In
chemistry
Chemistry is the science, scientific study of the properties and behavior of matter. It is a natural science that covers the Chemical element, elements that make up matter to the chemical compound, compounds made of atoms, molecules and ions ...
, the carbon-hydrogen bond ( bond) is a
chemical bond
A chemical bond is a lasting attraction between atoms or ions that enables the formation of molecules and crystals. The bond may result from the electrostatic force between oppositely charged ions as in ionic bonds, or through the sharing of ...
between
carbon
Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent
In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with o ...
and
hydrogen
Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-toxic, an ...
atoms that can be found in many
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
s.
This bond is a
covalent
A covalent bond is a chemical bond that involves the sharing of electrons to form electron pairs between atoms. These electron pairs are known as shared pairs or bonding pairs. The stable balance of attractive and repulsive forces between atoms ...
,
single bond, meaning that carbon shares its outer
valence electron
In chemistry and physics, a valence electron is an electron in the outer shell associated with an atom, and that can participate in the formation of a chemical bond if the outer shell is not closed. In a single covalent bond, a shared pair forms ...
s with up to four hydrogens. This
completes both of their
outer shells, making them stable.
Carbon–hydrogen bonds have a
bond length
In molecular geometry, bond length or bond distance is defined as the average distance between nuclei of two bonded atoms in a molecule. It is a transferable property of a bond between atoms of fixed types, relatively independent of the rest of ...
of about 1.09
Å (1.09 × 10
−10 m) and a
bond energy
In chemistry, bond energy (''BE''), also called the mean bond enthalpy or average bond enthalpy is the measure of bond strength in a chemical bond. IUPAC defines bond energy as the average value of the gas-phase bond-dissociation energy (usually ...
of about 413
kJ/
mol (see table below). Using
Pauling's scale—C (2.55) and H (2.2)—the
electronegativity
Electronegativity, symbolized as , is the tendency for an atom of a given chemical element to attract shared electrons (or electron density) when forming a chemical bond. An atom's electronegativity is affected by both its atomic number and the d ...
difference between these two atoms is 0.35. Because of this small difference in electronegativities, the bond is generally regarded as being
non-polar
In chemistry, polarity is a separation of electric charge leading to a molecule or its chemical groups having an electric dipole moment, with a negatively charged end and a positively charged end.
Polar molecules must contain one or more pola ...
. In
structural formula
The structural formula of a chemical compound is a graphic representation of the molecular structure (determined by structural chemistry methods), showing how the atoms are possibly arranged in the real three-dimensional space. The chemical bondi ...
s of molecules, the hydrogen atoms are often omitted. Compound classes consisting solely of bonds and
bonds are
alkane
In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which ...
s,
alkene
In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond.
Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...
s,
alkynes, and
aromatic hydrocarbon
Aromatic compounds, also known as "mono- and polycyclic aromatic hydrocarbons", are organic compounds containing one or more aromatic rings. The parent member of aromatic compounds is benzene. The word "aromatic" originates from the past groupin ...
s. Collectively they are known as
hydrocarbons
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ex ...
.
In October 2016, astronomers reported that the very basic chemical ingredients of
life
Life is a quality that distinguishes matter that has biological processes, such as signaling and self-sustaining processes, from that which does not, and is defined by the capacity for growth, reaction to stimuli, metabolism, energ ...
—the carbon-hydrogen molecule (CH, or
methylidyne radical
Methylidyne, or (unsubstituted) carbyne, is an organic compound whose molecule consists of a single hydrogen atom bonded to a carbon atom. It is the parent compound of the carbynes, which can be seen as obtained from it by substitution of other ...
), the carbon-hydrogen positive ion () and the carbon ion ()—are the result, in large part, of
ultraviolet light
Ultraviolet (UV) is a form of electromagnetic radiation with wavelength from 10 nm (with a corresponding frequency around 30 PHz) to 400 nm (750 THz), shorter than that of visible light, but longer than X-rays. UV radiation i ...
from
star
A star is an astronomical object comprising a luminous spheroid of plasma (physics), plasma held together by its gravity. The List of nearest stars and brown dwarfs, nearest star to Earth is the Sun. Many other stars are visible to the naked ...
s, rather than in other ways, such as the result of turbulent events related to
supernovae and
young star
Various methods and tools are involved in stellar age estimation, an attempt to identify within reasonable degrees of confidence what the age of a star is. These methods include stellar evolutionary models, membership in a given star cluster or s ...
s, as thought earlier.
Bond length
The length of the carbon-hydrogen bond varies slightly with the
hybridisation of the carbon atom. A bond between a hydrogen atom and an sp
2 hybridised carbon atom is about 0.6% shorter than between hydrogen and sp
3 hybridised carbon. A bond between hydrogen and sp hybridised carbon is shorter still, about 3% shorter than sp
3 C-H. This trend is illustrated by the
molecular geometry
Molecular geometry is the three-dimensional arrangement of the atoms that constitute a molecule. It includes the general shape of the molecule as well as bond lengths, bond angles, torsional angles and any other geometrical parameters that determ ...
of ethane, ethylene and acetylene.
Reactions
The C−H bond in general is very strong, so it is relatively unreactive. In several compound classes, collectively called
carbon acid
In organic chemistry, a carbanion is an anion in which carbon is trivalent (forms three bonds) and bears a formal negative charge (in at least one significant resonance form).
Formally, a carbanion is the conjugate base of a carbon acid:
:R3CH ...
s, the C−H bond can be sufficiently acidic for proton removal. Unactivated C−H bonds are found in alkanes and are not adjacent to a
heteroatom
In chemistry, a heteroatom () is, strictly, any atom that is not carbon or hydrogen.
Organic chemistry
In practice, the term is usually used more specifically to indicate that non-carbon atoms have replaced carbon in the backbone of the molecula ...
(O, N, Si, etc.). Such bonds usually only participate in
radical substitution
In organic chemistry, a radical-substitution reaction is a substitution reaction involving free radicals as a reactive intermediate.March Jerry; (1985). Advanced organic chemistry reactions, mechanisms and structure (3rd ed.). New York: John Wile ...
. Many enzymes are known, however, to affect these reactions.
Although the C−H bond is one of the strongest, it varies over 30% in magnitude for fairly stable organic compounds, even in the absence of
heteroatoms
In chemistry, a heteroatom () is, strictly, any atom that is not carbon or hydrogen.
Organic chemistry
In practice, the term is usually used more specifically to indicate that non-carbon atoms have replaced carbon in the backbone of the molecula ...
.
[Yu-Ran Luo and Jin-Pei Cheng "Bond Dissociation Energies" in CRC Handbook of Chemistry and Physics, 96th Edition
]
See also
*
Carbon–carbon bond
A carbon–carbon bond is a covalent bond between two carbon atoms. The most common form is the single bond: a bond composed of two electrons, one from each of the two atoms. The carbon–carbon single bond is a sigma bond and is formed bet ...
*
Carbon–nitrogen bond A carbon–nitrogen bond is a covalent bond between carbon and nitrogen and is one of the most abundant bonds in organic chemistry and biochemistry.
Nitrogen has five valence electrons and in simple amines it is trivalent, with the two remaining el ...
*
Carbon–oxygen bond
A carbon–oxygen bond is a polar covalent bond between atoms of carbon and oxygen. Carbon–oxygen bonds are found in many inorganic compounds such as carbon oxides and oxohalides, carbonates and metal carbonyls, and in organic compounds such as ...
*
Carbon–fluorine bond
The carbon–fluorine bond is a polar covalent bond between carbon and fluorine that is a component of all organofluorine compounds. It is one of the strongest single bonds in chemistry (after the B–F single bond, Si–F single bond, and H–F ...
References
{{DEFAULTSORT:Carbon-hydrogen bond
Organic chemistry
Chemical bonding