Carbon–hydrogen bond


The carbon-hydrogen bond is a bond between carbon and hydrogen atoms that can be found in many organic compounds. This bond is a covalent bond meaning that carbon shares its outer valence electrons with up to four hydrogens. This completes both of their outer shells making them stable. Carbon–hydrogen bonds have a bond length of about 1.09 Å and a bond energy of about 413 kJ/mol. Using Pauling's scale—C and H —the electronegativity difference between these two atoms is 0.35. Because of this small difference in electronegativities, the C−H bond is generally regarded as being non-polar. In structural formulas of molecules, the hydrogen atoms are often omitted. Compound classes consisting solely of C–H bonds and C–C bonds are alkanes, alkenes, alkynes, and aromatic hydrocarbons. Collectively they are known as hydrocarbons.
In October 2016, astronomers reported that the very basic chemical ingredients of life—the carbon-hydrogen molecule, the carbon-hydrogen positive ion and the carbon ion —are the result, in large part, of ultraviolet light from stars, rather than in other ways, such as the result of turbulent events related to supernovae and young stars, as thought earlier.

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. Such bonds usually only participate in radical substitution. 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.
BondHydrocarbon radicalMolar Bond Dissociation Energy Molar Bond Dissociation Energy
CH3−HMethyl104440
C2H5−HEthyl98410
2HC−HIsopropyl95400
3C−Htert-Butyl93390
CH2=CH−Hvinyl112470
HC≡C−Hethynyl133560
C6H5−Hphenyl110460
CH2=CHCH2−HAllyl88370
C6H5CH2−HBenzyl85360
OC4H7−Htetrahydrofuranyl92380
CH3CCH2−Hacetonyl96400