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Names | |
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IUPAC name Diatomic carbon | |
Systematic IUPAC name Ethenediylidene (substitutive) Dicarbon(C—C) (additive) | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
196 | |
PubChem CID | |
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Properties | |
C2 | |
Molar mass | 24.022 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Diatomic carbon (systematically named dicarbon and 1λ2,2λ2-ethene), is a green, gaseous inorganic chemical with the chemical formula C=C (also written [C2] or C2). It is kinetically unstable at ambient temperature and pressure, being removed through autopolymerisation. It occurs in carbon vapor, for example in electric arcs; in comets, stellar atmospheres, and the interstellar medium; and in blue hydrocarbon flames. [1] Diatomic carbon is the second simplest of the allotropes of carbon (after atomic carbon), and is an intermediate participator in the genesis of fullerenes.
C2 is a component of carbon vapor. One paper estimates that carbon vapor is around 28% diatomic, [2] but theoretically this depends on the temperature and pressure.
The electrons in diatomic carbon are distributed among the molecular orbitals according to the Aufbau principle to produce unique quantum states, with corresponding energy levels. The state with the lowest energy level, or ground state, is a singlet state (1Σ+
g), which is systematically named ethene-1,2-diylidene or dicarbon(0•). There are several excited singlet and triplet states that are relatively close in energy to the ground state, which form significant proportions of a sample of dicarbon under ambient conditions. When most of these excited states undergo photochemical relaxation, they emit in the infrared region of the electromagnetic spectrum. However, one state in particular emits in the green region. That state is a triplet state (3Πg), which is systematically named ethene-μ,μ-diyl-μ-ylidene or dicarbon(2•). In addition, there is an excited state somewhat further in energy from the ground state, which only form a significant proportion of a sample of dicarbon under mid-ultraviolet irradiation. Upon relaxation, this excited state fluoresces in the violet region and phosphoresces in the blue region. This state is also a singlet state (1Πg), which is also named ethene-μ,μ-diyl-μ-ylidene or dicarbon(2•).
State | Excitation enthalpy (kJ mol−1) | Relaxation transition | Relaxation wavelength | Relaxation EM-region |
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X1Σ+ g | 0 | – | – | – |
a3Π u | 8.5 | a3Π u→X1Σ+ g | 14.0 μm | Long-wavelength infrared |
b3Σ− g | 77.0 | b3Σ− g→a3Π u | 1.7 μm | Short-wavelength infrared |
A1Π u | 100.4 | A1Π u→X1Σ+ g A1Π u→b3Σ− g | 1.2 μm 5.1 μm | Near infrared Mid-wavelength infrared |
B1Σ+ g | ? | B1Σ+ g→A1Π u B1Σ+ g→a3Π u | ? ? | ? ? |
c3Σ+ u | 159.3 | c3Σ+ u→b3Σ− g c3Σ+ u→X1Σ+ g c3Σ+ u→B1Σ+ g | 1.5 μm 751.0 nm ? | Short-wavelength infrared Near infrared ? |
d3Π g | 239.5 | d3Π g→a3Π u d3Π g→c3Σ+ u d3Π g→A1Π u | 518.0 nm 1.5 μm 860.0 nm | Green Short-wavelength infrared Near infrared |
C1Π g | 409.9 | C1Π g→A1Π u C1Π g→a3Π u C1Π g→c3Σ+ u | 386.6 nm 298.0 nm 477.4 nm | Violet Mid-ultraviolet Blue |
Molecular orbital theory shows that there are two sets of paired electrons in a degenerate pi bonding set of orbitals. This gives a bond order of 2, meaning that there should exist a double bond between the two carbon atoms in a C2 molecule. [3] One analysis suggested instead that a quadruple bond exists, [4] an interpretation that was disputed. [5] CASSCF calculations indicate that the quadruple bond based on molecular orbital theory is also reasonable. [3] Bond dissociation energies (BDE) of B2, C2, and N2 show increasing BDE, indicating single, double, and triple bonds, respectively.
In certain forms of crystalline carbon, such as diamond and graphite, a saddle point or "hump" occurs at the bond site in the charge density. The triplet state of C2 does follow this trend. However, the singlet state of C2 acts more like silicon or germanium; that is, the charge density has a maximum at the bond site. [6]
Diatomic carbon will react with acetone and acetaldehyde to produce acetylene by two different pathways. [2]
The light of gas rich comets mainly originates from the emission of diatomic carbon. An example is C/2014 Q2 (Lovejoy), where there are several lines of C2 light, mostly in the visible spectrum [10] , forming the Swan bands. [11] C/2022 E3 (ZTF), visible in early 2023, also exhibits green color due to the presence of diatomic carbon. [12]
Photochemistry is the branch of chemistry concerned with the chemical effects of light. Generally, this term is used to describe a chemical reaction caused by absorption of ultraviolet, visible light (400–750 nm) or infrared radiation (750–2500 nm).
Intersystem crossing (ISC) is an isoenergetic radiationless process involving a transition between the two electronic states with different spin multiplicity.
Cyclobutadiene is an organic compound with the formula C4H4. It is very reactive owing to its tendency to dimerize. Although the parent compound has not been isolated, some substituted derivatives are robust and a single molecule of cyclobutadiene is quite stable. Since the compound degrades by a bimolecular process, the species can be observed by matrix isolation techniques at temperatures below 35 K. It is thought to adopt a rectangular structure.
In chemistry, a nitrene or imene is the nitrogen analogue of a carbene. The nitrogen atom is uncharged and univalent, so it has only 6 electrons in its valence level—two covalent bonded and four non-bonded electrons. It is therefore considered an electrophile due to the unsatisfied octet. A nitrene is a reactive intermediate and is involved in many chemical reactions. The simplest nitrene, HN, is called imidogen, and that term is sometimes used as a synonym for the nitrene class.
Sulfur monoxide is an inorganic compound with formula SO. It is only found as a dilute gas phase. When concentrated or condensed, it converts to S2O2 (disulfur dioxide). It has been detected in space but is rarely encountered intact otherwise.
Singlet oxygen, systematically named dioxygen(singlet) and dioxidene, is a gaseous inorganic chemical with the formula O=O, which is in a quantum state where all electrons are spin paired. It is kinetically unstable at ambient temperature, but the rate of decay is slow.
Photosensitizers are light absorbers that alters the course of a photochemical reaction. They usually are catalysts. They can function by many mechanisms, sometimes they donate an electron to the substrate, sometimes they abstract a hydrogen atom from the substrate. At the end of this process, the photosensitizer returns to its ground state, where it remains chemically intact, poised to absorb more light. One branch of chemistry which frequently utilizes photosensitizers is polymer chemistry, using photosensitizers in reactions such as photopolymerization, photocrosslinking, and photodegradation. Photosensitizers are also used to generate prolonged excited electronic states in organic molecules with uses in photocatalysis, photon upconversion and photodynamic therapy. Generally, photosensitizers absorb electromagnetic radiation consisting of infrared radiation, visible light radiation, and ultraviolet radiation and transfer absorbed energy into neighboring molecules. This absorption of light is made possible by photosensitizers' large de-localized π-systems, which lowers the energy of HOMO and LUMO orbitals to promote photoexcitation. While many photosensitizers are organic or organometallic compounds, there are also examples of using semiconductor quantum dots as photosensitizers.
Triplet oxygen, 3O2, refers to the S = 1 electronic ground state of molecular oxygen (dioxygen). It is the most stable and common allotrope of oxygen. Molecules of triplet oxygen contain two unpaired electrons, making triplet oxygen an unusual example of a stable and commonly encountered diradical: it is more stable as a triplet than a singlet. According to molecular orbital theory, the electron configuration of triplet oxygen has two electrons occupying two π molecular orbitals (MOs) of equal energy (that is, degenerate MOs). In accordance with Hund's rules, they remain unpaired and spin-parallel and account for the paramagnetism of molecular oxygen. These half-filled orbitals are antibonding in character, reducing the overall bond order of the molecule to 2 from a maximum value of 3 (e.g., dinitrogen), which occurs when these antibonding orbitals remain fully unoccupied. The molecular term symbol for triplet oxygen is 3Σ−
g.
Tricarbon is an inorganic compound with the chemical formula C
2(μ-C). It is a colourless gas that only persists in dilution or solution as an adduct. It is one of the simplest unsaturated carbenes. Tricarbon can be found in interstellar space and can be produced in the laboratory by a process called laser ablation.
A quadruple bond is a type of chemical bond between two atoms involving eight electrons. This bond is an extension of the more familiar types double bonds and triple bonds. Stable quadruple bonds are most common among the transition metals in the middle of the d-block, such as rhenium, tungsten, technetium, molybdenum and chromium. Typically the ligands that support quadruple bonds are π-donors, not π-acceptors.
Atomic carbon, systematically named carbon and λ0-methane, is a colourless gaseous inorganic chemical with the chemical formula C. It is kinetically unstable at ambient temperature and pressure, being removed through autopolymerisation.
A sextuple bond is a type of covalent bond involving 12 bonding electrons and in which the bond order is 6. The only known molecules with true sextuple bonds are the diatomic dimolybdenum (Mo2) and ditungsten (W2), which exist in the gaseous phase and have boiling points of 4,639 °C (8,382 °F) and 5,930 °C (10,710 °F) respectively.
There are several known allotropes of oxygen. The most familiar is molecular oxygen, present at significant levels in Earth's atmosphere and also known as dioxygen or triplet oxygen. Another is the highly reactive ozone. Others are:
In chemistry, bond cleavage, or bond fission, is the splitting of chemical bonds. This can be generally referred to as dissociation when a molecule is cleaved into two or more fragments.
Ethylene dione or ethylenedione, also called dicarbon dioxide, Carbon peroxide, ethenedione, or ethene-1,2-dione, is a chemical compound with the formula C2O2 or O=C=C=O. It is an oxide of carbon, and can be described as the carbon-carbon covalent dimer of carbon monoxide. It can also be thought of as the dehydrated form of glyoxylic acid, or a ketone of ethenone H2C=C=O.
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.
Methylene is an organic compound with the chemical formula CH
2. It is a colourless gas that fluoresces in the mid-infrared range, and only persists in dilution, or as an adduct.
Methylidenecarbene is an organic compound with the chemical formula C=CH
2. It is a metastable proton tautomer of acetylene, which only persists as an adduct. It is a colourless gas that phosphoresces in the far-infrared range. It is the simplest unsaturated carbene.
The helium dimer is a van der Waals molecule with formula He2 consisting of two helium atoms. This chemical is the largest diatomic molecule—a molecule consisting of two atoms bonded together. The bond that holds this dimer together is so weak that it will break if the molecule rotates, or vibrates too much. It can only exist at very low cryogenic temperatures.
In chemistry, the selection rule formally restricts certain reactions, known as spin-forbidden reactions, from occurring due to a required change between two differing quantum states. When a reactant exists in one spin state and the product exists in a different spin state, the corresponding reaction will have an increased activation energy when compared to a similar reaction in which the spin states of the reactant and product are isomorphic. As a result of this increased activation energy, a decreased rate of reaction is observed.