Carbon–carbon bond

Carbon–carbon bond

A carbon–carbon bond is a covalent bond between two carbon atoms.[1] 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 said to be formed between one hybridized orbital from each of the carbon atoms. In ethane, the orbitals are sp3 hybridized orbitals, but single bonds formed between carbon atoms with other hybridisations do occur (e.g. sp2 to sp2). In fact, the carbon atoms in the single bond need not be of the same hybridisation. Carbon atoms can also form double bonds called alkenes or triple bonds called alkynes. A double bond is formed with an sp2 hybridized orbital and a p-orbital that isn't involved in the hybridization. A triple bond is formed with an sp hybridized orbital and two p-orbitals from each atom. The use of the p-orbitals forms a pi bond.

Carbon has the unique characteristic among all elements to form long chains of its own atoms, a property called catenation. This coupled with the strength of the carbon–carbon bond gives rise to an enormous number of molecular forms, many of which are important structural elements of life, so carbon compounds have their own field of study: organic chemistry.

Branching is also common in C−C skeletons. Different carbon atoms can be identified with respect to the number of carbon neighbors:

  • primary carbon atom: one carbon neighbor
  • secondary carbon atom: two carbon neighbors
  • tertiary carbon atom: three carbon neighbors
  • quaternary carbon atom: four carbon neighbors
primary, secondary, tertiary and quaternary carbon atoms

Synthesis

Carbon–carbon bond forming reactions are organic reactions in which a new carbon–carbon bond is formed. They are important in the production of many man-made chemicals such as pharmaceuticals and plastics.

Some examples of reactions which form carbon–carbon bonds are Aldol reactions, Diels–Alder reaction, the addition of a Grignard reagent to a carbonyl group, a Heck reaction, a Michael reaction and a Wittig reaction.

See also

  • An extensive list is presented here: list of carbon–carbon bond forming reactions
  • The chemistry of carbon bonded to other elements in the periodic table:
CH He
CLi CBe CB CC CN CO CF Ne
CNa CMg CAl CSi CP CS CCl CAr
CK CCa CSc CTi CV CCr CMn CFe CCo CNi CCu CZn CGa CGe CAs CSe CBr CKr
CRb CSr CY CZr CNb CMo CTc CRu CRh CPd CAg CCd CIn CSn CSb CTe CI CXe
CCs CBa CHf CTa CW CRe COs CIr CPt CAu CHg CTl CPb CBi CPo CAt Rn
Fr Ra Rf Db Sg Bh Hs Mt Ds Rg Cn Uut Uuq Uup Uuh Uus Uuo
CLa CCe CPr CNd CPm CSm CEu CGd CTb CDy CHo CEr CTm CYb CLu
Ac Th Pa CU Np Pu Am Cm Bk Cf Es Fm Md No Lr
Chemical bonds to carbon
Core organic chemistry Many uses in chemistry
Academic research, but no widespread use Bond unknown / not assessed

References

  1. ^ March, Jerry (1985), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (3rd ed.), New York: Wiley, ISBN 0-471-85472-7 

Wikimedia Foundation. 2010.

Игры ⚽ Поможем сделать НИР

Look at other dictionaries:

  • Carbon-carbon bond — A carbon carbon bond is a covalent bond between two carbon atoms [JerryMarch] . 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 said… …   Wikipedia

  • Bond length — In molecular geometry, bond length or bond distance is the average distance between nuclei of two bonded atoms in a molecule. Explanation Bond length is inversely related to bond order, when more electrons participate in bond formation the bond… …   Wikipedia

  • Carbon-nitrogen bond — A carbon nitrogen bond is a covalent bond between carbon and nitrogen and one of the most abundant in organic chemistry and biochemistry [ Organic Chemistry John McMurry 2nd Ed.] .Nitrogen has five valence electrons and in simple amines it is… …   Wikipedia

  • Carbon–hydrogen bond activation — or C−H activation may be defined as a reaction that cleaves a carbon–hydrogen bond. Often the term is restricted to reactions involving organometallic complexes and proceeding by coordination of a hydrocarbon to the inner sphere of metal, either… …   Wikipedia

  • Carbon arc welding — (CAW) is a process which produces coalescence of metals by heating them with an arc between a nonconsumable carbon (graphite) electrode and the work piece. It was the first arc welding process ever developed but is not used for many applications… …   Wikipedia

  • Carbon — (), but as most compounds with multiple single bonded oxygens on a single carbon it is unstable.] Cyanide (CN–), has a similar structure, but behaves much like a halide ion (pseudohalogen). For example it can form the nitride cyanogen molecule… …   Wikipedia

  • Carbon fiber — or carbon fibre [See American and British English spelling differences.] (alternately called graphite fiber, graphite fibre or carbon graphite) is a material consisting of extremely thin fibers about 0.0002–0.0004 inches (0.005–0.010 mm) in… …   Wikipedia

  • Bond order — is the number of bonds between a pair of atoms. For example in nitrogen N≡N the bond order is 3, in acetylene H−C≡C−H the bond order between the two carbon atoms is 3 and the C−H bond order is 1. Bond order gives an indication to the stability of …   Wikipedia

  • Carbon ring — Carbon rings are rings of carbon atoms. Rings of five and six carbons are by far the most common, as they allow bond angles close to the ideal angle of 109.5 degrees. Rings of three and four are possible, but with bond angles of 60 and 90 degrees …   Wikipedia

  • Carbon dioxide — Carbon dioxide …   Wikipedia

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”