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Boratabenzene
Boratabenzene is the heteroaromatic anion with the formula 5H5BHsup>−. Derivatives of boratabenzene are ligands akin to cyclopentadienyl anion. sandwich or half-sandwich type complexes of many transition metals have been reported.{{cite journal , doi=10.1016/j.ccr.2015.07.014, title=Boratabenzene Rare-earth Metal Complexes, year=2016, last1=Cui, first1=Peng, last2=Chen, first2=Yaofeng, journal=Coordination Chemistry Reviews, volume=314, pages=2–13 Electronically related heterocycles are adducts of borabenzene. The adduct C5H5B.pyridine exhibits properties of boratabenzene anion, i.e., it has the character C5H5B−-N+C5H5. See also * borabenzene, silabenzene, germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, bismabenzene, pyrylium, thiopyrylium, selenopyrylium, telluropyrylium * 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 alter ...
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Silabenzene
A silabenzene is a heteroaromatic compound containing one or more silicon atoms instead of carbon atoms in benzene. A single substitution gives silabenzene proper; additional substitutions give a disilabenzene (3 theoretical isomers), trisilabenzene (3 isomers), etc. Silabenzenes have been the targets of many theoretical and synthetic studies by organic chemists interested in the question of whether analogs of benzene with Group IV elements heavier than carbon, e.g., silabenzene, stannabenzene and germabenzene—so-called "heavy benzenes"—exhibit aromaticity. Although several heteroaromatic compounds bearing nitrogen, oxygen, and sulfur atoms have been known since the early stages of organic chemistry, silabenzene had been considered to be a transient, un-isolable compound and was detected only in low-temperature matrices or as its Diels-Alder adduct for a long time. In recent years, however, a kinetically stabilized silabenzene and other heavy aromatic compounds with silico ...
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Borabenzene
Borabenzene is a hypothetical organoboron compound with the formula C5H5B. Unlike the related but highly stable benzene molecule, borabenzene would be electron-deficient. Related derivatives are the boratabenzene anions, including the parent 5H5BHsup>−. Adducts Adducts of borabenzene with Lewis bases are isolatable. Since borabenzene is unavailable, these adducts require indirect methods. 4-Silyl-1-methoxyboracyclohexadiene is used as a precursor to the borabenzene: : + → + MeOSiMe3 The pyridine adduct is structurally related to biphenyl. It is a yellow whereas biphenyl is colorless, indicating distinct electronic structures. The pyridine ligand is tightly bound: no exchange is observed with free pyridine, even at elevated temperatures. : The borabenzene-pyridine adduct behaves like a diene, not an analog of biphenyl, and will undergo Diels-Alder reactions.{{cite journal , doi=10.1021/ol061201w , title=1-Borabarrelene Derivatives via Diels−Alder Additions to Bora ...
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Structure Of Rh(C8H12)(C5H5BH) (OZUFAR)
A structure is an arrangement and organization of interrelated elements in a material object or system, or the object or system so organized. Material structures include man-made objects such as buildings and machines and natural objects such as biological organisms, minerals and chemicals. Abstract structures include data structures in computer science and musical form. Types of structure include a hierarchy (a cascade of one-to-many relationships), a network featuring many-to-many links, or a lattice featuring connections between components that are neighbors in space. Load-bearing Buildings, aircraft, skeletons, anthills, beaver dams, bridges and salt domes are all examples of load-bearing structures. The results of construction are divided into buildings and non-building structures, and make up the infrastructure of a human society. Built structures are broadly divided by their varying design approaches and standards, into categories including building structures, ...
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Arsabenzene
Arsabenzene (IUPAC name: arsinine) is an organoarsenic heterocyclic compound with the chemical formula C5H5As. It belongs to a group of compounds called heteroarenes that have the general formula C5H5E (E= N, P, As, Sb, Bi). This air sensitive liquid has an onion odor, and it decomposes on heating. Arsabenzene is also an ambidentate ligand that prefers to coordinate using η1(As)- or η6(π)-routes. The study of arsabenzene and related compounds was an important step in the understanding of compounds that contain multiple bonds between carbon and heavier elements. The study of heteroarenes was begun by Märkl, with the synthesis of 2,4,6-triphenylphosphabenzene. This is achieved by treating 2,4,6-trisubstituted pyrylium salt with phosphanes. The first derivative of arsabenzene was 9-arsaanthracene prepared by Jutzi and Bickelhaupt. Structure Arsabenzene is planar. The C—C bond distances of 1.39 Å, the As—C bond has a length of 1.85 Å, this is 6.6% shorter than the no ...
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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 subseq ...
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Telluropyrylium
Telluropyrylium is an aromatic heterocyclic compound consisting of a six member ring with five carbon atoms, and a positively charged tellurium atom. Derivatives of telluropyrylium are important in research of infrared dyes. Naming and numbering Formerly it was named tellurapyrylium. However this is misleading, as "tellura" indicates that tellurium substitutes for carbon atom, but actually tellurium is substituted for the oxygen atom in pyrilium. In the Hantzsch-Widman system it is called tellurinium. This is the name used by Chemical Abstracts. Replacement nomenclature would call this telluroniabenzene. Numbering in telluropyrylium starts with 1 on the tellurium atom and counts up to 6 counter-clockwise on the carbon atoms. The positions adjacent to the chalcogen, numbered 2 and 6 can also be called α, the next two positions 3 and 5 can be termed "β" and the opposite carbon at position 4 can be called "γ". Occurrence Because telluropyrylium is a positively charged cation, it ...
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Selenopyrylium
Selenopyrylium is an aromatic heterocyclic compound consisting of a six-membered ring with five carbon atoms and a positively charged selenium atom. Naming and numbering Formerly it was named selenapyrylium. However, this is misleading as "selena" indicates that selenium substitutes for a carbon atom, but actually selenium is substituted for the oxygen atom in pyrylium. In the Hantzsch-Widman system of nomenclature, it is called seleninium. This is the name used by Chemical Abstracts. Replacement nomenclature would call this selenoniabenzene. Numbering in selenopyrylium starts with 1 on the selenium atom and counts up to 6 on the carbon atoms. The positions adjacent to the chalcogen, numbered 2 and 6 can also be called α, the next two positions 3 and 5 can be termed "β" and the opposite carbon at position 4 can be called "γ". Occurrence Because selenopyrylium is a positively charged ion, it takes the solid form as a salt with non-nucleophillic anions such as perchlorate, tetra ...
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Thiopyrylium
Thiopyrylium is a cation with the chemical formula C5H5S+. It is analogous to the pyrylium cation with the oxygen atom replaced by a sulfur atom. Thiopyrylium salts are less reactive than the analogous pyrylium salts due to the higher polarizability of the sulfur atom. Among the chalcogenic 6-membered unsaturated heterocycles, thiopyrylium is the most aromatic, due to sulfur having the similar Pauling electronegativity as carbon and only a slightly higher covalent radius. In water, thiopyrylium reacts to it and forms a mixture of 2-hydroxythiopyran and 4-hydroxythiopyran. Thiopyrylium salts can be synthesized by hydrogen abstraction from thiopyran by a hydride ion acceptor, such as trityl perchlorate. The thiopyrylium analogue of 2,4,6-trisubstituted pyrylium salts can be synthesized by treatment with sodium sulfide followed by precipitation with acid. This reaction causes the oxygen atom in the pyrylium cation to be substituted with sulfur. See also * 6-membered aromatic r ...
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Pyrylium
Pyrylium is a cation (positive ion) with formula , consisting of a six-membered ring of five carbon atoms, each with one hydrogen atom, and one positively charged oxygen atom. The bonds in the ring are conjugated as in benzene, giving it an aromatic character. In particular, because of the positive charge, the oxygen atom is trivalent. Pyrilium is a mono-cyclic and heterocyclic compound, one of the oxonium ions. Salts Pyrylium and its derivatives form stable salts with a variety of anions. Derivatives Many important cations are formally derived from pyrylium by substitution of various functional groups for some or all the hydrogens in the ring. The 2,4,6-triphenylpyrilium, referred to as the Katritzky salt, (after Alan R. Katritzky) is an important example used in many modern examples of metal catalyzed cross-couplings. Chemical properties Like other oxonium ions, pyrylium is unstable in neutral water. However, pyrylium is much less reactive than ordinary oxonium ions bec ...
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Bismabenzene
Bismabenzene () is the parent representative of a group of organobismuth compounds that are related to benzene with a carbon atom replaced by a bismuth Bismuth is a chemical element with the symbol Bi and atomic number 83. It is a post-transition metal and one of the pnictogens, with chemical properties resembling its lighter group 15 siblings arsenic and antimony. Elemental bismuth occurs ... atom. Bismabenzene itself has been synthesised but not isolated because it is too reactive, tending to instead dimerize in a Diels-Alder addition. An unstable derivative with 4-alkyl substituents was reported in 1982. A stable derivative was reported in 2016. This derivative has two tri(isopropyl)silyl substituents in the ''ortho''-positions and was synthesized from aluminacyclohexadiene, bismuth trichloride, and DBU. References {{reflist, colwidth=30em, refs= {{cite journal , doi = 10.1021/jacs.6b08714, title = An Isolable Bismabenzene: Synthesis, Structure, and Reactivit ...
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Stannabenzene
Stannabenzene (C5H6Sn) is the parent representative of a group of organotin compounds that are related to benzene with a carbon atom replaced by a tin atom. Stannabenzene itself has been studied by computational chemistry, but has not been isolated. Stable derivatives of stannabenzene Stable derivatives of stannabenzene have been isolated. The 2-stannanaphthalene depicted below is stable in an inert atmosphere at temperatures below 140 °C. The tin to carbon bond in this compound is shielded from potential reactants by two very bulky groups, one tert-butyl group and the even larger 2,4,6-trisis(trimethylsilyl)methylhenyl or Tbt group. The two Sn-C bonds have bond lengths of 202.9 and 208.1 pm which are shorter than those for Sn-C single bonds (214 pm) and comparable to that of known Sn=C double bonds (201.6 pm). The C-C bonds show little variation with bond lengths between 135.6 and 144.3 pm signaling that this compound is aromatic. : Tbt-substituted 9-stannaphenanthrene wa ...
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Phosphorine
Phosphorine ( IUPAC name: phosphinine) is a heavier element analog of pyridine, containing a phosphorus atom instead of an aza- moiety. It is also called phosphabenzene and belongs to the phosphaalkene class. It is a colorless liquid that is mainly of interest in research. Phosphorine is an air-sensitive oil but is otherwise stable when handled using air-free techniques (however, substituted derivatives can often be handled under air without risk of decomposition). In contrast, silabenzene, a related heavy-element analogue of benzene, is not only air- and moisture-sensitive but also thermally unstable without extensive steric protection. History The first phosphorine to be isolated is 2,4,6-triphenylphosphorine. It was synthesized by Gottfried Märkl in 1966 by condensation of the corresponding pyrylium salt and phosphine or its equivalent ( P(CH2OH)3 and P(SiMe3)3).''G. Märkl'', 2,4,6-Triphenylphosphabenzol iAngewandte Chemie 78, 907–908 (1966)/ref> 500px, Synthesi ...
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