Triple bond
Chemical bond involving six bonding electrons; one sigma plus two pi bonds
- 2 min read
- 2 chapters
![(left) Chemical structure of triangular dehydrobenzo[12]annulene (tDBA); (right) high-resolution AFM image of tDBA on Ag(111). Inset shows the STM topography. Measurement parameters: Vtip=0 mV and A=6](/encyclopedia-data/v2/img/triple-bond.avif)
Related on Lably
Through Chemistry, Chemical bond and Atom
Bonding
Triple 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° bond angles, and occupy the x-axis in the cartesian coordinate system. The p-orbitals are perpendicular to the sp-orbitals on the y-axis and the z-axis. When the atoms approach each other, the sp orbitals overlap to form an sp-sp sigma bond. At the same time the pz-orbitals approach and together they form a pz-pz pi-bond. Likewise, the other pair of py-orbitals form a py-py pi-bond. The result is formation of one sigma bond and two pi bonds. However, with heavy enough atoms, relativistic effects comes into play and one ends up, not with pure sigma and pi bonds for the three bonds, but rather hybridizations of sigma and 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.
Sign in to keep reading
One more chapter is free with a Lably account.
Triple bonds between elements heavier than oxygen
Many elements beyond oxygen can form triple bonds. These bonds are common in some transition metals. Hexa(tert-butoxy)ditungsten(III) and Hexa(tert-butoxy)dimolybdenum(III) are well known examples, in which the metal-metal bond distance is about 233 pm. The former has attracted particular attention for its reactions with alkynes, leading to metal-carbon triple bonded compounds of the formula RC≡W(OBut)3
Additionally, phosphorus can exist as the highly reactive diatomic molecule diphosphorus, which has roughly half the bond-dissociation energy of dinitrogen.

