chemistry Chemistry is the scientific study of the properties and behavior of matter. It is a physical science within the natural sciences that studies the chemical elements that make up matter and chemical compound, compounds made of atoms, molecules a ...

, the carbon–hydrogen bond ( bond) is a

chemical bond A chemical bond is the association of atoms or ions to form molecules, crystals, and other structures. The bond may result from the electrostatic force between oppositely charged ions as in ionic bonds or through the sharing of electrons a ...

between

carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...

and

hydrogen Hydrogen is a chemical element; it has chemical symbol, symbol H and atomic number 1. It is the lightest and abundance of the chemical elements, most abundant chemical element in the universe, constituting about 75% of all baryon, normal matter ...

atoms that can be found in many

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

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 atom ...

, single bond, meaning that carbon shares its outer

valence electron In chemistry and physics, valence electrons are electrons in the outermost shell of an atom, and that can participate in the formation of a chemical bond if the outermost shell is not closed. In a single covalent bond, a shared pair forms with b ...

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 Atomic nucleus, nuclei of two chemical bond, bonded atoms in a molecule. It is a Transferability (chemistry), transferable property of a bond between at ...

of about 1.09 Å (1.09 × 10⁻¹⁰ m) and a

bond energy In chemistry, bond energy (''BE'') is one measure of the strength of a chemical bond. It is sometimes called the mean bond, bond enthalpy, average bond enthalpy, or bond strength. IUPAC defines bond energy as the average value of the gas-phase b ...

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 ...

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 polar ...

. In structural formulas 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 whi ...

alkene In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or at the terminal position. Terminal alkenes are also known as Alpha-olefin, α-olefins. The Internationa ...

alkyne \ce \ce Acetylene \ce \ce \ce Propyne \ce \ce \ce \ce 1-Butyne In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and n ...

s, and

aromatic hydrocarbon Aromatic compounds or arenes are organic compounds "with a chemistry typified by benzene" and "cyclically conjugated." The word "aromatic" originates from the past grouping of molecules based on odor, before their general chemical properties were ...

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; their odor is usually faint, and may b ...

. In October 2016, astronomers reported that the very basic chemical ingredients of

life Life, also known as biota, refers to matter that has biological processes, such as Cell signaling, signaling and self-sustaining processes. It is defined descriptively by the capacity for homeostasis, Structure#Biological, organisation, met ...

—the carbon–hydrogen molecule (CH, or methylidyne radical), the carbon–hydrogen positive ion () and the carbon ion ()—are created, in large part, using energy from the

ultraviolet light Ultraviolet radiation, also known as simply UV, is electromagnetic radiation of wavelengths of 10–400 nanometers, shorter than that of visible light, but longer than X-rays. UV radiation is present in sunlight and constitutes about 10% of th ...

of nearby

star A star is a luminous spheroid of plasma (physics), plasma held together by Self-gravitation, self-gravity. The List of nearest stars and brown dwarfs, nearest star to Earth is the Sun. Many other stars are visible to the naked eye at night sk ...

s, rather than in other ways, such as turbulent events related to

supernovae A supernova (: supernovae or supernovas) is a powerful and luminous explosion of a star. A supernova occurs during the last evolutionary stages of a massive star, or when a white dwarf is triggered into runaway nuclear fusion. The original ob ...

and young stars, as thought earlier.

Bond length

The length of the carbonhydrogen bond varies slightly with the hybridisation of the carbon atom. A bond between a hydrogen atom and an sp² hybridised carbon atom is about 0.6% shorter than between hydrogen and sp³ hybridised carbon. A bond between hydrogen and sp hybridised carbon is shorter still, about 3% shorter than sp³ 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 det ...

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 acids, 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 mainly used more specifically to indicate that non-carbon atoms have replaced carbon in the backbone of the molecular ...

(O, N, Si, etc.). Such bonds usually only participate in radical substitution. Many enzymes are known, however, to effect 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.Yu-Ran Luo and Jin-Pei Cheng "Bond Dissociation Energies" in CRC Handbook of Chemistry and Physics, 96th Edition

References

{{DEFAULTSORT:Carbon-hydrogen bond Organic chemistry Chemical bonding

Bond length

Reactions

See also

References