds so as to form a closed or partially closed mesh, with fused rings of five to seven atoms. The molecule may be a hollow sphere, ellipsoid, tube, or many other shapes and sizes. Graphene (isolated atomic layers of graphite), which is a flat mesh of regular hexagonal rings, can be seen as an extreme member of the family. Fullerenes with a closed mesh topology are informally denoted by their empirical formula C''n'', often written C''n'', where ''n'' is the number of carbon atoms. However, for some values of ''n'' there may be more than one isomer. The family is named after buckminsterfullerene (C60), the most famous member, which in turn is named after Buckminster Fuller. The closed fullerenes, especially C60, are also informally called buckyballs for their resemblance to the standard ball of association football ("soccer"). Nested closed fullerenes have been na ...
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Indigo Dye
Indigo dye is an organic compound with a distinctive blue color. Historically, indigo was a natural dye extracted from the leaves of some plants of the ''Indigofera'' genus, in particular '' Indigofera tinctoria''; dye-bearing ''Indigofera'' plants were commonly grown and used throughout the world, in Asia in particular, as an important crop, with the production of indigo dyestuff economically important due to the previous rarity of some blue dyestuffs historically. Most indigo dye produced today is synthetic, constituting several thousand tons each year. It is most commonly associated with the production of denim cloth and blue jeans, where its properties allow for effects such as stone washing and acid washing to be applied quickly. Uses The primary use for indigo is as a dye for cotton yarn, mainly used in the production of denim cloth suitable for blue jeans; on average, a pair of blue jeans requires just to of dye. Smaller quantities are used in the dyeing of wool a ...
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