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Structure and AFM image of dehydrobenzo[12]annulene, where benzene rings are held together by triple bonds

A triple bond in chemistry is a chemical bond between two atoms involving six bonding electrons instead of the usual two in a covalent single bond. Triple bonds are stronger than the equivalent single bonds or double bonds, with a bond order of three. The most common triple bond, that between two carbon atoms, can be found in alkynes. Other functional groups containing a triple bond are cyanides and isocyanides. Some diatomic molecules, such as dinitrogen and carbon monoxide, are also triple bonded. In skeletal formulae the triple bond is drawn as three parallel lines (≡) between the two connected atoms.^[1]^[2]^[3]


acetylene, H−C≡C−H	cyanogen, N≡C−C≡N	carbon monoxide, C≡O
Chemical compounds with triple bond

Bonding

The types of bonding can be explained in terms of orbital hybridization. In the case of acetylene each carbon atom has two sp-orbitals and two p-orbitals. The two sp-orbitals are linear with 180° angles and occupy the x-axis (cartesian coordinate system). The p-orbitals are perpendicular on the y-axis and the z-axis. When the carbon atoms approach each other, the sp orbitals overlap to form a sp-sp sigma bond. At the same time the p_z-orbitals approach and together they form a p_z-p_z pi-bond. Likewise, the other pair of p_y-orbitals form a p_y-p_y pi-bond. The result is formation of one sigma bond and two pi bonds.

In the bent bond model, the triple bond can also formed by the overlapping of three sp³ lobes without the need to invoke a pi-bond.^[4]

References

^ March, Jerry (1985). Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (3rd ed.). New York: Wiley. ISBN 9780471854722. OCLC 642506595.
^ Organic Chemistry 2nd Ed. John McMurry
^ Pyykkö, Pekka; Riedel, Sebastian; Patzschke, Michael (2005). "Triple-Bond Covalent Radii". Chemistry: A European Journal. 11 (12): 3511–20. doi:10.1002/chem.200401299. PMID 15832398.
^ Advanced Organic Chemistry Carey, Francis A., Sundberg, Richard J. 5th ed. 2007

[1] March, Jerry (1985). Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (3rd ed.). New York: Wiley. ISBN 9780471854722. OCLC 642506595.

[2] Organic Chemistry 2nd Ed. John McMurry

[3] Pyykkö, Pekka; Riedel, Sebastian; Patzschke, Michael (2005). "Triple-Bond Covalent Radii". Chemistry: A European Journal. 11 (12): 3511–20. doi:10.1002/chem.200401299. PMID 15832398.

[4] Advanced Organic Chemistry Carey, Francis A., Sundberg, Richard J. 5th ed. 2007

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@@ Line 1: / Line 1: @@
 [[File:Dehydrobenzoannulene.jpg|thumb|upright=1.4|Structure and [[Atomic force microscopy|AFM]] image of dehydrobenzo[12]annulene, where [[benzene]] rings are held together by triple bonds]]
-A '''triple bond''' in [[chemistry]] is a [[chemical bond]] between two [[atoms]] involving six [[Electron pair bond|bonding electron]]s instead of the usual two in a [[covalent bond|covalent single bond]]. Triple bonds are stronger than the equivalent [[covalent bond|single bonds]] or [[double bond|double bonds]], with a [[bond order]] of three. The most common triple bond, that between two [[carbon]] atoms, can be found in [[alkyne]]s. Other [[functional group]]s containing a triple bond are [[cyanide]]s and [[isocyanide]]s. Some diatomic molecules, such as [[dinitrogen]] and [[carbon monoxide]], are also triple bonded. In [[skeletal formula|skeletal formulas]] the triple bond is drawn as three parallel lines (≡)<!--may be encoded on WP as &equiv;--> between the two connected atoms.<ref>{{JerryMarch}}</ref><ref>''Organic Chemistry'' 2nd Ed. John McMurry</ref><ref>{{cite journal|doi=10.1002/chem.200401299|title=Triple-Bond Covalent Radii|year=2005|last1=Pyykkö|first1=Pekka|last2=Riedel|first2=Sebastian|last3=Patzschke|first3=Michael|journal=Chemistry: A European Journal|volume=11|issue=12|pages=3511–20|pmid=15832398}}</ref>
+A '''triple bond''' in [[chemistry]] is a [[chemical bond]] between two [[atoms]] involving six [[Electron pair bond|bonding electron]]s instead of the usual two in a [[covalent bond|covalent single bond]]. Triple bonds are stronger than the equivalent [[covalent bond|single bonds]] or [[double bond|double bonds]], with a [[bond order]] of three. The most common triple bond, that between two [[carbon]] atoms, can be found in [[alkyne]]s. Other [[functional group]]s containing a triple bond are [[cyanide]]s and [[isocyanide]]s. Some diatomic molecules, such as [[dinitrogen]] and [[carbon monoxide]], are also triple bonded. In [[skeletal formula|skeletal formulae]] the triple bond is drawn as three parallel lines (≡)<!--may be encoded on WP as &equiv;--> between the two connected atoms.<ref>{{JerryMarch}}</ref><ref>''Organic Chemistry'' 2nd Ed. John McMurry</ref><ref>{{cite journal|doi=10.1002/chem.200401299|title=Triple-Bond Covalent Radii|year=2005|last1=Pyykkö|first1=Pekka|last2=Riedel|first2=Sebastian|last3=Patzschke|first3=Michael|journal=Chemistry: A European Journal|volume=11|issue=12|pages=3511–20|pmid=15832398}}</ref>
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