Hexazine
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Hexazine
Hexazine (also known as hexaazabenzene) is a hypothetical allotrope of nitrogen composed of 6 nitrogen atoms arranged in a ring-like structure analogous to that of benzene. It would be the final member of the azabenzene (azine) series, in which all of the methine groups of the benzene molecule have been replaced with nitrogen atoms. The two last members of this series, hexazine and pentazine, have not been observed, although all other members of the azine series have (such as pyridine, pyrimidine, pyridazine, pyrazine, triazines, and tetrazines). Stability The hexazine molecule bears a structural similarity to the very stable benzene molecule. Like benzene, it has been calculated that hexazine is likely an aromatic molecule. Despite this, it has yet to be synthesized. Additionally, it has been predicted computationally that the hexazine molecule is highly unstable, possibly due to the lone pairs on the nitrogen atoms, which may repel each other electrostatically and/or cause electr ...
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Diazine
In organic chemistry, diazines are a group of organic compounds having the molecular formula . Each contains a benzene ring in which two of the C-H fragments have been replaced by isolobal nitrogen. There are three structural isomers: * pyridazine (1,2-diazine) 55px * pyrimidine (1,3-diazine) 45px * pyrazine (1,4-diazine) 50px See also * 6-membered rings with one nitrogen atom: pyridines * 6-membered rings with three nitrogen atoms: triazines * 6-membered rings with four nitrogen atoms: tetrazines * 6-membered rings with five nitrogen atoms: pentazines * 6-membered rings with six nitrogen atoms: hexazine Hexazine (also known as hexaazabenzene) is a hypothetical allotrope of nitrogen composed of 6 nitrogen atoms arranged in a ring-like structure analogous to that of benzene. It would be the final member of the azabenzene (azine) series, in which al ...s References {{Reflist Simple aromatic rings ...
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Tetrazine
Tetrazine is a compound that consists of a six-membered aromatic ring containing four nitrogen atoms with the molecular formula C2 H2 N4. The name ''tetrazine'' is used in the nomenclature of derivatives of this compound. Three core-ring isomers exist: 1,2,3,4-tetrazines, 1,2,3,5-tetrazines, and 1,2,4,5-tetrazines, also known as v-tetrazines, as-tetrazines and s-tetrazines respectively. 1,2,3,4-Tetrazines 1,2,3,4-Tetrazines are often isolated fused to an aromatic ring system and are stabilized as the dioxide derivatives. 1,2,4,5-Tetrazine 1,2,4,5-Tetrazines are very well known and myriad 3,6-disubstituted 1,2,4,5-tetrazines are known. These materials are of use in the area of energetic chemistry. The compound 3,6-di-2-pyridyl-1,2,4,5-tetrazine' has two pyridine substituents and is of importance as a reagent in Diels-Alder reactions. It reacts with norbornadiene in a sequence of one DA reaction and two retro-DA reactions to cyclopentadiene and a pyridazine with exchange of a ...
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Pentazine
Pentazine is a hypothetical compound that consists of a six-membered aromatic ring containing five nitrogen atoms with the molecular formula C H N5. The name ''pentazine'' is used in the nomenclature of derivatives of this compound. Pentazine is predicted to be unstable and to decompose into hydrogen cyanide (HCN) and nitrogen (N2). See also * 6-membered rings with one nitrogen atom: pyridine * 6-membered rings with two nitrogen atoms: diazines * 6-membered rings with three nitrogen atoms: triazines * 6-membered rings with four nitrogen atoms: tetrazines * 6-membered rings with six nitrogen atoms: hexazine Hexazine (also known as hexaazabenzene) is a hypothetical allotrope of nitrogen composed of 6 nitrogen atoms arranged in a ring-like structure analogous to that of benzene. It would be the final member of the azabenzene (azine) series, in which al ... References Azines (heterocycles) Hypothetical chemical compounds {{theoretical-chem-stub ...
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Pyridine
Pyridine is a basic heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid with a distinctive, unpleasant fish-like smell. Pyridine is colorless, but older or impure samples can appear yellow, due to the formation of extended, unsaturated polymeric chains, which show significant electrical conductivity. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Historically, pyridine was produced from coal tar. As of 2016, it is synthesized on the scale of about 20,000 tons per year worldwide. Properties Physical properties The molecular electric dipole moment is 2.2 debyes. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase ...
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Triazine
Triazines are a class of nitrogen-containing heterocycles. The parent molecules' molecular formula is . They exist in three isomeric forms, 1,3,5-triazines being common. Structure The triazines have planar six-membered benzene-like ring but with three carbons replaced by nitrogens. The three isomers of triazine are distinguished by the positions of their nitrogen atoms, and are referred to as 1,2,3-triazine, 1,2,4-triazine, and 1,3,5-triazine. Other aromatic nitrogen heterocycles are pyridines with one ring nitrogen atom, diazines with 2 nitrogen atoms in the ring, triazoles with 3 nitrogens in a 5 membered ring, and tetrazines with 4 ring nitrogen atoms. Uses Melamine A well known triazine is melamine (2,4,6-triamino-1,3,5-triazine). With three amino substituents, melamine is a precursor to commercial resins. Guanamines are closely related to melamine, except with one amino substituent replaced by an organic group. This difference is exploited in the use of guanamines t ...
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Tetranitrogen
Tetranitrogen is a neutrally charged polynitrogen allotrope of the chemical formula and consists of four nitrogen atoms. The tetranitrogen cation is the positively charged ion, , which is more stable than the neutral tetranitrogen molecule and is thus more studied. History Polynitrogen compounds have been well known and characterized by chemists for many years. The commonplace molecular (diatomic) nitrogen () was first isolated by Daniel Rutherford in 1772 and the azide ion () was discovered by Theodor Curtius in 1890. Discoveries of other related nitrogenous allotypes during the twentieth century include the aromatic molecule pentazole and the radical molecule . However, none of these complexes could be isolated or synthesized on a macroscopic scale like and azide; it was not until 1999 that a large scale synthesis was devised for a third nitrogen allotrope, the pentazenium () cation. This increased interest in polynitrogen compounds in the late twentieth century was due to t ...
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Octaazacubane
Octaazacubane is a hypothetical explosive allotrope of nitrogen with formula N8, whose molecules have eight atoms arranged into a cube. (By comparison, nitrogen usually occurs as the diatomic molecule N2.) It can be regarded as a cubane-type cluster, where all eight corners are nitrogen atoms bonded along the edges. It is predicted to be a metastable molecule, in which despite the thermodynamic instability caused by bond strain, and the high energy of the N–N single bonds, the molecule remains kinetically stable for reasons of orbital symmetry. Explosive and fuel Octaazacubane is predicted to have an energy density (assuming decomposition into N2) of 22.9  MJ/ kg, which is over 5 times the standard value of TNT. It has therefore been proposed (along with other exotic nitrogen allotropes) as an explosive, and as a component of high performance rocket fuel. Its velocity of detonation is predicted to be 15,000 m/s, much (48.5%) more than octanitrocubane, the faste ...
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Borazine
Borazine, also known as borazole, is a non-polar inorganic compound with the chemical formula B3H6N3. In this cyclic compound, the three BH units and three NH units alternate. The compound is isoelectronic and isostructural with benzene. For this reason borazine is sometimes referred to as “inorganic benzene”. Like benzene, borazine is a colourless liquid with an aromatic smell. Synthesis The compound was reported in 1926 by the chemists Alfred Stock and Erich Pohland by a reaction of diborane with ammonia. Borazine can be synthesized by treating diborane and ammonia in a 1:2 ratio at 250–300 °C with a conversion of 50%. :3 B2H6 + 6 NH3 → 2 B3H6N3 + 12 H2 An alternative more efficient route begins with sodium borohydride and ammonium sulfate: :6 NaBH4 + 3 (NH4)2SO4 → 2 B3N3H6 + 3 Na2SO4 + 18 H2 In a two-step process to borazine, boron trichloride is first converted to trichloroborazine: :3 BCl3 + 3 NH4Cl → Cl3B3H3N3 + 9 HCl The B-Cl bonds are subsequently c ...
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Hexaphosphabenzene
Hexaphosphabenzene is a valence isoelectronic analogue of benzene and is expected to have a similar planar structure due to resonance stabilization. Although several other allotropes of phosphorus are stable, no evidence for the existence of has been reported. Preliminary ab initio calculations on the trimerisation of leading to the formation of the cyclic were performed, and it was predicted that hexaphosphabenzene would decompose to free with an energy barrier of 13−15.4 kcal mol−1, and would therefore not be observed in the uncomplexed state under normal experimental conditions. The presence of an added solvent, such as ethanol, might lead to the formation of intermolecular hydrogen bonds which may block the destabilizing interaction between phosphorus lone pairs and consequently stabilize . The moderate barrier suggests that hexaphosphabenzene could be synthesized from a +2+2cycloaddition of three molecules. Currently, this is a synthetic endeavour which remains to b ...
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Journal Of The American Chemical Society
The ''Journal of the American Chemical Society'' is a weekly peer-reviewed scientific journal that was established in 1879 by the American Chemical Society. The journal has absorbed two other publications in its history, the ''Journal of Analytical and Applied Chemistry'' (July 1893) and the ''American Chemical Journal'' (January 1914). It covers all fields of chemistry. Since 2021, the editor-in-chief is Erick M. Carreira (ETH Zurich). In 2014, the journal moved to a hybrid open access publishing model. Abstracting and indexing The journal is abstracted and indexed in Chemical Abstracts Service, Scopus, EBSCO databases, ProQuest databases, Index Medicus/MEDLINE/PubMed, and the Science Citation Index Expanded. According to the ''Journal Citation Reports'', the journal has a 2021 impact factor of 16.383. Editors-in-chief The following people are or have been editor-in-chief: * 1879–1880 – Hermann Endemann * 1880–1881 – Gideon E. Moore * 1881–1882 – Hermann Endemann ...
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Allotrope
Allotropy or allotropism () is the property of some chemical elements to exist in two or more different forms, in the same physical state, known as allotropes of the elements. Allotropes are different structural modifications of an element: the atoms of the element are bonded together in a different manner. For example, the allotropes of carbon include diamond (the carbon atoms are bonded together to form a cubic lattice of tetrahedra), graphite (the carbon atoms are bonded together in sheets of a hexagonal lattice), graphene (single sheets of graphite), and fullerenes (the carbon atoms are bonded together in spherical, tubular, or ellipsoidal formations). The term ''allotropy'' is used for elements only, not for compounds. The more general term, used for any compound, is polymorphism, although its use is usually restricted to solid materials such as crystals. Allotropy refers only to different forms of an element within the same physical phase (the state of matter, such as ...
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Pentazole
Pentazole is an aromatic molecule consisting of a five-membered ring with all nitrogen atoms, one of which is bonded to a hydrogen atom. It has the molecular formula . Although strictly speaking a homocyclic, inorganic compound, pentazole has historically been classed as the last in a series of heterocyclic azole compounds containing one to five nitrogen atoms. This set contains pyrrole, imidazole, pyrazole, triazoles, tetrazole, and pentazole. Derivatives Substituted analogs of pentazole are collectively known as pentazoles. As a class, they are unstable and often highly explosive compounds. The first pentazole synthesized was phenylpentazole, where the pentazole ring is highly stabilized by conjugation with the phenyl ring. The derivative 4-dimethylaminophenylpentazole is among the most stable pentazole compounds known, although it still decomposes at temperatures over 50 °C. It is known that electron-donating groups stabilize aryl pentazole compounds. Ions The ...
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