Carbon

Carbon
Carbon (from Latin carbo 'coal') is a chemical

element; it has symbol C and atomic number 6. It is
Carbon, 6C
nonmetallic and tetravalent—meaning that its atoms
are able to form up to four covalent bonds due to its
valence shell exhibiting 4 electrons. It belongs to
group 14 of the periodic table.[14] Carbon makes up
about 0.025 percent of Earth's crust.[15] Three
isotopes occur naturally, 12 C and 13 C being stable,
while 14 C is a radionuclide, decaying with a half-life
Graphite (left) and diamond (right), two allotropes
of about 5,730 years.[16] Carbon is one of the few
of carbon
elements known since antiquity.[17]
Carbon
Carbon is the 15th most abundant element in the Allotropes graphite, diamond and
Earth's crust, and the fourth most abundant element
more (see Allotropes of
in the universe by mass after hydrogen, helium, and
carbon)
oxygen. Carbon's abundance, its unique diversity of
organic compounds, and its unusual ability to form Appearance graphite: black, metallic-
polymers at the temperatures commonly encountered looking
on Earth, enables this element to serve as a common
diamond: clear
element of all known life. It is the second most
abundant element in the human body by mass (about Standard atomic weight Ar°(C)
18.5%) after oxygen.[18]
[12.0096, 12.0116]
The atoms of carbon can bond together in diverse 12.011 ± 0.002 (abridged)[1]
ways, resulting in various allotropes of carbon. Well-
Carbon in the periodic table
known allotropes include graphite, diamond,
amorphous carbon, and fullerenes. The physical –
properties of carbon vary widely with the allotropic ↑
C
form. For example, graphite is opaque and black, ↓
while diamond is highly transparent. Graphite is soft Si
boron ← carbon → nitrogen
enough to form a streak on paper (hence its name,
from the Greek verb "γράφειν" which means "to Atomic number (Z) 6
write"), while diamond is the hardest naturally
Group group 14 (carbon group)
occurring material known. Graphite is a good
electrical conductor while diamond has a low Period period 2
electrical conductivity. Under normal conditions, Block p-block
diamond, carbon nanotubes, and graphene have the
highest thermal conductivities of all known materials. Electron [He] 2s2 2p2
All carbon allotropes are solids under normal configuration
conditions, with graphite being the most Electrons per 2, 4
thermodynamically stable form at standard shell
temperature and pressure. They are chemically
Physical properties
resistant and require high temperature to react even
with oxygen. Phase at STP solid
The most common oxidation state of carbon in Sublimation point 3915 K (3642 °C, 6588 °F)
inorganic compounds is +4, while +2 is found in
Density (near r.t.) amorphous: 1.8–
carbon monoxide and transition metal carbonyl
2.1 g/cm3[2]
complexes. The largest sources of inorganic carbon
are limestones, dolomites and carbon dioxide, but graphite: 2.267 g/cm3
significant quantities occur in organic deposits of diamond: 3.515 g/cm3
coal, peat, oil, and methane clathrates. Carbon forms Triple point 4600 K, 10,800 kPa[3][4]
a vast number of compounds, with about two
Heat of fusion graphite: 117 kJ/mol
hundred million having been described and
indexed;[19] and yet that number is but a fraction of Molar heat graphite: 8.517 J/(mol·K)
the number of theoretically possible compounds capacity diamond: 6.155 J/(mol·K)
under standard conditions. Atomic properties
Oxidation states −4, −3, −2, −1, 0, +1,[5]
Characteristics +2, +3,[6] +4[7] (a mildly
acidic oxide)
Electronegativity Pauling scale: 2.55
Ionization 1st: 1086.5 kJ/mol
energies 2nd: 2352.6 kJ/mol
3rd: 4620.5 kJ/mol
(more)
Covalent radius sp3: 77 pm
sp2: 73 pm
sp: 69 pm
Van der Waals 170 pm
radius
Theoretically predicted phase diagram of carbon,
from 1989. Newer work indicates that the melting
point of diamond (top-right curve) does not go
Spectral lines of carbon
above about 9000 K.[20]
Other properties
The allotropes of carbon include graphite, one of the Natural primordial

softest known substances, and diamond, the hardest occurrence
naturally occurring substance. It bonds readily with Crystal structure graphite: simple hexagonal
other small atoms, including other carbon atoms, and (black)
is capable of forming multiple stable covalent bonds
with suitable multivalent atoms. Carbon is a
component element in the large majority of all Crystal structure diamond: face-
chemical compounds, with about two hundred
centered diamond-cubic
million examples having been described in the
(clear)
published chemical literature.[19] Carbon also has the
highest sublimation point of all elements. At
atmospheric pressure it has no melting point, as its
triple point is at 10.8 ± 0.2 megapascals Speed of sound diamond: 18,350 m/s
(106.6 ± 2.0 atm; 1,566 ± 29 psi) and 4,600 ± 300 K thin rod (at 20 °C)
(4,330 ± 300 °C; 7,820 ± 540 °F),[3][4] so it sublimes Thermal diamond: 0.8 µm/(m⋅K)
at about 3,900 K (3,630 °C; 6,560 °F).[21][22] expansion (at 25 °C)[8]
Graphite is much more reactive than diamond at
standard conditions, despite being more Thermal graphite: 119–165 W/(m⋅K)
thermodynamically stable, as its delocalised pi system conductivity diamond: 900–
is much more vulnerable to attack. For example, 2300 W/(m⋅K)
graphite can be oxidised by hot concentrated nitric
acid at standard conditions to mellitic acid, Electrical graphite: 7.837 µΩ⋅m[9]
C6 (CO2 H)6 , which preserves the hexagonal units of resistivity
graphite while breaking up the larger structure.[23] Magnetic ordering diamagnetic[10]
Molar magnetic diamond:
Carbon sublimes in a carbon arc, which has a
susceptibility −5.9 × 10−6 cm3/mol[11]
temperature of about 5800 K (5,530 °C or 9,980 °F).
Thus, irrespective of its allotropic form, carbon Young's modulus diamond: 1050 GPa[8]
remains solid at higher temperatures than the highest- Shear modulus diamond: 478 GPa[8]
melting-point metals such as tungsten or rhenium.
Although thermodynamically prone to oxidation, Bulk modulus diamond: 442 GPa[8]
carbon resists oxidation more effectively than Poisson ratio diamond: 0.1[8]
elements such as iron and copper, which are weaker Mohs hardness graphite: 1–2
reducing agents at room temperature.
diamond: 10
Carbon is the sixth element, with a ground-state CAS Number atomic carbon: 7440-44-0
electron configuration of 1s2 2s2 2p2 , of which the graphite: 7782-42-5
four outer electrons are valence electrons. Its first
four ionisation energies, 1086.5, 2352.6, 4620.5 and diamond: 7782-40-3
6222.7 kJ/mol, are much higher than those of the History
heavier group-14 elements. The electronegativity of
Discovery Egyptians and
carbon is 2.5, significantly higher than the heavier
Sumerians[12] (3750 BCE)
group-14 elements (1.8–1.9), but close to most of the
nearby nonmetals, as well as some of the second- and Recognized as an Antoine Lavoisier[13] (1789)
third-row transition metals. Carbon's covalent radii element by
are normally taken as 77.2 pm (C−C), 66.7 pm
Isotopes of carbon
(C=C) and 60.3 pm (C≡C), although these may vary
depending on coordination number and what the Main isotopes Decay
carbon is bonded to. In general, covalent radius
decreases with lower coordination number and abundance half-life (t1/2) mode product
higher bond order.[24] 11
C synth 20.34 min β+ 11
B
Carbon-based compounds form the basis of all 12

C 98.9% stable
known life on Earth, and the carbon-nitrogen-oxygen
13
cycle provides a small portion of the energy C 1.06% stable
produced by the Sun, and most of the energy in 14
C 1 ppt (1⁄1012) 5.70 × 103 y β− 14
N
larger stars (e.g. Sirius). Although it forms an
extraordinary variety of compounds, most forms of
carbon are comparatively unreactive under normal conditions. At standard temperature and pressure, it
resists all but the strongest oxidizers. It does not react with sulfuric acid, hydrochloric acid, chlorine or any
alkalis. At elevated temperatures, carbon reacts with oxygen to form carbon oxides and will rob oxygen
from metal oxides to leave the elemental metal. This exothermic reaction is used in the iron and steel
industry to smelt iron and to control the carbon content of steel:
Fe3O4 + 4 C(s) + 2 O2 → 3 Fe(s) + 4 CO2(g).
Carbon reacts with sulfur to form carbon disulfide, and it reacts with steam in the coal-gas reaction used in
coal gasification:
C(s) + H2O(g) → CO(g) + H2(g).
Carbon combines with some metals at high temperatures to form metallic carbides, such as the iron carbide
cementite in steel and tungsten carbide, widely used as an abrasive and for making hard tips for cutting
tools.
The system of carbon allotropes spans a range of extremes:
Synthetic nanocrystalline diamond is the hardest

Graphite is one of the softest materials known.
material known.[25]
Graphite is a very good lubricant, displaying
Diamond is the ultimate abrasive.
superlubricity.[26]
Diamond is an excellent electrical insulator,[28] and has

[27]
Graphite is a conductor of electricity. the highest breakdown electric field of any known
material.
Some forms of graphite are used for thermal insulation
Diamond is the best known naturally occurring thermal
(i.e. firebreaks and heat shields), but some other forms
conductor.
are good thermal conductors.
Graphite is opaque. Diamond is highly transparent.
Graphite crystallizes in the hexagonal system.[29] Diamond crystallizes in the cubic system.
Carbon nanotubes are among the most anisotropic

Amorphous carbon is completely isotropic.
materials known.
Allotropes
Atomic carbon is a very short-lived species and, therefore, carbon is stabilized in various multi-atomic
structures with diverse molecular configurations called allotropes. The three relatively well-known
allotropes of carbon are amorphous carbon, graphite, and diamond. Once considered exotic, fullerenes are
nowadays commonly synthesized and used in research; they include buckyballs,[30][31] carbon
nanotubes,[32] carbon nanobuds[33] and nanofibers.[34][35] Several other exotic allotropes have also been
discovered, such as lonsdaleite,[36] glassy carbon,[37] carbon nanofoam[38] and linear acetylenic carbon
(carbyne).[39]
Graphene is a two-dimensional sheet of carbon with the atoms arranged in a hexagonal lattice. As of 2009,
graphene appears to be the strongest material ever tested.[40] The process of separating it from graphite will
require some further technological development before it is economical for industrial processes.[41] If
successful, graphene could be used in the construction of a space elevator. It could also be used to safely
store hydrogen for use in a hydrogen based engine in cars.[42]
The amorphous form is an assortment of carbon atoms in a non-crystalline, irregular, glassy state, not held
in a crystalline macrostructure. It is present as a powder, and is the main constituent of substances such as
charcoal, lampblack (soot), and activated carbon. At normal pressures, carbon takes the form of graphite, in
which each atom is bonded trigonally to three others in a plane composed of fused hexagonal rings, just
like those in aromatic hydrocarbons.[43] The resulting network is 2-dimensional, and the resulting flat
sheets are stacked and loosely bonded through weak van der Waals forces. This gives graphite its softness
and its cleaving properties (the sheets slip easily past one another). Because of the delocalization of one of
the outer electrons of each atom to form a π-cloud, graphite conducts electricity, but only in the plane of
each covalently bonded sheet. This results in a lower bulk electrical
conductivity for carbon than for most metals. The delocalization
also accounts for the energetic stability of graphite over diamond at
room temperature.
A large sample of glassy carbon
At very high pressures, carbon forms the more

compact allotrope, diamond, having nearly twice the
density of graphite. Here, each atom is bonded
tetrahedrally to four others, forming a 3-dimensional
network of puckered six-membered rings of atoms.
Diamond has the same cubic structure as silicon and
germanium, and because of the strength of the carbon-
carbon bonds, it is the hardest naturally occurring
substance measured by resistance to scratching.
Some allotropes of carbon: a) diamond; b)
Contrary to the popular belief that "diamonds are
graphite; c) lonsdaleite; d–f) fullerenes (C60, C540,
forever", they are thermodynamically unstable (ΔfG°
C70); g) amorphous carbon; h) carbon nanotube
(diamond, 298 K) = 2.9 kJ/mol[44]) under normal
conditions (298 K, 105 Pa) and should theoretically
transform into graphite.[45] But due to a high activation energy barrier, the transition into graphite is so slow
at normal temperature that it is unnoticeable. However, at very high temperatures diamond will turn into
graphite, and diamonds can burn up in a house fire. The bottom left corner of the phase diagram for carbon
has not been scrutinized experimentally. Although a computational study employing density functional
theory methods reached the conclusion that as T → 0 K and p → 0 Pa, diamond becomes more stable than
graphite by approximately 1.1 kJ/mol,[46] more recent and definitive experimental and computational
studies show that graphite is more stable than diamond for T < 400 K, without applied pressure, by
2.7 kJ/mol at T = 0 K and 3.2 kJ/mol at T = 298.15 K.[47] Under some conditions, carbon crystallizes as
lonsdaleite, a hexagonal crystal lattice with all atoms covalently bonded and properties similar to those of
diamond.[36]
Fullerenes are a synthetic crystalline formation with a graphite-like structure, but in place of flat hexagonal
cells only, some of the cells of which fullerenes are formed may be pentagons, nonplanar hexagons, or even
heptagons of carbon atoms. The sheets are thus warped into spheres, ellipses, or cylinders. The properties
of fullerenes (split into buckyballs, buckytubes, and nanobuds) have not yet been fully analyzed and
represent an intense area of research in nanomaterials. The names fullerene and buckyball are given after
Richard Buckminster Fuller, popularizer of geodesic domes, which resemble the structure of fullerenes. The
buckyballs are fairly large molecules formed completely of carbon bonded trigonally, forming spheroids
(the best-known and simplest is the soccerball-shaped C60 buckminsterfullerene).[30] Carbon nanotubes
(buckytubes) are structurally similar to buckyballs, except that each atom is bonded trigonally in a curved
sheet that forms a hollow cylinder.[31][32] Nanobuds were first reported in 2007 and are hybrid
buckytube/buckyball materials (buckyballs are covalently bonded to the outer wall of a nanotube) that
combine the properties of both in a single structure.[33]
Of the other discovered allotropes, carbon nanofoam is a
ferromagnetic allotrope discovered in 1997. It consists of a low-
density cluster-assembly of carbon atoms strung together in a loose
three-dimensional web, in which the atoms are bonded trigonally in
six- and seven-membered rings. It is among the lightest known
solids, with a density of about 2 kg/m3 .[48] Similarly, glassy carbon
contains a high proportion of closed porosity,[37] but contrary to
normal graphite, the graphitic layers are not stacked like pages in a
book, but have a more random arrangement. Linear acetylenic Comet C/2014 Q2 (Lovejoy)
[39] has the chemical structure[39] −(C≡C) − . Carbon in this
carbon n surrounded by glowing carbon vapor
modification is linear with sp orbital hybridization, and is a polymer
with alternating single and triple bonds. This carbyne is of
considerable interest to nanotechnology as its Young's modulus is 40 times that of the hardest known
material – diamond.[49]
In 2015, a team at the North Carolina State University announced the development of another allotrope
they have dubbed Q-carbon, created by a high-energy low-duration laser pulse on amorphous carbon dust.
Q-carbon is reported to exhibit ferromagnetism, fluorescence, and a hardness superior to diamonds.[50]
In the vapor phase, some of the carbon is in the form of highly reactive diatomic carbon dicarbon (C2 ).
When excited, this gas glows green.
Occurrence
Carbon is the fourth most abundant chemical element in the

observable universe by mass after hydrogen, helium, and oxygen.
Carbon is abundant in the Sun, stars, comets, and in the
atmospheres of most planets.[51] Some meteorites contain
microscopic diamonds that were formed when the Solar System
was still a protoplanetary disk.[52] Microscopic diamonds may also
be formed by the intense pressure and high temperature at the sites
of meteorite impacts.[53]
Graphite ore, shown with a penny for
In 2014 NASA announced a greatly upgraded database (http://ww
scale
w.astrochem.org/pahdb/) for tracking polycyclic aromatic
hydrocarbons (PAHs) in the universe. More than 20% of the
carbon in the universe may be associated with PAHs, complex
compounds of carbon and hydrogen without oxygen.[54] These
compounds figure in the PAH world hypothesis where they are
hypothesized to have a role in abiogenesis and formation of life.
PAHs seem to have been formed "a couple of billion years" after
the Big Bang, are widespread throughout the universe, and are
associated with new stars and exoplanets.[51]
It has been estimated that the solid earth as a whole contains 730
ppm of carbon, with 2000 ppm in the core and 120 ppm in the Raw diamond crystal
combined mantle and crust.[55] Since the mass of the earth is
5.972 × 1024 kg, this would imply 4360 million gigatonnes of
carbon. This is much more than the amount of carbon in the oceans or atmosphere (below).
In combination with oxygen in carbon dioxide, carbon is found in
the Earth's atmosphere (approximately 900 gigatonnes of carbon —
each ppm corresponds to 2.13 Gt) and dissolved in all water bodies
(approximately 36,000 gigatonnes of carbon). Carbon in the
biosphere has been estimated at 550 gigatonnes but with a large
uncertainty, due mostly to a huge uncertainty in the amount of
terrestrial deep subsurface bacteria.[56] Hydrocarbons (such as coal,
petroleum, and natural gas) contain carbon as well. Coal "reserves"
(not "resources") amount to around 900 gigatonnes with perhaps "Present day" (1990s) sea surface
18,000 Gt of resources.[57] Oil reserves are around 150 gigatonnes. dissolved inorganic carbon
Proven sources of natural gas are about 175 × 1012 cubic metres concentration (from the GLODAP
(containing about 105 gigatonnes of carbon), but studies estimate climatology)
another 900 × 1012 cubic metres of "unconventional" deposits such
as shale gas, representing about 540 gigatonnes of carbon.[58]
Carbon is also found in methane hydrates in polar regions and under the seas. Various estimates put this
carbon between 500, 2500,[59] or 3,000 Gt.[60]
According to one source, in the period from 1751 to 2008 about 347 gigatonnes of carbon were released as
carbon dioxide to the atmosphere from burning of fossil fuels.[61] Another source puts the amount added to
the atmosphere for the period since 1750 at 879 Gt, and the total going to the atmosphere, sea, and land
(such as peat bogs) at almost 2,000 Gt.[62]
Carbon is a constituent (about 12% by mass) of the very large masses of carbonate rock (limestone,
dolomite, marble, and others). Coal is very rich in carbon (anthracite contains 92–98%)[63] and is the
largest commercial source of mineral carbon, accounting for 4,000 gigatonnes or 80% of fossil fuel.[64]
As for individual carbon allotropes, graphite is found in large quantities in the United States (mostly in New
York and Texas), Russia, Mexico, Greenland, and India. Natural diamonds occur in the rock kimberlite,
found in ancient volcanic "necks", or "pipes". Most diamond deposits are in Africa, notably in South
Africa, Namibia, Botswana, the Republic of the Congo, and Sierra Leone. Diamond deposits have also
been found in Arkansas, Canada, the Russian Arctic, Brazil, and in Northern and Western Australia.
Diamonds are now also being recovered from the ocean floor off the Cape of Good Hope. Diamonds are
found naturally, but about 30% of all industrial diamonds used in the U.S. are now manufactured.
Carbon-14 is formed in upper layers of the troposphere and the stratosphere at altitudes of 9–15 km by a
reaction that is precipitated by cosmic rays.[65] Thermal neutrons are produced that collide with the nuclei
of nitrogen-14, forming carbon-14 and a proton. As such, 1.5% × 10−10 of atmospheric carbon dioxide
contains carbon-14.[66]
Carbon-rich asteroids are relatively preponderant in the outer parts of the asteroid belt in the Solar System.
These asteroids have not yet been directly sampled by scientists. The asteroids can be used in hypothetical
space-based carbon mining, which may be possible in the future, but is currently technologically
impossible.[67]
Isotopes
Isotopes of carbon are atomic nuclei that contain six protons plus a number of neutrons (varying from 2 to
16). Carbon has two stable, naturally occurring isotopes.[16] The isotope carbon-12 (12 C) forms 98.93% of
the carbon on Earth, while carbon-13 (13 C) forms the remaining 1.07%.[16] The concentration of 12 C is
further increased in biological materials because biochemical reactions discriminate against 13 C.[68] In
1961, the International Union of Pure and Applied Chemistry (IUPAC) adopted the isotope carbon-12 as
the basis for atomic weights.[69] Identification of carbon in nuclear magnetic resonance (NMR) experiments
is done with the isotope 13 C.
Carbon-14 (14 C) is a naturally occurring radioisotope, created in the upper atmosphere (lower stratosphere
and upper troposphere) by interaction of nitrogen with cosmic rays.[70] It is found in trace amounts on
Earth of 1 part per trillion (0.0000000001%) or more, mostly confined to the atmosphere and superficial
deposits, particularly of peat and other organic materials.[71] This isotope decays by 0.158 MeV β−
emission. Because of its relatively short half-life of 5730 years, 14 C is virtually absent in ancient rocks. The
amount of 14 C in the atmosphere and in living organisms is almost constant, but decreases predictably in
their bodies after death. This principle is used in radiocarbon dating, invented in 1949, which has been used
extensively to determine the age of carbonaceous materials with ages up to about 40,000 years.[72][73]
There are 15 known isotopes of carbon and the shortest-lived of these is 8 C which decays through proton
emission and alpha decay and has a half-life of 1.98739 × 10−21 s.[74] The exotic 19 C exhibits a nuclear
halo, which means its radius is appreciably larger than would be expected if the nucleus were a sphere of
constant density.[75]
Formation in stars
Formation of the carbon atomic nucleus occurs within a giant or supergiant star through the triple-alpha
process. This requires a nearly simultaneous collision of three alpha particles (helium nuclei), as the
products of further nuclear fusion reactions of helium with hydrogen or another helium nucleus produce
lithium-5 and beryllium-8 respectively, both of which are highly unstable and decay almost instantly back
into smaller nuclei.[76] The triple-alpha process happens in conditions of temperatures over 100
megakelvins and helium concentration that the rapid expansion and cooling of the early universe
prohibited, and therefore no significant carbon was created during the Big Bang.
According to current physical cosmology theory, carbon is formed in the interiors of stars on the horizontal
branch.[77] When massive stars die as supernova, the carbon is scattered into space as dust. This dust
becomes component material for the formation of the next-generation star systems with accreted
planets.[51][78] The Solar System is one such star system with an abundance of carbon, enabling the
existence of life as we know it. It is the opinion of most scholars that all the carbon in the Solar System and
the Milky Way comes from dying stars.[79][80][81]
The CNO cycle is an additional hydrogen fusion mechanism that powers stars, wherein carbon operates as
a catalyst.
Rotational transitions of various isotopic forms of carbon monoxide (for example, 12 CO, 13 CO, and 18 CO)
are detectable in the submillimeter wavelength range, and are used in the study of newly forming stars in
molecular clouds.[82]
Carbon cycle
Under terrestrial conditions, conversion of one element to another is very rare. Therefore, the amount of
carbon on Earth is effectively constant. Thus, processes that use carbon must obtain it from somewhere and
dispose of it somewhere else. The paths of carbon in the environment form the carbon cycle.[83] For
example, photosynthetic plants draw carbon dioxide from the atmosphere (or seawater) and build it into
biomass, as in the Calvin cycle, a process of carbon fixation.[84] Some of this biomass is eaten by animals,
while some carbon is exhaled by animals as carbon dioxide. The carbon cycle is considerably more
complicated than this short loop; for example, some
carbon dioxide is dissolved in the oceans; if bacteria
do not consume it, dead plant or animal matter may
become petroleum or coal, which releases carbon
when burned.[85][86]
Compounds
Organic compounds
Carbon can form very

long chains of Diagram of the carbon cycle. The black numbers
interconnecting carbon– indicate how much carbon is stored in various
carbon bonds, a property reservoirs, in billions tonnes ("GtC" stands for
that is called catenation. gigatonnes of carbon; figures are c. 2004). The
Carbon-carbon bonds are purple numbers indicate how much carbon moves
strong and stable. between reservoirs each year. The sediments, as
Through catenation, defined in this diagram, do not include the
Structural formula of carbon forms a countless ≈70 million GtC of carbonate rock and kerogen.
methane, the simplest number of compounds. A
possible organic tally of unique
compound. compounds shows that
more contain carbon than
do not.[87] A similar claim
can be made for hydrogen because most organic
compounds contain hydrogen chemically bonded to
carbon or another common element like oxygen or
nitrogen.
The simplest form of an organic molecule is the

hydrocarbon—a large family of organic molecules that
are composed of hydrogen atoms bonded to a chain of
carbon atoms. A hydrocarbon backbone can be
substituted by other atoms, known as heteroatoms.
Common heteroatoms that appear in organic
compounds include oxygen, nitrogen, sulfur,
phosphorus, and the nonradioactive halogens, as well
as the metals lithium and magnesium. Organic
compounds containing bonds to metal are known as
organometallic compounds (see below). Certain Correlation between the carbon cycle and
groupings of atoms, often including heteroatoms, recur formation of organic compounds. In plants, carbon
in large numbers of organic compounds. These dioxide formed by carbon fixation can join with
collections, known as functional groups, confer water in photosynthesis (green) to form organic
common reactivity patterns and allow for the compounds, which can be used and further
systematic study and categorization of organic converted by both plants and animals.
compounds. Chain length, shape and functional
groups all affect the properties of organic
molecules.[88]
In most stable compounds of carbon (and nearly all stable organic compounds), carbon obeys the octet rule
and is tetravalent, meaning that a carbon atom forms a total of four covalent bonds (which may include
double and triple bonds). Exceptions include a small number of stabilized carbocations (three bonds,
positive charge), radicals (three bonds, neutral), carbanions (three bonds, negative charge) and carbenes
(two bonds, neutral), although these species are much more likely to be encountered as unstable, reactive
intermediates.
Carbon occurs in all known organic life and is the basis of organic chemistry. When united with hydrogen,
it forms various hydrocarbons that are important to industry as refrigerants, lubricants, solvents, as chemical
feedstock for the manufacture of plastics and petrochemicals, and as fossil fuels.
When combined with oxygen and hydrogen, carbon can form many groups of important biological
compounds including sugars, lignans, chitins, alcohols, fats, aromatic esters, carotenoids and terpenes. With
nitrogen it forms alkaloids, and with the addition of sulfur also it forms antibiotics, amino acids, and rubber
products. With the addition of phosphorus to these other elements, it forms DNA and RNA, the chemical-
code carriers of life, and adenosine triphosphate (ATP), the most important energy-transfer molecule in all
living cells.[89] Norman Horowitz, head of the Mariner and Viking missions to Mars (1965-1976),
considered that the unique characteristics of carbon made it unlikely that any other element could replace
carbon, even on another planet, to generate the biochemistry necessary for life.[90]
Inorganic compounds
Commonly carbon-containing compounds which are associated with minerals or which do not contain
bonds to the other carbon atoms, halogens, or hydrogen, are treated separately from classical organic
compounds; the definition is not rigid, and the classification of some compounds can vary from author to
author (see reference articles above). Among these are the simple oxides of carbon. The most prominent
oxide is carbon dioxide (CO2 ). This was once the principal constituent of the paleoatmosphere, but is a
minor component of the Earth's atmosphere today.[91] Dissolved in water, it forms carbonic acid (H2 CO3 ),
but as most compounds with multiple single-bonded oxygens on a single carbon it is unstable.[92] Through
this intermediate, though, resonance-stabilized carbonate ions are produced. Some important minerals are
carbonates, notably calcite. Carbon disulfide (CS2 ) is similar.[23] Nevertheless, due to its physical properties
and its association with organic synthesis, carbon disulfide is sometimes classified as an organic solvent.
The other common oxide is carbon monoxide (CO). It is formed by incomplete combustion, and is a
colorless, odorless gas. The molecules each contain a triple bond and are fairly polar, resulting in a
tendency to bind permanently to hemoglobin molecules, displacing oxygen, which has a lower binding
affinity.[93][94] Cyanide (CN−), has a similar structure, but behaves much like a halide ion (pseudohalogen).
For example, it can form the nitride cyanogen molecule ((CN)2 ), similar to diatomic halides. Likewise, the
heavier analog of cyanide, cyaphide (CP−), is also considered inorganic, though most simple derivatives are
highly unstable. Other uncommon oxides are carbon suboxide (C3 O2 ),[95] the unstable dicarbon monoxide
(C2 O),[96][97] carbon trioxide (CO3 ),[98][99] cyclopentanepentone (C5 O5 ),[100] cyclohexanehexone
(C6 O6 ),[100] and mellitic anhydride (C12 O9 ). However, mellitic anhydride is the triple acyl anhydride of
mellitic acid; moreover, it contains a benzene ring. Thus, many chemists consider it to be organic.
With reactive metals, such as tungsten, carbon forms either carbides (C4−) or acetylides (C2−
2 ) to form alloys
with high melting points. These anions are also associated with methane and acetylene, both very weak
acids. With an electronegativity of 2.5,[101] carbon prefers to form covalent bonds. A few carbides are
covalent lattices, like carborundum (SiC), which resembles diamond. Nevertheless, even the most polar and
salt-like of carbides are not completely ionic compounds.[102]
Organometallic compounds
Organometallic compounds by definition contain at least one carbon-metal covalent bond. A wide range of
such compounds exist; major classes include simple alkyl-metal compounds (for example, tetraethyllead),
η2 -alkene compounds (for example, Zeise's salt), and η3 -allyl compounds (for example, allylpalladium
chloride dimer); metallocenes containing cyclopentadienyl ligands (for example, ferrocene); and transition
metal carbene complexes. Many metal carbonyls and metal cyanides exist (for example, tetracarbonylnickel
and potassium ferricyanide); some workers consider metal carbonyl and cyanide complexes without other
carbon ligands to be purely inorganic, and not organometallic. However, most organometallic chemists
consider metal complexes with any carbon ligand, even 'inorganic carbon' (e.g., carbonyls, cyanides, and
certain types of carbides and acetylides) to be organometallic in nature. Metal complexes containing organic
ligands without a carbon-metal covalent bond (e.g., metal carboxylates) are termed metalorganic
compounds.
While carbon is understood to strongly prefer formation of four covalent bonds, other exotic bonding
schemes are also known. Carboranes are highly stable dodecahedral derivatives of the [B12 H12 ]2- unit,
with one BH replaced with a CH+. Thus, the carbon is bonded to five boron atoms and one hydrogen
atom. The cation [(Ph3 PAu)6 C]2+ contains an octahedral carbon bound to six phosphine-gold fragments.
This phenomenon has been attributed to the aurophilicity of the gold ligands, which provide additional
stabilization of an otherwise labile species.[103] In nature, the iron-molybdenum cofactor (FeMoco)
responsible for microbial nitrogen fixation likewise has an octahedral carbon center (formally a carbide, C(-
IV)) bonded to six iron atoms. In 2016, it was confirmed that, in line with earlier theoretical predictions, the
hexamethylbenzene dication contains a carbon atom with six bonds. More specifically, the dication could
be described structurally by the formulation [MeC(η5 -C5 Me5 )]2+, making it an "organic metallocene" in
which a MeC3+ fragment is bonded to a η5 -C5 Me5 − fragment through all five of the carbons of the
ring.[104]
It is important to note that in the cases above, each of the bonds to

carbon contain less than two formal electron pairs. Thus, the formal
electron count of these species does not exceed an octet. This
makes them hypercoordinate but not hypervalent. Even in cases of
alleged 10-C-5 species (that is, a carbon with five ligands and a
formal electron count of ten), as reported by Akiba and co-
workers,[105] electronic structure calculations conclude that the This anthracene derivative contains
electron population around carbon is still less than eight, as is true a carbon atom with 5 formal electron
for other compounds featuring four-electron three-center bonding. pairs around it.
History and etymology

The English name carbon comes from the Latin carbo for coal and charcoal,[106] whence also comes the
French charbon, meaning charcoal. In German, Dutch and Danish, the names for carbon are Kohlenstoff,
koolstof, and kulstof respectively, all literally meaning coal-substance.
Carbon was discovered in prehistory and was known in the forms of soot
and charcoal to the earliest human civilizations. Diamonds were known
probably as early as 2500 BCE in China, while carbon in the form of
charcoal was made around Roman times by the same chemistry as it is
today, by heating wood in a pyramid covered with clay to exclude
air.[107][108]
In 1722, René Antoine Ferchault de

Réaumur demonstrated that iron was
transformed into steel through the
Antoine Lavoisier in his absorption of some substance, now known
youth to be carbon.[109] In 1772, Antoine
Lavoisier showed that diamonds are a form
of carbon; when he burned samples of
charcoal and diamond and found that neither produced any water and that
both released the same amount of carbon dioxide per gram. In 1779,[110]
Carl Wilhelm Scheele showed that graphite, which had been thought of as
a form of lead, was instead identical with charcoal but with a small
admixture of iron, and that it gave "aerial acid" (his name for carbon Carl Wilhelm Scheele
dioxide) when oxidized with nitric acid. [111] In 1786, the French scientists
Claude Louis Berthollet, Gaspard Monge and C. A. Vandermonde
confirmed that graphite was mostly carbon by oxidizing it in oxygen in much the same way Lavoisier had
done with diamond.[112] Some iron again was left, which the French scientists thought was necessary to
the graphite structure. In their publication they proposed the name carbone (Latin carbonum) for the
element in graphite which was given off as a gas upon burning graphite. Antoine Lavoisier then listed
carbon as an element in his 1789 textbook.[111]
A new allotrope of carbon, fullerene, that was discovered in 1985[113] includes nanostructured forms such
as buckyballs and nanotubes.[30] Their discoverers – Robert Curl, Harold Kroto, and Richard Smalley –
received the Nobel Prize in Chemistry in 1996.[114] The resulting renewed interest in new forms led to the
discovery of further exotic allotropes, including glassy carbon, and the realization that "amorphous carbon"
is not strictly amorphous.[37]
Production
Graphite
Commercially viable natural deposits of graphite occur in many parts of the world, but the most important
sources economically are in China, India, Brazil, and North Korea. Graphite deposits are of metamorphic
origin, found in association with quartz, mica, and feldspars in schists, gneisses, and metamorphosed
sandstones and limestone as lenses or veins, sometimes of a metre or more in thickness. Deposits of
graphite in Borrowdale, Cumberland, England were at first of sufficient size and purity that, until the 19th
century, pencils were made by sawing blocks of natural graphite into strips before encasing the strips in
wood. Today, smaller deposits of graphite are obtained by crushing the parent rock and floating the lighter
graphite out on water.[115]
There are three types of natural graphite—amorphous, flake or crystalline flake, and vein or lump.
Amorphous graphite is the lowest quality and most abundant. Contrary to science, in industry "amorphous"
refers to very small crystal size rather than complete lack of crystal structure. Amorphous is used for lower
value graphite products and is the lowest priced graphite. Large amorphous graphite deposits are found in
China, Europe, Mexico and the United States. Flake graphite is less common and of higher quality than
amorphous; it occurs as separate plates that crystallized in metamorphic rock. Flake graphite can be four
times the price of amorphous. Good quality flakes can be processed into expandable graphite for many
uses, such as flame retardants. The foremost deposits are found in Austria, Brazil, Canada, China, Germany
and Madagascar. Vein or lump graphite is the rarest, most valuable, and highest quality type of natural
graphite. It occurs in veins along intrusive contacts in solid lumps, and it is only commercially mined in Sri
Lanka.[115]
According to the USGS, world production of natural graphite was 1.1 million tonnes in 2010, to which
China contributed 800,000 t, India 130,000 t, Brazil 76,000 t, North Korea 30,000 t and Canada 25,000 t.
No natural graphite was reported mined in the United States, but 118,000 t of synthetic graphite with an
estimated value of $998 million was produced in 2009.[115]
Diamond
The diamond supply chain is

controlled by a limited number
of powerful businesses, and is
also highly concentrated in a
small number of locations
around the world (see figure).
Only a very small fraction of the

diamond ore consists of actual
diamonds. The ore is crushed,
during which care has to be Diamond output in 2005
taken in order to prevent larger
diamonds from being destroyed
in this process and subsequently the particles are sorted by density. Today, diamonds are located in the
diamond-rich density fraction with the help of X-ray fluorescence, after which the final sorting steps are
done by hand. Before the use of X-rays became commonplace, the separation was done with grease belts;
diamonds have a stronger tendency to stick to grease than the other minerals in the ore.[116]
Historically diamonds were known to be found only in alluvial deposits in southern India.[117] India led the
world in diamond production from the time of their discovery in approximately the 9th century BC[118] to
the mid-18th century AD, but the commercial potential of these sources had been exhausted by the late 18th
century and at that time India was eclipsed by Brazil where the first non-Indian diamonds were found in
1725.[119]
Diamond production of primary deposits (kimberlites and lamproites) only started in the 1870s after the
discovery of the diamond fields in South Africa. Production has increased over time and an accumulated
total of over 4.5 billion carats have been mined since that date.[120] Most commercially viable diamond
deposits were in Russia, Botswana, Australia and the Democratic Republic of Congo.[121] By 2005, Russia
produced almost one-fifth of the global diamond output (mostly in Yakutia territory; for example, Mir pipe
and Udachnaya pipe) but the Argyle mine in Australia became the single largest source, producing 14
million carats in 2018.[122][123] New finds, the Canadian mines at Diavik and Ekati, are expected to
become even more valuable owing to their production of gem quality stones.[124]
In the United States, diamonds have been found in Arkansas, Colorado, and Montana.[125] In 2004, a
startling discovery of a microscopic diamond in the United States[126] led to the January 2008 bulk-
sampling of kimberlite pipes in a remote part of Montana.[127]
Applications
Carbon is essential to all
known living systems, and
without it life as we know it
could not exist (see
alternative biochemistry).
The major economic use of
carbon other than food and
wood is in the form of
hydrocarbons, most notably
Sticks of vine and compressed the fossil fuel methane gas Pencil leads for mechanical pencils
charcoal and crude oil (petroleum). are made of graphite (often mixed
with a clay or synthetic binder).
Crude oil is distilled in
refineries by the
petrochemical industry to
produce gasoline, kerosene,
and other products.
Cellulose is a natural,
carbon-containing polymer
produced by plants in the
form of wood, cotton,
linen, and hemp. Cellulose
is used primarily for
A cloth of woven carbon fibres
maintaining structure in
plants. Commercially
Silicon carbide single crystal
valuable carbon polymers
of animal origin include
wool, cashmere, and silk.
Plastics are made from
synthetic carbon polymers,
often with oxygen and
nitrogen atoms included at
regular intervals in the main
Tungsten carbide endmills
polymer chain. The raw
materials for many of these
synthetic substances come
from crude oil.
The C60 fullerene in crystalline form
The uses of carbon and its compounds are extremely varied. It can
form alloys with iron, of which the most common is carbon steel.
Graphite is combined with clays to form the 'lead' used in pencils used for writing and drawing. It is also
used as a lubricant and a pigment, as a moulding material in glass manufacture, in electrodes for dry
batteries and in electroplating and electroforming, in brushes for electric motors, and as a neutron moderator
in nuclear reactors.
Charcoal is used as a drawing material in artwork, barbecue grilling, iron smelting, and in many other
applications. Wood, coal and oil are used as fuel for production of energy and heating. Gem quality
diamond is used in jewelry, and industrial diamonds are used in drilling, cutting and polishing tools for
machining metals and stone. Plastics are made from fossil hydrocarbons, and carbon fiber, made by
pyrolysis of synthetic polyester fibers is used to reinforce plastics to form advanced, lightweight composite
materials.
Carbon fiber is made by pyrolysis of extruded and stretched filaments of polyacrylonitrile (PAN) and other
organic substances. The crystallographic structure and mechanical properties of the fiber depend on the
type of starting material, and on the subsequent processing. Carbon fibers made from PAN have structure
resembling narrow filaments of graphite, but thermal processing may re-order the structure into a
continuous rolled sheet. The result is fibers with higher specific tensile strength than steel.[128]
Carbon black is used as the black pigment in printing ink, artist's oil paint, and water colours, carbon paper,
automotive finishes, India ink and laser printer toner. Carbon black is also used as a filler in rubber products
such as tyres and in plastic compounds. Activated charcoal is used as an absorbent and adsorbent in filter
material in applications as diverse as gas masks, water purification, and kitchen extractor hoods, and in
medicine to absorb toxins, poisons, or gases from the digestive system. Carbon is used in chemical
reduction at high temperatures. Coke is used to reduce iron ore into iron (smelting). Case hardening of steel
is achieved by heating finished steel components in carbon powder. Carbides of silicon, tungsten, boron,
and titanium are among the hardest known materials, and are used as abrasives in cutting and grinding
tools. Carbon compounds make up most of the materials used in clothing, such as natural and synthetic
textiles and leather, and almost all of the interior surfaces in the built environment other than glass, stone,
drywall and metal.
Diamonds
The diamond industry falls into two categories: one dealing with gem-grade diamonds and the other, with
industrial-grade diamonds. While a large trade in both types of diamonds exists, the two markets function
dramatically differently.
Unlike precious metals such as gold or platinum, gem diamonds do not trade as a commodity: there is a
substantial mark-up in the sale of diamonds, and there is not a very active market for resale of diamonds.
Industrial diamonds are valued mostly for their hardness and heat conductivity, with the gemological
qualities of clarity and color being mostly irrelevant. About 80% of mined diamonds (equal to about 100
million carats or 20 tonnes annually) are unsuitable for use as gemstones and relegated for industrial use
(known as bort).[129] Synthetic diamonds, invented in the 1950s, found almost immediate industrial
applications; 3 billion carats (600 tonnes) of synthetic diamond is produced annually.[130]
The dominant industrial use of diamond is in cutting, drilling, grinding, and polishing. Most of these
applications do not require large diamonds; in fact, most diamonds of gem-quality except for their small size
can be used industrially. Diamonds are embedded in drill tips or saw blades, or ground into a powder for
use in grinding and polishing applications.[131] Specialized applications include use in laboratories as
containment for high-pressure experiments (see diamond anvil cell), high-performance bearings, and limited
use in specialized windows.[132][133] With the continuing advances in the production of synthetic
diamonds, new applications are becoming feasible. Garnering much excitement is the possible use of
diamond as a semiconductor suitable for microchips, and because of its exceptional heat conductance
property, as a heat sink in electronics.[134]
Precautions
Gross pathology of lung showing centrilobular

emphysema characteristic of smoking. Closeup
Worker at carbon black plant of fixed, cut surface shows multiple cavities lined
in Sunray, Texas (photo by by heavy black carbon deposits.
John Vachon, 1942)
Pure carbon has extremely low toxicity to humans and can be handled
safely in the form of graphite or charcoal. It is resistant to dissolution or chemical attack, even in the acidic
contents of the digestive tract. Consequently, once it enters into the body's tissues it is likely to remain there
indefinitely. Carbon black was probably one of the first pigments to be used for tattooing, and Ötzi the
Iceman was found to have carbon tattoos that survived during his life and for 5200 years after his
death.[135] Inhalation of coal dust or soot (carbon black) in large quantities can be dangerous, irritating lung
tissues and causing the congestive lung disease, coalworker's pneumoconiosis. Diamond dust used as an
abrasive can be harmful if ingested or inhaled. Microparticles of carbon are produced in diesel engine
exhaust fumes, and may accumulate in the lungs.[136] In these examples, the harm may result from
contaminants (e.g., organic chemicals, heavy metals) rather than from the carbon itself.
Carbon generally has low toxicity to life on Earth; but carbon nanoparticles are deadly to Drosophila.[137]
Carbon may burn vigorously and brightly in the presence of air at high temperatures. Large accumulations
of coal, which have remained inert for hundreds of millions of years in the absence of oxygen, may
spontaneously combust when exposed to air in coal mine waste tips, ship cargo holds and coal
bunkers,[138][139] and storage dumps.
In nuclear applications where graphite is used as a neutron moderator, accumulation of Wigner energy
followed by a sudden, spontaneous release may occur. Annealing to at least 250 °C can release the energy
safely, although in the Windscale fire the procedure went wrong, causing other reactor materials to
combust.
The great variety of carbon compounds include such lethal poisons as tetrodotoxin, the lectin ricin from
seeds of the castor oil plant Ricinus communis, cyanide (CN−), and carbon monoxide; and such essentials
to life as glucose and protein.
See also
Carbon chauvinism
Carbon detonation
Carbon footprint
Carbon star
Carbon planet
Gas carbon
Low-carbon economy
Timeline of carbon nanotubes
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External links
Carbon (https://www.bbc.co.uk/programmes/p003c1cj) on In Our Time at the BBC
Carbon (http://www.periodicvideos.com/videos/006.htm) at The Periodic Table of Videos
(University of Nottingham)
Carbon on Britannica (https://www.britannica.com/eb/article-80956/carbon-group-element)
Extensive Carbon page at asu.edu (https://web.archive.org/web/20100618165649/http://invs
ee.asu.edu/nmodules/Carbonmod/everywhere.html) (archived 18 June 2010)
Electrochemical uses of carbon (https://web.archive.org/web/20011109080742/http://electro
chem.cwru.edu/ed/encycl/art-c01-carbon.htm) (archived 9 November 2001)
Carbon—Super Stuff. Animation with sound and interactive 3D-models. (https://web.archive.
org/web/20121109012854/http://www.forskning.no/Artikler/2006/juni/1149432180.36)
(archived 9 November 2012)
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Carbon

Carbon (from Latin carbo 'coal') is a chemical

The allotropes of carbon include graphite, one of the Natural primordial

Carbon-based compounds form the basis of all 12

Fe3O4 + 4 C(s) + 2 O2 → 3 Fe(s) + 4 CO2(g).

The system of carbon allotropes spans a range of extremes:

Synthetic nanocrystalline diamond is the hardest

Diamond is an excellent electrical insulator,[28] and has

Graphite is opaque. Diamond is highly transparent.

Carbon nanotubes are among the most anisotropic

A large sample of glassy carbon

At very high pressures, carbon forms the more

Carbon is the fourth most abundant chemical element in the

Carbon can form very

The simplest form of an organic molecule is the

It is important to note that in the cases above, each of the bonds to

History and etymology

In 1722, René Antoine Ferchault de

The diamond supply chain is

Only a very small fraction of the

Gross pathology of lung showing centrilobular

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