Carborazine

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Carborazine
Carborazine.svg
Names
Other names
1,4,2,5-Diazadiborinine
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C2H2B2N2/c1-3-6-2-4-5-1/h1-2H
    Key: ZADCQHPUUMQREX-UHFFFAOYSA-N
  • B1=CN=BC=N1
Properties
C2H2B2N2
Molar mass 75.67 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Carborazine is a six-membered aromatic ring with two carbon atoms, two nitrogen atoms and two boron atoms in opposing pairs. [1] [2]

See also

Related Research Articles

Boron nitride Refractory compound with formula BN

Boron nitride is a thermally and chemically resistant refractory compound of boron and nitrogen with the chemical formula BN. It exists in various crystalline forms that are isoelectronic to a similarly structured carbon lattice. The hexagonal form corresponding to graphite is the most stable and soft among BN polymorphs, and is therefore used as a lubricant and an additive to cosmetic products. The cubic variety analogous to diamond is called c-BN; it is softer than diamond, but its thermal and chemical stability is superior. The rare wurtzite BN modification is similar to lonsdaleite but slightly softer than the cubic form.

Heterocyclic compound Cyclic compound that has atoms of at least two different elements as members of its ring(s).

A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of these heterocycles.

A period 2 element is one of the chemical elements in the second row of the periodic table of the chemical elements. The periodic table is laid out in rows to illustrate recurring (periodic) trends in the chemical behavior of the elements as their atomic number increases; a new row is started when chemical behavior begins to repeat, creating columns of elements with similar properties.

Aromaticity Phenomenon providing chemical stability in resonating hybrids of cyclic organic compounds

In chemistry, aromaticity is a property of cyclic (ring-shaped), planar (flat) structures with pi bonds in resonance that gives increased stability compared to other geometric or connective arrangements with the same set of atoms. Aromatic rings are very stable and do not break apart easily. Organic compounds that are not aromatic are classified as aliphatic compounds—they might be cyclic, but only aromatic rings have enhanced stability.

Double bond Chemical bond involving four bonding electrons; has one sigma plus one pi bond

In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist between two different elements: for example, in a carbonyl group between a carbon atom and an oxygen atom. Other common double bonds are found in azo compounds (N=N), imines (C=N), and sulfoxides (S=O). In a skeletal formula, a double bond is drawn as two parallel lines (=) between the two connected atoms; typographically, the equals sign is used for this. Double bonds were first introduced in chemical notation by Russian chemist Alexander Butlerov.

Bicyclic molecule

A bicyclic molecule is a molecule that features two joined rings. Bicyclic structures occur widely, for example in many biologically important molecules like α-thujene and camphor. A bicyclic compound can be carbocyclic, or heterocyclic, like DABCO. Moreover, the two rings can both be aliphatic, or can be aromatic, or a combination of aliphatic and aromatic.

Oxazole

Oxazole is the parent compound for a vast class of heterocyclic aromatic organic compounds. These are azoles with an oxygen and a nitrogen separated by one carbon. Oxazoles are aromatic compounds but less so than the thiazoles. Oxazole is a weak base; its conjugate acid has a pKa of 0.8, compared to 7 for imidazole.

Triazine Aromatic, heterocyclic compound

Triazines are a class of nitrogen-containing heterocycles. The parent molecules' molecular formula is C3H3N3. They exist in three isomeric forms, 1,3,5-triazines being common.

Borazine Chemical compound

Borazine, also known as borazole, is a 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. Borazine is a colourless liquid with an aromatic smell.

1,2,3-Triazole is one of a pair of isomeric chemical compounds with molecular formula C2H3N3, called triazoles, which have a five-membered ring of two carbon atoms and three nitrogen atoms. 1,2,3-Triazole is a basic aromatic heterocycle.

Cyclic compound Molecule with a ring of bonded atoms

A cyclic compound is a term for a compound in the field of chemistry in which one or more series of atoms in the compound is connected to form a ring. Rings may vary in size from three to many atoms, and include examples where all the atoms are carbon, none of the atoms are carbon, or where both carbon and non-carbon atoms are present. Depending on the ring size, the bond order of the individual links between ring atoms, and their arrangements within the rings, carbocyclic and heterocyclic compounds may be aromatic or non-aromatic, in the latter case, they may vary from being fully saturated to having varying numbers of multiple bonds between the ring atoms. Because of the tremendous diversity allowed, in combination, by the valences of common atoms and their ability to form rings, the number of possible cyclic structures, even of small size numbers in the many billions.

Homoaromaticity Special case of aromaticity in which conjugation is interrupted by a single sp³ hybridized carbon atom

Homoaromaticity, in organic chemistry, refers to a special case of aromaticity in which conjugation is interrupted by a single sp3 hybridized carbon atom. Although this sp3 center disrupts the continuous overlap of p-orbitals, traditionally thought to be a requirement for aromaticity, considerable thermodynamic stability and many of the spectroscopic, magnetic, and chemical properties associated with aromatic compounds are still observed for such compounds. This formal discontinuity is apparently bridged by p-orbital overlap, maintaining a contiguous cycle of π electrons that is responsible for this preserved chemical stability.

1,2-Dihydro-1,2-azaborine Chemical compound

1,2-Dihydro-1,2-azaborine is an aromatic chemical compound with properties intermediate between benzene and borazine. Its chemical formula is C4BNH6. It resembles a benzene ring, except that two adjacent carbons are replaced by nitrogen and boron, respectively.

1,4,2-Dithiazole is a heterocyclic compound consisting of an unsaturated five-membered ring containing two carbon atoms, one nitrogen atom, and two sulfur atoms. 1,4,2-Dithiazole compounds may be formed by the reaction of nitrile sulfide with various reactive species; for instance thiocarbonyls via a 1,3-dipolar cycloaddition reaction. These compounds may be protonated by strong acids to give synthetically useful aromatic cations.

Boroles represent a class of molecules known as metalloles, which are heterocyclic 5-membered rings. As such, they can be viewed as structural analogs of cyclopentadiene, pyrrole or furan, with boron replacing a carbon, nitrogen and oxygen atom respectively. They are isoelectronic with the cyclopentadienyl cation C
5
H+
5
(Cp+
)
and comprise four π electrons. Although Hückel's rule cannot be strictly applied to borole, it is considered to be antiaromatic due to having 4 π electrons. As a result, boroles exhibit unique electronic properties not found in other metalloles.

Boron monofluoride or fluoroborylene is a chemical compound with formula BF, one atom of boron and one of fluorine. It was discovered as an unstable gas and only in 2009 found to be a stable ligand combining with transition metals, in the same way as carbon monoxide. It is a subhalide, containing fewer than the normal number of fluorine atoms, compared with boron trifluoride. It can also be called a borylene, as it contains boron with two unshared electrons. BF is isoelectronic with carbon monoxide and dinitrogen; each molecule has 14 electrons.

Trihydridoboron, also known as borane or borine, is an unstable and highly reactive molecule with the chemical formula BH
3
. The preparation of borane carbonyl, BH3(CO), played an important role in exploring the chemistry of boranes, as it indicated the likely existence of the borane molecule. However, the molecular species BH3 is a very strong Lewis acid. Consequently it is highly reactive and can only be observed directly as a continuously produced, transitory, product in a flow system or from the reaction of laser ablated atomic boron with hydrogen.

Methyldiborane

Methyldiborane, CH3B2H5, or monomethyldiborane is the simplest of alkyldiboranes, consisting of a methyl group substituted for a hydrogen in diborane. As with other boranes it exists in the form of a dimer with a twin hydrogen bridge that uses three-center two-electron bonding between the two boron atoms, and can be imagined as methyl borane (CH3BH2) bound to borane (BH3). Other combinations of methylation occur on diborane, including 1,1-dimethylborane, 1,2-dimethyldiborane, trimethyldiborane, tetramethyldiborane, and trimethylborane (which is not a dimer). At room temperature the substance is at equilibrium between these molecules.

Borazocine Chemical compound

Borazocine is a polar inorganic compound with the chemical formula B4H8N4. In this cyclic compound, the four BH units and four NH units alternate.

Borocarbonitrides

Borocarbonitrides are two-dimensional compounds that contain boron, nitrogen, and carbon atoms in a ratio BxCyNz. Borocarbonitrides are distinct from B,N co-doped graphene in that the former contains separate boron nitride and graphene domains as well as rings with B-C, B-N, C-N, and C-C bonds. These compounds generally have a high surface area, but borocarbonitrides synthesized from a high surface area carbon material, urea, and boric acid tend to have the highest surface areas. This high surface area coupled with the presence of Stone-Wales defects in the structure of borocarbonitrides also allows for high absorption of CO2 and CH4, which may make borocarbonitride compounds a useful material in sequestering these gases.

References

  1. Srivastava, Ambrish Kumar; Misra, Neeraj (2015). "Introducing "carborazine" as a novel heterocyclic aromatic species". New Journal of Chemistry. 39 (4): 2483–2488. doi:10.1039/c4nj02089h.
  2. Bonifazi, Davide; Fasano, Francesco; Lorenzo-Garcia, M. Mercedes; Marinelli, Davide; Oubaha, Hamid; Tasseroul, Jonathan (2015). "Boron–nitrogen doped carbon scaffolding: organic chemistry, self-assembly and materials applications of borazine and its derivatives". Chem. Commun. 51 (83): 15222–15236. doi:10.1039/C5CC06611E. PMID   26411675.